update: my boss wants to hire us out for our “unique talents and skills” that have nothing to do with our jobs

It’s a special “where are you now?” season at Ask a Manager and I’m running updates from people who had their letters here answered in the past. 

Remember the letter-writer whose boss wanted to hire them out for their “unique talents and skills” that had nothing to do with their jobs? Here’s the update.

I found using the suggested phrasing “I freelance in that field and it would be a conflict of interest” to be a helpful way to express my concerns politely. I think it helped my boss feel less like I was shutting them down personally and more making it about general business norms.

One of your suggestions, “I do that for fun and I’m not interested in doing it professionally,” helped me to see how crazy of an ask this was. I could see how someone might naively ask about making cupcakes for an event, or taking photos. None of the three of us asked about adding our skills to this business were asked to make our hobbies part of our job. Two of us were asked about adding our services that are related to our master’s degrees and one to a field of work that they left over a decade ago. Fields that have professional certifications and titles that are unrelated to the company.

The company was and is very successful. It provides a much needed service in my community. But as it grew with more employees and in servicing more clients, it started to become very disorganized. A few months after the infamous meeting, I was asked to start coming to in-person events. My boss knew my availability and that I was only working this job because I could work from home. These events took place during regular working hours for my full-time freelance jobs and my boss hoped I could take a day off my full-time job occasionally and come in. I was asked two days before Thanksgiving if I could work from home for a couple hours on Thanksgiving Day (I was hosting my family on Thanksgiving). We had some in-person trainings that were rescheduled multiple times with little notice because of family emergencies from other staff. One of those reschedules happened while I was on a family vacation, so my boss used my emergency contact to get ahold of me to see if the new training time would work. Another time, my boss asked to meet with me quickly on a weekend to drop off something, and then was two hours late.

I said no to all of these last-minute asks and reschedules that conflicted with my full-time job and I didn’t wait around when my boss was late. I couldn’t event attend some of the rescheduled meetings or trainings because I couldn’t find a sitter with two days notice. But this type of thing started happening several times a month and I started to resent it.

While I do feel my boss has their heart in the right place, the last-minute requests started to really add up. By late winter, I couldn’t discount it as being “new” to running a company anymore. They were showing me who they were and how disorganized they are. I kept hoping they’d get it together. That’s on me! So I put in my notice a few months ago. Even though I worked such few hours, I feel like I’ve gained so much time back.

In the original letter you made up a name for my boss, “Craig.” My boss is actually non-binary and fairly young. While I know this wasn’t the intent of your advice, I felt differently about the situation when I started to think about my boss being an older man named Craig making these same requests. (I am a cis queer woman in my forties.) I liked my boss personally, and it was clouding my professional judgement of them. I excused a lot of behavior I wouldn’t if my boss had been a different person. This has given me a lot of reflect on personally.

I’ve briefly spoken to my previous boss a few times since I left, and we seem to be on good terms. I wish them success in their company and growth in their professionalism. I’ll always root for them and their business goals. But I’m much happier not being behind the scenes anymore.

{ 66 comments… read them below }

  1. Garblesnark*

    I’ve been on a journey of realization in this area, too. I’m queer and disabled, and early in those identity journeys, I found that people with an experience of marginalization were usually better equipped to have a lot of sensitive conversations with me. But I overcorrected into assuming people with an experience of marginalization were just better, and that isn’t true. Now I’m coming back to center, which is that marginalization often informs perspective and experience, but can’t make a person good or bad or equipped.

    1. Silver Robin*

      Just want to give you some kudos here because I see that exact overcorrection *everywhere* and it can be really frustrating. I definitely think social media contributes to it just by dint of putting folks into highly specific boxes for algorithm purposes. Reinforces “only people exactly like me are good/fun/interesting” while in the physical world that is patently false. But I also think you are quite insightful in noting how marginalized folks were better able to respond to your experiences with sensitivity and that created a positive bias towards those folks. That makes complete sense! And, it is not the full picture.

      1. Covert Copier Whisperer*

        Thank you, that really helps give shape to similar thoughts I’ve been having about this tendency, but wasn’t sure how to put into words.

