going into business with my boyfriend’s family, taking an interviewer on a tour of my current company, and more

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

1. Going into business with my boyfriend’s family

I have been with my boyfriend for six years now, and lived with him for five. I’m extremely close with his family, especially because my own family lives across the country, to the point that I’ve been invited to holiday events even when my boyfriend was unable to attend, and generally feel treated the same as him and his siblings.

Recently, his sister has come up with a business idea that springboards off the current brick-and-mortar store that she and her mom (same as boyfriend’s mom) run together. The plan is for it to be much less of a small-business thing, but it will still be a family-run thing as it’s a website and my boyfriend and his brother are web developers, I have some particularly helpful experience, and their father has run a larger business.

They are super enthusiastic about the skills I can bring to the business and naturally have already slotted out a place for me. I’m really enthusiastic about helping them and being part of the business (however inadvisable that might seem) but I want to raise the subject of the fact that I’m just attached by girlfriend status, but in a much nicer way.

My boyfriend is not likely going to scoff at my mentioning this sort of thing. We talk about “would one of us be able to handle the rent on our own?” every time we move into a new apartment, and I’m not at all worried that his family would suddenly try to edge me out if my boyfriend and I were to break up. But I’d like to discuss how we’d handle it if we wanted our space from each other after a possible break-up and if we no longer wanted to work together. I’m not sure if I ought to stress that we’re doing well as a couple and I’ve no plans on breaking up, or how to word this properly or even if it’s something I should just leave it alone and think “we’ll deal with it when we get there” due to how long we’ve been together happily.

You should absolutely talk about this and, depending on what’s decided, you might need to get something in writing about it.

When things are good, it’s very easy to think, “Even if we broke up, we’d handle things amicably. We love each other and we’re good people, so we’ll be able to figure it out.” But life can throw curveballs that you can’t predict, and plenty of people who thought they’d have kind, healthy break-ups instead have hostile ones. So it’s pretty important that before you get entwined with this family business, you lay out plans for what you’d do in a worst-case scenario — because as much as you feel like family right now, if things do go south, that can change pretty quickly.

You could say it this way: “I love that y’all make me feel like family, but to protect everyone, I want to recognize that I don’t have the same family ties that you do, legally or otherwise, and figure out how we’d handle things if Percival and I ever weren’t together. Obviously I hope that won’t happen and there’s no reason to fear that it will, but if we’re going to go into business together, I want to make sure we’ve thought through how we’d handle things if that ever changed.”

One potentially clean way to do it would be for you not to be a partner in the business, but instead to provide your services as a contractor. That’s an easier relationship to break off if you ever need to.

2. Offering to take an interviewer on a tour of my current company

I work in a highly technical field — design and installation off large IT infrastructures, like server rooms. I have had an interview with several SVP’s at a new company two weeks ago, but nothing seems to be moving forward.

As the job is all about systems engineering, what about inviting one of the interviewers to my current company for a tour and to show examples of my work? It may sound awkward, but the new company actually is an on-site customer of my current company, so seeing new company people in the our building is completely normal. And there would be absolutely no suspicion from my current management. My goal here is to further impress the new company by showing physical examples of my work. What do you think of this out-of-the-box approach?

No, don’t do it. That’s a misuse of your current company’s trust in you — and the prospective employer is likely to see it that same way.

Two weeks ago seems like a long time when you’re waiting to hear back about a job, but on the employer side, it’s not that long. Give them time to do whatever they’re doing. If they want more information from you, they’ll come back and ask.

3. My boss won’t let me work more hours to catch up on my backlog

I’m in a role where I am effectively acting as an entire department. This arrangement generally works okay, but I recently fell ill and had to take a couple of days off to recover. When I got back to work, I had a lengthy backlog of work to complete and have been struggling to catch up. The problem is that I’m now involved in so many (inescapable) meetings that it is now a month later and I’ve accrued over 60 unfinished tasks.

As a number of staff at my workplace have remote access, I requested this as well so that I could do some work from home, but this request was rejected due to my boss wanting me to have a good work/life balance (when I leave work, I should leave work at work). I’m grateful for the thought, but I’m getting increasingly more stressed out by having such a large backlog of work and no way to alleviate it. I’ve addressed this directly with my boss on a couple of occasions and they insist that some things just won’t get done, but I’m having a hard time adjusting to that mindset (I’m usually relentlessly on top of everything).

I love my job and my boss. I genuinely appreciate their intentions, but it appears that their efforts to not stress me out are failing miserably. I need to get this work done in order to keep sane, I just don’t know how to convince my boss that I need the flexibility of remote work. What do I do?

Well, your boss is telling you very clearly that she doesn’t want you working those kind of hours. And it sounds like she’s also told you that it’s fine for some things not to get done. The next step here is to sit down with her and figure out exactly what those things should be, so that you can officially move them off your list and cut down the number of things still on it.

You should tell her what you can get done in a regular 40-hour week and what will still be left over, and ask her how to prioritize things, and what things to jettison entirely. More here on how to do that. The solution is for the two of you to get aligned on how you’re going to get your workload down to a manageable level, not for you to work unreasonable hours just because you took time off.

4. We’re short staffed and they won’t hire anyone for at least another month

I work in reception at a small company (under 30 people). My department normally has three people, but we had someone leave before Thanksgiving and we have not hired anyone else. The employee who left gave almost a month’s notice. The department can run with two people (though not as smoothly as with three), but if either of us has to be out for any reason the department is really hard to run with just one person.

The biggest issue for me is that I’m a single mom and it is not uncommon for me to have to miss work when the school is closed or my child gets sick. Having two people in the department instead of three creates so much more pressure to not take a day off for any reason.

I just found out today that they may not hire anyone until after the first of the year. The position takes a long time to train people on, so reasonably, my coworker and I are the whole department until probably February (and that is IF they hire someone early in January). I don’t mind doing an extra person’s work for the time being, but I feel like they are being unfair expecting neither me or my coworker to need a day off for the next two months. Is there any way to impress on them how uncomfortable it is to be short-staffed like this near the holidays when people might want a day off to see family? Or when schools might be closed for snow?

I did speak to the HR lady (she’s the one who told me we won’t be hiring until the first) and she said basically to take care of my family if I needed to and not worry about the department being short staffed. But a few years ago when work was taking their time to hire a second person for the dept (I was the only one in the dept at the time) and my son got strep throat and was ordered by a doctor to stay home, I had work calling me all day every day asking where stuff was, asking when I would be back, asking how to do stuff, etc. The HR person was not here when this happened, so I don’t think she realizes what the culture at work is like when the department is short. When we have three people, it’s no problem if someone needs a day off. What can I do?

Take off the time you need to take off, and don’t answer calls from work while you’re out.

The HR person is giving you permission to do it, and that’s what you should do.

It’s not outrageous that your company doesn’t want to deal with hiring around the holidays; a lot of employers don’t. It would be problematic if they were telling you that you couldn’t take any days off during this period, but they’re not. It sounds like you’re the one who feels like you can’t take any days off, but they’ve clearly told you that you can. Take them at their word. And if you and your coworker both end up sick on the same day, then you both call out. This is what happens when a department is short-staffed, and they’ll muddle through.

5. Declining a job offer because of a drug test

What is the best way to decline a job because of a drug test? I recently applied for a position and made it all the way to the offer stage, when I was informed that I’d be required to pass a drug test post-offer to accept the position. I live in a state where recreational marijuana use is legal, and I use it nightly to help me fall asleep. However, even though recreational marijuana is legal in the state, because it is banned at the federal level, the courts have ruled that employers can consider it an “illegal drug” for the purposes of drug testing, and even someone with a medical marijuana card would not be protected. Drug tests aren’t common for my field, so I was really caught off guard when this employer brought it up. I am not comfortable on an ethical level with drug testing as a general practice (there are professions where they make sense), and would likely decline to take one even if I could pass the test.

I declined the position on the basis of “general fit,” but I am wondering if there is a better way to do that? Is there a way to ask about drug testing earlier in the process?

Nope, you can’t really ask about drug testing, unfortunately. It just comes across way too much like “I use illegal drugs,” to the point that the idea of a candidate asking the question is an old standby in (bad) jokes about hiring. This is ridiculous, of course; you should be able to inquire about what kinds of invasions of privacy you might be subjected to as part of a job, but like so many things with hiring, convention isn’t aligned with what’s logical.

In the future, if you find yourself in a similar spot, I urge you to be up-front about the reason you’re turning down the offer; it’s important that employers hear that they’re losing good candidates over their commitment to meddling in what you do in the privacy of your home on evenings and weekends. Say it this way: “I object to drug testing on privacy grounds, so I’ll need to decline the offer.”

