required to jump in the pool to get a day off, recovering from over-sharing, and more

It’s five answers to five questions. Here we go…

1. Employees had to jump into the pool to get the holiday off

My relative works in property management and sent me a video last Wednesday of them and their coworkers jumping into the apartment complex pool in their uniforms. The property’s owner had sent them a message: “You want Monday off? I want video of you jumping into the pool in uniform.” He has done batty things in the past, so they knew they wouldn’t get a day off for Independence Day otherwise and did it. I was so disgusted with the abuse of power and the bullying aspect of making subordinates debase themselves just to get the most common secular holiday in the U.S. off. Waiting until a few days before so they couldn’t make plans is just the icky icing on the gross cake. Is this as banana crackers as it seems?

Eh, I’d assume it was intended as a silly kind of team-building thing, not an abuse of power, unless there’s other context that makes it clear he was just doing it to be an ass. To be clear, I don’t like it — if you can give people the holiday off, just give it to them — but lots of places have occasional “do this silly thing for a prize” activities without being bullies. (That doesn’t mean this guy isn’t a bully, of course.)

2. I’ve been over-sharing at work — how do I reset?

I work for my husband in a small business. He has been in the field for many years and I recently changed careers to join him. We have a successful business with a crew of 10 and I work in the office with someone he has known for years who has done the business administration, including bookkeeping, and who knows all of the company details.

Due to personal reasons I have not been able to learn the business yet, so we hired another woman to join us in the office who has business experience. The plan is for the three of us to be interchangeable with all of the office duties but, being the wife of the owner, I will eventually be 50% partner (or even company owner).

Now here’s the problem: ME! I am the epitome of an “over-sharer.” I am secure and stable but have no problem telling anyone who will listen my entire dysfunctional early life story at the first opportunity of meeting them! And it’s a very colorful background. I don’t feel conflicted about my past, I just happen to identify as “survivor” of my past more than the woman I have become. I know better, I just can’t seem to help myself and now I’m extremely embarrassed!

My husband is a private person and also a natural leader. He addressed it with me and I have no excuse! He said I lack leadership and he is right. I’m intelligent but have no personal boundaries and this new employee I’ve been over-sharing with has been with us less than a month. How do I gain back my dignity that I robbed from myself? My plan is to learn the business inside and out and be the most valuable person my husband has within the next year and keep the other two in the office with us, but 1) I don’t know the business yet and 2) I feel really stupid for my lack of professionalism. Do you have any advice on how I can potentially undo my mistake so I can be taken seriously?

All you can do is be scrupulously professional from here on out. That’s not to say you can only talk about work, but resolve that the non-work conversations you have with colleagues will be on subjects that are in no way personal or intimate. In fact, while you’re working on recalibrating your sense of boundaries, pick three non-work topics that you know are safe and stick to those — for example, pets/movies/sports or cooking/books/travel. (Or you could engage in no non-work talk at all, but as the boss’s wife there’s a risk that if you go from really talkative to work-topics-only, people will read into the shift in ways you don’t want or will perceive it as chilly.)

In case you’re tempted to find a way to address this with colleagues (like to apologize for crossing boundaries with them): I would not! Talking about what’s happened and what you’re resolving to do differently may itself end up feeling to them like further over-sharing. The most convincing way to signal things will be different is to just do things differently. Seeing the change will be more convincing than an apology or declaration would be anyway.

In time, people will see you’ve reset, and if you sustain the change you won’t be marked forever by the way you began. People will appreciate that you course-corrected!

One other thing: I don’t know if this has been the case with you or not, but sometimes people who over-share also talk a lot in general — and people are more likely to worry about cutting you off when you’re the boss’s wife. Watch how often they initiate conversations vs. how often you do and pay attention cues that they might want to wrap up the conversation and turn back to work (if you’re not sure, you could default to wrapping up social conversations after five minutes or so, at least while you’re recalibrating).

3. My friend wants to hire me and isn’t taking no for an answer

I have been asked to consider an administrative support role in a team led by a friend of mine. We’ve never worked together, but I used to do administrative support in her field. I intentionally left that field several years ago because it was emotionally taxing, had systemic issues in how support staff were treated, and required me to give more of myself to my job than I was happy giving. I also moved out of administration entirely and have no desire to return. I work in a much lower paying industry now, but it is a better fit for me and it works well for my family too.

I am not a good candidate for the role she has describes. It would be an incredibly busy role, with tight deadlines and long hours, and needing extremely close attention to detail. It is a role for a high energy, high-capacity person. I am not that person at this point in my life, and I have no desire to be.

I have said plainly that I do not want the role she’s offered. I have said I am happy with my current role. I have said the role is not a good fit for me. I have said that as my husband and I are trying to get pregnant again, I do not want to take on a new role when I may take a year’s parental leave soon. Every time she counters by telling me that I’ll be so good at it, and then she offers me a higher salary than she did the previous day.

It’s been three weeks. I’ve started avoiding her. Please help.

Stop giving her reasons, and just tell her no — and say it’s your final answer and you don’t want to keep discussing it.

So: “Jane, thank you for the offer, but it’s not work I want to do. More money won’t change my mind. That’s my final answer, and I’d be grateful if we could leave it there.” (She’s a friend, so I’m suggesting softer language here than I might otherwise.)

If she keeps bringing it up after that: “It’s making me really uncomfortable that you keep pushing this after I’ve told you it’s not something I’m interested in. It’s been starting to make me avoid talking to you, and I don’t want that.”

4. Was in wrong in my response to a vague invitation?

I work in a mostly technical role but it also has financial impacts to my company and the work we do is audited so accuracy and focus are crucial. I lead my team in all aspects except those that are HR-related. Covid pushed back many of our very large, very high-profile projects to all launch right before October 1.

A partner recently reached out with a meeting invite. The subject was “quick check-in” and the body only said, “I would like to better understand this process.” WHAT PROCESS? My team has more processes than we know what to do with. My processes have processes, so I really did need more insight on what she was asking for, but I also need to be mindful of my time with our impending project launches. I replied politely asking clarifying questions, explaining that I wanted to ensure the right team members were on the call with her but I wasn’t clear on what process she was asking about. I also suggested that perhaps I had missed an attachment or the request was in reference to an email string that I wasn’t included in.

She very curtly canceled the meeting stating that she understood if I am too busy to meet.

So now my professional anxiety is flaring. AITA? Should I have just met with her and hoped it wasn’t a waste of both of our time? Should I reach out in a few weeks and invite her to schedule time? My direct leader is the epitome of a “hand holder” so I’m sure she wouldn’t have pushed back.

Nah, what you did sounds very reasonable, and her response sounds strange. Of course you need to know what the meeting is about so you can figure out how to prioritize it and figure out who needs to be there. One option is to reply back saying, “We do have a packed schedule right now, but I want to make sure you get what you need. Can you tell me more about what you were hoping to cover, so I can suggest times that would work and ensure the right people from my team are involved?” (That said, I wouldn’t be surprised if it turns out she doesn’t have a specific agenda and instead is a person who just feels better connecting one-on-one for relationship purposes. If so, maybe you can offer a short call — with a hard stop — with a team member who isn’t you.)

5. Freelance agency keeps paying me late, but they give me a lot of work

I work as a freelance graphic designer, usually doing a few weeks or months at a time at a few regular design agencies. One of these agencies has awful IT and timesheet systems that often fail (not being able to log in) or there are issues with getting information to complete them before my last day (job numbers and such). I track all my hours, but often the timesheet completion falls to staff to do after I’ve left and don’t have access anymore. Recently I found out one timesheet hadn’t been done for a month by this person.

The issue is that the finance department will simply not pay invoices if timesheets aren’t completed and, even if they are, invoices are consistently paid very late. This causes a lot of cashflow issues for me (standard freelance gripe, right?) and they don’t answer emails or the auto-reminders sent out. It’s beyond frustrating that things out of my control are holding the process up.

The work and company are otherwise great and I have a good relationship with them, but the constant payment issues are really making me not want to work with them anymore. Is there a polite way to say “I can’t work for you until the systems are sorted out” without burning bridges, or should I just grin and bear the 2-3 month payment delays without income? I don’t want to come across as a diva but the issues are causing a lot of problems for me. Should I let them go as a client and hope I get enough work from the other agencies? What’s the best way to handle this?

It’s not diva-like to expect to be paid on time and without repeated reminders. One thing some freelancers do is to include late fees (or early payment discounts) in their contracts … but a lot of places won’t agree to that (especially if they use lots of freelancers and have a standard system they won’t deviate from). Particularly if you want to work for them more than they need to hire you, that won’t always work but you could consider whether it’s worth trying.

You can also talk with your contact there about the problem, explain you can’t continue to have payment come in months late, and ask what can be done to get you paid on time. That may or may not make a difference. Sometimes it will, and other times their system just sucks and your contact won’t have much influence over it.

The big question I’d ask yourself is: If you knew this was never going to change, would you want to keep working for them anyway? If so, you might need to accept that this place pays three months later than everyone else and plan accordingly. But if it’s a deal-breaker for you, you can take a harder line with your contact and let them know you won’t do more work until this gets fixed. For example: “I really like working with you and would love to continue. But the payment delays have caused cash flow issues on my end, so I’d want to be assured that’s been fixed before I take on more projects.” (Alternately, is it realistic to request payment in advance, perhaps pointing to the continued problems and the grace you’ve extended them previously? Some places will do that if they really value you and if your contact has the sway to get it done.)

Read an update to this letter here

{ 476 comments… read them below }

  1. Annie J*

    I like Alisons response to op2, though I think it’s also worth considering the power imbalance here.
    The other two employees may have felt that they have to listen to, and be sympathetic for, the backstory presented by theOP due to her being the bosses wife.
    I know if I was in that position, and my managers spouse was working with me as a colleague, constantly i’d be on eggshells very wary how I behave and what I say in case i offend her, and this gets back to the boss.

    1. allathian*

      Yes, me too. And that’s just one reason why I would never want to work for a family business as an outsider.

      1. June*

        Being held a captive audience at work for personal laundry airing is definitely uncomfortable.

        1. Former Child*

          Yes. AND the wife is supposed to be learning the job from these two while they also do their work. She’s interfering w/that while also distracting them from training her. If they have time for all this — working, training her, and listening to her —
          right now, then why will they need all three of them later?

          I’d suggest she see a work coach or therapist to deal w/intrusive personal issues and ALSO
          I’d suggest she ask herself if she really wants this job or is avoiding it. Is her role well defined? Maybe not. She says “work FOR my husband” not “WITH my husband” and become the most valuable person, but he’s got a long-term one who sounds like that. Does she even want to do this? Is it interesting to her?

    2. The Prettiest Curse*

      Yup, the thought of the power imbalance alone and how uncomfortable the over-sharing may be making the employees should be a big incentive for the OP to stop this behaviour. However, as the family member of a chronic over-sharer who is an incessant talker, I have to say that unless the OP addresses the reasons for this behaviour, they won’t be able to stop. At this point, the over-sharing might be an ingrained habit. So unfortunately, the OP in this case may need to address this with a therapist.

    3. MusicWithRocksIn*

      Its hard enough being comfortable around the bosses wife, but if enough had been said in these over shared moments I don’t know if I would ever be comfortable around her. There was a discussion of it on this site recently and someone else used a phrase that really resonated with me which was ‘forced intimacy’ which really hits the nail on the head for how I feel when someone over shares with me. And every time I’ve been around the super over sharers again my awkward/uncomfortable level went to 10 and I did everything possible to keep from being alone with them, or be in any position to hear more. If I thought part of my job was being an audience for the bosses wife’s ongoing monologue of ‘This is my tragic life’ I would be looking for a new job so quick.

      1. Carol the happy elf*

        I first read about “Forced Intimacy” in Gift of Fear.
        It’s a technique where a person is manipulated into a position they would never place themselves (?) in. Also “Forced Teaming”.
        These are situations where the use of “We”, “Our”, and “Us” invokes a nonexistent relationship, and enforces artificial togetherness where it benefits one person, but exploits the other.

        “Captive audience” comes to mind, too.
        It’s extremely disconcerting when a power distribution is so unequal, especially in a small core business.
        One of my psych classes dealt with this, and the professor compared it to a circular weather pattern. Some weather patterns are enormous; the energy they transmit is huge, (think about the circles hovering over the map on the TV news) but since they cover such a massive area, the spin is slow and doesn’t cause much destruction.
        On the other hand, a tight circular rotation can spin much faster around a smaller center.
        “That’s a tornado, folks!”

        1. Ellie*

          This is in no way the same as ‘forced teaming’ – they are employed by the same organisation. This is a real, actual, work team. Its normal to want to talk to your coworkers, and to express yourself in terms of ‘we’ and ‘ours’ if you’re on the same team and are all trying to accomplish the same goals.

          If the bosses wife is an oversharer then that can be annoying, but it is in no way comparable to being approached by a strange man on the street, who uses ‘we’ and ‘our’ in order to manipulate you. The employees aren’t trapped there, they could excuse themselves or put their headphones on, or go and do something else. There’s no suggestion that they’re being forced to engage in any way.

          I think people are being really unkind to the OP. I’ve known many oversharers, and it is a lot more annoying when they’re in a position of power over you, to be sure. But they’ve mostly been well-meaning. If the OP can dial it back to professional friendliness from here on then it sounds like it could be a great place to work.

    4. SheLooksFamiliar*

      ”I like Alisons response to op2, though I think it’s also worth considering the power imbalance here.”

      Agreed. At two previous employers, the owner’s wife was an active part of the business. One worked as hard as anyone and knew the business inside and out; she ‘talked shop’ and asked our opinions on certain work issues, but never got into anything personal. The other was okay at her job and her life was an open book.

      I also walked on eggshells around both of them, wondering when my casual work question or comment would get reported to the husband. And when they talked about a difficult customer, their own workload, car problems, the family, etc., I smiled and said nothing. I can’t remember anything awful happening but being on constant alert was tiresome.

      1. quill*

        I got that at my ‘start up experience’ but without any of the boss’ family being involved – just, a culture of expecting everyone to already have the answers, the idea that anything you spoke of on the premises would get back to the boss who would have OPINIONS about your personal life even if it was how you should cook your dinner / where you should buy a car. (Sus Vide and Lexus were constantly promoted by the boss, nevermind that he knew he wasn’t paying us Lexus money.)

    5. Meep*

      Yeah I was emotionally blackmailed and abused because my manager was having issues with her marriage or with her boyfriends. She would come in and tell me I needed to break up with my boyfriend anytime she was fighting with her husband or a boyfriend (sometimes both at the same time). Once she told me to buy a house under his nose and make him sneakily pay my mortgage for me. I knew far too much about her life and she tried to dig up dirt on mine to judge it. There is a good reason she isn’t allowed over to my house.

      OP 2 needs to knock it off and find a (non-work) friend to vent to.

      1. LutherstadtWittenberg*

        These are completely different issues. You’re condemning the OP for things she’s not doing. She shouldn’t overshare, certainly. That makes everyone feel awkward and stifled. No one will feel as if she’s a true colleague; she’ll forever be considered the boss’ wife no matter what she contributes. However, she isn’t haranguing people to end relationships or buy property under false pretenses. She isn’t blackmailing coworkers.

    6. MHA*

      Yep. It’s much harder to cut off a chatty coworker (and even moreso when the person is sharing something very personal where it would seem rude to blow it off with a mere “Aw, sounds tough, anyway I have to get going,”) when they’re your boss! I occasionally have to cover at another office and I always dread it, because I’ve literally never been able to escape without the manager at that location holding me hostage for at least 45min worth of going over every sadbadterrible thing that’s happened in her life since I saw her last. (Once it was an hour and a half!)

      Thankfully it doesn’t sound like the LW is THAT far gone, and it’s great that she’s recognizing the need to nip this behavior in the bud! But thinking of it from this perspective of reinforcing a power imbalance– something she’s doing to other people, not just something she’s doing to their perception of her– may make it easier to remember to keep that behavior under control.

  2. Observer*

    #5 – Another thing to consider is charging your client a higher rate. If you are going to be paid late, at least you should be compensated for the aggravation.

    1. Pennyworth*

      I’d charge 20% more, with a 20% discount for on-time payment. You end up either getting paid on time or getting a significant income increase.

      1. Amy Farrah Fowler*

        Agree. Or possibly a sliding scale late charge. Early Payment – $X – 10%, On-Time Payment – $X, 1-30 days late $X + 10%, 31-60 days late $X + 20%, 61-90 days late $X + 30% and so forth. If they end up paying $120-130 for $100 worth of work a few times, either they will learn, or at least you will be compensated for your trouble!

        Alternatively, you could ask for a “retainer” of sorts to be paid up front that amounts to some percentage of the estimated scope of the project or require pre-payment for future projects.

        There are a number of different ways to work this. You have to figure out which you are most comfortable suggesting and which you think the company would be most likely to agree to.

        1. Amy Farrah Fowler*

          In re-reading your letter, I also noticed that the tech issues on their side with time sheets are a part of the delay, but not all of it. So to help with that side, could you claim you are unable to work on their project until you have correct permissions/log-ins that you need for time sheets? For example, do you have enough projects/other work that you could legitimately say: “I have you on my list and this project will likely take x hours/weeks, but I’m unable to begin until I’m able to access the system to log my time. Currently, I don’t have that access. I will check back tomorrow, and get started then if the access is available. Essentially you’re returning the timesheet problem back to the company and creating situation where they can’t just keep ignoring the “missing stair” of the time sheet issue if they want you to work with them.

          1. Person from the Resume*

            But it sounds like the problem is at the end after the project ends. She loses access, but hasn’t been able to complete her timesheet because of technical problems so someone else has to complete and submit it for her.

            1. Zephy*

              I read it as she was missing key info for the timesheet so she couldn’t complete it before losing access, like project codes (sounds like they’re on a billable-hours type of system or she’s paid out of the project’s individual budget) – surely that information isn’t generated upon project completion, she should just ask for all of that upfr0nt. If she has any kind of proposal/ticketing system that she uses, it would probably be easy to add a space for that kind of billing information.

          2. Where’s the Orchestra?*

            I would add having the access to the time sheet extended a day past the end of the project needs to happen so that contractors are not left stranded when the system glitches on their last day.

            Really it sounds like this time card system needs a major revamp to get the glitches fixed. It’s up to OP if they are willing to keep working with this company with the payment headaches it entails.

            1. quill*

              Yeah, and likely this is either going to require actual IT repairs, revamping the system (seems like it kicks them out on the last day? Maybe) or acquiring a new system, so if LW is otherwise happy working with this company, make the fuss NOW so they’ll actually spend money to fix it, and look for improvements in 3-6 months.

      2. Parenthesis Dude*

        If she normally charged $100 for a project and started charging $120 for a project, then that would be a 20% increase. But a 20% discount would put her pay at $96, because it would result in a 20% discount of the base price ($100 to $80) plus a 20% discount of the increase ($20 to $16).

        So, she’d want to offer a 15% discount or 16.66666% if you want to be exact.

      3. Boof*

        It sounds like this is the sort of company it may be hard to adjust things for – presumably LW needs to hand in the invoice and they won’t know for 100% certain when it will be paid so it’s hard to change the fees. If the company is almost always late I would just raise my rates for them enough to make it worthwhile. If they become better about it then perhaps lower the rates in the future back to what everyone else pays who pays on time. Much simpler.

    2. AdAgencyChick*

      Yes, absolutely this. If they reliably pay you, just reliably late, then they’re probably worth keeping as a client at a rate that’s worth the wait.

      In my experience on the other side (ie, hiring freelancers), my hands are tied by my company’s system. As I understand it, we pay pretty quickly if the freelancer gets their timesheets done and approved on time; some managers are better at doing the approval quickly than others. Since our system is pretty rigid and doesn’t allow for late fees (or a sliding scale of rates for the same freelancer), if I were on the other side, I’d ask for a higher rate across the board to make up for any managers who don’t approve timesheets quickly.

    3. learnedthehardway*

      This, and charge a certain amount of the fees up front to start the work.

      I will say, I have an aggravation tax for certain clients. It’s WELL deserved with the client I started it for, as there is a surprise (of an unwelcome variety) in every project.

    4. JJ*

      The fact that they do timesheets within the employer’s system (and not invoicing) says to me that OP5 is not in control of their rate and they wouldn’t be able to enforce any kind of late fee or early bonus.