        1. NotBatman*

          I think there’s tremendous joy and relief in finding someone who *gets* an aspect of your life that most people don’t. Like, disability is the kind of thing that huge swathes of people don’t understand and can be huge jerks about — i.e. that archived letter linked recently where LW was tracking every second of a coworker’s sick time out of the conviction that they “didn’t look sick” — and it’s often wonderful to find a coworker who does understand.

          …which can then lead to being too forgiving if that coworker starts doing crap like “oh by the way, can you work a few hours on the biggest secular holiday in our country, with 2 days’ notice?” I get where this LW is coming from, and wish them all the best.

        2. Silver Robin*

          I am often the only representative of social defaults in my group of friends outside of work (everyone else is some kind of marginalized that I am not) and from time to time there are jokes about “all [insert social default] folks are boring” or “we [marginalized] have the superior Y” or “Z behavior is clearly a [marginalized] thing”.

          Most of the time it is blowing off steam or jokes and nothing too serious is meant by it. But at the same time, I sometimes respond with an amused but pointed look because I am the exception to those statements and it does nobody any favors to flatten people into monoliths.

      2. tree frog*

        Well, and part of it comes from the relief of finding a group of people you feel relatively safe and comfortable around, particularly if you’re used to a lot of mistreatment by the wider world. It is a really awful feeling when those people turn around and treat you badly as well.

    2. Festively Dressed Earl*

      “All skinfolk ain’t kinfolk” is a tough lesson to learn and an even tougher lesson to balance.

      1. the cat's pajamas*

        This reminds me of the Geek Social Fallacies, especially the one about ostracizers are evil, therefore calling someone out on their bs also makes you evil.

  2. Falling Diphthong*

    I appreciate the detail about imagining the same actions from a different person. Bit of a recurring theme is “On paper the forest gremlin’s actions seem really bad, but because I personally know and like the forest gremlin my brain is coming up with a lot of reasons this might be okay.”

    1. Sloanicota*

      Honestly, this is the biggest disconnect between letter writers and the commentariat – having been both, it’s easy to be black-and-white from the outside; this boss sucks and isn’t going to change, this partner is abusive and you need to leave them; this family member is someone you should grey rock or go noncontact with. But of course, when these characters are people you know personally and intimately, you know they’re not a villain. Which doesn’t mean, however, that their actions/choices might be very far off base.

      1. Six for the truth over solace in lies*

        This is why I’ve leaned back heavily from the really strong rhetoric around how Bad someone is.

        A couple years ago I asked a question (not here) about something my boss was doing with regards to travel expenses, and I got a lot of “your boss is toxic, doesn’t care about you, and is probably going to try to push you out.” And I must say, my first thought was “well I know for a fact that’s not true, given how hard he lobbied for me in X, Y, and Z situations. so maybe nothing this person says is accurate to my situation?”

        Righteous indignation feels good, and so does sorting people into heroes and villains, but neither of those are useful as *advice.*

        1. Zeus*

          Absolutely this. It’s something I’ve noticed both here and other online places – I’ve been privately thinking of it as “the AITAfication of the internet”. People want a hero and a villain in every story, and if there isn’t a clear dichotomy (as there isn’t in most situations in real life) they have to invent one.

          All bosses are evil, all landlords are evil. You can’t make a mistake in a relationship, it’s either gaslighting or weaponised incompetence. Every third or fourth person you meet is a narcissist, despite the fact it’s a very rare diagnosis.

          It gets exhausting, doesn’t it?

        2. Squirrel Nutkin (the teach, not the admin)*

          I might have seen it here on Ask a Manager, but one internet comment that has stayed with me is about how righteous indignation can be very dangerous — in our minds it justifies bad (sometimes awful) behavior towards the person/group at whom we are feeling righteously indignant.

    2. Fluffy Fish*

      It’s a version of “they’re a good employee/boss” then proceeds to list 20 reasons why there’s no way on this green earth they are “good” anything.

      People can be likeable but very very very bad at their job.