{ 288 comments… read them below }

    1. Venus Supreme*

      I agree with this! I’ve had jobs in the past where I was the sole person in the department and I’ve made something I call a “Bible” – all important login information, numbers, and basic information about the company (in a physical folder) that would help the Average Joe perform basic tasks in my position. Someone else I know follows this “If I got hit by a bus” attitude, that is essentially how the department could survive if, God forbid, someone got hit by a bus. We’ve adopted that a little bit in my department and it does help if we’re one or two people down!

      1. Gadfly*

        I called it the ‘if I call out rich’ book. The story being that if I win the lottery or an unknown wealthy relative dies, I won’t be answering my phone, and I wouldn’t expect anyone else to. That way people laughed but got the point that the unexpected happens (hit by bus was ‘too depressing’ and kidnapped by aliens was ‘too weird’)

    2. Elizabeth West*

      Yep. Someone did that at a past job because they were leaving, just in case the company didn’t hire anyone before they did (they did not). I found it invaluable during my training–and I followed that practice ever since. I always make a FAQ.

      A bus could hit me, a meteor could fall, I could get lucky and suddenly become fabulously wealthy–you never know.

  1. Cynicaal Lackey*

    My former employer required drug testing. I had smoked a little pot the week before my interview and was worried if I would pass or not. i did and accepted the job. Three or four years later, when I knew my boss well enough we got to talking about drug tests. He told me, that unless the position was for delivery drivers where they were very cautious; they disregarded the pot results and just looked for signs of hard drug use. Perhaps this employer is equally enlightened.

    1. Ask a Manager* Post author

      The issue, though, is that the OP considers it an unreasonable invasion of privacy (I agree) and wouldn’t want to work there regardless of whether she’d pass the test (nor would I).

      1. Artemesia*

        I agree and wish more people would do it. I have never had to take a drug test but 5o years ago I had to sign a loyalty oath for a summer work program while I was in college — it still rankles and I wish I had walked away from the opportunity rather than compromise my integrity by submitting to police state tactics.

        1. Dan*

          For several years, I held jobs that required drug tests. I used to work on the ramp around aircraft and drive 10,000 gallon fuel trucks, as well as tow multi million dollar jets. New hire drug tests, for cause drug tests, and random drug tests were a given.

          I just can’t get in the mindset that drug testing for office jobs is so unconscionable that I would turn down an offer from a company where I really wanted to work. While I’m all for grass roots change, this isn’t a battle that I’m willing to fight.

          There are things that would make me think long and hard — if a job prohibited alcohol use off the clock, I’d probably have to pass. If a job restricted my ability to travel freely around the world, I’d have to think long and hard. (My company does a lot of classified work, if I got into that line of our business, the foreign travel that I do would become a concern.) We all have to pick and choose what battles are worth fighting.

          1. Amber*

            Yeah I’m in agreement. I’m a former soldier and had to take regular and random drug tests so I’d have no problem doing it especially if the job has safety concerns.

            1. Princess Consuela Banana Hammock*

              But you were both in fields where drug testing was significantly related to your job functions (national security). OP#5 has noted that they’re ok with drug testing in limited contexts, but the job to which they applied isn’t one of them.

              FWIW, a lot of people find drug tests intrusive and overly invasive when balanced against personal privacy. In general, I think it’s useful for employers to figure out if they actually need the data they’re looking for or whether they’ve chosen a blunt tool that’s a bad proxy. Most times, drug tests fall into the “blunt tool that’s a bad proxy” bucket.

          2. Ask a Manager* Post author

            That’s your prerogative, but I don’t want to derail the conversation with people’s personal opinions that they don’t mind being drug tested. The OP does, and that’s what her question is about; let’s keep the conversation focused on what she’s asking.

            (And a heads-up that I’m now at times deleting off-topic threads, given how derailing and unwieldy some off-topic threads have been becoming.)

            1. RP*

              To that point – should we be comparing an unmentioned drug test to say an unmentioned background check or credit check? these would be all invasions of privacy that should have been brought up earlier in the process.

          3. Nerdy Canuck*

            The jobs you’re describing, though, are all jobs where drug testing as a safety measure makes sense – but I think maybe we’ve come to accept this idea that just because it makes sense there, it’s acceptable where it doesn’t make sense?

          4. Bartlett for President*

            It’s worth noting that I live in a state that has legalized recreational marijuana. So, testing for pot use (and making decisions based on testing positive) is akin to doing the same for alcohol use.

            1. Gadfly*

              Except not because of the federal issue for now. And issues for multi-state businesses or those dealing with contracts from out of state.

      2. Gaia*

        I agree with you and the OP. Unless the job involves safety or public trust and there is reason to believe the employee is under the influence of these drugs *while working* it is a violation of their privacy. Employers almost never test for alcohol.

      3. Amy the Rev*

        I knew someone once who, as a non-drug user, intentionally failed a drug test so that she could leave the job:

        One of my co-workers back when I was a beachfront lifeguard in high school didn’t want the job, but her parents essentially made her take it (and pulled strings to get the position for her). This poor girl had a phobia of blood, and since our town beaches were relatively calm, the majority of our work was dealing with cuts/scrapes and other bleeding injuries from people getting cut up on barnacles, etc. We had all talked to our supervisor about her having a blood phobia, but her hands were tied because the girl’s parents had clout with the town officials (and we were all town employees) so she couldn’t fire her.

        We all had to submit to a drug test at the beginning of each summer, and failing meant you couldn’t be rehired until the next summer. So what did this poor, straight-edge girl do? She intentionally failed the drug test the following summer so that no matter what strings her parents pulled, she couldn’t go back to lifeguarding. I still don’t understand why her parents were so hell-bent on her being a lifeguard, but glad she got out.

        1. Marillenbaum*

          That’s intense! Poor girl, I can’t imagine how tough it must feel when your parents simply do not listen to you about a phobia. And who is so caught up in wanting their kid to be a lifeguard?

    2. ..Kat..*

      But if the employer is not “enlightened ,” a positive drug test could be a problem for the rest of one’s employment life time.

      1. Natalie*

        How do you figure? The results of pre-employment drug tests aren’t shared with anyone. No one’s going to know you once had an offer pulled.

        1. No, please*

          True. I’ve known a few people who were fired due to marijuana in their test results. Not one of them had those bad tests come up in interviews with new jobs.

          1. Emilia Bedelia*

            But… how would anyone find out?
            The employer who pulled the offer would not be called for a reference. Unless there is serious concern about the employee that goes beyond just failing a drug test, I really doubt that the employer would make any effort to spread this information to other potential employers.
            For the lab/test facility, I believe test results like that would fall under HIPAA and would therefore be fairly protected.
            I’m all for skepticism and being careful, but I think “problem for the rest of one’s working life” is a bit dramatic.

            1. ..Kat..*

              HIPAA applies to patients. You are not the testing clinic’s patient. The potential employer gets the results and can do whatever they want with the results.

          2. OhNo*

            They should be, though, shouldn’t they? The testing clinic shouldn’t tell anyone other than the company requesting the test (because HIPAA), and I sincerely doubt anyone would know that you applied at a particular company and were declined an offer unless you told them.

            Or is there something I’m missing?

          3. No, please*

            They left those jobs off their resumes. At least two of the people started jobs that had policy changes so they were randomly pulled. One person was recovering from cancer. The prescription marinol was still in their urine.

              1. No, please*

                Yes. This person had a supervisor willing to back them up if the prescription could be shown. I’m not sure if it was just too stressful for them to deal with or what. But finding work hasn’t been a problem for that person.

            1. Retail HR Guy*

              But testing facilities ask about prescription medications and check prescribed medications against the test results. They will then only go on to report a failed drug test to the employer if the prescriptions can’t account for the results. This is to save the employer from ADA lawsuits. Unless something goes terribly wrong no one is going to get fired for taking a legal prescription.

          4. Natalie*

            I’m not assuming they’re wrapped in ironclad secrecy, but based on my own experience and that of all the potheads I know (which is a lot) pre-employment drug test results are not typically shared with other employers. It has nothing to do with privacy rules, it’s simply a function of the fact that there’s no typical reason Employer B would know that Employer A had pulled an offer a couple of months ago. *Maybe* in an extremely small, chatty industry.

          5. LBK*

            How do you envision that a hiring manager would end up contacting someone a candidate only interviewed with and never worked for? How would they even know?

    3. Rick*

      While AAM’s advice is appropriate for the OP, since the OP is objecting on ethics grounds, other readers may want to know how to handle the situation if they still want the job.