      Honestly OP I’d start looking for someone to fill that client’s gap and break up with them, they’ve shown you they’re not going to prioritize getting you paid, and I doubt anything you say can fix their broken system. (For context, I’ve been full-time freelancing for 5 years and I’ve never experienced this in an agency setting…I’d bet that agency is dysfunctional in more ways than that).

      1. OP#5*

        I have a day rate as a freelancer but I have to submit timesheets within the systems that agencies use. I can add late fees to invoices which I have been doing but it’s not made any difference.

        It’s a shame really because the agency and team are great otherwise. I’ve since worked with another agency on a well known client so fingers crossed they become a regular booker. I probably won’t work with the problematic agency for the foreseeable future as it causes too many cashflow issues never knowing when invoices will get paid.

    5. Cakeroll*

      This is also where talking to the contact as Alison suggests might be informative – they might say there’s nothing they can do about the timesheet problems, but that they have an option to switch the payments to a non-hourly fee-for-service setup that’s processed by a separate AP group.

      From the other side of this – after months of headaches with managing time approvals and pre-approvals in a complicated management system for freelancers, assuming it’s just what I had to do, one of my contacts at the management system suggested out of the blue “oh you know we can just switch them all to regular weekly payments, right? Do you wanna do that?”

      (Subtext because I’m far from an expert, but the talk about being required to use their systems, and log time in their timesheets are setting off employee/independent contractor classification alarms for me too)

      1. OP#5*

        The way it works in UK agency freelancing is more day rates and like independent contractors, rather than hourly/project based. The bookings are ad hoc, either week by week (or longer contracts) or sometimes a few days at a time, and timesheets usually get submitted and invoices sent on a weekly basis. Some freelancers end up on rolling contracts or as permalancers, but recent IR35 laws in UK are trying to stamp out ‘disguised employee’ ways of working (won’t go into that as it’s been a messy rollout). So it’s usually weekly invoicing cycles. In some sense that’s good because it prevents large sums being owed for projects, but it still affects cashflow when payments are late (especially if the contract states 30 day terms).

    6. Momma Bear*

      And/or require a deposit so that at least some of the funds are provided upfront. When I freelanced, I used an automatic invoice system that nagged them for me at intervals. That seemed to help in 1. it looked more professional and 2. it followed my contract for warnings about unpaid invoices.

      1. OP#5*

        I’ve got auto-payment reminders set up on my accounting platform but they’ve largely gone ignored, as well as emails to the finance person and cc’d their boss, and other contacts. They wouldn’t agree to a deposit as all payments are dependent on the timesheets (so they know what to bill client accounts for work done). It sucks but that’s how it is done here, and normally it works well if both sides act professionally.

    7. OP#5*

      OP#5 here. Thanks for all your replies. You’re right in that I don’t have control over the systems in place which is where a lot of the frustration lies. The way it works where I am (UK based) is freelancers get hired at a certain day rate and during the week of booking, we get various projects to work on (or just one, whatever the agency needs). Project managers give us the various job numbers for projects we’ve worked on but sometimes we have to chase and they aren’t entered in properly in the system. At the end of the week, we complete and submit timesheets (usually on the agency systems but sometimes we just send them to the resource manager.. it depends on the agency and how they work) – this agency has their own system I have to log into and input time against job numbers. It’s not something I can leverage over the agency because I’m pretty much like an employee during that time, rather than a freelancer that takes on individual projects in my own time (if that makes sense). The day rate is agreed beforehand and is usually industry standard. Charging ahead isn’t usually the way to do it for agency based freelancing unfortunately. I did actually add accumulating late fees though (within legal government guidelines) and send many reminders which were ignored (payment of late fees for other invoices were also ignored). Sometimes they pay without issue, but I’ve had problems before with late payments and systems not working as described, so it’s not even consistent.

      We have an industry freelancing platform here that acts as a middle man between agencies and freelancers, but the irony is that I was asked to bill the agency directly as a favour to them.

      BTW I’m still waiting for the invoice, it’s been over 3 months. I don’t think these systems will be fixed any time soon so I will most likely part ways for the foreseeable future.

    1. Peter Piper Picked a Peck of Pickled Peppers*

      Me too. I used to be a chronic oversharer. I eventually trained myself out of it. My behaviour also made more sense when I got my early-40s ADHD diagnosis. Poor impulse control, and all that. But having some practical tools to curb it would certainly have helped!

  3. Allison K*

    #5 – I’m confused why they need timesheets from you at all – if you’re a freelancer, part of that is getting to accomplish the work in whatever hours you want, without them monitoring your time spent. Theoretically, you should be able to just invoice, even if it’s for an hourly rate. Timesheets are for employees.

    1. alienor*

      Depends on how the design agency is billing their clients. I’ve done agency work where hours had to be tracked and billed against specific projects, so even freelancers needed to report that they’d worked 12.5 hours on project X, 6.75 hours on project Y and so forth.

    2. Ask a Manager* Post author

      Some freelancers are paid by the hour, some by the project. It just depends. (Also, there’s no hard and fast rule that freelancers must be able to choose their own hours; the determination of independent contractor vs employee is based on the totality of the circumstances, not any one individual factor.)

    3. 2 Cents*

      This isn’t true for how all design / ad agencies work either. Usually, they’ve outlined for the client that design work will be X number of hours. If those hours go over because of client changes, then extra $$ is charged by the agency, so tracking the number of hours by everyone (freelancers and employers) is key.

    4. OP#5*

      Hey, OP#5 here. Freelancing in agencies usually involves being a bit like an employee, with set hours and projects that we have to track like employees do. The problem is that if we don’t get the information (like job numbers) to input, or if there are IT issues and we physically can’t log into the timesheet system before our contract ends (eg. Monday – Friday booking) then we have to rely on others completing the timesheets for us. And no invoice payments can be made without the timesheets being entered and submitted, even if I send the invoice. It’s a bad system.

  4. Naomi*

    Could making a day off contingent on jumping in the pool be an ADA violation, if an employee couldn’t jump in the pool because of a disability?

    1. Willis*

      Yeah, I think I’d characterize it more as mean than silly. There are loads of legit reasons people wouldn’t want to randomly jump in a pool in their clothes around coworkers and trying to force people to do so in order to get the holiday is a dumbass move in my book. I feel like this is maybe something you’d have te

      1. Willis*

        Argh…wasn’t done. Was going to say it sounds like something that would happen with teens at a summer camp not a adults in a property management office. If you want a team building thing, pick something that’s more universally accepted as fun. I thought that was generally the goal for most team building activities.

        1. Mongrel*

          “If you want a team building thing, pick something that’s more universally accepted as fun.”
          Good luck on finding that unicorn of an activity.
          Cash bonuses or time off are the only things I can think of that are universally appreciated

          1. Roscoe*

            Ha, yeah, just what I was thinking. If someone can find this magical activity that everyone will find fun, they will solve a lot of workplace issues around the world.

          2. Willis*

            Sure, it’s hard to find an activity every single person thinks is a great time. But, that doesn’t mean you just give up on trying and ask everyone to do dumb stunts instead.

            1. Mongrel*

              Why not cut out the middleman and just give them the day off? Why the desperate need to try to find something that will suitable for everyone?

              No silly stunts, no off the wall ‘Team-Building’ exercises, no artificially inflated sales targets, no “You can only leave early if you come to the barbecue” or any of the other requirements for ‘Mandatory Fun’* if you want to have a long holiday weekend, just let people have the long weekend to do with as they please.

              *Some of these are from personal experience, not in the letter.

          3. anonaccountant*

            I feel like there’s a lot of room between cash bonuses and jumping in a pool…

            It doesn’t have to be super fun for everyone, but it shouldn’t be actively embarrassing and uncomfortable (as this would be for many people).

        2. EPLawyer*

          Not to mention what the residents think seeing everyone jump into the pool with their clothes on. (also public pool, ewwwwwww).

          1. LW1*

            I second the ewwwwwwww, even on a good day, but… the property is just north of section 8 housing, no available showers (you’d theoretically shower at your apartment), & the maintenance team is horribly underfunded (500+ units, enough pest control budget to treat 4 units per month). I was told the pool is only 5′ deep, but you can’t see the bottom. I need a shower just typing that out.

        3. Guacamole Bob*

          This is the kind of thing that’s effective as team building because it strengthens the bonds of the employees to each other in an alliance against management.

      2. Insomniac*

        This point is excellent, in addition to so many points of why the freak not to ask employees to do this – so many women, and indeed men, would not want to get wet around coworkers because … I don’t know… wings, body shapes, makeup, clothing color/transparency, feeling appropriate.. so many reasons more than I can imagine!

        1. Banana Bread*

          I don’t want to go off-topic here, but what are “wings” in this context?

            1. Artemesia*

              I was thinking pads with wings — and there is a reason a lot of teen girls would not want to be forced into jumping into a pool while clothed. The poster probably meant wigs —

          1. Insomniac*

            Oh no, wigs!!! Misspelling. I worked in dermatology for a few years and you would be surprised how many more people wear wigs than you know. Speaking of hair, a lot of hairstyles just shouldn’t get wet without costing a bunch of money and time.

            1. Perilous*

              “Wings” actually made sense to me – my mind jumped to maxipads, and I wouldn’t want to jump in a pool while wearing a maxipad!

              1. Mallory Janis Ian*

                I was thinking of flabby back-of-arm skin, which my MIL calls her “middle-age wings”.

            2. Casey*

              Yes! I wear a wig, so I can usually tell when someone else is wearing one, and it’s more common than you think.
              And no, I would NOT want to jump in a pool with it and mess it up and get chlorine in it. Unlike hair attached to my head, I can’t just get in the shower when I get home. I have to take it to a salon to get it washed and set for me

          1. hamsterpants*

            This is the worst! Not only is it uncomfortable, could ruin your clothes, and could ruin your carseats, but there are A LOT of conditions (such as having female reproductive organs) that mean you shouldn’t keep your skin sitting in wet clothes for very long.

            1. Observer*

              Well, Boss wants this done in uniform, so at least no one has to worry about the clothes – if they look terrible from the chlorine, that’s on Boss.

            2. Aquawoman*

              I was thinking my eczema wouldn’t be happy with me having chlorine on my skin for an extended period of time.

              1. PT*

                If there is a public swimming pool, the law typically says there must be a shower somewhere nearby too.

        2. LW1*

          Exactly! Plus picking your kids up from daycare after work, plans immediately after work, concerns about infecting an open wound in nasty pool water (their property’s pool is super gross, but even if it weren’t, it’s still a public pool), childhood trauma around water… We could think of a hundred reasons this is bad, from the merely inconvenient to the possibly life-threatening.

      3. MCMonkeybean*

        Yeah, if the wording in the letter is literally what his message said I have to disagree with Alison. It seems like an extremely weird and mean thing to ask.

        1. LW1*

          It was exactly that. He has a history of being petty, too. He’s the owner of the property, while the employees work for a management company. Years ago, when they switched management companies, the owner wanted the employees to stay with the property & switch employers. One employee had surgery scheduled, & since switching employers meant no insurance until after the scheduled surgery, they felt they had to stay with the employer & switch properties. They realized this was a mistake & returned to the property in 4 months. The owner denied this employee a promotion 5+ years later due to “disloyalty” & specifically cited leaving the property as the reason for this belief.

    2. Elena*

      Probably only if it came up and they refused to change the rules for that person. I mean, it’s not great anyway! But it’s not an ADA violation, for example, to require people to stand during their shift, unless someone requests to sit and is denied

      1. Dr. Rebecca*

        This; ADA accommodations are more concrete than they are theoretical/potential.

    3. I'm just here for the cats*

      My first thought was, I can’t swim! And I’m afraid of jumping into water because of something that happened when I was in swim classes (hence why I can’t swim very well).
      If I didn’t jump does that mean I would have to work? Or would everyone have to work because not the entire team jumped?

          1. I want to go to Brighton!!!*

            But a little sea bathing would set your mum up forever, Lizzie B!

      1. LW1*

        I’m not sure if this was case-by-case or all-or-nothing. I don’t think his message was that specific, & everyone jumped. There were some who shared your fears, though – people who don’t swim well & have had bad experiences. I’m told the water is 5′ deep, & the owner’s attitude was that everyone there was tall enough to just stand up.

    4. Mina, The Company Prom Queen*

      True. Also, they didn’t consider that fact that some people can’t swim. That could be dangerous.

      1. Artemesia*

        To graduate from college (public university in PNW) I had to jump into the pool fully clothed and swim to the end and back without drowning. Of course people prepared for that and could schedule it. I assume people with health restrictions would have a way out but don’t know. I have always thought requiring people to know how to swim would be a wise school requirement.

        1. TeacherTurnedNurse*

          But why? Why do I need to be able to swim to obtain an unrelated degree?

          someone who is a terrible swimmer.

          1. Ooh! I know this one!*

            It’s a water safety thing. I went to a university with a swim requirement. It was located on a river, and the folklore was that the parents of a student who had drowned gave a large donation to the university on the condition that all students be required to know how to swim.

    5. Esmeralda*

      If they didn’t accommodate, I’d think so.

      But I have a hard disagree with Alison on this one. Team building??

      I can think of all sorts of reasons why people do not want to do this:
      Can’t swim
      Can’t swim with their clothes on
      Chlorinated pool water will ruin their clothes and shoes
      They now have to shower and put on clean clothes
      Cleaning their now wet and chlorinated clothes
      Afraid of the water
      The wet t-shirt effect. I personally have no desire to get wringing wet and make my nipples and underwear show.
      Ruins make up (if you wear it). Messes up your hair — for people who really style their hair, I can’t imagine they’d be happy about it.

      What happens if someone jumps in with their clothes and gets hurt?

      It’s a terrible idea. Find another way to have people show their team spirit (I’m rolling my eyes so hard). Or just give them the time off.

      1. LW1*

        This! Plus, there’s no indication this was a team-building thing. Their org doesn’t do that sort of stuff. They also don’t do a lot of marketing stuff that this would support. It seems to just be for the owner’s amusement.

    6. SK*

      Yeah. I’m actually allergic to cold temperatures. With daily medication it’s not a huge issue, but the one thing my doctor told me NEVER to do is jump in any cold pools. It could genuinely send me into anaphylaxis.

      1. Firecat*

        Oh man I was allergic to the cold but thankfully grew out of it by 12. I would get these huge welts if I toched snow with my bare hands or swam in cold water.

  5. bookartist*

    LW1 – I am more aligned with you than Alison here. The owner is getting off on the power imbalance here – when they says jump, employees have to literally jump to get what they’re dangling in front of them. Owner does not have team building in mind here.

    1. SG*

      It’s hard to know without having more context, knowing what the tone was, what type of boss he is, etc. All we know is that, “He has done batty things in the past.” I see Alison’s point, but without knowing more details, it does seem like a pretty extreme ask. I mean, getting out of the pool in sopping wet clothes and then (conceivably) having to drive home like that? Ugh. Plus, what about people who can’t swim or are afraid of getting in the water, which is not unusual.
      I can imagine other silly, more benign requests, like everyone has to tell a joke, or everyone has wear their t-shirt backwards or inside out, or wear red, white, and blue. I mean, those are kind of dumb too, but pretty low-stakes.

      1. Red Wheelbarrow*

        Yes, or worse, having to take the bus and/or subway home while soaking wet. I hardly ever disagree with Alison, but my take here is closer to the LW’s–it sounds pretty gross and at least in the vicinity of bullying.

        1. allathian*

          Yes, this. I think that any action that requires employees to open up in a way that makes them vulnerable to each other can become bullying in some circumstances.

          People who are comfortable around each other can also often lower their fences a bit and allow themselves to be vulnerable around each other. The trouble is that you have to be comfortable to do it, and most team building events are based on forcing people to be vulnerable with the idea that this shared embarrassment/vulnerability will also make them more comfortable around each other and thus more effective at their jobs, and it just doesn’t work that way. I detest all sorts of forced team building with a passion of a thousand suns.

          In that situation I’d be very tempted to refuse to participate and call in sick on the holiday…

          1. Mina, The Company Prom Queen*

            Agreed. Forced vulnerability just breeds resentment, not bonding. Can’t people just do their jobs in a generally pleasant environment, earn straightforward pay, get straightforward benefits, and call it a day? Forced camaraderie is so stupid. Work relationships happen organically over time. You can’t force it.

        2. Allypopx*

          Absolutely agree. I think Alison is way too soft on the boss here. This is a pretty extreme ‘team building’ activity, especially so close to a standard federal holiday that they clearly have the capacity to give employees off.

        3. ToTiredToThink*

          Same! I was like – they likely don’t have a change of clothes on them, so to then be walking around, soaking wet in their work clothes? That’s not good.

          1. LW1*

            This is part of what bothered me, and I should have put it in the letter. They had to send the videos (took turns jumping/filming) midday, but they’re not done until 6pm, & no one brought a change of clothes because they had no expectation they’d need it. Plus, most employees there have longish commutes (30 min average), & most of them have kids to pick up on the way home. Several also have second jobs they do right after work, & since the “uniforms” are regular clothes worn on a schedule (no logo/company name), they usually don’t bring a change for that. All of this is known by the owner.

      2. Anon For This*

        I was thinking about having to explain that you need to go buy tampons before you can jump in the pool.

        I wouldn’t be surprised if it weren’t at all maliciously meant – that from the boss’s perspective it was a silly joke followed by a day off, rather than a deliberate attempt to exercise petty power over his underlings. But that still indicates a lack of imagination that is a liability in someone who does have power over other people. He isn’t thinking of the people who really do want the day off, but have good reasons for not jumping in a pool fully clothed – from minor annoyance and discomfort, to public embarrassment, to more complicated health and safety issues.

      3. Solana*

        Also, what if a person has a medical issue? Say a recovering wound that MUST stay dry and/or covered to prevent infection? What if they have a catheter that has to stay sterile?

    2. Anonymouspenguin*

      I admit, I do wonder if the majority of staff are women. I know I would find it pretty gross to have to participate in a (possibly surprise) wet t-shirt contest at work.

      1. Speaks to Dragonflies*

        I was coming here to mention this. If the uniforms are of the kind and type that would work well in a wet T-shirt contest,then that adds another layer of WTF to this regardless of how any of the employees present. Not only could this be an impromptu wet T-shirt contest, what about folks that have body image issues? Its possible that this isn’t a reason, but SG and Red Wheelbarrow mentioned having to travel home sopping wet, and thats bad enough to think that this boss is ,at best, clueless and out of touch. At worst, its like Bookartist says. A powerplay of making the employees “jump when he says” and possibly a chance to get their creepy jollies.

    3. I'd Rather Be Eating Dumplings*

      I would LOATHE that particular “challenge”, but I definitely know people who would think it was hilarious and playful and fun — -and not understand why others didn’t feel the same.

      I assume these are the same people who constantly ask quiet people “what’s wrong?”.

      1. WS*

        Yes, my brother (a programmer) had a job in a workplace that was very into the “zany” “fun” atmosphere (things like having to jump into the pool fully dressed and document it sounds about right) and he quit pretty fast – it would have been faster except he broke his arm during one of these fun events and was put on fully paid leave for a month). But most of the people there really enjoyed it and considered it a perk of the job!

        1. Empress Ki*

          If he was in the US, the treatment needed for his broken arm would incur spending lot of money.
          I hope your brother made then pay for that too.

          1. WS*

            Not in the US, so that wasn’t a problem. But we’re pretty sure the time off at full pay was to avoid a Worksafe investigation!

          2. Quickbeam*

            Injuries from any required activity (US) are covered by Worker’s Compensation. Even team building or “fun” activities. So all medical would be covered as well as a likely settlement (tax free payment) if there is surgery or any lingering disability.

          3. Ace in the Hole*

            In the US, treatment for an arm broken during a work activity would be covered by worker’s compensation and would not cost the employee anything.

      2. Guacamole Bob*

        My kids have the last swim lesson in the evening, and one night while they were getting changed after lessons the staff had a meeting on the pool deck that ended up with a guy in uniform khakis and a polo shirt jumping into the pool fully clothed – I couldn’t hear details, but it looked like some sort of bet/challenge/zany fun type thing. But there are key differences to the situation in the letter: he works at a pool, to start with, not doing a totally unrelated job at a facility with a pool on site. I’m pretty sure he’s some sort of shift supervisor at the very least so the power differential goes the other way, there are changing facilities on site and most of the staff probably have extra clothes stashed there, etc.