      1. Kyrielle*

        Or amazing at some parts of their job and horrible at others. I have worked for people who were incredible at managing people and terrible at understanding tech, and who are the reverse. Neither is entirely fun, and whether they look like “a good boss” depends on the particular situation you’re viewing them in. And if they end up leaning into their strengths most times but you’re writing about one of their weaknesses, it’s easy to see they’re a bad boss…and harder to say that with conviction when you know all the ways they’re good, as well as the one they’re terrible at.

    3. Filthy Vulgar Mercenary*

      Which is why I think societally we need to be trained to think of people as layered, rather than all good or all bad.

      It would get rid of a lot of that second guessing you just described, I think, as well as the invalidating responses like “what do you mean she makes her employees cry every day? But she’s so well respected in her field! [or, what do you mean he committed an awful crime, he’s such a kind person]”.

      It would provide folks with context to be like “oh, here’s another example of how people can be more than one thing and both things can be true about them”

      1. Slow Gin Lizz*

        Which is why I think societally we need to be trained to think of people as layered, rather than all good or all bad.

        I agree! It’s really unfortunate how black and white everything is these days. Is it harder to look deeper and figure out nuance and layers to each person’s personality or the situation at hand? You bet! But I wish more people did it, because it would give more people common ground. Sigh.

      2. Helewise*

        This has been a big part of my own personal growth over the past several years and I’ve found it really powerful. We really are so very complex. Being able to look at all the shades of gray in a person (and in myself!) can be confusing but also opens doors to understanding both people and ideas with more depth.

      3. Statler von Waldorf*

        While I agree with Filthy Vulgar Mercenary in spirit (awesome screen name BTW) , it’s never going to happen for scientific reasons.

        Based on observations on the brains of monkeys and the size of the social groups they form, there appears to be a hard limit on on how many people the human brain can actually conceive of as real and layered individuals instead of one-dimensional cartoon versions of people. That number is between one hundred and two hundred people. My brother is in my shortlist, so I can see him as a layered individual with both positives and negatives. My mailman is not, and in my head all he is “the friendly guy with the bright red hair and beard.” My apathy towards the mailman is nothing personal, it’s just how the human brain works.

        This appears to explain why we are literally incapable of the complex empathy you are describing. If you want more details on this, go and google “monkeysphere” which will hopefully explain the science behind this better than I can.

        1. Silver Robin*

          I am going to push back on that a little bit, based on my own experiences. I know that study and I think it is mostly true, I also think that study was about meaningful relationships, not like, whether people are…people. I can keep the information about birthdays or preferences or whatever in my head regarding roughly 100-200 folks, but everyone outside that is “generic human”. And I also think it is 100-200 people *at a time*. I do not think it is a static list.

          So two things:
          1) I personally try to focus on seeing the people *I am currently interacting with* as multilayered and complex. My best friend from college is not here right now, the mail carrier is. I can deal with the person in front of me (or in the article I am reading, the show I am watching, the story I am hearing) and treat them as complex and multilayered. Usually we are only dealing with a handful of people at a time, so it is manageable. With practice, this does become easier and easier to do. In fact, if you are good at customer service, this is kind of what you do all day, which absolutely wears down that emotional muscle.

          2) To do #1, create an emotional/intellectual checklist of sorts when dealing with “generic human” that reminds you that people are complicated and layered. You do not need to *know* what those layers are to be able to respond to them as such. For me, that means asking a lot of questions and reminding myself/others that we do not know the whole story. That goes in a positive direction (the mail carrier is late! AGH. Turns out it is raining and that slows everything down) and a negative direction (the mail carrier is nice to me, but who knows if they are nice to everyone).

          Also, once the group of humans is too big to see the individuals, you just apply the above to the group. It scales. And I am not trying to say that this is easy or obvious or whatever, I just think it is actually possible for use to train our monkey brains to treat >200 folks as complex people without having to break that 100-200 limit.

          1. Statler von Waldorf*

            I sincerely and honestly admire your optimism.

            However, I just spent two hours trying to explain how to explain to a group of roughnecks how to fill out a very simple one page form. This is why I admire your optimism, but I don’t share it. The vast majority of humanity that I have known simply doesn’t have nor do they care to acquire the emotional muscles required to task switch in the way you describe.

            1. Silver Robin*

              How is “filling out a task form” the same as “seeing a person as a complex being”?