      I recommend disclosing anything that would appear on the drug test as soon as the employer mentions there will be a drug test. After all, they’ll see it anyway. It’s very likely the employer won’t care, like in Cynicaal Lackey’s experience. By being upfront, you’ll establish a much better relationship with the employer. Also, if the hiring manager knows about it before the test results return, she will be prepared to fight for an exception, if necessary.

      The same advice applies to criminal background checks. Both drug tests and background checks may be intimidating and frustrating, but the company may actually much more lenient than it appears.

      1. Koko*

        I agree with this. It goes along with the idea that you remove the stigma from something by normalizing it. If you live in a state where recreational marijuana is legal, ideally you would be confident enough to say something like, “I understand there’s a drug test required for this office job. I would never come to work under the influence if any substance, but like many adults I do occasionally drink alcohol or smoke marijuana on evenings and weekends. Before we continue I want to make sure we’re not wasting either of our time, and that evidence of alcohol and marijuana use outside of work will not be considered disqualifying for the position.”

        A friend of mine stayed at the Four Seasons in Vail, CO – very ritzy, fancy hotel. He went down to the concierge to ask about local entertainment and dining options, and along with recommending a few restaurants and other attractions, without missing a beat the concierge said, “And there’s a lovely boutique cannabis shop just down the road,” and pointed it out on the map. He told me that was the moment he realized everything had changed, when this high-class concierge recommended a quality cannabis shop just the same as he recommended a fine dining establishment.

        It’s normal if we treat it like it’s normal!

        1. Colorado*

          In my own experience working in an industry that almost always drug tests, this is not true. Most companies don’t care if it’s legal in the state, it’s still federally illegal. I haven’t witnessed any exceptions to this. You don’t pass the test, you don’t get the job. And I’m against it personally and would love to see it normalized, it just isn’t there yet.

          1. Koko*

            There are people up-thread, though, saying that their company ignores marijuana results because they are only concerned about hard drugs, but drug tests are usually sold in panels and its cheaper to get a 10-panel with 1 you don’t care about than to try to get the other 9 panels individually or in other combinations.

            1. Otra*

              I also live in Colorado and every job I’ve been offered required a drug test. I have a friend who works in HR who mentioned, as others have, that her company ignores marijuana and focuses only on hard drugs. This was after it became legal in Colorado that her company changed the policy.

      2. Christine*

        While working for temp agencies, they have a standard statement regarding drug testing. I was with 3 different ones at the same time. Only 1 required the drug testing, and it was when I was assigned to work for a government defense contractor. All of the positions were administrative in nature.

        When clearly stating that drug testing is required, or may be required by their clients it’s a prescreening tool. If someone is using drugs heavily they will not apply in most instances. It’s posted in the lobby of temp & contract agencies. Suspect people fill the applications out, hard to just walk about but do not go through the interview process. Saves them time in the long run.

        I got used to it when I was in the military, so no big deal. But others that haven’t had jobs requiring it, can fully understand their unwillingness to participate if there isn’t a safety issue or a security clearance required. I’m leaning towards us admin people being told that we might be submitted to it, or it is required as part of the application process — that is being used as a pre-interview screening process.

    4. Just Jess*

      I’ve been an AAM lurker forever and now have to say that regularly testing candidates and employees and disregarding the results is an interesting concept. I’m an IO psychologist and I immediately wondered if any employer has ever consistently done this and then went back through the positive/negative drug tests to see if the results affected different performance variables. Then you would have scientific reasons for not hiring candidates based on drug tests. Conversely, you could save time and money by eliminating useless testing.

      It would also be interesting (in a sad way) to see if minorities were intentionally/unintentionally denied employment because they tested positive for marijuana while other groups were more likely to have the results disregarded. But then you’d have to make sure that you’re taking into account the racial makeup of delivery drivers versus non-drivers because of the stricter policy, etc…. Fascinating.

      1. Morning Glory*

        It would be interesting to see if there’s an association, but it would be important not to assume causation if you notice a performance discrepancy between negative and positive testing.

        A person could be both under-performing and using marijuana or other drugs due to a health issue, or personal issues, etc. – in those cases, the underlying cause would cause the person to under-perform even if they weren’t taking recreational drugs.

        1. Natalie*

          Ideally you’d look at multiple people, so you could see whether it was a pattern rather than a one-off.

          1. Morning Glory*

            I really hope this isn’t going too off-topic, but I love statistics so want to address. A pattern is association, not causation. It could be a million people, but all you would be able to show from Just Jess’s idea is association.

            1. Miss Nomer*

              This is true, but since they’re not really trying to do a big statistical write up, maybe association is all they need. There may be confounding variables in there, but it’s possible all the company would care about is a correlation. It’s kind of like how you screen out poorly written cover letters even for non-writing jobs. It’s not that being a bad writer is the cause of being a subpar worker, it’s that the same people who don’t care enough to spell check a cover letter are probably also subpar workers.

      2. Koko*

        I’m not sure if there have been studies of really task-specific performance metrics for employees, but I do know there have been studies that found that companies who implement drug testing do not increase their productivity. Drug test makers often pitch to companies that the cost of testing will be offset by the increased productivity from not having dead weight druggies on the payroll, but many independent studies have failed to confirm this.

        1. Emilia Bedelia*

          It seems to me that if you can’t tell someone is a dead weight druggie in interviews, then they’re not dead weight. Conversely, I’ve know a lot of dead weight non-druggies.
          This is just my opinion, perhaps,but hiring unproductive slackers is something that could be prevented by, I don’t know, interviewing the person and checking references? So maybe it does actually save money- the money that would be spent on actually making an effort in hiring people.

  2. Artemesia*

    #5. I noticed that the medical history form you fill out at the doctor’s offices where I go (a large city university run medical complex) which used to ask about illegal drug use not words it as ‘using any illegal drugs besides marijuana’. And we aren’t even a state where it is legal. I liked Alison’s advice here especially for a state where it is legal.

    #1 My husband advised a family member about a startup where he was to work for equity noting that they could fire him one day before he vested and essentially steal his labor for a year — so was he confident they were ethical people. He was confident. They used him to set up their business (it was an on line business) and then fired him one day before he vested, stealing his labor for a year. I have sense learned of something similar happening to a couple acquaintances. Absolutely do not work for the boyfriend’s family without an iron glad contract that protects your interests. A relationship where you talk about being able to afford the lease on your own is not one to rely on people’s good graces. ‘They would never. . .’ Don’t bet on it. THEY do it all the time. Look at divorces. I have always appreciated Carolyn Hax’s advice to think about how your future partner would be likely to behave if you divorced; some people behave very badly and viciously and they are generally the people you always knew would be jerks in those circumstances.

    1. MillersSpring*

      I agree with this advice–think of all the people who have been caught off guard that their partner was cheating.

      However, were the OP’s rent conversations with her BF (whether one of them could handle the rent on their own) maybe about whether one of them lost their job?

      1. OhNo*

        I know friends of mine have had that conversation with past partners, and it was always a combination of “What if one of us loses our job?” and “I want to make sure you’ll have a safe, comfortable place to live if we ever break up”.

        That said, I don’t think how nice the OP’s boyfriend is is a good indicator about how the rest of the family will feel if they break up. The boyfriend might be the nicest guy in the world about, but the mom/sister/other relatives might decide it’s all the OP’s fault and she should burn for it. Absolutely get an agreement in writing, just to cover your bases.

      2. Kimberlee, Esq*

        I feel like it was included as a demonstration of openness; that part of why OP feels good about going into business with his family is that he, and they, have demonstrated a responsible level of openness and practicality that is somewhat divorced from emotions and feelings. Being able to talk about whether or not the rent situation becomes untenable in the event of a breakup up-front is, to me, a sign of maturity and reasonableness.

    2. Gadfly*

      Look at it like co-parenting. It generally is best to have everything in writing because even the best of people sometimes disagree on whose weekend it is. OP, don’t just make it about you/boyfriend. Maybe Daughter will decide to have a young-life crisis and decide to charter ships in St Thomas (a friend of mine just did that, dumping a long held job to do it…) Maybe Mom and Dad will split up–should your share of the company be dependent on their divorce decree? Maybe someone will embezzle–who decides how to handle that? Setting down how people can leave and when they can be fired/forced out is good for everyone.

    3. Nerdy Canuck*

      #1: I wouldn’t take the conversation about being able to afford the lease on their own as indicative of stability or anything like that – especially given the way it comes across in the letter, it seems like them not taking the relationship for granted. Honestly, it’s just smart – and it means that they have the kind of freedom where this whole time, they’ve been choosing to be together rather than feeling like they don’t have an out.