        I’d detest the situation in the letter.

        1. L.H. Puttgrass*

          Excellent point. A good (well, not horrible) team-building exercise would be if the property owner offered to jump in the pool with all his clothes if the team meets some sort of goal. Making employees jump in the pool with their clothes to get a holiday? Even if it was in jest (which immediately triggers, “Geez, can’t you take a joke?” type problems), it’s punching down and in poor form.

      3. Falling Diphthong*

        Yes. I’d connect this a bit to the second letter–if you’re the boss, you get a lot less feedback that your jokes aren’t funny, that your idea of fun bonding has the employees glaring daggers at your back, etc.

    4. Galgal*

      Totally agree with you, bookartist. On the face of it, this is workplace bullying and a massive abuse of power, and the owner is clearly enjoying it, even if they are trying to convince themselves that it’s “harmless”.

    5. Person from the Resume*

      The LW also hit another power issue. The employees did not know until the Wednesday before the weekend of they would have Friday off. I like more time to plan my weekend than that. They may have had to already refuse activities/events that require a longer lead time than 2 days notice.

      I don’t think there’s anyway this is team building. Bad team building, maybe, if the boss and the employees all jumped in the in their clothes. Without the boss joining in, he’s just on some sort of power trip.

      1. londonedit*

        Yeah, I used to work for a boss who would often randomly decide to close the office at lunchtime, especially the Friday before a holiday weekend. Which was great in theory, but when train tickets are extortionate between 3pm and 7pm and you finish work at 5, you’re going to book the 7.30pm train for your weekend away. And while I wouldn’t sniff at free time off, it was always a bit galling when the boss came in at 10 and said ‘Right everyone! We’re closing up at lunchtime! Go and enjoy yourselves!’ and you ended up with a suitcase to lug around and six hours to kill.

        1. TastefullyFreckled*

          This reminds me of ExJob, where the rule was friday afternoons of a long weekend were off “workload permitting”. Which meant that the client-facing people rushed to get their work orders in that morning, but never accounted for any extra time for the afternoon off, so everyone who actually carried out the work never got to enjoy this “benefit”.

          I’ve never been happier to have been laid off.

      2. SheLooksFamiliar*

        This reminds me of my high school fast-food job in the 70s, and some managers love to spring last-minute contests on. We could compete for holiday time off, leave a shift early, trade workstations, get a free meal, etc.

        Some were quizzes about the menu, work process, company info, stuff we all were supposed to know. But most were athletic contests or feats of strength, like holding a 50-pound container of shortening the longest. One contest was to see who could skate around the kitchen fastest. We had plenty of grease, why not put it on our shoes and skate? The loser had to mop up. The girl who lost was tiny and could barely heft the industrial mop, but she lost ‘fair and square’ according to our manager.

        Nope. Some of us had inner ear and balance issues – at least, this girl and I did – but we all wanted time off.

      3. Person from the Resume*

        Arg! Actually the 4th of July was observed on Monday this year (and I knew that), but it’s the same idea. Not a lot of time to make plans especially travel if you don’t know if you need to be back in time to work on Monday or Tuesday.

    6. Schwanli*

      Yes, almost always I think Alison’s answers are spot on, but I disagree with her this time. It’s at best thoughtless bullying, and at worst a very conscious desire on the manager’s part to exercise their power over employees who need the job and naturally want whatever time off they can get. Especially not giving them enough notice of the holiday for them to plan around it.

    7. Hornswoggler*

      I agree with bookartist. I immediately think of women who might be menstruating, people who might have allergies to pool chemicals, pregnant women, people with a fear of water, people with hearing aids or expensive glasses, people with medical conditions such as stoma or who wear a prosthetic (either a limb or perhaps following breast surgery).

      That’s quite apart from those who’ve just had an expensive hairdo or who might be wearing particularly lovely silk underwear for a tryst later on.

      I’m really surprised that Alison is so laid back about this one. I think it’s flipping outrageous.

      1. RagingADHD*

        Pregnant people can swim just fine. It’s actually recommended as a low-impact exercise. I get what you’re saying about health conditions, but I don’t know where you’re getting the notion that pools are a problem for pregnancy.

          1. RagingADHD*

            Do you think they’re specifically doing a belly flop or going off a high-dive platform?
            No, hopping off the side is not going to cause “significant discomfort” to the average pregnant person. Especially fully clothed. Especially since you’re not even that big until over halfway through.

            Honestly, the imaginations going on here.

            1. quill*

              Depends on how far along you are and how mobile you are at that point. I’m imagining the possibility of discomfort, not the inevitability of it.

        1. Hornswoggler*

          Yes, I know. The implication seems to be jumping off the side of the pool into the water. Obviously it depends how far along you are – my friend who is currently 8 months gone would probably feel it wasn’t a good idea.

    8. Metadata minion*

      Yeah, I’m a bit surprised at Alison’s reply. The fact that the owner sent the video to his brother, presumably without the employees’ knowledge or consent, is also not ok.

      1. Creeped Out*


        I really disagree with Alison on this one.

        This boss is a horrible person. Thoughtless and foolish at best, a nightmarish bully at worst.

    9. HannahS*

      Also…not everyone can swim! It’s a foolish thing to ask everyone to do, on so many levels.

    10. Aquawoman*

      I agree. It seemed to me that if the employees thought that they really wouldn’t get Monday off without jumping in the pool, there is a history that points more toward bullying than silliness gone wrong. I also don’t really feel like giving someone a major holiday off is a plus as much as taking it away is a minus. Two hours off on a random Friday is a carrot; not getting 4th of July holiday is a stick.

    11. GothicBee*

      This is the kind of thing that if you hear about it without context, it’s pretty obviously a bad idea, but in certain workplaces it would go over okay. A lot of it depends on the team’s reaction to it and whether the boss is the kind of person who would stop if someone objected or push it. I’m not so sure about property management, but I could easily see this being something done by workers at a summer camp or a park or something, especially if it’s a bunch of young people in the same type of demographic. I’m not saying it’s a good idea, but I don’t think I’d jump to “bully who gets off on it” without more context from the people directly involved.

      Plus it’s really unclear here if the relative was offended by it or just sent the video because they thought it was funny. At most if I were the LW, I’d encourage the relative to speak up if they felt like anyone was being discriminated against or hurt by this, but I wouldn’t try to talk them into seeing this as the actions of a horrible boss if they otherwise like the guy.

      1. LW1*

        My relative shared the video with me because they were PISSED about it; I also saw some pics of them leaving at the end of the day, sitting in the car & still so wet their clothes were transparent & sticking to their body. This is hours later & after trying to dry off with the office supplies/facilities. The owner isn’t liked or trusted by the staff. They pretty much all did the jumping videos purely because they knew they’d have to work Monday if they didn’t. For context, the employees are generally 30s+ with families & non-exempt hourly workers. They don’t hang out together on the weekends or generally socialize with each other. It’s not that kind of organizational culture that would encourage them to be friends or do any kind of team-building exercise.

  6. Reluctant Manager*

    OP #5: I worked for a company that always had a million reasons why payments needed to be tracked and processed and resubmitted. Turns out accounting looked inept because the company has a cash flow problem; when they filed for Chapter 11, an lot of freelancers got screwed.

    Obviously may not be the case here, but don’t put all your eggs into one basket. When they drag their feet paying you, they’re essentially borrowing money from you without interest.

    1. I'd Rather Be Eating Dumplings*

      Obviously may not be the case here, but don’t put all your eggs into one basket. When they drag their feet paying you, they’re essentially borrowing money from you without interest.

      Seconded. If you keep working with them, make sure you’re cultivating other connections and taking on plenty of other clients — they may not be in financial trouble, but you know for sure they’re unreliable.

    2. Falling Diphthong*

      Thirded: When one company gave me lots of run-around on how I would actually be paid later, they soon went bankrupt, leaving me one of many many creditors.

      In that case I was able to get my money from a third party because a) 1 person on the inside shared what had happened with the freelancers; b) Someone in that group figured out who at the client would be excited to learn that all those contracts in which we gave up copyright on our work in exchange for money were now non-binding.

      1. Reluctant Manager*

        That’s not always the case–bankruptcy law can be fickle, and it depends on the type of bankruptcy, so one should always consult a bankruptcy-specialist lawyer. But if it worked out for you, great!

    3. TreeFrogEditor*

      First-time commenting just to echo this. OP#5 brought up many (not-good very-bad) memories of my very first job out of college: I was an unpaid-intern turned freelancer turned in-house-contract-worker-with-no-benefits, and there were HUGE RED FLAGS all over the place that I didn’t recognize due to my age/inexperience (most of them probably already obvious to Alison’s readers).

      Like the LW, when I freelanced, payments almost always came late and I had to hound Payroll for my checks. When I came to work in-house (I KNOW, again, I was young), I found out why: the company was horribly mismanaged and constantly on the brink, and freelancers were often lied to. They were told payment delays were due to [XYZ excuse] when the real reason was “We’re broke until the next client pays.” I had barely worked in-house for 6 months when the company filed for bankruptcy. I jumped ship before it was totally sunk but last I heard, lots of those freelancers didn’t see the money that was owed to them from the final few months.

      Working for that company was obviously a huge mistake but was also sadly educational on what a terminally dysfunctional small business looks like. Obviously I have no idea whether OP#5’s client is in a similar boat, but it’s tingling my spidey senses.

    4. OP#5*

      OP here. Totally agreed.. I do have a few agencies I’ve worked with for many years and have definitely had experiences with being given the runaround by awful agencies before too. It’s infuriating that they put their budgeting problems onto us freelancers. I’ve been freelancing a long time so know the game well unfortunately. This agency is a big one in my town and I’ve been working with them for many years. The IT has always been terrible but not to this level. I guess this was their third strike, so they’re out.

  7. Heidi*

    For Letter 4, it sounds like the partner didn’t really have a specific process in mind, at least not one that required the involvement of other staff. It’s possible that your request for specifics made her realize that she didn’t want to do the work of coming up with any.

    1. Willis*

      I thought she sounded confused…like maybe she even meant to email someone else who would know the context but then cancelled the meeting and sent that weird note once she realized it. Alison’s suggestions are good and I don’t think the OP did anything wrong here.

      1. Unkempt Flatware*

        Agreed. This happens so often in my job—someone just wanting to put a block on my calendar and call it, “collab meeting”—that I have to defend my own time like OP did.

      2. Falling Diphthong*

        Yes, I was thinking this might have been sent in error. Could be “Wait why is someone from Spouts replying to my email to Llamas? Oh dang…” Or “As a new team leader I should reach out to all the people at level W and ask them to brief me on the process” and then the replies made it clear that this was far too vague. She didn’t know what she didn’t know.

      3. GothicBee*

        To me it sounded a lot like what I’ve experienced when dealing with someone who is so confused they don’t understand what questions to ask. They’ll ask really vague, general questions and then when you come back and ask for clarification so that you can help them, they get angry and defensive because they don’t understand enough to formulate a good question or expand on the context. I feel like the LW’s response was good and would work for most reasonable people.

      4. Meep*

        I saw it more as she didn’t know what was going on and wanted to be in the “know” but realized she doesn’t even know what to ask. I have a coworker who has been asking for a “workflow” for a month now. Never mind I gave it to her already. She doesn’t know anything based on her own refusal to learn (sales at an engineering company with no formal background). So she just continues to ask for the same thing over and over again and make it out to be someone else not giving her what she needed.

    2. lailaaaaah*

      Same here. This happens so often with IT- people send in incredibly vague emails like ‘this isn’t working’ or ‘I want to go over things with you’, and the ones who do have a specific thing in mind often get upset when you can’t think of it off the top of your head. You definitely didn’t do anything wrong by asking for clarification!

      1. Cookie D'oh*

        Agree. I work in IT and get vague emails all the time. I’m happy to share about processes or the business logic implemented in our software, but I need some frame of reference. That will help me prepare and make the meeting more productive. The OP didn’t do anything wrong.

        1. quill*

          My hack for getting good IT responses is to always have the context on hand. After all, I am (usually) only getting one error to fix, they have a few dozen.

    3. Mongrel*

      Having worked IT support; people are perfectly capable of asking context-less queries and assuming that you know what they’ve got in front of them.

      1. Koalafied*

        I don’t do support as a main part of my job, but I’m the resident expert admin in a couple of different marketing tools, and it galls me how often people will just report that they “can’t login” or are “unable to [complete x task]” with absolutely zero additional information. Do they really think that’s going to be enough to get their problem solved, or have they just not spent a single second of time considering whether it’s enough before sending their message? What is the thought process?

        1. Green great dragon*

          I do get that that’s not helpful (and I always try to give more details) but I suspect the thought process is ‘I don’t know what Koalafied needs to know but they will ask for the details they need’. Trained perhaps by chat/phone support which require personal details/security/order number before discussing an actual problem and my personal bugbear – chat functions into which I type a full description of the problem, which transfers me to someone else, whose first question is ‘so what is the problem?’.

        2. Falling Diphthong*

          Like Dragon, I think the process might be “State my basic problem to the person who answers the phone, and they will direct me through the labyrinth to the person who can actually do the thing.”

          I’ve been making lots of medical appointments, for example, and so I open with the basic information and then we determine if the person on the phone can help me reschedule, or do I need to leave a message for the nurse, etc.

          1. Le Sigh*

            Yeah, same. Most of the time when I frontload the information, I then get, “Ah, okay, that’s actually a different person/dept.” and then I get redirected and have to repeat myself (and likely waste that person’s time). So I start with the central issue to save us all time, and then save the details for when I’m in the right place.

    4. Daisy*

      It sounds to me like she doesn’t really know what OP does and wanted it explained. Like, by ‘process’ she meant ‘role’ or ‘department’ but was embarrassed to say so.

      1. Person from the Resume*

        I think this is it too. Agree with hamsterpants below.

        It could be terminology confusion though. You say you have many many processes. From the outside it may seem that your department has one big over-arching process and that is what was being asked about.

        OTOH I sure wish reddit’s Am I The A$$hole (AITA) hadn’t caught on so much. Nobody had to be the a$$hole in this situation. LW wording the question as AITA as such leaves out the possibility of misunderstandings and assigns a right and wrong person in the situation.

        1. Yorick*

          OP was afraid they had done something wrong, and it makes sense for them to ask so somebody could comment NAH (no a*holes here)

    5. hamsterpants*

      My guess is that someone told her that she should talk to you about what your process is and she scheduled the meeting without really understanding what she was supposed to talk to you about.

      I’ve also had managers not understand what my work is and schedule hour-long meetings in the busy part of my day just to learn more about what I do and how it fits into what the org does. Not even evil people trying to waste my time, but when Project X is three hours away from a critical deadline, the last thing I want is to be going through my standard slide deck about what Project X is and having a curious but not-very-involved manager ask tons of questions and make a lot of suggestions that would have been useful six months ago but now would require a dramatic structural change to implement. Meetings like this is why I now guard my time.

    6. Rebecca*

      It seems like someone who is floundering and wanted some informal help to maybe prioritize projects or learn what is required for some of them. These are things it sounds like she should know, but because of Covid projects kept getting delayed so she never learned what she needed to. She is now embarrassed that is doesn’t know and came to LW as a coworker rather than to a boss for that reason. She wants some help knowing where to start or what components are required for a project. Have an informal lunch to see how bad it is. Maybe she is very competent and knows how to do the work, and just wants to make sure she isn’t missing anything, or maybe she is totally in over her head, in which case it would be good to let someone know so her work doesn’t fall to you.

    7. Pinkbasil*

      It also depends on what partner means. At my husband’s company it’s the most senior people, and if one of them sends a vague meeting request to learn more about what he’s doing he will absolutely carve half an hour our of his schedule to see what they want to know.

      1. Allypopx*

        I assumed it meant external partner but that’s a good point. If it’s like a part-owner of the company then yeah, find the time. But I still think I’d have at least asked clarifying questions so I could come prepared.

        1. Pinkbasil*

          Yes — no matter what a partner is in this context, it was rude of that person to reply to the email curtly. They should have done the OP the courtesy of providing a little more context or apologizing if they’d accidentally emailed the wrong person.

  8. Bowserkitty*

    OP #3 – this reminds me of an older letter from an LW who eventually gave in to her former coworkers’ persuasions after continually declining and it ended up being HORRIBLE – I think they ended up letting her go or something? Definitely put your foot down!

    1. allathian*

      Yeah, this.

      I think it’s time to escalate this a bit. If Alison’s script doesn’t work, there’s always the nuclear option of ending the friendship, or at least putting it on hold until they’ve hired someone else. This friend is no fun to be around if all she wants to do is hire the LW as an admin.

      1. Zelda*

        I’m already questioning how much of a friend this person is if they can’t take no for an answer– is LW even a person to them, or just an NPC to slot in where needed?

        1. Cj*

          I think it must be this one: “my former coworkers hired me to work for them … but it was a bait and switch, they fired me, and I’m ashamed”. You should be able to search for it.

          So, so sad.

  9. McThrill*

    #5: Unfortunately, what you’re experiencing here is more the tule than the exception when it comes to freelancers. Even huge, prestigious institutions like the New Yorker usually take up to three or four months to pay freelancers despite having the infrastructure and accounting to do so promptly.

    The main reason? Profit, unfortunately. A percentage of freelancers will cut their losses and stop chasing bills after a certain point, since taking a company to small claims court is prohibitively expensive and time consuming, meaning the company got away without having to pay. It’s scummy but legal, except in New York where a recently passed law requires all freelance bills to be paid within 30 days.

    1. Observer*

      since taking a company to small claims court is prohibitively expensive and time consuming

      Small claims court should not be so expensive, so if this is actually happening the they are taking advantage of people’s ignorance of the system.

      It’s scummy but legal

      No, it’s not legal. It could be legal to delay payment, but it’s not legal to NOT pay at all. “They didn’t chase us enough” is totally NOT a legal defense. Again, if that’s what is happening they have decided that whatever cost saving is worth the absolute illegality of withholding payment from any freelancer who doesn’t have the wherewithal to chase for several months.

      1. Annie J*

        It’s not just wherewithall, it’s time, labour, energy, and in many cases a great deal of money and there is no guarantee that the money you get back will cover the costs of legal feeS, not to mention if the company goes into bankruptcy.
        while you are right that it’s not technically legal, enough companies get away with it that it might as well be.
        Best just to avoid it all together in not work for that company again if you can afford not to do so, either that or apply some kind of charge for lateness.

        1. Observer*

          you are right that it’s not technically legal

          This not just a “technical” issue – it’s flat out illegal.

          enough companies get away with it that it might as well be

          That’s nonsense. Even if it’s true that a lot of companies do this and get away with it, that doesn’t make it “as good as legal”. It’s not and any company or person that works on that assumption is asking for trouble.

          Best just to avoid it all together in not work for that company again if you can afford not to do so

          That’s valid and certainly something to think about. But it stands totally independently of the (il)legality of such a tactic. Anyone who is dealing with this kind of behavior should protect themselves or walk if they can, regardless of why the company is doing this.

          1. McThrill*

            No one here is arguing over whether this is illegal or a terrible thing to do – it is, on both counts. But going to court and fighting against it in numbers that will make companies stop doing it requires resources that most freelancers don’t have or can’t afford. When even prestigious mags like Rolling Stone take ~100 days to pay their photographers for their shoots, it honestly doesn’t matter what the letter of the law says. Until major changes like the “freelance isn’t free” act show up across the country, freelancers will always be in this position because the costs of going to court (in both time and money) are much easier for a company to absorb than a single person who doesn’t get any paid time off.

            1. Observer*

              Oh, I agree that it’s a terrible thing to do, and also that often free-lancers are stuck dealing with this regardless of legality. But I was responding to a comment that this is actually legal, and a response that this is only “technically” illegal.

              Neither is true. Let’s call a spade a spade. It’s the first step in recognizing the problem.

              I think it’s important to call it out. On a number of occasions Alison has called out certain industries as being problematic. Often people react by saying that it’s not ok to call those industries problematic just because they do things differently. Except that it is NOT just “different”. It is most definitely problematic.

              You are saying that this problem is prevalent is magazine publishing. Which means that the norms in magazine publishing are not just DIFFERENT – they are ILLEGAL (and not “just technically”).