              But I will also note, that I very carefully said “this is possible” not “most people do this”. I described a set of practices I apply to my own life to show that it is possible only, not to make a claim about the majority of humanity.

              1. Statler von Waldorf*

                The politest version I can come up with is that they both require more mental muscles than I have observed in a significant percentage of the population. I do admin support work for oilfield workers, as a result I have a very different (and much dimmer) view of the mental abilities of the general public than most of the commenters here. Based on that salary survey, most of the people commenting here are white collar workers working with other professionals. I work with oil rig workers, which includes a lot of the dumbest and most bigoted people on the planet. Thus, I view things differently sometimes.

                And yes, you did say “this is possible.” However, you originally said “I think societally we need to be trained to think of people as layered, rather than all good or all bad.” I agree with the former, but not the latter. Yes, it is possible for individuals to do this, and I have a lot of respect for people who do so. That is not the same as training society to do this, which is simply not going to happen because of the monkeysphere and was the idea I was pushing back on.

          2. R*

            +1 to Silver Robin’s comments! I use very similar internal prompts which have now become habits, and I think they help me think about people in a more nuanced way. (Maybe this jerk saved someone’s life this morning! Maybe this nice person is really a murderer!)

            For example: Sometimes I get really spun up about strangers being jerks in passing, and I’ve started saying to myself “Maybe they are grieving” or “Maybe they will feel really bad about that this afternoon”. Just helps me remember that there’s a full person behind the character who made a brief appearance in my story.

            1. Natalie*

              I’ve started doing that kind of reframing as well. “Oh, maybe he’s lost,” etc. and I do feel like it helps me to be kind, patient, and compassionate.

              But I’ve found that it’s only useful to me if I’m the one initiating it. When my sister says, “Maybe she was just confused,” I find myself getting kind of annoyed about it.

              People are complicated.

              1. Silver Robin*

                Yeah external prompts can feel invalidating of the emotion that you are currently feeling. I am frustrated, stop telling me not to feel this perfectly valid frustration! I liked that person, why are you bursting my bubble about feeling good about them?? I usually try to affirm the emotion first before adding the prompt, and that seems to work better, but everything depends on the particular people and particular situations.

                I mean, I honestly roll my eyes at my internal reminders too sometimes, but I go with it. I just want to be mad, stop reminding me to be a kind person! Waahhhh! But then I get over it and move along.

        2. unpleased*

          I would suggest that we don’t even need to fall back onto studying non-human primates to understand human social and cultural behavior. We can just study humans. While we are primates, we do things at a degree of sophistication that other primates don’t (never mind that we’re not monkeys, we’re apes, and there are real distinctions there). The reliance on things like this to understand our behavior allows us to excuse things that we shouldn’t, and to not demand more of ourselves, which it is in our evolutionary powers to be able to do. The scientific reasoning here is like the bare minimal behavioral floor and personally I want more for myself than that. That kind of complex empathy is perfectly within human power.

      4. Irish Teacher.*

        Yeah, I’m reminded of my boss during my work experience year who was a genuinely kind person and deeply committed to the kids we worked with, working much longer hours than contracted for or paid for (which yeah, became problematic as it meant that there was a sense the rest of us should do likewise) and even offering to go to visit a young man who she had worked with in his youth in prison, on Christmas day, but…who also lied constantly and about the most ridiculous things to the point you had to doubt everything she said (and did this to the kids too, who often believed her; she once asked “how come you’ll believe Irish Teacher and not me?” when one of the kids checked with me about something she said), had days when she got really hyper (or perhaps more like manic) and would start shouting over you while you were trying to discuss something with somebody else you were working with and as I mentioned on a previous post today, tended to undermine us to the kids. Oh and she didn’t always (or ever) seem to realise how far was “too far” with teasing and was genuinely shocked when one of the kids finally told her “you really upset me when you keep teasing me about that!” (I had realised this ages before but as a work experience student, I hadn’t the confidence to advocate for the kid. I should have, but I really didn’t know how.)

        She genuinely did mean well, would go out of her way to help us and was genuinely horrified and apologetic when that kid told her they were actually upset and weren’t just “playing along with the joke” and I strongly suspect she had some mental health problems that were contributing to her actions (and it was the turn of the millennium when there wasn’t the same understanding of or support for a lot of mental health issues). And I must say the kids and their families adored her. But for all that, she wasn’t a good boss in many ways.