      1. MK*

        It is smart, but it speaks to a lower level of commitment; the relationship may be stable and is obviously long-term, but it’s also one in which the partners are not able or willing to say “I believe that this will last a lifetime and I am ready to take the consequences if I am wrong”. There is nothing wrong with that, but it’s something to take into consideration when you are planning on going into bussiness with a romantic partner.

        To not stray more from the point though, I think the OP mentioned this to say that she and her partner are able to have practical discussions about what would happen if they broke up; it sounds to me more as if she cannot figure out how to have a similar discussion with his family without them questioning the relationship in turn.

        1. YetAnotherAnon*

          A little off-topic, but I’d say that discussing if one person could afford the rent isn’t necessarily indicative of a lower level of commitment. It’s just good planning – what if one person’s fired, or wants to go back to Uni, or develops a health condition that prevents them from working, etc., etc.

          On topic, getting something in writing is definitely a good plan. If something personal does end up affecting the business, it’ll be much easier to work out the logistics when there’s a plan already in place.

        2. TL -*

          I also don’t think it’s a low level of commitment. For some people, love doesn’t trump practicality. And there’s more than a bit of “I’m here because I choose you, not because I can’t afford rent without you,” to it, which to me is really romantic. (Because the latter happens. A lot.)

          1. Judy*

            My husband & I have been married 20 years. Due to changing circumstances and job moves, we’ve bought 3 houses over that time. Each time we’ve worked out if one of us could afford the house, just in the case of death, disability, illness, etc. In the early years, my husband actually went back to school full time for his master’s. Underbuying your housing situations, if you have that privilege, is a great way to help your peace of mind.

          2. Myrin*

            I agree. You can be completely committed to your partner (as in “I want to be together forever”) and still be realistic in terms of “something might happen in the future that makes it so that we won’t be together anymore”.

          3. Natalie*

            Agreed. I bought my house as an officially single person, but I was seeing someone I was pretty into. I didn’t set my price assuming he’d move in soon and help me with the mortgage, I bought at the level I could afford on my own. And we did end up getting married, so clearly it had nothing to do with my not being invested in the relationship.

          4. Mephyle*

            You can be completely committed to your partner (as in “I want to be together forever”) and still be realistic in terms of “something might happen in the future that makes it so that we won’t be together anymore”.

            To draw in something that was mentioned above, “something might happen in the future that makes it so we won’t both be bringing an income into the household.”
            Thinking about whether you can carry the lease alone isn’t even necessarily a hypothetical scenario about ‘if we’re not together in the future,’ but can be ‘if we’re poorer together in the future’.

        3. MsCHX*

          I think she just doesn’t want her “what if?” questions to be taken as “OMG are you guys having problems?!?” because people can be that way. And maybe she already knows they ARE that way??

          not able or willing to say “I believe that this will last a lifetime and I am ready to take the consequences if I am wrong”.

          But why? As someone going through a divorce no.no.no. The “consequences” are often higher than you can ever imagine. Don’t take a chance on marriage. Be as certain as you can be.

          And +1 on it being practical. Even with a married couple, you’d be doing yourself a HUGE favor if your living expenses could technically be covered by one person. I know it often can’t…but yeah that’s a huge stress removed if it could be.

          1. Koko*

            it’s also one in which the partners are not able or willing to say “I believe that this will last a lifetime and I am ready to take the consequences if I am wrong”

            Some people, because of their personality and beliefs, are never going to feel that way. Maybe they are naturally pessimistic. Maybe they have been betrayed by someone before and are not willing to take that risk again, no matter how much hope and confidence they feel that they won’t be burned again. Maybe they are on the spectrum or just not sentimental, so they don’t get caught up in these kind of ideas about the emotional implications of planning for remote possibilities.

            1. myswtghst*

              Completely agreed. As someone who just is more pragmatic than romantic by nature, I can absolutely believe my husband and I will be together forever but still want to be able to have open, honest conversations with him about what could happen in the future and how it could impact us.

              1. Gadfly*

                Same here. And since there are his two kids and experience living on alimony, and some discussion of if we want another kid, that gets even more important so we have a mutually agreed upon answer if something happens to either of us.

            2. OP1*

              Yea, I definitely agree with this. I’m definitely not uncommitted to my boyfriend, and I’m honestly an almost naïvely optimistic dewey-eyed girl when it comes to thinking about bad stuff happening (I still get super surprised and shocked whenever anyone dies on Game of Thrones because part of me thinks that now is going to be the time when everyone’s just going to be happy)

              It just seems smart to me, because I know that when you still love each other is honestly the best time to decide what’s fair because you still want your partner to be happy, which might not be true in the future.

            3. Hrovitnir*

              I am perhaps overly pragmatic, but I really wish it was normalised to be practical. No one who gets completely screwed in a divorce saw that coming, come on. It doesn’t mean you assume it’s going to go horribly, it means taking care of both of you.

              I also agree re: wanting to be with someone because you want them, not because you need them, being romantic.

      2. MK*

        I forgot to say, I think Alison’s advice applies regardless fo their relationship status, because the personal and the professional relationships do not (or should not) develop in tantem. What if ten years from now the OP is blissfully married with children to the boyfriend, but want out of the bussiness to do something else? Or the bussiness develops in a way that makes her skills irrelevant? What if she gets hit by a bus, with no close relatives, unmarried and without a will, dies (sorry!) and her share of the bussiness goes to some random distant cousin as next of kin? It’s not really about “what happens if we break up”, it’s “the bussiness must be set up in such a way as to cover certain eventualities”.

        1. KellyK*

          I like this. Any contingency planning that will be necessary if the couple splits up will also be necessary in lots of other circumstances. It might help take the focus off “What if we break up?” to consider a break-up just one of many unexpected things that could happen, whether it’s a crisis like death or illness or just a change in plans for her, or for anybody else in the family.

          1. Ama*

            Yeah, I’ve had unfortunately several instances in my family where a family member was unable to work for a long period of time due to illness or injury — including some harder to navigate, chronic issues that come and go. It’s just a good idea to have some guidelines in place if the OP (or one of the boyfriend’s family members) are in a position where they can’t contribute to the business at the expected level.

        2. LBK*

          Yeah, I agree – I would take this from a much more general perspective that getting into business with family can get messy sometimes for a variety of reasons, so it’s just cleaner and simpler for everyone to lay things out in clear, legal terms. I wouldn’t hone in on the possibility that the OP and the boyfriend would break up, because realistically that’s not the only way this arrangement could go sour (there are plenty of horror stories about family businesses on AAM for the OP to peruse).

        3. Princess Consuela Banana Hammock*

          Yes, agreed. I think it’s important to think about this as contingency or “disaster” planning. Leaving aside the rent conversation, in general the best time to create agreements about what happens if things fall apart is at the beginning or at a point where everyone is still high on life and working together. Trying to sort this out in the middle of a crisis or when feelings are hurt makes detangling the personal relationship from the professional entity extraordinarily difficult (and often impossible). And this of course goes for every owner/stakeholder in the business, not just OP#1.

          It’s also useful to do this kind of planning because it helps you identify your financial priorities and core needs, and it also helps guide you through determining what sorts of practices you want to adopt to help ameliorate unexpected events that threaten the business’ stability (e.g., procuring insurance, creating a business savings account or contingency fund, ensuring there’s a smooth exit plan if someone needs to drop out and pull out their equity).

      3. OP1*

        I didn’t mention the conversation about leases to indicate that we are in a particularly stable relationship, just that I wasn’t worried about how my boyfriend might react if I were to bring this issue up.

    4. Christine*

      Could you explain what you mean by “vested” in your employment? the one year anniversary? I have a an idea, but would like to make sure I fully understand. Thank you Artemesia.

      1. Catalin*

        Vested (sorry, just butting in here) indicates that the party has met the criteria for the deal to finalize: it often refers to a period of time, like how a life insurance policy won’t apply if the insured party hasn’t had it for at least N months. It’s common for a year to be the unit of measurement.

        Generally speaking, it’s a crappy deal for the person seeking services/payment/unicorn tears and a great way for the company to insure against losses by making the recipient (effectively) invest in the company before receiving services/payment/leprechaun pants.

        1. Koko*

          Another place it commonly pops up is with retirement matches. My company contributes a few percentage points of our salary every year to our retirement account, and matches any additional amount we contribution up to a capped percent – but it takes 3 years to be fully vested. If you quit in less than a year the company would take back all the money they’d put in your account, it would be like you never actually got that benefit. More than one but less than two years, you get to keep half of the money. More than two but less than three, 75%.