      2. McThrill*

        Maybe “legal” was the wrong term to use, but it’s common and not punished enough that it in practice there’s no real difference. And yes, the cost savings to the company outweigh having to pay back the 2 or 3% of freelancers who take them to court over it. It’s not a matter of just not being persistent enough – While you could take them to court and probably get paid for your outstanding invoice when you win, doing so would require several days of your time (during which you couldn’t work on other projects) as well as several extra hours filing paperwork, talking to lawyers, etc. Even if you win the case, it’s most likely a net loss for a small freelancer due to the time spent. It’s super crappy but the system is overwhelmingly stacked against freelancers in most ways.

        1. Ask a Manager* Post author

          Yes — and depending the terms of your contract, you might need to take them to court in a state across the country from where you are and be required to appear there in person (happened to me; fortunately they paid up while I was still deciding whether to do that). Going forward all my contracts are going to list my own state as the deciding jurisdiction.

    2. nonprofit writer*

      McThrill: Can you tell me more about this NY law about paying freelance bills within 30 days?

      1. McThrill*

        Mannheim Steamroller posted about it just above you, and I was wrong – It’s not a state law, but a city law.

    3. OP#5*

      OP here. I’m actually UK based so not sure of NY/USA laws but these issues seem to be universal in freelance land. In UK, the guides set are B2B payments should be within 60 days (unless there’s a different contract agreement). After 30 days we can start adding daily interest and can also charge a set ‘debt collection’ fee (the government website has specific £ amounts set out for that). My contract stated payment within 30 days of invoice so they’ve broken their own contract. I can take them to small claims court here and the process is pretty straight forward (we even have a right to bankrupt companies to get payment :o , not that it’ll come to that). Normally it’s a fee dependent on the amount being recovered, and some mediation process beforehand.. need to look into it more. I’m still chasing the invoice.

  10. Insomniac*

    Aliiiiisoooooonnnn! LW1 – I really thought you were not going to go in this direction given past responses to employers abusing their powers. I’m included to agree with LW1 here – no one should have to jump into a pool for a common holiday off (especially when these proprietorial are usually closed for July 4?!). Besides the disability issue part of it – what if a female
    employee was menstruating and wearing a pad? What if they had a staph infection (kind of common when people shave… or maybe that’s just me? I’ve had several in my life when I shaved). What if they don’t swim? Shallow water doesn’t feel safe to people who don’t swim unless you walk in.. I know because I taught adult swimming for many years back in the day! What if you’re going somewhere later? What if the employer has a sadistic streak with challenges for work perks? What if you really don’t want to? I think these reasons are all valid and there’s got to be so many more.

    Also, where does the slippery slope start? That’s even more of an issue even if someone doesn’t care about the previously mentioned stuff. I’d be so irritated if I wasn’t into it.

    1. Insomniac*

      ** sorry, by “I thought you” I mean Alison. And Alison, FYI I deeply respect your advice and have written in! This is a story that makes me feel gross though. I’m curious to see if I’m in the minority though.

      1. Despachito*

        No, you are not.

        I find it deeply humiliating and unprofessional, and can hardly imagine any context in which it would be even remotely O.K.

      1. Insomniac*

        For sure .. just for me, I would actually find this to be pretty outrageous. There’s many things I accept as “annoying and questionable, but just the way things are.” Personally, I wouldn’t lump this into that category. This may dredge up some divided responses. Or, I could be in the minority, but this is something that would really, really bother me.

        1. Annie J*

          But I think this falls into a different category,
          There are certain silly things like being forced to tell a joke or sing a song and everyone can have a laugh about it afterwards because it didn’t really affect you after it’s done but this is jumping into water which means that when you come out of the water you’ll be soaking wet.
          I don’t know of many people who have multiple uniforms at work, so chances are you’ll be wearing those sopping wet clothes for awhile, besides that though really people feel very uncomfortable around water, I should know I’m one of them.
          being socially pressured to jump into a pool so I can get a holiday seems excessive end pointless, and the boss engaging in it, well if feels like he’s on a power trip.
          Even if everyone in the video is smiling and laughing, there is a possibility that some of them are just putting on an act, also did they give consent to be filmed in this situation, do they all know that a video video exists?

          1. Insomniac*

            I agree – this is not your normal silly stunt. It’s a different category for me completely.

            1. allathian*

              Yeah, me too. I think that there’s one category for silly stunts that can be got past without incurring any expense or spending a lot of time, like wearing a silly hat provided by the employer, wearing your t-shirt inside out (provided you can change in private), etc. It’s a whole different matter if fixing things afterwards is time-consuming or incurs any expense, no matter how small, for the employee.

              But if employees are responsible for laundering and ironing their own uniforms, like I was when I worked for a fast-food place as a college student, jumping in the pool is an even bigger ask.

              1. Allypopx*

                Other commenters have also called out disability or potential sexualization. Potential gender and race issues. And just the overall power trip vibe. There’s a lot of reasons this is a no-go.

            2. Allypopx*

              Same. The response also seems out of sync with similar responses Alison has given, I’m really surprised by the advice.

            3. fhqwhgads*

              I’m not saying the jumping in the pool thing is in any way good or acceptable, but Alison’s take read to me like: the boss doing this is more likely to be an idiot than a monster. No more, no less. And it does make a difference in he way you’d attempt to respond…if you were to attempt to respond. Hence all the caveats about not having enough information.

          2. Nanani*

            This. It’s not just a prize, it’s time off – and time off is part of your compensation.
            “jump in a pool to get your paycheck” wouldn’t be ok, right? This shouldn’t be laughed off either.

            1. Colette*

              What about “jump in a pool to get a bonus”? There’s no indication that this was a day they were supposed to have off; it could be an extra.

        2. Chocolate Teapot*

          Based on re-reading the letter, I get the impression the boss often pulls similar stunts. (The employees had been told they would not get a day off for Independence Day, then all of a sudden boss comes up with the silly pool jumping requirement)

          Slightly off-topic, but what normally happens in the US when a public holiday falls on a weekend? Is the day off transferred to the following Monday, or do employees get a day off in lieu, either of their own or the company’s choosing? I forgot to ask yesterday!

          1. PollyQ*

            Almost universally, if the holiday is on a Saturday, then workers get the Friday off, or if it’s on a Sunday, workers get the Monday off.

            1. PollyQ*

              … although retail & food service may not fully close at all on some holidays, and some public holidays are defined to be on specific weekdays of specific months, e.g., Memorial Day, which is the last Monday in May, and Thanksgiving, which is on the 4th Thursday of November.

              1. londonedit*

                That’s what happens here in England – the early May holiday is defined as the first Monday in May, the spring holiday is the last Monday in May, the August holiday is the last Monday in August. The only time you get an extra day if the holiday falls on a weekend is over Christmas – if Christmas Day, Boxing Day or New Year’s Day fall on a Saturday or Sunday, then the Monday after the weekend will be a holiday (or Monday/Tuesday if Christmas Day is a Saturday and Boxing Day is a Sunday). The only other public holidays are Good Friday and Easter Monday, which obviously are set days each year. And of course people in retail jobs/jobs that need coverage/shift work etc may end up working on those holidays, but they’ll either get a day off in lieu or if they’re paid hourly then it’ll be time-and-a-half or whatever.

                1. EPLawyer*

                  Hubby is in manufacturing with a union in the US. Working the holiday is TRIPLE time. The plant is closed for Thanksgiving and Christmas, but he works every other holiday bringing home that sweet, sweet cash. I don’t care. Being self-employed, I can work that day uninterrupted by clients and then take another day off with Hubby.

          2. Willis*

            The day off usually transfers to the Monday or sometimes the Friday. For Juneteenth which fell on a Saturday, the day people had off was generally the Friday before. For the Fourth of July, it was on Monday. (For places open Mon-Fri that gave people days off for those holidays.)

            1. I'd Rather Be Eating Dumplings*

              And for many places that don’t close, there is time and a half on those days. Certainly when I worked retail in CA, holidays tended to be popular with the team (not sure if this was a company policy or law, although I’m inclined to suspect the latter).

              1. Haven’t picked a user name yet*

                It is generally not law, at least not for retail/food service, but if the company pays time for the holiday, then they need an additional incentive to have shifts filled, hence time and a half or double time. Even if they don’t offer paid time for a holiday, it can often be difficult to fill a regular shift on those days because kids are off or activities planned, so additional compensation is required to keep the business running.

          3. doreen*

            Depends on the employer , and I’m not sure you can generalize beyond saying that at most decent jobs, you won’t lose the holiday. I’ve had jobs where all holidays that fell on a day off get you an extra day of leave, ones where Sat holidays were observed on Friday and Sunday holidays on Monday and at at my current job, Sunday holidays are observed on Monday, but we get extra leave for holidays that fall on Saturday.

        3. Kimmy Schmidt*

          I’m with you Insomniac. And I tend to be someone who likes team-building activities, silly contests, games, and harmless pranks! This feels so icky to me.

        4. Observer*

          just for me, I would actually find this to be pretty outrageous

          This *IS* outrageous. But it could still be not bullying but sheer stupidity. I mean look at all of the letters we see here, and all of the crazy stories that hit the news about outrageous “team building” activities or “fun activities” that are far from fun.

          One that’s not gross that comes to mind was the boss who was penalizing people who did not participate in extreme physical sports on weekends – even people with physical disabilities that had ZERO in office relevance.

          I’ll add a link in my response.

        5. RussianInTexas*

          This is an activity that would legit start a panic in me.
          I can’t swim, and I don’t jump in to the water, and I may curl up in a ball and cry if I have to do this to get a day off at work.

        6. Esmeralda*

          Agreed. This is an outrageous request for the reasons you set out, and other reasons too.

      2. Tuppence*

        I think I’m in the minority so far, but I come down more on Alison’s point of view on it. The staff had a few days’ advance warning so they could prepare accordingly e.g. bring a change of clothes with them so they wouldn’t have to go home soaking wet. The LW doesn’t mention that anyone had a specific disability/fear/haircare requirement that would have made this prohibitive; they don’t even describe the nature or colour of the uniform.

        It’s a stupid thing to require employees to do, but it doesn’t feel necessarily ‘debasing’ or abusive or bullying just on the facts. Honestly, it sounds to me like the owner is trying to market his business with Tik Tok or Instagram videos to present it as a “FUN” place to work or patronise (in which case obviously the right thing to do would be to ENGAGE staff in silly stunts, rather than require them). Of course if he has a history of blatantly abusing his power over the staff then that’s something else, but it’s not clear from the information presented in the letter.

        1. I'd Rather Be Eating Dumplings*

          Yeah, if it was posed as a ‘challenge’ and not a requirement, I could see it fitting into certain workplace cultures. When I worked a summer camp, for example, we had some stuff akin to that (although we were all teens and young adults, and the work was very physical and required swimming anyways).

          But this is heavily culture-dependent and I think also relies on a good boss who you know won’t penalize you for sitting stuff out.

          1. Empress Matilda*

            They are getting penalized for sitting out, though. If you jump in the pool, you get the day off; if you don’t, you have to work.

            Even if it’s a situation where they need to have a minimum number of staff working on the holiday, and he’s using this bizarre method to decide who it should be – it’s still a penalty, because lots of people don’t have the opportunity to participate. If people are being denied even the chance at a day off because they’re menstruating or whatever, they’re absolutely being penalized for not participating.

          2. quill*

            Yeah, at a summer camp, swimming, perhaps at a moment’s notice, is part of the job description unless otherwise negotiated. In this context? It’s not, so it should not be sprung on people.

        2. allathian*

          Yes, if it’s posed as a challenge rather than a requirement, and those who declined to participate wouldn’t be penalized in any way, my response to this would be different.

        3. it's me*

          Maybe I haven’t had enough coffee yet but I didn’t interpret the letter as saying they had a few days’ advance warning. I thought it was saying a few days’ advance from the holiday, meaning they had no time to make plans assuming they had the day off. I didn’t get an idea one way or the other as to when they were told that they had to jump in the pool, and if anything, just saying “Monday” implies this happened on Tuesday at the earliest, and the person told the LW about this on Wednesday. Happy to be corrected if I’m confused.

        4. Vina*

          The OP commented elsewhere that there wasn’t advanced warning – it was “make this video today” and no one had a change of clothes: “They had to send the videos (took turns jumping/filming) midday, but they’re not done until 6pm, & no one brought a change of clothes because they had no expectation they’d need it.”

          I’m also curious whether everyone on staff knows how to swim – there are plenty of places in the US at least where many people don’t. The whole thing feels like a “technically okay but so many ways in which it’s not feasible for people so you’re denying them a day off for inalienable reasons”

        5. LW1*

          Point of clarification: they didn’t get a few days’ notice for jumping in the pool; the owner told them on Wednesday that he wanted video that day for them to have Monday off for the 4th. I left a lot of details out of the letter for brevity’s sake, but there’s a history of petty tyranny from this owner & no history or indication of using such a video for marketing purposes. The uniforms are regular clothes worn on a specific schedule, with the maintenance team in khakis & polos. I see why Alison wrote what she did given the lack of context in my letter, though.

      3. Greige*

        I think there’s some forgivable transparency error here. If you’re someone who would find this extremely costly/inconvenient to impossible, it seems obvious that it’s an inappropriate ask. To those people, whole scenario sounds obviously intended to harm employees, whereas to the boss, those issues might seem like outliers.

        I’m not giving a pass to the boss, here. If you’re going to decide to demand something unusual in exchange for a job benefit, it’s on you to think through and probably seeking feedback on the possible consequences for employees. Commenters have pointed out multiple traditionally marginalized groups that would be more likely to have a problem with this. Boss didn’t think get feedback, or worse, doesn’t have enough women/POC/disabled people on staff or in his circle to even ask.

      4. jtw*

        I’m with you, Alison. I actually thought the LW1 was going to say that the boss should be mindful of people who can’t swim or have reasons for not joining in that would deter them from taking advantage of the offer. From my take, thee leap to bullying was rather a large one. We don’t know the history or context any more than the LW provided, so unfortunately, I do think your assessment is fair. No, it’s not a great idea, but I didn’t see it as an abuse of power as much as just a thoughtless and insensitive promotion. If I hated it, I’d tell the manager that I am not able to participate in the activity for personal reasons and thus would like another option at taking a common national holiday off. And, I’d start looking for another job.

        1. Allypopx*

          There it is, thank you. That’s exactly what was not landing with me on the team-building argument.

      5. MCMonkeybean*

        There is a lot of room though between silly and the worst thing ever, of course.

        It seems we are all in agreement that the ask was unreasonable, but maybe not agreeing on whether the way it was asked was equally unacceptable. I don’t know if the letter writer was paraphrasing at all, but I cannot imagine many scenarios where “if you want X then I better see you do Y” is delivered by The Boss in a light-hearted way. I don’t usually come down so hard on misguided “fun” at work but it’s hard to me to hear that in anything other than a somewhat malicious manner. Even just reading about it made me feel deeply uncomfortable.

        1. LW1*

          That part was a quote. “You want Monday off? I want video of you jumping into the pool in uniform” was his exact message to the property staff. FWIW, he doesn’t communicate with the staff directly often, though it happens enough to not be A Big Deal when he does. This definitely isn’t how they normally approach holidays off, though.

      6. Colette*

        I wonder whether there’s a correlation between the people who are outraged by this and the people who go out of their way to find something indirect for OPs to do instead of using their words.

        I think this was a pretty ridiculous request from the manager, but in the employee’s shoes, I’d either do it or say no; either way, it wouldn’t be a big deal.

        1. Roscoe*

          I mean, the crazy thing is we don’t even know what the employees thought about it. The LW is a friend of one of the employees, and its not even clear that the person who sent the video was upset.

          People on this site like to find the every nefarious reason possible for something. Digging up things that are real, but not common, to show how he is a monster. So many what ifs, when we know NOTHING about the stuff.

          This could be a staff of people in their 20s who found it hilarious. Or a staff of people in their 50s who were horrified. I’m 40 myself. 10 years ago, I probably would’ve thought this was funny. Now I’m more like “eh, I may not want to do it, but I don’t think its as absurd as people are acting like”.

    2. Allonge*

      It’s a really bad move for sure, but it’s also one of those things where speculating here on all the things that could make it horribly wrong is useless. What if all the employees are young men, are on a swim team, have two changes of uniforms on site and jump in the pool every Friday anyway?

      Again, it can be bullying and worse and at minimum it’s misguided.

      1. Green great dragon*

        Yeh, I can certainly think of a set of circumstances under which this would be annoying but not that bad, but a much wider set of circumstances where it feels really inappropriate – I too would feel more uncomfortable with this than it sounds like Alison would be.

        It matters a lot whether they knew in advance, and could bring a change of clothes and have the appropriate underwear/period products – though I still would not be happy.

      2. Emilia Bedelia*

        Seconded. All of the reasons that were listed initially are good reasons for the boss to not ask people to jump in the pool. But the context really is what matters. Considering that OP is not even writing about something that happened to them, what can be said other than “It’s wacky, but not necessarily illegal”?
        If someone were writing in to say “My boss said I have to jump in a pool to get the day off and I have 4 medical reasons that I can’t”, the answer would be very different. But without any other context. it’s probably likely that the employees have weighed the situation and concluded “my boss does batty things sometimes and isn’t going to change”. There’s nothing actionable here for OP to do.

        1. allathian*

          I’m hoping that the residents of the building complain about building management employees wearing something other than swimwear in the pool just before a holiday. Shoutout to Seeking Second Childhood below.

          1. Emilia Bedelia*

            And what if the pool is closed to residents, but is still being filled and maintained due to local regulations for pool maintenance? (which is the case for my condo complex)
            The point here is that neither we nor the OP have enough info to do anything about this.

          2. Roscoe*

            I mean, why would they complain? I couldn’t see myself being that upset. Hell, this could be an apartment complex of all people in their mid twenties who find this type of thing great.

      3. Koalafied*

        I agree with this take. I don’t think it was a great idea but I think you have to evaluate it in context of this specific company and set of employees, not in terms of how it would go over at a multinational corporation with thousands of employees who should be assumed to represent the full diversity of traits and conditions, or at hypothetical small business with hypothetical employees who have particular traits and conditions.

        Not the same thing exactly, but I’ve worked at a place where I pushed back on a proposed team building activity that was highly physically demanding because I knew not everyone on our medium sized team (~2 dozen people) was in great shape and that they might be too embarrassed to speak up, and also that we had enough staff that we weren’t all already aware of each other’s level of physical ability just from casual conversations and observations. I’ve also worked at a place where the head of the organization took our entire staff of 3 people to do a ropes course as a team building activity, and didn’t take issue with it because we were specifically 4 people who were young, physically active, and talked about hiking, running, yoga, and other activities we all frequently engaged in enough that it was possible for the boss to know ahead of time that we’d all enjoy the ropes course. I would never suggest a ropes course as a general good idea, but with our specific company it was a good activity and we all enjoyed it – just because something isn’t a good idea on all contexts doesn’t make it a bad idea in all contexts.

        1. Colette*

          Yeah, exactly. Maybe one or more of the employees had serious issues with it, or maybe they all thought it was in good fun. We don’t know; the OP is not an employee there.

        2. Elsajeni*

          Yeah, my main question to the OP would be — did your relative who this happened to feel like it was bullying (or mean, unreasonable, an abuse of power, etc.)? Was the tone of them showing you the video “look at this awful thing Fergus made us do” or “haha, check out what Fergus made us do”? Like, I agree that there are lots of good reasons not to make your employees jump in the pool in exchange for a day off, and if the manager wrote in I’m sure we would all tell him so! But if none of those reasons came up and the actual employees involved weren’t bothered by it, there’s no real point in getting mad about all the ways it could have gone badly or upset people.

      4. Empress Matilda*

        Yeah, I think the bullying aspect is kind of a red herring. It sounds to me like the OP was looking for a gut check on whether or not this is a reasonable kind of team building activity. We can go back and forth all day on whether or not it meets the specific definition of bullying, but I think most of us can agree that it’s certainly not reasonable.

    3. Archangelsgirl*

      Do they want the video for a social media post? That’s the first thing that came to my mind because of the request to wear uniform and I just popped in to say make sure that’s not happening without authorization because that would be a big overstep to me.

    4. M / P*

      I agree with you. I am similarly surprised by Alison’s response here. Yes, for many people it’s just a silly request but for many it’ll be a humiliating ordeal. Pushing your employees to do something potentially physically unsafe and in some circumstances humiliating for a basic workplace perk borders on bullying in my view.