        1. EnigmaticallyEvil*

          Wow, it sounds like you’re describing my current boss. The care and compassion, dedication to the work, real brilliance, and well-meaning are all there. But the erratic behaviour, mania, lying, and tantrums are making it hard for me to see myself staying in the role in the long term. Oof. People are complicated, layered. And it’s sometimes very hard to parse the costs/benefits of staying engaged.

      5. not nice, don't care*

        I think that’s a great idea, until I get to people who use their privilege/votes/rights to do harm to others. Then I don’t care what good qualities you might have. They are negated by hostile actions.
        Or as we say in my household ‘even hitler loved dogs’

    4. Elitist Semicolon*

      My version of this a sort of Bitch Eating Crackers assessment: I ask whether I’d be reacting badly to the behavior/comment/issue if it came from a coworker I personally like or from a good friend. If the answer is “no, I’d let it slide,” then that’s a sign that I need to step back and think about what’s really fueling my reaction. If it’s “yes, but I’d reframe my response,” then I try to do that as best I can. If it’s “yes, and my response would be the same,” then I still try to reframe because what might be acceptable in a personal conflict probably isn’t in a work conflict.

      I like the forest gremlin mental image, though. :)

      1. Silver Robin*

        I do this too! “Would this be annoying in isolation/from a loved one? Would it be worth saying something about? Does it actually affect me or is it just tacked on because [other issue] is sapping all my good will?”

  3. WellRed*

    I’m glad this worked out and I’m not surprised things devolved into chaos. I just reread the original post and still can’t figure out what Craig was trying to accomplish.

    1. Chauncy Gardener*

      Same here! It’s amazing to me that the company is really successful too. It sounds like everyone’s running around with direction that keeps wildly changing.

      I’m so glad you’re out, OP.

    2. Mango Freak*

      Honestly, I’m dealing with someone now who might be like this. They’re leading a large (unpaid, hobby-ish) project and seem to be driven not by goals or consequences, but by the Ideas! that seize them and the things they personally feel like doing. Very magpie-like…but don’t expect them to forget the shiny Idea! Just the conversation where you explained why it wouldn’t work.

      My Craig truly has trouble considering or understanding other people’s POVs, and they don’t seem to learn from feedback or even, so far, consequences. But they are very nice. I genuinely like them, so it’s frustrating and hard to extricate yourself sometimes.

    3. AcademiaNut*

      I see similarities to the really enthusiastic but erratic and inexperienced junior employee letters we get sometimes – they’re brimming over with what are to them cool ideas, but lack focus and the experience and wisdom that can tell good ideas from bad ones, or see the complications in implementation. Throw in leadership of a passion project they’re devoting all their time and energy to plus chronic disorganization and some personal charisma and good intentions, and you could get the letter writer’s situation.

  4. Murfle*

    OP’s former boss sounds like someone who doesn’t think that working from home or freelancing is “real work”. So many independent professionals experience this sort of entitlement to their time from friends and family — it must have been really disheartening to have an employer feel the same way. OP, I’m glad you got out of there with minimal damage!

  5. Sloanicota*

    A minor point but – a while ago there was a letter about emergency contact info and I felt like I was the only one saying I didn’t want to give managers additional, easier access to that information if they could already get it through HR … since then there’s been several letters about whacko bosses misusing the information. If you have a non-whacko boss, perhaps the risk of abusing the info is less than the risk of a worker being in an urgent after-hours accident where every second counts, but I have had mostly bosses who would get tunnel vision if they wanted to schedule a training but I was on vacation. Sorry to see you did too, OP.

  6. Slow Gin Lizz*

    Sorry, but no matter how young or inexperienced a company owner is, that’s no excuse for asking someone two days before Thanksgiving to work on Thanksgiving. Unless they work in a 24/7 coverage field and the person asking had a family emergency and needed someone to cover for them, that’s just completely bananacrackers.

    1. Craig’s Former Employee (LW)*

      Yes! This ask was the turning point for me because I couldn’t write it off as naïveté.