      2. LBK*

        When you work for equity (ie partial ownership in the company) instead of a regular paycheck, you typically have to work for a certain amount of time before you actually have a lega right to that equity (“become vested”) and ergo actually get paid for your work. So if you get fired before your equity vests, you don’t get your partial ownership (which would have entitled you to a portion of the company’s profits) so you don’t get paid.

        I don’t really know how this is legal since it seems to violate the FLSA, but it does happen.

      3. Artemesia*

        This is common in start ups that pay in equity. You don’t get the promised equity in the business until you have been there a year. So if they can by contract fire you, they can simply steal your labor by firing you just before your equity is legally yours. Since people work for essentially nothing in promise of this pay off it is disastrous when they are treated like this. It is not uncommon.

        I use it as an example for the OP in that believing that the people you are dealing with would never cheat you is not a valid business model; people cheat each other all the time and in the case of a social relationship with a boy friend and his family you can expect to be treated badly if you break up. The people treating the employee or partner badly is always someone who ‘would never do that.’ People have no trouble justifying behavior that is in their own interest.

    5. Michele*

      Re #5, I don’t think my doctor’s office even uses the work illegal. I think they have some sort of blanket non-prescription question that lumps everything in together from vitamins and “medicinal herbs” to herion.

      Re #1, I would not be surprised if your husband’s family member considered what they said as fair warning to justify unethical behavior. I remember an ill-fated year working for a family owned business. I had asked them what kind of turn over they had during the interview. They said that it was higher than they liked but they were working hard to bring it down and minimize it. Naïve thing that I was, I took that to be good. Then, when they laid me off, they added insult to injury by saying that I knew they had high turnover and should have expected it.

      1. Rusty Shackelford*

        Re #5, I don’t think my doctor’s office even uses the work illegal. I think they have some sort of blanket non-prescription question that lumps everything in together from vitamins and “medicinal herbs” to herion.

        If this is part of your medical history (as opposed to a drug test for employment purposes), they specifically don’t refer to “illegal” or probably even “drugs” because patients tend to assume that means they’re only looking for heroin use and not St. John’s Wort or vitamins or whatever supplement you might be taking.

        1. Artemesia*

          The forms I have been filling out here for years specifically asked for non prescription drugs and then separately for, I think, recreational drugs. At any rate, it was clear that it was an illegal drug category. Recently the forms changed to say ‘other than marijuana’.

    6. Venus Supreme*

      I came here to comment that what Artemesia’s husband went through is the SAME EXACT THING my father went through, and he was working for close family friends (to the point he was in one of the family member’s wedding parties and I used to play with their kids). They used him for his labor and skill then fired him one day before he vested.

      When it comes to money, people can turn downright nasty. OP1, protect yourself and your assets! I’m so glad you’re thinking about this now when your relationships with your boyfriend and his family are healthy and well.

      1. Artemesia*

        It wasn’t my husband — he was advising another family member of the risk and counseled against agreeing to the contract. But the point stands and you are yet another example of how people screw people over most unexpectedly.

      2. Lissa*

        I just…these “firing one day before” situations are so horrifying to me. I can’t help but wonder how those conversations go. “Hey friend, actually we were planning to screw you the whole time, and now we’re doing it. Bye!” or like, is there some kind of pretext where they pretend it wasn’t the plan all along and the firing was with cause and it was just coincidental . . ?

  3. MillersSpring*

    OP2: If you gave a tour to the prospective employer, then took a job with them, it would look really bad and possibly burn bridges with your current employer. After you leave, your current employer would have reason to question every tour, vendor meeting and client decision you made. Don’t exploit your current responsibilities.

    1. Grits McGee*

      Maybe I’m looking at this through AAM-tinted lenses, but it seems like any approach to interviewing that is described as a “out-of-the-box” (rather than “targeted” or “industry-specific”) = bad idea.

      1. MoinMoin*

        My thought as well. Reading that question I could understand where the OP was coming from, but when she described it herself as an “out of the box” idea I just thought, “If that’s how you describe it, you should know the answer.” Like when a product describes itself as fancy it’s a dead giveaway that the product is not, in fact, fancy.

      1. Jesmlet*

        I’ve never heard this saying before but I (unfortunately) have some friends who should hear something like this. Definitely stealing this for the future.

      1. Zombeyonce*

        OP, your post makes me wonder if there is a larger issue here. If missing 2 days for being sick (a totally reasonable thing that is pretty common for a lot of people) makes you so behind a month later, I think that either your workload is unreasonably large for one person or you are taking on too much that others can do.

        Is it possible to delegate any of this work to someone else? Your manager saying some tasks don’t need to be done as quickly as you want makes me think those tasks are far less important which leads me to think that it doesn’t have to be you doing them. Even just reprioritizing your work could decrease your stress level. I don’t mean this in an unkind way at all, but do you feel that you have any issues with perfectionism? I have found that letting go of the ideal of a perfect work product not only decreases my stress but also allows me to spend less time on things with no decrease in managerial satisfaction; I used to be much more critical of my work when something just being done was all that really mattered, not that it was perfect.

        If that isn’t the issue at all, could talking to your manager about your workload in general help? In a healthy workplace, you should only be getting that far behind in your work if you miss a couple of days if your department is shortstaffed and you didn’t mention that being an issue. If this is your regular workload, I think you have too much going on.

        1. Zombeyonce*

          I just saw your response to another comment below indicating that you are shortstaffed, so my response may not be useful (then again…). But I think that it’d be helpful to you to find out if that vacant position is going to be reposted and when.

  4. AcademiaNut*

    For LW #1 – even if you’re marrying into a family business (or join the business when married, or start up a business with your spouse, or have a business are getting married) it’s a very wise idea to talk about this, and sit down and figure out how it will work, and what will happen if you split up, and actually draft a document with the help of a lawyer.

    Even when you’re dealing with reasonable people, divorces and breakups can get messy, and it can get a lot worse when there is money involved. And it can work both ways – facing losing your job if you split up and leave the family, or for the family, an angry ex who owns part of the business.

    1. Princess Consuela Banana Hammock*

      +100! The best time to plain for what happens if something goes wrong is when you’re in good headspace and nothing looks like it will go wrong. Alison’s advice is helpful for all areas of life that overlap with your bf and his fam.

        1. JaneB*

          Maybe also worth doing even with family ties, so that you have a plan for when things change – emotions can run very high, and you just don’t know when someone will, say, meet the new love of their life and decide to go live off the grid in Australia with them, or whatever – making good logical plans and putting them on paper when all is going well just seems like a good idea for any situation where multiple people’s effort and income are involved…

          1. Colette*

            Agreed. They should talk agree what will happen if anyone wants out, or they want want someone to leave (for not holding up their end of the bargain, for a breakup, etc.). The plan for the OP may be different, but they should think about it for everyone.

    2. Lora*


      My aunt and uncle were married 30 years, raised four kids, were happy from every appearance. Then he had an affair and dumped her and they had to divide up a lot of assets. It got ugly fast. That was 10 years ago and they still won’t be in the same room together at holidays. Grandparents were married 60 years and as soon as my grandmother went to the nursing home with pneumonia, grandad started having an affair with, as he put it, “the prettiest lady in the retirement home, she’s 10 years younger than me!” He was 92. I was married to my dear ex for 15 years, and the first 10 or so were smooth sailing – he only developed a drug/hooker habit in the last few years, and although *he* was fairly chill about being kicked out, his girlfriend harangued him endlessly for a year about “make sure you get alimony!” Per my lawyer, when you own a business or assets >$500,000 – $1M, that’s when divorces turn into a battlefield, because that’s when it becomes financially worth it to have a huge expensive legal fight. When both of you are just arguing over who gets the DVD collection, that’s easier to settle out of court.

      People change, often surprisingly. I think of all the serial killers whose neighbors swear they never suspected a thing, he seemed so nice, etc.

      There are companies who make it work, just…not a lot.

      1. SimontheGreyWarden*

        This is the main reason why my best friend and I have kept our tiny jewelry business just the two of us. Even though I am married, we have never brought him on (not even to help with the books) because we don’t want any potential entanglements. I may know the friendship and the marriage would never end, but at the same time, the business needs to be protected.

      2. Venus Supreme*

        Yup, after 25+ years of marriage to my mom my father suddenly developed a drug addiction. Everyone was shocked! You never know what the future will hold, and I’ve learned that you have to protect your assets.