    5. whistle*

      I’m with you, Insomniac. I’m terrified of water and absolutely hate having my head underwater. Not exactly something I want to share with coworkers. To get a major holiday day off. That should be part of my compensation to begin with.

      I don’t see how this is any different than taping your mouth shut or dunce caps.

      1. Keep me dry at work*

        Agree. I think this is shaming and completely problematic. I like to swim, so my personal concerns are different. I wonder if part of the issue here may have to do with age. I would have hated this when I was 20, but lots of people seemed to like such nonsense the . Now, at 38, I would hate it even more, and I’ve noticed that my attitude is more expected and in the majority than it was when I was younger.

      2. D'Euly*

        Well, because the boss is saying “jump in for a perk,” not “if I don’t like what you say in a meeting I’m pushing you in.” That’s quite a large difference.

        1. Despachito*

          I consider the “jump in for a perk” to be an ugly demonstration of power (I have the power over you and therefore I can make you do silly things as I see fit) , it reminds me of that proverbial donkey and a carrot and I find it deeply humiliating.

          The dunce caps and taping your mouth shut would have me quit on the spot (unless I would support someone whose life would depend on my job). What an utter horror.

        2. Not So NewReader*

          But it’s not a perk. This is like calling sick time or a paycheck a perk. It’s not a perk. Holidays off is part of their compensation package. Just as one should not joke about subordinates paychecks they should not “joke” about other benefits the subordinates receive.

          They have already earned the holiday time, so now they have to earn it again, really?

          I have to ask if this was a group of men, would the boss still have done this???

    6. Falling Diphthong*

      I think it was a bad thing to do.

      But we are many layers out from anyone who can do anything about the situation: boss -> employees -> friends of employees -> person friend asked for advice on boss. “Your friend is right to feel annoyed, but doesn’t have a legal case” is the sum of it, with exact gradations of annoyance not changing that.

    7. RagingADHD*

      Tangent: no, staph infections aren’t that common, from shaving or anything else. If you get multiple staph infections, you should probably talk to your doctor about what’s wrong, and/or be more careful about the razors you use.

      And pools are chlorinated or salted to kill bacteria.

  11. Admin Ana*

    I like the answer to no.2. I’m on the different end of the spectrum though. I’m not a really talkative person and would also like to keep my personal life separate from my work life so when the need calls for it I also pick random topics to talk about. When they talk about food/pets/travel, I can amiably contribute and engage without divulging too much but still keep things friendly. I also ask them questions instead of sharing, so the conversation can keep flowing without having to contribute anything but my engagement in their story. I actually do listen and am interested when I ask so it’s a win-win for me, I get to remain a private person and Bob from accounting won’t think I don’t like him because I don’t talk to him.

    1. EPLawyer*

      Oooh asking questions is ALWAYS a good thing. Just don’t be intrusive. Which probably takes some effort if you are an oversharer you might think EVERYONE wants to talk about their life story. But do the same thing as what you would talk about, only ask questions instead. Then really listen. You ask the new employee if they have pets and it turns out they have a cat. LEARN THE PET’s name. Then you can ask about the pet. Friendly chitchat accomplished without you sharing a darn thing. Bonus, the employee thinks you care about them as a person which goes a long way towards office team building.

      1. Koalafied*

        Yeah, a great way to become a better listener is to challenge yourself to find follow-up questions to what someone shares with you, to which you genuinely interested in hearing the answer. So many of us have a bad habit of spending the time sometime else is sharing just waiting for a polite opportunity to share our own stuff once they stop talking.

        When I was trying to become a better listener the way I challenged myself was to think of it like homing-in on the interesting: there’s this input (question) – result (answer) – input – result iterative process you’re controlling. What was the most interesting (to me) part of what they just said, and what can I ask to see if they’ll talk more about that?

        A protip: “How has that been?”/”What was that like?” work really well in a wide range of contexts – they show interest that reaffirms for the speaker that they won’t bore you if they go into more detail, and they’re broad enough to let the speaker choose how to answer.

        For example, “My husband and I recently moved in with his parents to save up for a down payment on a house.” Asking, “what has that been like so far?” means they could just as easily answer with, “my in laws are kooks” as they could with, “we’re making great progress saving and have already started casually looking at a few houses, just to see what’s out there,” or, “their house is near a park and I’ve really been enjoying having one so close by,” and so on – all responses that can set up different conversations to follow – are we sharing stories about ridiculous people, talking about the joy of window shopping on Zillow, or talking about parks or what our favorite features are to have in a neighborhood? Most people (assuming they want to be talking to you or anyone at all) will answer those type of open ended questions with something that puts the conversation in territory they’re comfortable with and will be able to speak more easily about with fewer pauses and less need to feel guarded.

  12. Viette*

    #2 – I’m glad the husband took the OP aside and addressed it! It sounds like it was addressed in a pretty constructive way, too. The OP is embarrassed and wants to fix it, but seems to have internalized the criticism well and is seeking help.

    I know that hiring a family member to work at your business is extremely fraught, but the fact that the husband is willing and able to give corrective feedback sure is a hopeful sign. If you’re going to hire your spouse to give them a good job, you should also coach them to be a good employee and hold them to some kind of a standard.

  13. SS Express*

    OP2, it sounds like you are really beating yourself up. You say things like “I lack leadership”, “I have no personal boundaries” as though these are hard facts about the person you are. You talk about feeling stupid and robbing yourself of dignity. This all sounds extreme and quite sad. Alison’s tips for changing your behaviour are solid, but I also want to encourage you to seek therapy/mental health support of some kind if you can, because it sounds like you have a really negative view of yourself at the moment and nobody deserves to feel like that.

    1. nonee*

      Yeah I got a vibe from this letter that makes me worry that OP thinks her husband is automatically right in all situations just because he’s “such a good leader”. I don’t want to read too much into it, but OP, I hope self-reflection is part of this journey too!

      1. MusicWithRocksIn*

        At first I was kinda getting the vibe that she was taking her husband’s advice too hard – but after reading the whole thing, it felt more like she’s the kind of person who tends to more… dramatic reactions? Everything with her is either the best or the worst – she can’t be a good employee unless she is the absolute most valuable person in the office, which seems like a pretty big goal. My feeling is she is just a big personality type that takes everything up to ten – her life story – her work goals – her self criticisms are all amplified. Which, maybe I’m projecting because my last boss’s wife that worked in the office was a total Effie Trinket and everything was a ‘big big big day!’ and I saw her react the same way to criticism, but that was the feeling I had by the end of the letter.

        1. MEH Squared*

          This was my take as well.

          LW #2, in addition to the over-sharing, it seems as if you magnify everything. I can certainly relate to this, it’s being a weird kind of perfectionist. I can’t just do something well, I have to be the best. In your case, going from not knowing anything about the business to knowing everything about it is too big a leap and a kind of wishful thinking.

          Do you WANT to work for your husband and be co-owner? I can’t tell from your letter if you do or if it’s just what you think you need to do. If you do actually want to do this, then part of what you need to do is sit down with your husband and figure out the logistics, including the training you need.

          Lastly, I also think you could benefit from therapy in dealing with your self-view and in deciding if this is truly what you want to do.

        2. SuperDiva*

          Yes, there’s a lot of all-or-nothing thinking here. “I have no leadership skills…I must become indispensable to the business!” As someone with an anxiety disorder who is prone to this same thing, it’s really hard to live with, and to break out of. (Not diagnosing OP, just offering my perspective that this behavior can come out of something more than just having a dramatic personality.) Therapy can really help to work through these insecurities and fears, as well as process where the oversharing is coming from, and build strategies for dialing it back and feeling confident about regaining your colleague’s professional trust.

        3. RB*

          Yes, my take as well, but this is very concerning to me, as these kinds of people don’t make great managers, in my experience, and she is aspiring pretty high.

    2. traffic_spiral*

      Yeah, there’s just too much swinging to extremes here. First she’s 100% ok telling people everything, now she’s mortified; she plans to learn literally everything about the business inside and out, “be the most valuable person [her] husband has,” and eventually be co-boss, but also she “lacks leadership?”

      Maybe calm down a bit. It seems OP is deeply emotionally invested in being the co-owner of this business, to the point of serious distress every time she makes any mistakes, and that’s not healthy. Not everyone is cut out to be a small business manager and not everyone is cut out to work alongside their spouse. Maybe just plan to give it the ol’ college try for a year, and see if it work out, or if the old career would be a better fit.

    3. OhNo*

      Agreed. That plus not being able to learn the job/industry “for personal reasons” leads me to believe that some kind of therapy or support might be really helpful here.

      Start course-correcting on the oversharing, of course! And if that’s all you have the capacity for right now, that’s fine. But sometimes these things become a case of treating the symptoms rather than the underlying cause, so it couldn’t hurt to dig in a little bit and see if you can start working on that underlying issue, too.

    4. Observer*

      . Alison’s tips for changing your behaviour are solid, but I also want to encourage you to seek therapy/mental health support of some kind if you can, because it sounds like you have a really negative view of yourself at the moment and nobody deserves to feel like that.

      Very much this.

    5. Workerbee*

      I kinda was getting that vibe too, that OP #2 is taking what her husband thinks about her to heart–and he might NOT be 100% right. Now she’s got all these layers of anxiety-sounding “issues” to work through. I know I wouldn’t take it kindly if my own spouse told me I lacked leadership.

      My thoughts tend toward “this may not be the job/situation for you” but that’s not what she was asking for.

    6. mf*

      Yeah, the “I lack leadership” bit was a yellow flag to me. The LW sounds like she doesn’t have a lot of self confidence and takes feedback very, very personally. Luckily therapy can help with that!

      1. ecnaseener*

        But she was just quoting her husband. She didn’t say whether she believes it, but either way her boss is the one who said it. (I do question why he said it! It doesn’t seem that relevant to the over-sharing problem.)

    7. Boof*

      Yes I’m worried OP2 is expecting themselves to go from what sounds like “no business experience” to “know business inside and out” and “be at most valuable person” in a YEAR? OP, seriously consider how many years of experience your husband has, the person who was hired along with you, the person your husband has worked with for years; I bet they all have more than a year of experience. I bet they have many years of experience. I think you are setting yourself up for disappointment if you expect yourself to be at their level in just a year; it probably takes 6 months just to learn the basics!!
      OP2 you sound very enthusiastic but please along with Allison’s advice on how to not overshare, examine why you’ve made this change (is it for yourself? For your husband?), what you are really hoping to get out of it (why do you want to be the best at this? For emotional validation? For financial security? etc) and try to identify more concrete and doable steps and checkpoints. Maybe come up with set of goals and check it with your husband, the person working with your husband, and the person hired with you to see if they are realistic. If you don’t meet, say, 3 month goals, figure out if it’s because they were too ambitious etc.
      Finally, be ready to admit if you tried and things aren’t working that it’s ok! Its better to back out gracefully than to go down in flames if something isn’t for you. Not saying that will happen, but maybe if you have your plan B, the anxiety won’t be so great about making plan A happen.

  14. july*

    I, too, wouldn’t jump on a pool for one day off but either I have been indoctrinated to put up with a lot of bs or it’s really not that deep. They technically don’t have to jump in the pool and the question also comes from an outsider of the business so I don’t know what batty bananas things the owner has subjected his staff to do, if there are exemptions to the crazy things he’s asking his employees to do, so yes, it is as bananas crackers as it goes but not something I would call my lawyer about unless we’re presented with more details.

  15. Kate, short for Bob*

    OP3 some additional language you can use with your friend:

    “yes, I could probably do the job, but I would hate it. And while you’re wasting time trying to get me to change my mind, you’re missing out on hiring someone who would excel because they’d also enjoy the work”

    And then go on to “but we’ve talked about this and it’s not going to happen”, starting with a jokey tone and moving to a concern for her grasp on reality maybe. But she might just need to hear that you’d hate it and she’s missing other opportunities to move on.

    1. lailaaaaah*

      Idk, I think with people like that, anything beyond ‘no’ just gives them more things to argue with (“nooo, you’d love the work! I don’t want anyone else!” etc etc.)

      1. allathian*

        Yeah, I get the same feeling. That’s why it’s entirely possible that this friendship isn’t salvageable. I dumped a friend faster than she could blink when she joined a “cult” (MLM scheme) and wouldn’t take no for an answer when I told her I wasn’t interested. I stayed friends with another friend who also joined a MLM, because she sold products that I actually could use. I even hosted a sales party in my apartment once, and I was very open about what it was and didn’t hold it against any of my friends who declined the invite. My friend even got a few repeat customers from my party.

      2. Tía Teapot*

        If she hasn’t directly said “I hated that job, I hated the work itself, I would not be good at it now, it made me miserable, best decision I ever made was to leave it behind and find better work even though it pays less”, then she should. In as much detail (and possibly rant, since this is a friend) as she feels like. Accompanied by a flat “no, and please stop asking.”

  16. Jinni*

    I’m a little outraged by the pool thing. Menstruation is one issue. Transparent clothing another. Inability to swim or fear of the water yet another.

    Despite all of that, my first thought?

    What if they’re all black women with processed (straightened) hair. We’re only half a second past (California at least) passing a law barring discrimination against women wearing their hair naturally as it grows out of our heads.

    Despite that MANY black women I know either wear wigs to avoid costly/time consuming hair care or straighten their hair for work which would not withstand a pool dunking. So what now we’d be left to address our hair on our day off? This is so over the top for me, I can’t even…

    1. Insomniac*

      I think your answer highlights some of the issues with what happens when there isn’t diverse leadership. I’m in big agreement with all your reasons listed and it is unsurprising that a lot of considerations in response to this issue came from what sounds like white gaze.

      1. Roscoe*

        I mean, I’ll be honest, I’m a black guy and I didn’t really think of that either. Sometimes its just people not thinking. Everything isn’t about the white gaze, or sexism. Sometimes its just a simple case of thinking something would be funny until people list reasons why they wouldn’t find it fun or funny.

        1. Aquawoman*

          Not thinking is itself a problem–it perpetuates nondisabled white male as the norm.

          1. Empress Matilda*

            Exactly this. A lot of discrimination comes from a place of thoughtlessness rather than outright evil – but at the end of the day, it’s still discrimination.

          2. Roscoe*

            I mean, we have no information on the race or ability status of this manager. Like, again, sometimes things are just thoughtless, but I don’t know that you can decide anything about his motivations and what he sees as the norm based on the info we have.

    2. PayMeInChocolate*

      There are also the hidden medical conditions. Chlorine and bleach like products makes my skin breakout. I would work the holiday before I subject myself to a week of rashes and itching.

    3. The Original K.*

      We had to do the ice bucket challenge at work when that was a thing. I was the only Black person on the team (the company was very, very white). My hair is curly and I wear it naturally but I insisted that we do the challenge at the end of the day so I could properly deal with my hair at home afterward. (I didn’t cite my hair as a reason with the team because I wasn’t comfortable with them – I think I said “freshen up afterward” or something.) There were showers on site so the rest of the team wanted to do it at lunch, but I put my foot down.

      I love swimming and water but curls can take a while to deal with afterward.

      1. Jinni*

        This^^^ I have natural hair, but I still need a plan, and a one-off work thing isn’t really a ‘plan’ I want to manage.

      2. OyHiOh*

        I hear you on needing time to deal with curls.

        I’m white with moderately curly hair (mostly tight S waves, some soft finger width coils). I have a dinner party tonight and have spent more time than non-curly people would imagine planning when to condition vs shampoo my hair and timing of post workout shower so that it looks it’s best on a workday evening instead of looking best when I arrive at work. I too love swimming, and I find that my hair is generally pretty resilient, but I can’t really just jump in a pool and towel it off after.

    4. A New CV*

      I’m a white lady with rainbow coloured hair. I have no idea what chlorine would do to my hair dye, never mind what my leaking dye would do to the pool. This sounds like a plan by a white cis man who has no idea about other people.

      1. Metadata minion*

        That’s usually not going to be an issue if you’re just briefly jumping in, unless you’re using the single-use washable dye.

      2. Empress Matilda*

        Even something as benign as a new tattoo or a piercing. There are lots of reasons people may not want to jump into a pool!

    5. learnedthehardway*

      The entire thing reads as management that is harebrained and at best, doesn’t care about their employees.

      And that’s not a good look.

    6. New Bee*

      Black woman here and yeah, do I think this is the Worst!Boss!Ever! No. But do I see this situation as a breeding ground for microaggressions (“Can I touch your hair?”; “Why does it look like that?”; *Insert joke about Black people not being able to swim*,etc.). Yep.

  17. rd*

    LW5, what happens when you use your own software to make a timesheet and sent that along with your invoice?

    1. OP#5*

      Unfortunately I have to use their system like full time employees do (for this particular agency). Some agencies use excel sheets, it just depends. I normally use text editor to track time for myself throughout the day/week/booking then use the info to input timesheets. Some agencies use their own systems that link to finance department and are very rigid in how they work, despite the issues they cause.

  18. Onion Rings*

    Letter #1 makes me feel uncomfortable because this feels dehumanizing, as the OP said. No one should have to dance for their time off, no matter what kind of job they do. One thing I’ve gotten from this column is that time off is something built into a good workplace as part of supportive environment, and workers should take vacation they’ve earned without feeling guolty. Just because these employees aren’t white-collar doesn’t mean they deserve a stable, predictable schedule with breaks any less–plus
    this reinforces the idea that basic amenities are favors, not rights.

    1. river*

      You have hit the nail on the head. Nobody should have to dance for their time off. Well said. Even if it’s “all in fun”, it’s so unnecessary. The thin edge of the dehumanizing wedge.

    2. RabbitRabbit*

      This. Especially after the year we’ve had, why do you have to do something that complicated for a day off?

      The boss at best sounds like he thinks we’re living in some wacky comedy film, where jumping into the pool means a minute of being soaking wet and then you just change the scene and everyone’s all totally normal again (and no one has hair/body issues that complicate it).

      We used to have “team building” afternoon outings at a nearby restaurant/bar, with games, free food, a few drink tickets. Sounds lovely until you realize we were expected to stay there, in a loud bar which made conversation (especially for the hearing impaired) very difficult, for around 4 hours. Some of us started leaving after about 2-3 hours, but upper management would come later and be mad that not everyone was there/that people were getting time off without being at the department party, so they handed down the edict that if you left, you had to go back to work. So a few coworkers and I did just that.

    3. Galgal*

      Onion Rings, you’ve summarised it beautifully. The entire scenario is disgusting.

    4. londonedit*

      Exactly. I could maybe, in a ‘zany’ sort of workplace, see a boss saying ‘Hey! If one of you jumps in the pool fully clothed, you can all finish at lunchtime before the holiday weekend!’. I still don’t love that, but there’s likely to be one person who’d do it and then everyone gets an extra little perk. But not ‘I will only grant you this public holiday if you all jump in a pool’. It just seems incredibly miserly.

      1. meyer lemon*

        Yes, if the boss thought employees really wanted to jump in the pool, he wouldn’t have to hold a day off over their heads to make them do it. In a way, I would find it less objectionable if it was just a bonus non-holiday day off. Making it a common holiday just reinforces the fact that he’s making employees jump through hoops to get a perk that most workplaces freely allow.

    5. it's me*

      Yeah, I’m irritated by it precisely because of the plausible deniability of “C’monnnn, it’s just funnnnn” for something where you should have the day off anyway. It’s not a property management thing, my apartment complex has no problem whatsoever taking holidays off, lol.

    6. L.H. Puttgrass*

      “No one should have to dance for their time off.”

      Yes! Thank you!

      I’m amazed that Alison isn’t seeing this.

      1. Ask a Manager* Post author

        I’m not clear on why you think I’m not. I would never do or recommend something like this, and I would advise against it if the manager wrote in. I think it’s gross, as I’ve said. But I also don’t think there’s enough info in the letter from someone who doesn’t even work there to know if it’s bullying or not. A bad idea, yes.

        1. L.H. Puttgrass*

          “You want Monday off? I want video of you jumping into the pool in uniform.” How can that not be bullying? It may be unintentional bullying, if you want to give the owner credit(?) for cluelessness, but it’s still exploiting a power dynamic. Or is bullying only bullying if it’s malicious?

          I think what a lot of us are getting at here is that something can be both “intended as a silly kind of team-building thing” and an abuse of power. The former doesn’t excuse the latter, IMO (and opens up the door for a lot of icky “I was just trying to have some fun—can’t you take a joke?” kind of excuse-making).