      I didn’t do it, by the way. I didn’t work Thanksgiving. I had a lovely day hosting my family.

      1. Slow Gin Lizz*

        Good for you! Like, what even could he possibly have needed you to do that needed to be done on the most major holiday in the US??? Poor Craig, I hope they figure out better leadership skills going forward, but they do sound like they’re all over the place….

        1. Craig’s Former Employee (LW)*

          The sad part was their life partner asked them not to work the holiday so they could attend a family gathering. The phone call to me invovled the phrasing, “What do I have employees for if not to delegate work so I can take time off now and then?” The sentiment was true…delegation is important. But the mark was truly missed in this instance.

          And nothing. Absolutely nothing needed to be done on Thanksgiving. Nothing bad happened that no one checked in either! lol.

      2. ferrina*


        Totally agree with you and Slow Gin Lizz- unless you work in a 24/7 field, there is absolutely no reason to consider Thanksgiving for a work event. This is a huge red flag of someone that doesn’t understand that other people’s time has value.

        1. M2RB*

          Agree – sure, first responders have to work, and utility workers have to be on call in case the power/water/gas go out, but …. you know going in to those jobs that the work is 24/7. And your work gives you overtime/holiday pay and/or comp time because you work on those holidays. Two days’ notice in a field that isn’t already well-known for 24/7 work is absolute BS.

          1. Slow Gin Lizz*

            Right? I have a friend who is an OT and works at a school. The school has all kinds of administrative ridiculousness that drives her crazy and she really doesn’t see herself at her school for the next 15 years she has until retirement. But she really loves the fact that she never has to work on weekends or holidays; pretty much any other type of OT position (at a hospital or rehab center) requires 7 days a week coverage. Not necessarily 24/7, but definitely someone needs to be there on holidays. (I’m confused about this b/c it seems to me that OT is the kind of thing that can wait a few days for treatment, but I guess if someone is having emergency surgery and needs hand or shoulder mobility work asap, then that makes sense.) Anyway, in this case, she definitely would know going in that she’d have to work weekends/holidays and would get compensated for it.

  7. JSPA*

    People who have realized that all things are potentially possible in their private lives can bring a particular energy into their work lives.

    Depending where an employee is in their own life, this can be freeing & inspiring…or land like an endless shower of bull puckey.

    If you’re a bit older, a lot of outside-box thinking isn’t novel and creative… it’s the same “bad boundaries” and “duplicate scheduling” and “unrealistic expectations” and “cult of personality” and “labor law violations” that come around, cyclically, masquerading as the hot new disruptive trend.

    IMO, when an org hires on the basis of vision and inspiration, they need to think hard about where the actual skill, time and perspiration will come from (and no, you can’t include cult-like devotion nor magical thinking nor parallel universes in that calculation).

    1. goddessoftransitory*

      I agree with all of this.

      Ideas, big thinking, inspiration are all valuable and needed qualities in life and at work. Everybody can think of a “nothing” job they loved because the atmosphere and leaders had those qualities, and “dream” jobs that sucked dead rats because of toxic leadership.

      But really? Truly? Ideas are a dime a dozen. Even good ones. Even great ones. There isn’t a person alive who hasn’t had at least one really fantastic notion, a game changer, a “leave the world better” level idea. But that’s not all that’s needed.

      You need organization. Knowledge (both personal and the trust to find those who have what you don’t.) Ability to synthesize different working styles. Vision to see problems and unintended consequences and plan for them. Patience to slog through the minutiae.

      The problem with the Craigs of the world is that they get overinvested in the stream of Great Ideas they’re generating and refuse to focus on the debris that can pile up in their wake as they hop around, leaving a frustrated and exploited workforce, “sad” and “disappointed” that there’s no one who can share their vision of a glorious future, while their reports are struggling with switchback decisions, sudden announcements, uncertainty and exhaustion.

  8. Unkempt Flatware*

    I had a boss who relied on the, “but we’re friends! I’m sure they’d be willing to drive two hours to attend a surprise meeting with us!” thing with clients/contractors/vendors/senators. He doesn’t have many friends left.