    3. Natalie*

      Another reason you want to talk about this now is succession planning. Even if every single things goes swimmingly for decades, some of you will probably retire at some point. My step dad is in that position with his business partner, who doesn’t want to retire but can’t afford to buy him out. My stepdad doesn’t have any legal ability to force the issue.

      1. Zahra*

        Very good point! My father died 15 years ago and two friends had parents die between then and now. The only succession that went without a hitch was my father’s. A big part of it was that there was time to do a family reunion to hash out the details and tell everyone what the plan was. It was very important to do so, because he owned a business with his brother, a business in which all 5 of his brothers and his sister worked in at some point and thus were emotionnally attached to it. Having a clear plan where everyone knew what was going to happen let them get used to the idea long before he died instead of processing the information while grieving for him.

    4. Emmie*

      Family business conflict is the hardest to resolve for business attorneys. It’s like a divorce with tons of emotional investments. I applaud OP for approaching the conversation now, and the commentor who suggested the OP also address the departure of other family members from the business. It’s a tough conversation now, but it preserves family relationships for years to come.

    5. Sadsack*

      Yes, and if the boyfriend or the family balks at the idea of an agreement in writing (“but we’re family!!!”), just say no and stick to it. If they are not reasonable enough to agree that an agreement would be good for all sides, then imagine what it may be like to work for them.

      1. Artemesia*

        ‘Yes, but its business’ like they say in the movies when they off someone. Just like people who plan to be roommates even for a vacation house, should sit down and formalize agreements about potentially contentious issues, so they have a way to handle things like eating each other’s food, different cleaning standards, someone’s boyfriend moving in essentially without permission or paying etc etc. The time to make sure the rental goes smoothly is BEFORE it starts and when the issues are largely abstract. Same with how to leave a business or wind it down or deal with issues of a break up and someone wanting to move on. It is easier when it is a future possibility and not an emotional present conflict.

        1. Princess Consuela Banana Hammock*

          Yes! This is why lawyers always want folks to do prenups. A prenup doesn’t mean you don’t love your partner or you’re not “in it” for life, it means that you acknowledge that life can throw things at you that you don’t expect, and it’s better to make decisions from a place of grace/love/consideration than a place of trauma.

          Similarly, contingency planning, dissolution plans, internal policies, etc., are ways to take the pain and uncertainty and high drama out of an already stressful situation.

          1. Natalie*

            A friend of mine and her now-husband did a prenup, and their lawyers wouldn’t even let them set a date until the pre-nup was finalized. That way neither party felt pressured by the timeline to just agree to whatever.

  5. paul*

    OP 4: how far before thanksgiving and did they try to hire if it was more than a month or so out? If it was someone leaving a week or so before, it’d be totally normal for an employer not to hire someone until the new year. Between people being out, people having pre-committed travel plans, etc, I know I’ve seen more than a few companies have an unofficial policy of shelving it till after Christmas if someone leaves any time in mid November through December. That’s by no means universal, but it isn’t uncommon.

    OP 1: To paraphrase an old manager of mine: Never defecate where you eat. Getting tangled up in business with romantic partners, particularly ones you ain’t married to, is just a mess waiting to happen.

  6. Anon1*

    OP 1: Unless you have worked with your boyfriend in the past, you may want a way to be able to exit the business easily even if you don’t break up. Once I had to work with my long term boyfiend on a year long work project. Even though we have a great relationship, it was tough. When things were stressful at work, it would bleed into our relationship outside of work. We also saw each other ALL the time. We now both work at different jobs and it’s so much better.

    1. Yetanotherjennifer*

      This is a good point. Someday, OP, you may want to move on to a different job. Maybe because work with the family has gone sour but maybe instead because of a great opportunity. How will the family handle that? How will the business handle that? You know the expression “it’s not personal, it’s business? A family business is very personal. It can be difficult to navigate as a member of the family and it can be even more difficult for someone who isn’t.

    2. Michele*

      I have always wondered how married couples handle running a business together. At the end of the day, I can go home and vent to my husband about the jerk at work. They can’t do that. And like you said, they never get a break from each other. I love my husband dearly, but I could not spend 24 hours a day with him.

      1. LBK*

        From my limited anecdotal experience, they don’t. A ton of them get divorced, especially if the business tanks.

      2. Artemesia*

        I wonder that too. I love my husband and we are now retired and sharing a tiny condo 24/7 but I could never ever have worked with him full time. And I like him. I would think the odds of one liking the partner after 10 years of working together especially with the stresses of a small business would be low.

      3. Koko*

        I work with my partner and we interact a modest amount at the office each day (we’re both Teapot Makers but he’s on the milk chocolate team and I’m on the dark chocolate team, so we rarely touch the same projects but coordinate on a lot of departmental work).

        It works for us because we’re both introverted, so we’re both extremely comfortable sitting in the same room quietly doing our own thing and not speaking to each other for hours. We’re also comfortable saying to the other, “I need to go be alone for a while,” if we’re not naturally on the same wavelength already, and the other will understand and give that.

        It’s an extremely useful skill to have when you’re traveling for an extended time with someone. I have permanently ruined friendships by traveling with someone who didn’t give me enough space or alone time and it changed the way I felt about them. There is a girl I used to be very close with but we took a trip together and afterwards I could never not see her as annoying. Total BEC effect.

        My partner and I, on the other hand, can rent a criminally small and depressing extended stay hotel room and go six hours stuck inside it because of heavy rains outside, without speaking to or even much looking at each other despite being 6 feet away from each other. Every now and then he might read me a passage out loud from the book he’s reading that he thinks is really good, or I might stare out the window and make some idle comment about the wind picking up, but then it’s right back to comfortable silence. It’s one of the things I love most about him/our relationship.

      4. Princess Consuela Banana Hammock*

        Like LBK, I have rarely seen these work over the long haul if both partners are really involved in running the business. The only times I’ve seen it work are (1) where both spouses own the business, but one is essentially a silent partner and does not get involved with day-to-day management or personnel decision-making; or (2) where the partners are in subordinated roles and they’re both super ok with that. Even then, it can create a huge amount of tension.

      5. Elizabeth West*

        I’ve worked for two different sets of married bosses–one got on really well, from all appearances, and the other wouldn’t surprise me if they split up. AFAIK they are still together, but they sure screamed a lot.

    3. OP1*

      This is an excellent point that I hadn’t even thought of. Again, I’m pretty optimistic about this being fine, especially since we won’t actually be working too close together (he’s doing web development, I’m doing photography and sales stuff) but I’ll still have a talk about that, too. Thanks for the excellent suggestion.

  7. Nerdy Canuck*

    I wonder if OP3’s boss wants to keep things at a reasonable workload to help make the case that there’s actually too much for one person?

    1. StressBalls*

      Hi, OP#3 here! I’m not sure about managements agenda, but I do know that two other positions could exist in this department. One staff is off on a mat leave and the other position is vacant, not reposted. This should be a short term situation, but I’m just having trouble coping (it’s more my anxiety about falling behind)!

      1. Jaydee*

        Then absolutely talk to your boss about which things to prioritize and which things you can let slide. If you are anxious about falling behind, but it isn’t actually necessary to do all the things, then it’s really just a matter of finding out which things aren’t necessary and reframing in your mind what it means to be on top of your workload versus falling behind.

      2. Emilia Bedelia*

        So it seems like they know they’re understaffed and have decided that not getting all the work done is an acceptable solution.

        If they really wanted the work to get done, they’d hire someone else. Or, they would have given you remote access already. By not doing either of those things, your boss is pretty clearly saying “this is not a priority for me… or you”. Please don’t look at it as “falling behind”- you’re in a triage situation.

        1. StressBalls*

          True, it’s a mindset change. I just am one of those people that likes a short task list so nothing ever surprises me or so I can handle urgent requests without affecting timelines. Doing my best to adapt!

          1. Kyrielle*

            Perhaps, when you prioritize with your boss, you can move those items off your list. Don’t think of them as “never getting done” or “going undone” but as “deferred” or (even better) “assigned to unfilled position”.

            If you ramp up and do all the work anyway, people higher up than your boss may also decide the position *never* needs to be filled. Let them see what it’s like when it’s not and people are working a reasonable amount – it’s the best way to ensure that they do move on filling it after the holidays. :)

          2. Jadelyn*

            Create multiple lists. I have A, B, and C lists. A is for all the immediate tasks that will cause serious trouble if I don’t get them done quickly – employee status changes, recruiting stuff, special projects for executive leadership. B is for the secondary stuff that is important and needs to get done, but lacks the ticking time bomb element of the items on list A – for me, that’s a lot of HRIS-configuration-related stuff that we’ve got workarounds in place for, because we can manage without the fix short-term but it does need to get done moderately soon. And the C list is for “nice to have” tasks – first-inquiry-type analysis tasks (the idle kind of “I wonder what would happen if we did XYZ?” thing that doesn’t have a specific project attached), adding special functionality to existing reports, research on upcoming legal changes.