        2. L.H. Puttgrass*

          Oh, and I think part of the reason we’re taken aback at your answer is that it doesn’t really sound like what you just described above.

          LW1 asked, “Is this as banana crackers as it seems?”, to which the answer, for me anyway, is “Heck yes!” Maybe there’s some mitigating circumstances, but from the text of the letter (and taking the LW at their word), this is (1) wacky, and (2) mean.

          Your response led with, “I’d assume it was intended as a silly kind of team-building thing, not an abuse of power,” and compared it to “do this silly thing for a prize” activities. Yes, your answer also mentions that you don’t like it, but the answer as a whole reads like you don’t think it’s a big deal. Your posts in the comments thread are a little stronger on this not being okay, but that does not come across in your original answer.

        3. Not So NewReader*

          I think that what is missing here is an agreed upon definition of bullying.

          From Stop Bullying dot gov under “What is bullying?” (This is as applied to children.)

          The first ingredient is imbalance of power.

          The second ingredient is:
          “Repetition: Bullying behaviors happen more than once or *have the potential to happen more than once.*”

          There is absolutely no doubt in my mind that the boss will require more dog tricks from people to “earn” their basic benefits promised to them on hiring. OP indicates he has done other stuff and I don’t doubt it. This isn’t something people come up with right away, they usually work their way up to something of this level.

          OP, encourage your relative that they can find a better place to work.

    7. The Original K.*

      No one should have to dance for their time off, no matter what kind of job they do.
      Perfectly stated. There was a whole long thread last week about how we should normalize just saying we’re not feeling well rather than giving detailed explanations when we’re sick. We’ve also talked about normalizing a) taking all the time off that you’re offered; b) telling, rather than asking, that you’re taking time off; c) not oversharing about why you’re taking time off because you don’t need to justify taking it. This pool thing falls into this category – just give people the day off, don’t make them bow and scrape for it.

      1. Despachito*

        “No one should have to dance for their time off, no matter what kind of job they do.”

        Exactly, and I’d add that no matter what kind of dance is required.

        The objections of getting wet clothes, un/curled hair, non-swimmers etc. although valid, are red herrings here – even if the boss required a different “dance” with no such inconvenience (such as, putting on a silly hat and singing a silly song), it would still be humiliating and unprofessional, just for the donkey-and-carrot element in it. (I am going to give you a perk but I want you to earn it by humiliating yourself).

    8. Nanani*

      Yes! If it was really a contest for IDK, food coupons or a nice spoon, that would be one thing, but for holidays off? It crosses a line.

  19. Virginia Plain*

    I think Alison is being kinder to the boss in #1 than he deserves. I thinking making people jump into a pool fully clothed to get a last minute chance to have a commonly observed public holiday off is more mean than silly. What does he do for an encore; poke employees with a stick until they dance the Macarena on the street outside the office or else they have to work in Christmas Day?
    I really don’t see how this is better than the bosses who paraded employees with lower sales targets round the office in dunce caps. Frankly I’d rather do that than jump into a swimming pool in work clothes and have to get home when I was all wet. Damp musty car seats anyone? Having to stand up on the bus all the way home? And wet underwear – ugh remember that nasty feeling from early childhood when you’ve had a small accident?
    That boss is a w@nker imho.

  20. Speaks to Dragonflies*

    OP-3…One last reason to use before you use Alisons advise.This is something I’ve used with my dad,and it worked pretty good. Tell them that you dont mix business with pleasure. If you went to work for them, then the friendship would have to end, and that you value the friendship more than the job. If I were in your shoes, and they still pressured me to work for them, I think I would be reevaluating the friendship anyway.

    1. JustaTech*

      I’ve applied this same reasoning to not joining a friend’s Patreon for his farm: as a friend I want him to be happy and healthy and take time off to be with his kid. As an investor in his farm I want him out there working. To me these two things are incompatible, so I gifted the friend some money but refused to invest.

      Working with friends can be challenging, working *for* friends is even harder.

  21. Seeking Second Childhood*

    Re: OP1
    Here’s hoping those uniforms are 100% polyester, because otherwise there are going to be a lot of really faded uniforms. Pool-safe levels of chlorine are rough on clothing. Is this guy going to make them replace faded cotton uniforms at their own cost?
    I’d also be uncomfortable with this because the employees are now on film doing something that is usually against pool rules–wearing street clothes into the pool.
    Unfortunately I have no advice to go with this except that I personally would be polishing my resume.
    (And if I were a resident I’d be complaining because that’s an awful lot of street dirt & unwashed bodies in the pool just before a holiday. I have to wonder if the pool is even safe for use before a treatment. )

    1. allathian*

      Thanks for bringing up the residents’ POV here. I honestly hadn’t even thought about it, but now that you said it, their reaction alone should be enough to nip this in the bud…

      1. Seeking Second Childhood*

        I freely admit I’m a little extreme on this because of severe ear infections caused by bad water at waterparks and hotel pools as a kid. I’mean one of the few people I know who *always* showers before getting in a pool. Shoes & underpants that have been worn all day? Nopety nope nope if I hear about that I’m complaining to management.

      2. Keymaster of Gozer*

        And having a load of very wet staff squelching their way through the site afterwards because I seriously doubt any brought towels/change of clothes.

        (I got thrown in a pool many years ago fully clothed and had a long and very unpleasant journey home afterwards dripping muck all over the bus)

    2. Mannheim Steamroller*

      This boss would probably respond to resident complaints by firing those employees for “using” the pool in their street clothes.

    3. Phony Genius*

      The main problem with jumping in a pool wearing street clothes is that the dyes in the clothes and fibers that fall off, especially cotton, can foul up the pool’s filtration system. And these employees probably have some responsibility for maintaining that system. So, yes, the residents may very well complain. And since they don’t know that the owner told them to do it, they’ll demand action be taken against the employees.

    4. Where’s the Orchestra?*

      Not much of a swimmer here (I can swim just fine, but hate it after years of forced laps as part of injury rehab process), and I have to agree that I as a resident would be horrified if I saw the staff of the complex having to jump into the pool. It would make me seriously question what if anything is going on in the brain of that manager.

  22. Matt*

    #4: sounds to me like just one of those “got a sec” requests that some people (those who formerly just walked into your office or cold-called) seem to prefer to giving more info in writing, or even using just email. Annoying for dedicated “email persons” like me, but nothing to overthink. However I don’t think you (OP 4) were in the wrong – if anything it was a gentle reminder that some to most people find more written info useful before agreeing to a meeting …

  23. Speaks to Dragonflies*

    OP-5… If theres no contract stating terms for payment, and you can’t add on late fees, can you add a “hassle tax”to your invoice? Or raise your rates enough to cover the cash flow issue?
    Something else, and I would guess you’re already doing part of this, is document document document! Try to have all correspondence in writing, with dates and times, as proof that you’ve been sending in your timesheets. Can you also CC or BCC someone higher up than the payroll/timekeeper folks as further proof that you are, in fact, sending in your timesheets? Paying late is something that companies seem to do alot. They are floating their debt over to you and it’s a load of horse excrement that they do, and I would bet it’s because you’re the least likely to be the squeaky wheel.

    1. OP#5*

      Have done all of this, the issue is still ongoing :( There’s been some movement but the promised ‘will be paid on Monday’ hasn’t materialised.

      I have a set day rate so can’t really raise that ad-hoc, although I’ve recently increased it generally for inflation etc. It’s definitely super frustrating that company budgeting issues (if there are any) are put onto independent freelancers – how is it our problem?

  24. Oska*

    LW1: Okay, going way out on a limb here, but all those Youtube videos of people (especially wedding parties) falling into pools? It’s apparently a kink thing. (Watching, not participating, or at least I think so.) I only read that in the webcomic Oh Joy Sex Toy, and can’t find the comic now, so, pinch of salt, but that plus the power play had my hackles up. :\

  25. RebelwithMouseyHair*

    OP2, I had the same happen to me. I had a great job that I loved, but this friend was adamant I’d prefer working for her (as admin too, and I’m chronically disorganised, so it would have been dangerous for her to take me on!). Also, she worked with her husband and they had a volatile relationship, and I was afraid of being caught in cross-fire.

    After a bit, I adopted the strategy of showing my friend just how bad I’d be. For example, I complained loudly that my boss interrupted me when I was filing my nails to talk about business (in fact, I keep my nail file in with my pens and pencils because I sometimes file my nails to soothe my brain, it helps me to think things through, but I didn’t bother to explain that little detail). Then I complained that the boss didn’t like it when I arrived late (which was fair enough because I always had to leave on the dot to pick my kids up from school). Then I complained that we weren’t getting a Christmas bonus (knowing that for my friend, this wouldn’t be on the table either).
    She stopped bugging me and got a divorce, and our friendship didn’t last all that long either.

    1. PayMeInChocolate*

      It sounds like you made the right choice, you probably would have been fired or let go as a casualty of the divorce. I worked part-time for a friend and was constantly pressured to work more hours because I was a friend and needed to help more. That friendship ended when I had to quit.

      1. Falling Diphthong*

        I absolutely foresaw firing as a casualty of the divorce.

        It’s the business version of an affair: “Both of us are miserable! Let’s drag in more people!” And then there are just more miserable people.

  26. Klio*

    Letter one’s wet clothes sound like a good way to get staff catching many different bugs. I guess the boss is also “come in ill or never come back”.

    1. Cheesesteak in Paradise*

      That’s a myth. Being wet doesn’t make you sick. Miasmas don’t make you sick either. Virus laden respiratory secretions make you sick.

      1. Klio*

        Being cold from water logged clothes can most assuredly give a some help to all those diseases trying to get ahold.

  27. jtw*

    OP 4: After a quick glance at the few replies for this one, I wish to add another observation. We don’t know what the OP’s email actually said or how it read. I am not suggesting they lied, not at all. Rather, our own perceptions of how we communicate, especially via email, can vary considerably from how others perceive them. While devoid of our physical nonverebal cues, there is still a sense of tone and voice that can come through in emails. I’ve managed a few people who think nothing of rather curt, unthinking, or pushy emails, when the recipients have reported back to me (or I was already on the thread to see for myself). Often, the writers think they’ve done a bang-up job of ‘communicating’ professionally; when, I might be gritting my teeth at what I’m reading and dreading dealing with the fallout.

    I say this, too, because the OP’s letter itself rings very strongly of frustration and ire. So, while I don’t know what was actually said in her follow-up email, I might suggest the OP take that into consideration. I don’t deny, however, that some managers/bosses are in fact clueless and may respond curtly. But, communication is a two-way street, and this can be a learning experience for how to manage upwards.

    1. Matt*

      This is certainly possible. I remember one coworker who I never met in person over a long time, but I got some todo lists for the web apps I developed which he was supposed to check in terms of style guide, accessibility/usability issues etc. – those were always in a very “curt”, “sharp” tone as perceived by me, and I always dreaded his emails. One day I was to meet him in person – I have to admit, I was a bit afraid. It turned out that he was a real nice person if you sat next to and talked with him, a complete opposite of his email style …

    2. Observer*

      You could be correct.

      Nevertheless, I still don’t think that the OP did anything wrong. The original request was unreasonable. Unless the OP was overtly rude, allowing some frustration to show when being asked for something like this is not the end of the world.

      1. jtw*

        Not saying the OP did anything wrong, but I also don’t know that the request was unreasonable or unusual. “The subject was “quick check-in” and the body only said, “I would like to better understand this process.”

        Not ideal, no. But this happens all the time. And, the OP’s all-caps take on it, “WHAT PROCESS?” indicates a high level of frustration (that’s how I read it and I do realize that’s only one way to do so). Because of this, I have seen many people do themselves an injustice in that ‘that tone’ comes through in written communication. I’ve done it. I’ve managed several people who’ve done it. It’s another side of the token I think may be overlooked here, and may have contributed to the ‘curt’ cancellation and overall response.

        Or, perhaps what we see as a curt cancellation may have been that manager recognizing that her request for such a meeting was premature or otherwise unnecessary based on the OP’s reply, and simply decided not to press forth and it was as simple as that.

        Or, yes… it could have been out-rightly stupid and the manager is a tool. My point is, there’s a large piece of context missing that to me, having been in what seem similar situations, may just be due to how we communicate our emotions through our written words.

        1. AJR*

          Agree with what you are saying. I have been in a similar position as the meeting requester – asking for meetings with others based on vague directions from a supervisor, or receiving vague clues in project meetings that this person is someone I need to talk to. Or sometimes I try to set up meetings with others to build relationships and learn about other areas of the organization (this type of interaction and background knowledge is immensely useful for the type of work I do, which is cross-organizational), as Alison described. If there’s pushback then I may feel chagrin and cancel, especially if the reason why I’ve gotten in touch is because someone else gave me vague directions to do so.

          In the normal non-WFH world, I would maybe try to have a much less intensive 2-5 minute interaction with this person as they pass in the hall, or have a short, casual one-on-one interaction with them before or after a meeting. In the normal non-WFH world, there’s usually more than one way to get the information you need, and you don’t have to do detective work about what other divisions are doing with vague clues and hints. Of course, in the WFH-only, online world, the only way to get some of this information is by imposing on people and directly asking for meeting time, which is part of why I hated mandatory WFH so much.

          1. AJR*

            To add to what I wrote above: if I know someone is up against the wall with a deadline, I would try to avoid requesting an informational meeting with them, but if I have no way of knowing their workload then I can’t space this out in this way.

            If the meeting requester was curt or brief in canceling the meeting, it might be that their frustration was not with the LW but rather with the person who sent them on a goose chase by directing them to the LW. It’s not the best, but sometimes that is what is happening.

            1. Observer*

              If the meeting requester was curt or brief in canceling the meeting, it might be that their frustration was not with the LW but rather with the person who sent them on a goose chase by directing them to the LW. It’s not the best, but sometimes that is what is happening.

              I think that this is highly likely. So, OP, you didn’t do anything wrong here, but consider that this person may be in an uncomfortable position as well.

              1. jtw*

                Precisely. It’s a reminder that most everything we think “is about us” likely isn’t, and it’s better to consider the full spectrum of what might be going on, if only to help reduce our anxiety over what may be perceived as a bad interaction.

  28. Keymaster of Gozer*

    OP2: oh mate, been there, learnt the hard way (turns out nobody in the office will respect you if they’ve all been told, multiple times, about the bad bits of your past. And current. It’s how I learnt to keep my gob shut about a few mental issues)

    I couldn’t pull it back at the firm I did that in. People simply knew too much about me (and in several cases were actually scared of me – the whole mental health equalling dangerous person trope that I wish would sod off) and I didn’t have a handy mind wipe to hand.

    But, if you’ve not got to that tip-off point there’s definitely the ‘be the most professional person ever for as long as you can be’ option. Over time, adopting that role can a) become second nature at work (confession: I’ve not quite managed it if the words I just used on this motherboard are anything to go by) and b) enable you to notice the culture and people around you to get a better view of where the true limits of friendly conversation are.

    Basically, listen more than you talk.

    1. PayMeInChocolate*

      I cringe still at the memory of one of my first jobs and cornering a co-worker in the break room and giving them every detail of my latest marriage counselling session. I needed to vent but that poor person was not the right choice.

      1. Keymaster of Gozer*

        Definitely having a sympathetic cringe along – the guy I first unloaded my issues onto during a bad day wrote me an email later saying how he did not appreciate anybody bringing emotional ‘stuff’ to him and I was never to do it again.

        20 odd years ago that was. Gods I was so, so clueless.

        1. Something Something Whomp Whomp*

          an email later saying how he did not appreciate anybody bringing emotional ‘stuff’ to him and I was never to do it again.

          FWIW, his reaction sounds like an unusually heavy-handed way of setting boundaries and dealing with a social faux pas at work. Unless I’m missing something here, it really doesn’t sound like you were bringing all of the cringeworthiness to that scenario.

          1. Keymaster of Gozer*

            I did cry a lot over getting that email but on reflection of several decades I had laid some…pretty heavy stuff down that would probably be triggering to quite a few people. So, yeah he was actually a fairly abrupt person who really didn’t appreciate people dumping their emotional stuff on him. I’m paraphrasing the email because heck who keeps 20 year old cringe material?

  29. EventPlannerGal*

    OP2, Alison has given great advice about your actual question but I just want to encourage you to take a step back and breathe. You sound extremely down on yourself and almost panicked, and I don’t think that’s necessary! You haven’t shot someone, you’ve overshared some personal information. It happens! It’s embarrassing right now but you’ll be fine! There’s no need to shame-spiral about robbing yourself of dignity and how can you ever recover your professionalism – you just need to try your best to stay conscious of what you’re saying and not let your mouth run away on you. I hope that’s not an overstep but you just sound so very down on yourself and I don’t think you need to be.

    1. OP#5*

      Thank you :) I’m glad they had a good resolution in that case! I’m in UK so thankfully don’t have to worry about health insurance on top of the financial stuff but it’s still very frustrating. I use Xero for accounting (another hat to wear as freelancers.. we’re actually really business owners) so have auto-reminders and read receipts all set up. The problem is just with internal agency processes and a lack of urgency sorting out any issues on their end.

  30. Richard Hershberger*

    LW1: Riddle me this: What is the practical difference whether the behavior is motivated by bullying or by team building? Bonus question: What does this say about team building exercises in general?

    1. Allypopx*

      I think in general the way you handle or respond to things is different if you know it’s malicious. We tend to be more forgiving of well-intentioned behavior, less afraid of repercussions, more tolerant of the individual prescribing the behavior. But that’s mostly interpersonal and psychological, and your question was practical. Practically – I still think this is awful and it shouldn’t matter what the intention was.

    2. The Original K.*

      Someone upthread pointed out that team-building is when the boss jumps in the pool with you, and I agree. I mentioned having to do the ice-bucket challenge at work and I can at least say that our boss (VP) did that with us.

      1. Mallory Janis Ian*

        When we did the ice bucket challenge at work, only the highest bosses participated and the rest of us watched. They were representing all of us when they did it, but I’m glad we didn’t all have to.

    3. Falling Diphthong*

      If you’re considering an ongoing relationship with the person, their motivation matters to some degree–if this is a well-intentioned person they might listen to feedback. If not, the advice is that your boss is a jerk and isn’t going to change.

      “Team building” can be “the managers brought in food and grilled lunch for everyone” or “the whole office went to the local ice cream shop” or “we had a fun Friday afternoon of opt-in egg-spoon races and cheering and eating cupcakes and general bonhomie.” In a functional office, most team building gets done by doing the work together, but some broader bonding options are pleasant breaks and may give you a chance to learn just who “Joan in Accounting” is.

    4. Not So NewReader*

      What is the practical difference whether the behavior is motivated by bullying or by team building?

      Well first off the “beneficiary” of the experience has to see something as team building. IF they perceive it as bullying then there is absolutely no difference. Just as beauty is in the eye of the beholder, team building is in the eye of the recipient.

      What does this say about team building exercises in general?

      I will try to be as unbiased as I can. As a consumer I do not want to pay for employees bonding experiences. I just want to pay a fair/reasonable price for a product.
      As a supervisor, the biggest team building experience I have ever seen is watching the group’s collective eyes open super wide when they saw the staggering amount of production they were capable of. Success is the ultimate team builder.
      As an employee I don’t want to waste time on non-work related things. I could be at home doing something important to me. I am fully capable of building or not building work relationships with people. I do not want Papa Employer making sure I feel loved.

      In OP’s example a great question to ask would be what is the result of this team building exercise? One (or more) posters mentioned it above: Most of the employees now HATE this employer down to the cellular level. And it will show in their work. Errors will increase, breakage will increase and so on. Oddly, nothing will be deliberate. It’s a side-effect of not caring any more.

  31. Texas*

    I feel like the fact that the manager in #1 required a video of jumping into the pool pushes it quite definitively into “making employees debase themselves for the manager’s pleasure” territory. That is absolutely unacceptable behavior from the manager, and the video makes it even ickier.

    1. Violet Fox*

      Yeah, whatever happened to everyone has a right to not be on camera and not be recorded?

  32. Roscoe*

    #1. while this isn’t great, I feel like your reaction is a bit much. Using words “disgusted”, “bullying”, and “abuse of power” seem a bit over the top.