    1. Peanut Hamper*

      Sadly, I’ve worked for a lot of people like this in the past and their solution is to always just hire more people and try to turn them into friends.

      Sorry, but that’s not why I have a job.

  9. Salty Caramel*

    “Hire” is not the word I would use to describe what he wants to do. I am so happy to hear the LW is out of there.

  10. MassMatt*

    The update makes it seem as though the big problem is the boss being disorganized and having bad boundaries. This is an improvement, IMO, compared to the original letter.

    The original letter really gave me the creeps, I get that OP still likes them (though from a distance) but I would not have been been diplomatic when the original “Hire you out for your ‘unique skills’ ” idea was made. My first thought was “You are my boss, at this job. You are not my pimp!”

    1. tree frog*

      With the full context, I think it all makes sense coming from a naive/excited younger person working for a small organization that means a lot to them. There is a point where outside the box thinking collides with reality.

    2. Craig’s Former Employee (LW)*

      It was a very weird and wild meeting-the hiring us out one. While definitely not the norm of what I experienced working there, it stands out as the one absolutely crazy ask.

      After that meeting, there seemed to be some doubling down on asking more from employees and crossing professional boundaries. So I kind of think it was the start of a change in business practice for my boss or a loss of their perspective?

      I’m glad it never got quite so crazy again with the asks, but it definitely made me weary and on alert about other asks.

      1. sparkle emoji*

        I’m sure you have a better sense of this LW, but as a spectator, I don’t think this business will be open much longer.

        1. Craig’s Former Employee (LW)*

          I think if my former boss quits trying to diversify business offerings and sticks with the niche market and clients they have perfected working with; everything will be great for them. If they keep trying to have more offerings in more locations and manage more people; they will fail. When I went freelance, I was told “If everyone is your client, no one is your client.” That has been so true for me. But it may take my former boss longer to see the big picture. Which includes not diversifying job descriptions excessively.

          1. BikeWalkBarb*

            Since you said they were modeling it after ideas from a similar business I wondered if it was a bit of panic about potential downturns in the core and wanting to diversify (at random! bad idea!) to hedge against a potential dip in profits.

            Branding gets over-used as a reason to do lots of things but this felt like one of those times a brand manager needed to say “How is this on brand for us?” and stick to that line.

            1. goddessoftransitory*

              Amazon is a perfect example of this. They succeeded wildly in permanently changing how consumers think about shopping and spending money. It really was one of the biggest alterations in society for the last century at least.

              And it’s not like they’ve vanished or anything, clearly. But they keep trying to “revolutionize” all sorts of different shopping experiences and often their “vision” simply doesn’t synch up with reality. There’s a big article in The Seattle Times about their attempts to change the grocery industry and how it’s fallen flatter than a dime store pancake, for instance. Reading it, you can feel the frustration of a lot of these visionary types that the general shopping public won’t grasp their amazing concept and just start doing things they way they want.

              And every time one of these ventures don’t work out, hundreds of people lose their jobs as that section is shut down.

          2. MsSolo (UK)*

            The vibe coming across is they’re bored – they’ve done the thing, done it well, and now they’ve lost interest in continuing to do it when they could do a new thing in a new place – they want to be in a place of change, not a place of stability. If they hire someone else to run the existing business while they explore new markets things might work out, but if they’re constantly hunting for that New Job Energy and accustomed to the power of being CEO I’m sceptical they’ll be able to separate the two roles sufficiently.

      2. MCMonkeybean*

        I guess it’s better than the other way around, where the asks start small and then gradually get more and more unreasonably until you suddenly realize you’ve lost all of your work boundaries!

  11. Marzipan Shepherdess*

    My first thought on reading this letter was to wonder if the manager thought that their subordinates were either indentured workers or enslaved people because that’s the only context in which this proposal would make sense!

    Workers who are freely hired and paid (as all employees are supposed to be in America c. 2024) can usually take side or “gig” jobs if they choose, but those arrangements – and all the money earned from those side jobs – are the province of the worker. This sounds suspiciously as if the employer wanted to “hire out” their employees for lucrative side jobs and keep the extra profits for themself while continuing to pay the employees their usual salary.

    This isn’t the 19th century, folks – it doesn’t work that way!

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