            I consider it an okay day if everything on list A gets done and nothing more. A good day, I get all of A and some of B done, or at least progress made on B. A great day sees all of A and B completed and some progress on one or two items from C. The partitioning really helps me keep from getting overwhelmed by keeping my focus narrow and my priorities clear – maybe it could help you, too?

      3. Michele*

        First of all, I love your name.
        Second, is it possible to bring in a temp to cover the easier tasks?

        1. StressBalls*

          Why thanks, me too! :) A temp is unfortunately not in the cards, but the mat leave staff member should be back in 5 months, so there’s that!

          1. Mabel*

            This situation is not tenable because you really do need to be able to take days/weeks off when you’re not sick. It doesn’t sound like you’re ever able to use any vacation time. :(

          2. Zombeyonce*

            5 months is too long for you to have this kind of anxiety. I like Jadelyn’s advice above of creating A, B, and C task lists and ignoring C and most of B until more staff arrives.

      4. Trout 'Waver*

        I don’t want to overdiagnose, so feel free to disregard this if I’m off base. But you talked about being very stressed and anxiety, chose ‘StressBalls’ as a user name, and talk here about having trouble coping. Make sure you’re taking care of your mental hygiene. Do something nice for yourself this weekend!

      5. Artemesia*

        If you weren’t falling behind then there would be no need to replace the missing person. WHy do it when you can get it all done.

      6. nonymous*

        The nice thing about having a long backlog is that you and your boss have an opportunity to implement some systems improvement & reset expectations.

        For example, you and your boss might identify a category of tasks that simply won’t be addressed by your team going forward. Maybe you run reports for other teams and it’s high time that they learned to do it themselves? Or there’s a pesky newsletter that no one really reads?

        Having a list of real data, you can start saying things like “I’ve noticed that 50% of this list are custom change requests from the teapot designers. Why are there so many changes if we’ve been making the same teapots since 1975?” Perhaps what is really needed is that the teapot designers need software access rights to be able to change the teapot color. This is a totally different mindset than a production environment, and it’s something that your boss/management should have an eye on (or you can gently steer them that way).

  8. Gadfly*

    OP1– one thing about contracting: be careful if you do that to not just work for free or close to it for the family rate… easy trap to fall into, full of love

  9. hbc*

    OP2: Absolutely not. It’d be one thing if you sincerely had a business reason for inviting them and steered it a little more towards your projects, but even then, it’s icky. Your current company might not suspect at the time, but you would torch any positive feelings there once they found out how blatantly you deceived them. And if a candidate offered this up to me, I would either 1) blow your cover with an offhand comment at reception because it wouldn’t have occurred to me that you had a secret tour out in the open, or 2) move you way down the list because you’ve shown you don’t respect your employers.

    Unless you can go to your boss and say, “I’m talking to Client about a potential job offer and am bringing the interviewer out next Tuesday,” this is a really, really bad idea.

    1. Artemesia*

      This. I’d never hire someone who offered to betray their employer on my behalf. It is like marrying the guy you cheat with.

    2. Marty*

      It’s worse than that, trade secrets are serious business. Without permission from your current employer, this would almost certainly be a violation of your employment contract / NDA. You, and your new employer would likely be liable in a lawsuit. If you suggested it to me, I would place your name in the “never hire” file. I might even let your current employer know. If I found out one of my employees had made this offer, I would immediately fire them for cause.

      1. EngineerBob*

        Making a lot of assumptions here. Does the employee have a contract? Did he/she sign an NDA? And simply taking a somebody on a walk through tour of a data center is not exactly divulging trade secrets. However you would be well within your right to stamp the file “never hire”. But going to the employees boss and getting them fired could easily get you and your company in a nasty law suit. That’s crossing the line.

  10. Pineapple*

    LW 4 Could you create a handbook for occasions when you and your coworker are out sick? Create a digital and a physical copy and have it labelled in a bright folder somewhere prominent. It’d also be useful for when the new hire comes on board

    1. Lemon Zinger*

      Agreed, this seems like a project that would benefit everyone. In OP’s current situation, I’m sure management would see this as something to prioritize.

  11. Poster Child*

    Intereting theme in #3 and #4…it is often our own internal struggle causing stress rather than the employer. In both cases the employer/boss/HR are saying the OP should chill out. Do the best you can do, but also live your life outside of work. Some tasks really aren’t that critical (nice to have not need to have).

    1. StressBalls*

      OP#3 here! Internal struggle, or in this case, sometimes crippling anxiety. I’m trying to manage my workload and the inability to do that is stressing me out. I can normally overcome my anxiety by being organized and ready for anything but I’m finding myself being more frazzled and unprepared nowadays.

      1. A.*

        I feel for you, I have been there! I encourage you to sit down with your boss and get priorities for the back logged tasks. When I did this, I discovered my boss was trying to get justification to fill an open position and did not want me working overtime to do everything because that would show we didn’t need another person. If your boss does not want you working overtime to get everything done there might be a bigger plan.

        I know it’s hard to let go (sometimes feels impossible) when you have anxiety; please make some time to take care of yourself too.

      2. Natalie*

        Are you pursuing any treatment (psychological or other) for your anxiety? It sounds like it’s having a significant negative affect on your life, and it doesn’t have to be this way.

        1. StressBalls*

          Yes, I previously was treated for anxiety with medication, but with the help of a counselor I found some coping techniques that have made the anxiety less powerful. I haven’t required medication for my anxiety for the past 5 years as a result, I embrace the fact that sometimes I’m just frazzled. For situational panic attacks I also have a medication I can take, but that’s also not been required for the past 5 years. :)

          1. StressBalls*

            It’s truly unfortunate that’s my coping techniques involve organization and time management lol

            1. Natalie*

              Yeah, it’s good to have other options for situations you don’t have much control over. Might be worth giving your old therapist a call, just for a short term.

              1. TL -*

                I’m seconding this – maintenance therapy! Like taking your car in for a tune-up; doesn’t mean you wrecked it completely, but sometimes you’re still going to need the oil changed and tires aired up.

                1. StressBalls*

                  It’s possible you both might be on to something… unfortunately I moved cities and haven’t set myself up with someone locally. I may have to make some time for that; maybe I can use all that “work/life” balance free time I’ve been gifted, lol.

                2. Natalie*

                  @ StressBalls, give your old therapist a call. They might be open a few phone/Skype sessions, even if they don’t typically do that, or they may have someone to refer you to.

                  I don’t mean to be pushy about this, I just know from experience that anxiety is very much like that metaphor of the frog in boiling water. It ramps up to a 10 so slowly you don’t even notice, and you forget what being a 4 felt like.

                3. LBK*

                  Totally agree – this situation would have me digging up my old therapist’s business card. She had explicitly told me that I could call her for maintenance if needed down the road but even if yours didn’t, I’m sure they aren’t going to turn you away. At the very least they’d probably help you with a referral to someone local.

            2. Artemesia*

              Maybe you need to work on reframing this as an opportunity for the management to fully understand the need to staff up. You are doing them a favor by not working overtime for free to hide the understaffing.

      3. Observer*

        That’s very rough. But, your manager may have a really good reason for not allowing you to work the extra hours. So many companies have a culture that doesn’t respect work / life balance, etc. and she may be concerned about inadvertently causing or exacerbating this kind of issue at your workplace.

        When I got one of our staff a smart pone for work use, I had to explicitly tell her that although she’s likely to get emails with middle of the night time stamps, NO ONE expects her to answer them at that time, and that it’s totally acceptable for her to turn the phone off after hours. (And she generally DOES ignore late night emails, which really is just fine. But I needed to be very clear about it.) Those of us that work those hours love the flexibility, but if you are not careful, it can lead to people who do NOT love it to feel pressured to take part in that kind of thing.

      4. hbc*

        Is it possible for you to redefine what “managing your workload” means? When you’re understaffed, the goal cannot be that 100% of your work gets done. It just can’t. So you need to redefine a successful week or day as doing 100% of tasks X and Y, and giving accurate delivery times on tasks A, B, and C, even if you’re saying you can’t do a 1 hour task for 2 months. Run it by your manager, and then tell people who complain that they can take it up with him.

        Do whatever tricks you need to remind yourself of what good performance actually is in this situation. Working from home is a failure in your duties, but leaving low priority tasks for later is not.