    Sometimes there are silly things people have to do. The fact that this didn’t even happen to you and you seem so over the top angry for someone else is also concerning. Was your friend even upset, or did she just think it was stupid and in good fun? Sometimes being upset on other people’s behalf just isn’t your place. Trust me. The amount of well meaning white people who I’ve had be upset on my behalf (I’m a black man) is ridiculous sometimes, and doesn’t look good

    1. Texas*

      There’s a huge difference between “Hey everyone! We’re jumping into the pool in our uniforms as a team-building activity” and “You want Monday off? I want video of you jumping into the pool in uniform.”

      While I think the former is also not a good idea for a place of work, I wouldn’t call that bullying or an abuse of power. The latter, however, reminds me of an episode of Undercover Boss where the manager forced the waitresses to race each other eating plates of beans without their hands (face down in plates) and whoever finished first got to go home early.

      I agree that there isn’t anything for LW to do, because they’re not part of it. But even if all the involved employees were okay with it, it’s still not an acceptable action on the part of the manager.

      1. Willis*

        Yes! I thought of that Undercover Boss episode (at Hooters) as soon as I read this letter. I feel like that manager thought it was just good, silly fun too. Sometimes you can be a bully who thinks you’re just a harmless fun guy. Holding the holiday over someone’s head to get them to do a prank sounds more like the former to me, but I think the better point is that it’s a stupid thing, which a manager should not do, regardless of whether we can universally agree to brand him a “bully” via the internet.

        1. MCMonkeybean*

          “Sometimes you can be a bully who thinks you’re just a harmless fun guy.”


  33. Pocket Mouse*

    OP 5: I like the suggestion above to charge a higher rate, then give a discount for on-time pay—it seems these clients need an incentive to pay you on time, and/or a reduction in the barriers for the same.

    From your end, is it possible to write into the agreement that you only start work after you have all information (job numbers, etc.) you need for timekeeping and payment purposes? For the agency with the tech issues, can you speak with regular employees and find out how they navigate timely pay, or with Payroll to see if there is an alternate format you can submit that would work and/or ease the burden of anyone who has to complete your timesheets after you’ve left?

    1. OP#5*

      I’ve worked at this agency for many years and the regular staff and other freelancers gripe about timesheet systems a lot. The agency seems in no hurry to change the IT company or systems in place, and freelancers get caught in the crossfire unfortunately. There’s no alternative method (apart from others doing the timesheets for us when the system is working again, which I’ve had to rely on before and the person didn’t do for a month). I might try the surcharge/discount method but it’s not that usual here, and likely that I won’t work with this agency in future. It’s not the first time this has happened.

  34. Dr. Rebecca*

    For LW5: I used to work at a warehouse. One client was more than six months in arrears when I suggested to my boss that we…stop filling their orders until they paid up. He retorted “but they’re one of our biggest customers!” and I replied “not if they’re not paying us.”

    Like Alison said, imagine this isn’t going to change, and act accordingly.

    1. Sola Lingua Bona Lingua Mortua Est*

      We go through this with one of 10 largest clients–but instead of arrears, we subsidize their business with us by forgiving invoices and zero-rating services. The fear that they’ll leave is palpable with some coworkers, and the fear they won’t leave is with others.

      I wouldn’t be surprised if there’s a commission or other monetary incentive (beyond the interest-free loan) involved somewhere. Some things are so stupid they can only exist to grease hands.

      1. Dr. Rebecca*

        *nods* “Expanding our reach into the Detroit metro area” was the reason given. Dude. They have other suppliers of picture frames, we’re not going to be it.

        1. Sola Lingua Bona Lingua Mortua Est*

          At least if we saved the money until February and then set it on fire, we’d get the warmth from it!

    2. OP#5*

      Yeah that’s so true. In my situation the invoice is usually for the week of work preceding it. I’d get booked Monday – Friday, do timesheet on Friday and send invoice from my own accounting system after that. Then trust that everything will be smooth on their end. In this case there were delays outside my control so they basically just ignored payment reminders, daily late fees applied and other emails asking for payment ETA. There’s been some movement so hoping it’s resolved today or in the next few days.

  35. ResuMAYDAY*

    I think there would be some value in OP2 addressing her oversharing. After all, she has set a precedent. The new employees could be bracing themselves for the next verbal unload, or could decide that it’s OK to bring *their* crazy weekend stories into the office. Changing the unwritten rules now could throw the employees off kilter. I wouldn’t do it formally, like in a meeting or a memo, but just bring it up as casual conversation.
    “I probably surprised you when I told you so much about my colorful background. I’ve always been an over-sharer but I know that also means you become a captive audience. Sorry about that! I’m working on it and need to keep in mind that this is an office. Blerg! Hey, do you have that sales report ready?”

    1. Allypopx*

      Eh I wouldn’t address it unless it comes up. The husband found it out-of-sync enough to pull OP aside, and sometimes naming these things can blow them up into a bigger deal than they are. There are different scripts if those scenarios happen but there are also downsides to being so pre-emptive, I’d wait it out and see what happens.

      1. ResuMAYDAY*

        Well, now she has two options: address it or don’t. She can pick the one that works for her.

    2. LITJess*

      I worry that without giving herself enough time to practice “under sharing”, addressing it could accidentally turn into another platform for over-sharing. Better to just focus on building up those small chat topics and professional boundaries. By the time OP has that down, hopefully addressing it will no longer be necessary.

    3. Falling Diphthong*

      While I think people may not just notice your new leaf, and there’s sometimes value in alerting them that you are aware you overstepped in the past… this sort of announcement goes better when the affected people are your peers.

      And if the resolution to do better doesn’t actually come through, as with so many resolutions, the subordinates nodding along to your latest promises can’t do anything about it.

      (For OP, I go with the upthread advice to get some counseling re the extremes, and to focus on 1) not oversharing; 2) some aspect of the business, not the whole thing. Deal with this in chunks.)

  36. SJ*


    Lots of people have pointed out issues with jumping in the pool in general, what puts this over the top for me is ** send the boss video of you jumping in the pool fully clothed **. Someone pointed out downthread there is a market for these videos online for, uh, NSFW reasons, but even aside from that — once it’s on video and in someone else’s hands, it’s completely out of your control. Is boss gonna be watching these at random times when he wants to feel superior? Show them to friends at parties for a laugh? Throw them up on the projector at staff meetings later on? Yuck. Yuck! I hate everything about this. LW1 your instincts are good, trust them!

  37. CatCat*

    #1, I’d be deeply uncomfortable having to jump in a pool for a day off. I would be extremely conscious of my clothes adhering to my body when wet (I have a very large bust). I also can’t imagine sitting around in wet clothes covered in chlorinated water until I got home. I would absolutely feel bullied as I lost out on a day off over this. As a bonus, I’m sure I could expect my boss to comment on my lack of participation on how I’m “no fun” or trying to get me to believe a video of me with wet shirt clinging to my breasts was just a “silly team-building exercise.” No effing way.

      1. Not So NewReader*

        Labeling people works until it doesn’t.

        There is an employer here who labels everyone a thief. The turn over is very high. Unemployment has caught on to this and pushes people’s applications through.

  38. Mannheim Steamroller*

    Re:Letter #1…

    Does the boss do the pool thing for all requested days off, or was yesterday a special case (because Independence Day was a Sunday)? Would this be worth reporting to the state labor department?

  39. blackcatlady*

    LW#1: Are these part time hourly employees? If they are full time, is there a hiring contract specifying holidays, vacation and sick leave time? If the work agreement already specifies set holidays why do they have to jump in the pool?

    1. Valancy Snaith*

      Contracts are exceedingly rare for employees of all kinds in the States. I highly doubt there was a work agreement with set holidays.

    2. Not So NewReader*

      A lot of this type of thing goes on with lower paid workers here. You have to beg for everything.

  40. Mannheim Steamroller*

    Re: Letter #5…

    If other freelancers have the same experience, then maybe all of you can band together and “blacklist” this company as a client.

    Also, if the client is based in New York City, then the City’s “Freelance Isn’t Free Act” may apply. Keep track of the amount and age of all outstanding bills and consult an attorney if necessary.

    1. OP#5*

      Based in UK and there’s a website for rating agencies by freelancers but sometimes freelancers will just keep their head down to get more work, even if payments take a long time (especially in Britain!). I know others who work there and need the work more than the hassle.. especially after the pandemic and how long we’ve been under lockdown here. I understand, everyone has their own reasons. I’m not sure if other freelancers that have been there before that I don’t see any more have had similar issues and have just decided not to work there any more.

  41. Workfromhome*

    #2 This is not meant to be unkind but the best thing the LW can do is find another job. I understand that her husband owns the business. He is entitled to hire who he wants within the confines of the law. BUT if the business is important here the LW needs to exit this situation . The oversharing isn’t even the biggest issue (although it is one of them)

    Here is what other employees see:
    Someone has been brought into the business with NO knowledge of the business.
    Someone was hired for a jib they have so little aptitude for that they needed to hire an additional person to “cover” for her lack of experience.
    After a certain period of time this person who has no experience and no qualifications that would get her hired for this job is going to become a cow owner of the business and essentially the “boss” of all the employees (even the one who was specifically hired to cover her lack of experience. ).
    This person who has no experience, needs to be covered for but cant be dismissed because they are the bosses wife also has shared many things about her past life that would lead people to believe she’s not at all qualified for this job let alone to be “their boss”

    Even if LW stops oversharing 100% right now the damage is done. Unless there is some miracle where the LW suddenly learns the business overnight and comes up with some ground breaking ideas that improve the company she is always going to be seen as the Boss’s wife who is not their boss because of who she married. She will always be the incompetent person who’s bossing them around making way more money than them despite the fact that they do her work for her.

    If the owner wasn’t to make her 50% partner due to marriage he can. Make her a silent partner and if she wants to work go find a job somewhere else where she can get a job on her own merit. Everyone wins.

    1. Allypopx*

      You’re right. This is so common in family run businesses and one of the reasons they’re notoriously awful to work for.

    2. El l*

      Yeah, I understand that spouses work together, but am not sure how it makes sense in this case. There has to be a compelling reason – besides cost minimization – for bringing them in, and I just don’t see it here.

    3. traffic_spiral*

      Yeah. Also, I’m no shrink* but it seems that she’s taking a basic correction very very hard, and combine that with the “My plan is to learn the business inside and out and be the most valuable person my husband has,” thing, and… she might not be able to compartmentalize “work” vs “marital” feelings enough to be in business with her husband. She’d probably be happier in a job where a mistake was only a reflection of her as an employee and not (as she seems to feel) a reflection on her as a wife.

  42. Lucious*

    LW5: it’s unlikely they’re going to change. Odds are you’re not the only one impacted by their lackadaisical finance team, and clearly resolving the delays is not a priority for that organization.

    A choice is at hand; if they refuse to change, make plans under the assumption you won’t get paid until 3 months after the due date on future work . Or consider ending the business relationship.

    1. Obscure*

      When companies pay late I find it’s more often than not by design rather than incompetence. It’s a sad reality that pretty much any company here in the UK beyond a certain size will have at least ones person who’s sole job is to chase late payers.

    2. OP#5*

      I’m in UK and yeah that’s been my main consideration, whether to sever ties at this point (this is the third or fourth time this has happened, otherwise it’s been ok and have worked with them regularly for years). It’s partly by design and partly by systems that keep failing and a terrible IT department that is very blase about everything. No shade to IT as they work hard but I’ve never seen more issues than this company. Will most likely not work with them again.

  43. June*

    The pool jumping is ridiculous and goes far beyond team building. Some people cannot swim. Some people have medical issues. Yes. It’s way over the top.

  44. Gray Lady*

    I’m just plain afraid to jump into a pool. I don’t think it rises to any kind of disability, it’s just that I’ve never really learned to swim well and am fairly uncomfortable around water. I don’t mind going into a pool, down the steps, and standing around where I can touch the bottom or floating on something, but jumping in isn’t going to happen. I’d be deeply upset if I were denied a day off that other people got, because of this.

  45. Okapiokapi*

    #1 reminds me of a roommate I had once. Roommate thought I should go with her to a particular social activity, that I wasn’t interested in. She thought I just needed convincing. So as a “joke,” she stole a stuffed animal off of my bed and sent me a picture of it hogtied in the trunk of her car, saying I would get it back when I agreed to go to the social event. It felt like a joke, and we both had a good laugh right up until I made it clear that I still didn’t want to go to the social event. She refused to return the stuffed animal until I agreed to go. She kept it hogtied in her trunk for TWO WEEKS, and I only got it back days after the social event, and she gave me a little upset speech about how she’d been trying to teach me a lesson about how I needed to socialize more (read: hang out with her, because sharing a room wasn’t enough hanging out for her?).

    It’s…regardless of actual harm, a joke with an ultimatum attached isn’t really a joke. It’s an attempt to manipulate someone else. This joke would be okay if the employees knew that they could talk to the boss about why they don’t want to/can’t jump in the pool, and would be respected. Is it worth making a fuss over? Probably not. But it cna and should reflect badly on the boss.

    1. Allypopx*

      That’s…wow. I’m sorry that happened. But your overall point is very well put.

    2. Not So NewReader*

      I see the roommate is now an ex-roommate. That’s good.

      The fact that she carried this on for weeks is … uh…. concerning.

      I hope you told her there is no circumstances ever that taking your stuff is acceptable behavior.

  46. lilsheba*

    On number 1, first of all why are you required to wear a uniform to work in property management? Secondly I DESPISE “team building” games like this. They are designed to humiliate people and that’s it. My old job did a bunch of humiliating “games” like this and I refused to participate.

    1. Jinni*

      In bigger complexes, and multi-complex apartments the property management folks are often required to wear uniforms to identify themselves to tenants. It can be a bit concerning to see random street-dressed (unfamiliar) folks using passkeys to get into apartments and otherwise accessing tenant-only areas of the building. I’m talking hundreds/thousands of apartments.

      1. NotAnotherManager!*

        Yep. I haven’t lived in a multi-unit building in a while now, but nearly every one I lived in had some sort of uniform (logo’ed polo or dress shirt for the office staff, coveralls or similar for the maintenance staff) for those who worked there. Only the tiny, 8-unit building where the owner lived onsite and did the “management” part themselves didn’t have some sort of logo’ed or uniform for staff.

    2. Valancy Snaith*

      Is it that unusual? Most property management I’ve encountered is maintenance-type work–taking care of the lawns, pools, repair work, and I’d certainly expect workers in that vein to be wearing a uniform, especially for a company large enough to have multiple employees in that role.

      1. UKDancer*

        Yes the concierge at my block of flats wears a uniform. The cleaner and gardener also wear overalls with the company logo. I’d say it’s fairly normal for residential property.

        1. lilsheba*

          It’s not normal here. I’ve lived in small buildings and a large one with over 600 units and the only time I’ve seen a uniform is on maintenance, which I get. But not office staff. That seems weird to me.

  47. voyager1*

    I am not surprised by folks pushing back on the pool thing, but I think Alison is right on this one. No it isn’t the greatest thing to ask employees to do…

    Honestly I don’t see anything wrong with LW1 and the pool jump, but caveat is that be done for marketing purposes or social media post. I could see a company doing that.

    If jumping into a pool would have gotten me out of working many holidays over the years, I could dive into that. Working holidays sucks.

  48. animaniactoo*

    LW3 – You might try acknowledging her push that you’d be good at it. She may be reading your other reasons as cover for “I don’t think I could do this well and am trying to politely decline”.

    So it is possible that saying “Yes, I think I would be good at it too and I appreciate how much you believe in me. But for all the reasons I stated before, I am not a good fit because I don’t want to be doing this kind of work again. It is more stress than I want to take on. So when I say “it’s not a good fit”, it’s not because I don’t think we would work well together or I would suck at the job. It’s because it’s work that I just don’t want to do right now/again/whatever.”

    I think there may be another piece in here where she is having a problem finding other good candidates that she trusts… and if you know someone else who might be a good fit… maybe a referral? Or asking straight up how hard she’s looked for other people to fill the role and where/how she’s looking?

  49. LadyByTheLake*

    I am an attorney and one of my clients (a Fortune 50 company) changed their invoice software. It was TERRIBLE and their support for external vendors trying to submit invoices was even worse. I spoke to my contact at the company and (gently) raised concerns and expressed that it would be difficult to continue providing them services if I could not be assured of timely payment. She passed along my concerns and it turned out that a lot of external vendors had raised similar issues. They focused on fixing the problems, and from then on, when I had problems, I reached out to my contact — once I made it their problem to help me (and I could do that because I had a good relationship with my contact), change happened pretty quickly.

    1. NotAnotherManager!*

      I am always amazed at how companies, including large ones, have terrible (or terribly run) A/R and A/P systems. I worked with one a few years ago whose finance department took their sweet time sending out invoices, and we’d get six to twelve month old invoices in batches. A lot of our ordered services are on behalf of clients, and, if the client’s matter is closed, we can no longer invoice those services – our team even does a last call for invoices before project closure to ensure we get everything paid. We finally had to write into our contracts that invoices not received within X days of service or X days of last call would have to be written off. I’m not surprised about A/P systems being a mess but the A/R system… well, you’d think people’d want to get paid.

    2. OP#5*

      Contract stated 30 day payments which they broke themselves. The company seems in no hurry to replace the IT company or timesheet systems. Unfortunately freelancers are in no short supply so me not working with them any more probably won’t make a difference even if our relationship has been great. I will never understand why companies run this way.

  50. animaniactoo*

    LW5 – you’d have to gauge how well this might work. But when I was a freelancer, I had a limit of how many jobs I hadn’t been paid for yet before I would take on additional work. So… is there an avenue here to say “I have 4 invoices waiting over 2 months for payment, I can’t take on more work until those are paid.”?

    If not, I would work on building up additional clients while you accept that they will always be 2-3 months behind – which means that you count on the invoices paid out from 3 months ago, not the ones submitted in the past month – until you get to a point where you are no longer as dependent on them for work and can say things that could be relationship ending like “As soon as I’ve been paid for the previous work, I will be happy to take on another project for you.” and “I have a late fee now for all work that is not paid within X days of invoice submission.”

    1. OP#5*

      Definitely. I’ve not worked with them since and probably won’t do again as it’s not the first time this has happened. Since writing I’ve done a contract/booking with a new agency so hopefully they book me again and become a regular. It’s always hard to drop a client you’ve worked with for a long time and trust you’ll get others. Everything I do is word of mouth too but it’s been working so far.

  51. Penny Parker*

    #1 In my opinion this is an outrageous abuse of power; I adamantly disagree with Alison. I am also pretty upset that she is condoning this abuse of power. I would suggest looking for a new job STAT. There are many jobs out there on the level of “property management” and employers are begging for workers right now. Let this employer lose all of his workers and then maybe he might understand to quit his abuse.

    1. Disgusted*

      I too was extremely surprised at Alison’s take on the pool jumping. It is a flagrant abuse of power of the, “I’m the boss and if I say, jump. You jump!” variety. Only in this case, it is a literal jump. I am just agog that Alison believes it’s NBD.

      For me, there is no way I would ever participate. The overriding reason, to be accused of oversharing, is that I have a larger than average chest for a woman and my entire life and in ALL of my jobs, I have had to endure at best “teasing” and “off handed comments” and at worst, outright sexual harassment over my chest. I have ceased to be astonished at ways men, but sometimes women, will engineer a situation to draw even more attention to my chest. “but it’s all in good fun!” is the response when I refuse. “Fun for whom?” is my retort, which usually gets me a smirk and a wink.

      I would view this pool jump as a wet t-shirt contest. Period.

        1. M / P*

          I think it’s the “Eh” at the start of your response which to me read as a bit dismissive.
          I have to admit the letter made me pretty angry (at the boss) and yeah, I would have enjoyed a more cutting response. Maybe for some of us the letter just hit a nerve. Just saying.

          1. June*

            “Eh” comes off as “no big deal”. It is a big deal. Maybe not the WORST deal. But not an “eh”.

        2. MCMonkeybean*

          Well, you referred to it as “silly” twice which isn’t usually a word people use to describe things that they DO think are a big deal.

      1. Not So NewReader*

        I think that unless a person has been harmed by this type of thing it can be tough to appreciate how much impact crap like this has.

    2. Observer*

      I am also pretty upset that she is condoning this abuse of power.

      Exaggerating is not going to help you make your point. While I think it’s worse than Alsison does, she isnot condoning it. There is a difference.

        1. Allypopx*

          I don’t think it’s bizarre. Your medium is written communication, miscommunications happen. A few people have pointed out some tonal words (“silly”, “eh”) that, clearly unintentionally, feel pretty dismissive of the concerns.

        2. jtw*

          It does seem bizarre. There’s loads of emotion tied up here, alongside very good observations and input. But you did say it’s wrong. You did say that there’s context missing (and I agree, there is). You even said that this guy may very well be a bully. What I see in your reply is room for interpretation of the events because of the aforementioned missing context.

          Yes, what this boss did was wrong, but we don’t know what his intentions were. Maybe it was to show his hand as boss. Maybe it was just a silly social media prank he put little or no thought (or empathy) into. In any case, speaking up in these situations with reasons why it’s such a bad idea may help that boss learn from his mistakes. Or, it may piss him off – and then you know what you’re dealing with.

      1. El l*

        Yeah, I think we’ve reached the point in the discussion where it’s all pure “mood affiliation.”

        In other words: Everyone who doesn’t think it’s the “worst thing ever” … will now get called “the worst thing ever.”

  52. Lyra Silvertongue*

    OP #2 some of the language in your letter feels a little concerning. You’re being hard on yourself and presenting your husband as perfect. It’s pretty harsh to tell your wife that they “lack leadership” even if there’s some truth there. You left your career for this, but you haven’t been trained in the business. I don’t know. I hope you’re doing okay.

    1. Ginger Baker*

      I had the same takeaway. It sounds like a…disproportionately harsh dressing-down from a boss, and especially from one who supposedly cares for you. I’m not suggesting people should treat “family” employees differently, mind – I think the level of “you are TERRIBLE” that seems to have come across in that conversation is demotivating and unhelpful to anyone. There is a difference between being direct and honest and tearing someone down. Given that this is your husband, I am strongly concerned that work/personal boundaries are not going to be strong enough to withstand you having this job, and would highly caution against continuing here. You left a career (that I presume you were succeeding in, or at least doing moderately well and were respected in) to work for your husband’s business. Why? Is it because he recognized that you have valuable skills his business would benefit from (in which case, I would expect a lot better support from him as a boss)? Is it because the business is struggling and it made more “financial sense” to hire someone he could get away with paying a very low wage? (Yellow/orange flag) Is it because he wants you under his control more (so he can tell you how terrible your work is??)? (Bright red flag all over, red flags galore.) I would give some very serious consideration to what the motivations were to bring you on and whether those reasons are beneficial *to you* versus returning to your previous career (which will only get harder once you’ve been sufficiently brainwashed that you can’t do anything right…)

      1. traffic_spiral*

        Ok, let’s be fair, we don’t know exactly what the husband said to her. There’s no way to tell that these things came from him as opposed to her catastrophizing a bit over a reasonable correction about over-sharing, and being told “if you want to be in a position of authority over people you can’t go telling them all your private issues.”

        That being said, regardless of whether it’s coming from him or her, I agree that working with her husband isn’t a good fit for her.

        1. pamela voorhees*

          It could be that this has turned into a game of telephone. I can see the husboss saying something like “people in leadership at the company cannot do this”, which was heard as “you have no leadership skills.” Could also be that “you have no leadership skills” is exactly what the husband said, but he and LW have a relationship built on really blunt language and it doesn’t bother either of them. Regardless, it’s probably always a good idea to seriously think about “do I want to work at the same place as my spouse.”

    2. El l*

      Yeah, for as much as I wonder whether it was a good idea for her to join the company…I also wonder if the situation is really as bad as LW portrays it.

      There’s some real oscillation between factual statements and extremely emotional statements.

      And when things appear factual, they sometimes don’t make sense. I don’t see how both of these statements can be true at the same time: “I am secure and stable…I don’t feel conflicted about my past, I just happen to identify as “survivor” of my past more than the woman I have become.”

      This whole situation smells of unreliable narrator.

      1. Lyra Silvertongue*

        Maybe so, I don’t feel qualified to judge that or not. I just feel that the LW is being really down on herself and it seems like there’s maybe more for her to think about there than just the oversharing thing. Catastrophizing or not, this doesn’t seem like a healthy workplace situation for them right now.

  53. TeaWrecks*

    #1 – I disagree with Alison and I do think it’s a horrible abuse of power. Anyone who is scared of the water, people who wear wigs, hairpieces, or head coverings that shouldn’t get wet but also they shouldn’t be forced to remove them in front of co-workers, people who are menstruating and wearing a pad, people who may have a skin condition for which chlorine is irritation or aggravates it, people with wearable medical or gender affirming devices, etc… These and other things are all situations that should not have to be revealed in a work setting just to get a day off, nor should they be forced to work if they otherwise would have the day off just because they can’t get in the pool.

    1. Lucious*

      Context matters. Even a “hello” is an abuse of power depending on the situation it’s said .

      We cannot tell from the letter if the boss is trying to promote team building but is going about it wrong, or if they’re heading down Power Trip Boulevard as you’ve pointed out. Either situation is bad news, but there’s no proof yet it’s the second scenario.

  54. Lora*

    LW5, nothing but sympathy. This is exactly why I got out of consulting / contract work – huge Fortune 100 companies that refused to pay bills for literally years on end. Found out from other vendors, they were getting screwed over for the same ridiculous lengths of time; one was carrying a $1mio balance for them and hadn’t been paid in a year. They obviously HAVE the money, it’s not even a cash flow or “gosh this crazy SAP system!” problem, it’s literally that they are the big dogs and can afford to ignore vendors until they feel like remembering to pay up. Basically you’d get paid whenever there was an audit showing that you hadn’t been paid – which was mayyyybe every couple of years. So you’d have to carry these huge “everyone owes me” balances and the options were, sue them and end the business relationships (hard, because they were indeed major players and word travels) or just let them coast (which, I can’t afford personally).

    This also extended to how they pay employees: some hadn’t gotten bonuses they were owed in over a year, some hadn’t gotten the correct pay rates in five years, some had their taxes completely screwed up by Payroll and somehow this was never the Fortune 100 companies’ faults for employing the worst accountants in the universe.

    Most important thing I learned in MBA school: finance fraud is a LOT more common than anyone imagines, because there are a lot of finance and accounting people who can’t do basic math, and the ones who can do math are mostly smart enough to not get caught.

    1. OP#5*

      Don’t get me started on finance for-profit capitalism! Dealing with finance people really feels like dealing with sociopathic robots sometimes, they just don’t care at all. I tend to resort to what I can do legally. In UK there are some protections at least. But I definitely won’t be working for them again and since they broke their own contract, the ‘you’re not allowed to encourage other freelancers not to work for this company’ clause is moot too (not kidding, that was in the contract).

  55. Former Retail Lifer*

    OP #1, are you sure you have all the context here? This is something my property management company does, but it’s done as a fundraiser. It’s supposed to be voluntary but you almost have to do it. That being said, it has no bearing on days off and if anyone said it did, it would be a joke trying to convince you to do it.

    1. Valancy Snaith*

      This is pretty well where I’m falling. This is a few degrees removed from the actual scenario and there’s a lot of opportunities for information to get lost in the game of telephone.

  56. mreasy*

    I can’t help but think – as folks have alluded to – that the pool jumping could absolutely not be an innocent prank…but the way the supervisor can get an eyeful of the parts of employee bodies usually covered by shapeless uniforms, now skintight. It’s really gross.

  57. Hiring Mgr*

    On #1, tying it to a vacation day is the part that’s a little off in my mind. Nobody wants to play these dumb games

    Separately, what happens if everyone jumps in? They close that day because there are no employees?

  58. RussianInTexas*

    I can’t swim. I don’t get in to a pool or the ocean (I don’t go in to lakes or rivers at all) deeper than my waist.
    I suppose I would never have a holiday then.

  59. ENFP in Texas*

    OP#3 – Just say “I’ve already told you no, thank you. Please stop asking me.” and either change the subject or walk away any time she brings it up. If she is so disrespectful of your boundaries, is she really someone you want to be friends with?

  60. Texan In Exile*

    All I could think of with LW1 is what a bad boss Miranda Priestly is in The Devil Wears Prada, which I watched again this weekend.

    She made Andrea tell Emily that Emily wasn’t going to Paris.

    She would move meetings to a day or more early, then be ticked off that people weren’t ready.

    She blamed Andrea for not getting her out of Miami when there was a hurricane and her (Miranda’s) flight was cancelled.

    And again – she decided Emily’s work was not up to par, but rather than speak to Emily, she decided that Andrea would go to Paris instead. And she made Andrea tell Emily.

    I am still angry.

  61. Lizard*

    #1 – The devil on my shoulder would tempt me to be the first to jump in, then yell out, “Whoops, forgot I was menstruating!” to force the boss to cancel the rest of the event. But he’d probably make everyone go to work instead of giving everyone the day off.

  62. pamela voorhees*

    LW #2 – First off, I want to say that I admire you’re trying to address this issue. I really do. So many people go their entire lives without realizing that they’re making someone uncomfortable. I wish you all the best in working with this issue.

    Allison has great suggestions, but here’s mine, from a quarantine in a group chat with an oversharer — people remember how many times you ask about them, talk about what they want to talk about, etc. If you’re oversharing, you’re likely making folks uncomfortable not just with these very intimate details of your life, but the fact that you have jumped into talking about your life, not theirs. They notice how many times it’s about you vs. it being about them, and three years from the last time they speak to you, they will remember absolutely nothing about your life but they will remember that you never asked about them once. Along with the “safe topics” is asking about their own lives — again, not intrusively, and not as a way to set yourself up to talk more, but actually creating a space for them to talk instead.

    Here’s how conversations with Oversharer Melissa From my Group Chat go –
    Me: I saw a movie this weekend.
    Melissa: Which one?
    Me: Birds of Prey
    Melissa: Oh I loved Birds of Prey, Harley Quinn is my favorite character, I really liked xyz, [talks about herself for another thirty minutes]

    Here’s how the good version of this would go –
    Me: I saw a movie this weekend.
    Melissa: Which one?
    Me: Birds of Prey
    Melissa: Did you like it? Where’d you go see it, at the nice place downtown? [continues to ask other person-centered focused questions]

    People love to talk about themselves. Let them. And don’t jump in with your own opinions, your own thoughts, “I had an uncle who died too”, whatever it is no matter how relevant it seems. Just let them talk, and occasionally ask a light question. If your sentence contains the words “I” or “me”, you’ve goofed.

  63. drpuma*

    OP2, a couple practical suggestions for you –

    Not long ago I participated in a workshop where they asked extroverts to follow the “three before me” rule – be mindful of who’s speaking, and make sure 3 different people have contributed to the conversation before you share again.

    Try to retrain your brain to only answer the question that’s being asked. Part of making conversation is folks asking about your weekend or how you spent the fourth of July holiday. You can just say “we watched the fireworks with my sister,” that answers the question just fine. It doesn’t have to be “we watched the fireworks with my sister, she and I have a super close bond because when we were kids we survived…” Maybe even practice while you’re away from work.

  64. RagingADHD*

    The pool-jumping boss is dumb and eye-rolly. But the pearl-clutching going on in the comments is ridiculous.

    When you get hired for a job, your days off are stated up front. If you don’t want to work somewhere that doesn’t guarantee this or that holiday, fine. Nobody in this scenario is losing PTO that they would otherwise be entitled to. They are potentially getting extra PTO, and they have to jump through stupid hoops to get it.

    I’m also not sure how some of these extreme health conditions being mentioned would even be relevant for uniformed property-management employees. IME, those folks are doing manual labor involving heavy lifting, ladders, power tools, landscaping, etc that would not be able to be performed by people with wheelchairs, stomas, and so forth anyway.

    1. Willis*

      Lots of property management is done by people in offices! Our property management company has a whole office full of people, including receptionists and roles like that. I think apartment community leasing agents would also often fall under a the umbrella of the property management company. It’s a lot of other stuff besides property maintenance.

      1. GraceRN*

        Yes. Looking through these comments I’m noticing many folks have a rather narrow understanding of PM company employees. Many PM companies hire office-based employees in various roles: accountants, maintenance request coordinators, office managers, administrative coordinators, account-payable clerk, receptionists, etc, etc. Many of them have to wear uniforms like a polo shirt/button down shirt with the PM company logo.

      2. RagingADHD*

        In uniform?

        When I worked admin in property management, and in the various property-management offices I’ve dealt with as a customer, I’ve never seen the office staff in uniform. They just wear office clothes.

        I certainly have never seen a leasing agent in uniform.

        1. NotAnotherManager!*

          Polo shirts with the company logo and a pair of khakis are very common in the management office of complexes in my area and where I went to college. Not universal, but common enough that that’s what I envisioned while reading OP’s letter.

    2. Nanani*

      “When you get hired for a job, your days off are stated up front.”

      No? Not for a lot of jobs anwyay.

      1. RagingADHD*

        Eh? Nobody I know in any line of work, including retail and hospitality, started a job with absolutely no idea (or opportunity to find out) what days the business was closed, what holidays were observed, and what the general policy was for taking PTO.

        If you’re taking jobs without having this conversation, I suggest you start doing that.

    3. NotAnotherManager!*

      Know if you have the day off or not isn’t the issue. The issue is the boss offering extra PTO to people willing to discomfort/inconvenience themselves in a manner that he specifies and is unrelated to their job/job performance. This is not you can take the day off if you’re doing community service or you worked the last holiday or you exceeded your rental quota or you’re attending a veteran’s event or even if your whole extended family is coming to a barbecue at your house – the price of the day off is to do something many would find unpleasant and provide video proof (to someone who’s judgment seems suspect, so who knows what he’d do with the footage). To say nothing of the potential wet t-shirt contest feeling aspect of it that could embarrass some staff.

      1. Despachito*

        “The issue is the boss offering extra PTO to people willing to discomfort/inconvenience themselves in a manner that he specifies and is unrelated to their job/job performance. ”

        Exactly this!

    4. Observer*

      IME, those folks are doing manual labor involving heavy lifting, ladders, power tools, landscaping, etc that would not be able to be performed by people with wheelchairs, stomas, and so forth anyway.

      You seem to have both a very narrow view of what people in property management do, and who can do those jobs. Property management does NOT require only fit young men with no hair.

  65. GraceRN*

    #4: This is one of those rare times that I disagree with Allison’s response. I receive meeting requests like this from time to time. I can totally relate. My initial reaction is many time similar to LW4’s. Where I work, sometimes it comes about because my name/my work was mentioned in some meeting, and a partner/boss got an idea that they can use my help with something, but they weren’t sure exactly what or how yet, and they decided to extend a meeting request to explore. When I met with them, it’s usually more of an open-ended, “Q&A style” meeting where they learn more about what I do and I learn about what they do. We usually leave with some general ideas on how we can work together in the future. I’ve learned that these meetings aren’t a waste of time: if I meet with them sooner rather than later, even just briefly, like 10-15 min, I can use the time to educate them on what I do/how I do things, and that bit of understanding can help prevent more vague requests like this in the future.

    When I get an email like this, I usually write back with an open-ended response: “Sure, we can find a time to meet. I’ll be glad discuss any topic related to my work that you’re interested in. Please feel free to let me know if I should come prepared with anything.” That usually opens the door for them to say for example “Oh yes actually I am dealing with this project now and I heard you helped Partner Esmeralda with their latest project, I am wondering if you have any ideas that might help me.” or “Actually nothing specific right now, but I would like to get a general sense of your processes. I might need your help for future projects.” I can then gauged the urgency, adjust the meeting length, and my level of preparedness based on their response.

    I can see LW4’s frustration. I’m guessing LW4 is in goal-oriented mode, and didn’t want to deal with non-specific requests. I get that. For me, I have to remind myself that people aren’t perfect. Just because they didn’t write the most clear, most on point email doesn’t mean their request isn’t valid. I don’t know exactly how LW4 responded in their email, but I think where LW4 got into this pickle with the partner is they asked for specifics too soon, and the partner unfortunately interpreted it as a refusal to meet, or even an aggression. Perhaps the partner were already very aware that they didn’t know technical things and felt insecure, and responded defensively.

  66. azvlr*

    OP#2, I have adopted what I call The Sonia Rule. I sat next to someone who is very devoutly religious in a faith that emphasizes chastity for unmarried members, rather vanilla ideals of marital relations, and a value on large families and getting married.

    I’ll admit that when I first met her, I was not thrilled to learn we’d be cubemates because others of her faith treated me very badly growing up and were always very pushy and discriminatory with me. Important to the story is that she was unmarried. Based on what I knew of her faith, and what I gleaned as I go to know her, she was very unenlightened in the sexuality department. Surprisingly, she was well-studied on some serious topics usually ignored in her faith, and never, ever judgmental about them. I was always professional towards her. Sonia turned out to be an insightful and gracious person, and over time I grew to respect here a great deal.

    Sonia and I sat next to another person who was less familiar with Sonia’s religious practices, and a classic oversharer. I personally didn’t mind when our co-worker would talk about some of the details of her daughter’s birth, nursing, or getting a tattoo in an intimate place, but it always made me cringe on Sonia’s behalf.
    I made a rule for myself that if it is something I wouldn’t share in front of Sonia, then it didn’t belong in a work conversation. It has served me well, to the point that I think some people are really surprised when they get to know me outside of work.

  67. TeapotNinja*

    #3, counter the job offer by asking for an absolutely ridiculous amount of pay. When your friend says that’s unreasonable, tell her that amount is what counters all the negative aspects of the job and is the lowest you could go.

    That should put an end to your friend hounding you for a job you don’t want. If she still does it, repeat the same number to her.

    1. Colette*

      The OP should just say no; there is no reason to ask for an unreasonable salary. What would she do if the friend said “OK, that works for me”? She doesn’t want this job. She should just say no.

  68. Jane*

    OP#1: Your story raises all kinds of red flags for me, which other have shared, so I won’t rehash. Being allergic to chlorine, if I were one of those employees, I guess I wouldn’t get the holiday off.

  69. FreelanceWolf*

    #5 – The thing to take into account with freelance clients who *constantly* pay late, is that in the case of bankruptcy (which is more frequent with places with cashflow issues) you can be stuck holding the bag on a lot bigger amount than you would normally be comfortable extending a client, just through them ordering a lot of work.

    In my industry you sometimes just have to assume late payment as a “cost of doing business” because of how the revenue streams work, and no one in the industry will agree to late payment fees (no matter how you couch them).
    However I learned early on the importance of putting a limit on the volume of invoices I’ll let a single client accrue. I discovered at one point (to my horror) that I had a late paying client owing me >$50,000. I just hadn’t noticed because their work was lots of small orders, and it was during a period I was very busy. Thankfully I didn’t get burned (although it took over a year to get their account down to a manageable level), but after that I made sure to set a strict limit at which I wouldn’t do any more work. It’s saved me now with two client bankruptcies that were a blow – but not catastrophic as they had both been cut off. Also one of my worst clients for timely payment switched to letting me charge a credit card on file for work because they were tired of being cut off every other week and scrambling to get me a payment… which turned them into a perfect paying customer overnight!

    1. OP#5*

      Definitely a good plan and 50k.. yikes! As my situation is usually day rates and weekly invoicing, it’s easier to track at least. I’ve not been there since this contract and won’t go back. I don’t think they’re at bankruptcy level as they’re quite a large agency so it’s just bad systems.

  70. ChickenChains*

    I’m going to push back on #1. I can’t swim. Does that mean I don’t get the day off?

    1. Mannheim Steamroller*

      Yes. PTO is part of your compensation but using it is conditioned on your demonstrated ability to swim.

  71. Brain the Brian*

    Not to pile onto the comments about the pool quite some time later. But people with epilepsy can trigger unexpected seizures triggered by jumping into water — and because they’re in water, proceed to drown as they have a seizure. Plenty of otherwise well-managed, invisible health conditions that someone might not otherwise be predisposed to share with their employer could make the pool an impossible task for some people.

    1. Anon4This*

      This happened to one of my employee’s teenagers last year. He went into the water, had a seizure, and didn’t come back up. Because his epilepsy was recently diagnosed and they’d only just got his medication dosage at what seemed to be the right level, his dad was watching him more closely (thank goodness) and pulled him up from the bottom before the lifeguard even realized something was amiss. But his dad freely admits that, had he not been so on edge and the diagnosis not been so new, he might have missed it and the kid could have drowned.

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