        1. StressBalls*

          Managing my workload has shifted definitions over the course of this job. It started as 100% completion, and has shifted to only high priority tasks. Of the 60 tasks on my list 30 of them are high priority and have due dates attached to them, hence the stress! I’ve started needing to tell people their timelines will not be met (which isn’t hard for me, I’m very deadline driven). My boss has my back on that and sometimes I refer requesters to my boss for validation of my prioritization. She doesnt mind stick handling that for me, again which is appreciated.

          1. LBK*

            I completely understand what you’re going through, because I’m also someone who is extremely uncomfortable letting things go unfinished even if my boss tells me it’s okay. I think you just have to sit down with your boss and develop a really explicit metric for what does and doesn’t need to get done – effectively, what you need to do is redefine success for your job so that it no longer means “get everything/all the high priority items done” or hitting a vague target like “getting as much done as you can.”

            Directions like “don’t worry about it” aren’t actionable for someone with anxiety because worrying about it is all we do. You need more explicit permission to let yourself consider your work complete, and that needs to be more measurable otherwise you’re always going to be concerned that you’re not doing enough.

          2. Princess Consuela Banana Hammock*

            I completely agree with what Alison and folks have said. OP#3, I’m also someone who likes the satisfaction of clearing her “to do” list and gets stressed by not being able to turn in high-quality work on a specific timeline.

            This isn’t a time management problem—it’s a load management problem. And when that happens, all the processes that normally work (organization, planning, mental health) start to come apart. As LBK noted, I think the only way for you to feel like you have more control over your workload (i.e., feel like you can do the organization and time management needed) is to sit down with your boss with a full to do list grouped by project area and organized by deadline. Print out a copy for her. Go literally line by line through that list to figure out what’s a priority, what can be shelved, and what should be transferred to someone else for completion. If you do that and still have 30 high priority tasks, then go back through those 30 with her, again, and do the same thing (prioritize, shelve, transfer) until you reach a reasonable load for each week/timeframe.

            In this specific circumstance, you need your boss to be more actively engaged in determining your workload, and I think it will save you a lot of stress, anxiety, and heartache if you can get her to step up and go through this process with you. Talking her doesn’t mean you’ve failed at your job—it means that you’ve exercised as much leadership as you can within your sphere of control, and now you need your boss to do the same. Right now you’re so caught in fielding demands that you’re not getting a chance to step back, breathe, and reassess. Go ahead and do that, now, and enlist your boss in making sure that reassessment happens!

            1. LBK*

              I think this is a great roadmap. The one suggestion I might add:

              Talking her doesn’t mean you’ve failed at your job—it means that you’ve exercised as much leadership as you can within your sphere of control, and now you need your boss to do the same.

              If you want to feel like you’re taking charge a little more and not just running to your boss for help, you might try to go through the prioritization exercise on your own first (sorting everything into the do/shelve/transfer buckets) and bring that to your manager for review, rather than starting it from scratch with her.

      5. Victoria Nonprofit (USA)*

        Oh man, I feel you. I also struggle with anxiety (and once had to leave a job over it).

        Early in my career, I handled it the way it sounds like you do — just doing tons of “extra” work; checking email over weekends just to be sure nothing had happened that would stress me out on Monday morning (… and in doing so stressing myself out on Saturday afternoon instead).

        These days I manage it in a few ways:

        1) I took a job with a workload I can get done in my working hours.
        2) I bring my computer home with me over the weekend, in case I get sick and want to work from home on Monday, but otherwise I leave it at work (and don’t have emails sent to my phone).
        3) If there’s something I actually need to get done outside of work — the last time this happened it was because a foundation had asked for more information with 6 hours notice before a grant deadline — I’ll do it, but if that becomes too frequent I raise the issue with my boss.
        4) I do a lot of calming activities to chill my brain out (coloring, meditation, etc.).

  12. Mazzy*

    The backlog question – I’m very curious what type of work it is and how long it will take to catch up. I was in a similar place recently and we eventually hired someone else. My backlog of 50 things was about three months of work, though

    1. StressBalls*

      OP#3 here! It’s data analysis primarily but there are also customer support functions and project management functions to my role; if I was left alone and not in meetings, I could catch up in maybe 1-2 weeks; I’m usually super efficient!

      1. Harper*

        Ha, I feel you about those meetings! I’m in a project currently just like that — We’d be done if we didn’t have to meet about it. :D

      2. Aglaia761*

        Are these scheduled meetings, impromptu meetings, or both? Is it possible for you to shift things around or schedule 1 day of no meetings so you can focus on tackling the backlog?

        1. StressBalls*

          Unfortunately both! And they are related to a high profile project so I can’t necessarily decline. I’ve already started blocking off my calendar for a few days a week but some people ignore that.

  13. 80cm / hour @ 10A DC*

    #1: So you’ve known this guy and his family for 6 years now, and you’ve been living with him for 5 of those years, and his family apparently thinks you’re wonderful. And now they’re getting serious about offering you a role in a family business they want to start.

    When I step back and take a look at it, it seems to me like they want you to marry the boy. I’m not a lawyer, but if you’re in a community property state, and you and your husband own part of the biz, I believe there are some protections that kick in in the event of divorce. And / or the business aspect may lead to y’all drawing up a pre-nup, which could be a good thing. When it’s just a couple, pre-nups are often non-starters; but when you’ve got other members of the family involved, it could go a lot more smoothly.

    Finally, it sounds like y’all get along really well, and that’s probably the biggest indicator of success. Many people hold the attitude that doing any kind of business with a family member is the start of A Very Fast Descent Into Hell. And if the “business” in question is buying a used SUV from the bum who married your niece, this may well be true. But there are tremendous numbers of successful family-owned businesses out in the world. Arrangements like this *can* work – I’ve seen it happen: Back around 1994 I built and maintained a website for a small family law firm in Alaska – really good people, a joy to work with. One day Ward, the head of the firm, called me up and said “You’ve done a great job, but we just don’t need you anymore.” I responded “Hey, it’s cool – but, are you guys alright?” And Ward laughed and said “I’m more than alright – I’m doin’ great! I just got married and my wife is the best thing that ever happened to me! Umm … but she’s a designer and an artist and she wants to take over the website.” I said something like “Dude – go with God!”

    I just looked them up, and the firm and the couple are still going strong.

    1. anon for this one*

      Finally, it sounds like y’all get along really well, and that’s probably the biggest indicator of success.

      Oh, not necessarily. I love my brother-in-law to death, but if my financial success depended on his motivation and follow-through, I’d have murdered him long ago. And I might not have realized that he was fun and caring and sweet but completely irresponsible when I was only six years into my relationship with my spouse, as the LW is.

      1. Artemesia*

        And she may want to leave the business but not the guy — to save the relationship or because she finds she really doesn’t want to work for Uncle Harry after all and so there needs to be a clear process for selling her share or whatever.

    2. Princess Consuela Banana Hammock*

      I just want to note that if you’re unmarried, you can contract into the same protections that community property provides. Where people get into trouble is when they don’t come up with agreements before going into business, and that problem exists whether you’re married or not. Community property just provides a backstop to protect the more vulnerable spouse in the event of death or divorce. I would not suggest/encourage folks to get married in order to trigger those protections.

      OP#1, this whole thing will be cleaner if you can convince your bf’s family to separate the business relationship from the personal relationship. Regardless of whether they’re on board with that, definitely explain that it will be helpful for the group to deal with uncertainty (and to protect each person!) in the future if you can all enter into business agreements with each other before you join the biz.

    3. Manders*

      Strangely, I know tons of lawyers whose wives are their web designers, marketers, or admins. It seems to be a really common dynamic, I work for a couple that functions that way right now.

      I think part of what makes it work is the fact that it’s pretty rare for a small law firm to go bankrupt unexpectedly. There may be lean times, but it’s unlikely that the business will go under in a way that leaves both members of the couple out of work. Most of the successful family businesses I’ve seen have a similar dynamic: there’s still some stress about money, but there’s at least one rainmaker in the family. And in the dysfunctional ones, you could tell that the rainmaker was hard to work with, but the other family members were stuck because getting out would mean losing a job *and* an immediate relative.

      1. 80cm / hour @ 10A DC*

        I’ve been out of the WebDev biz for many years, and many aspects of it have changed. But what you say rings true, based on my experience.
        And, honestly, one of the reasons I chose lawyers and law firms as my “niche” was because they always had money to pay me.

  14. Kate*

    I would be sure to review the drug test form before declining. We test for drugs, because of a client contract we have that requires it – we make everyone do it so it’s not discriminatory, not just the people who work on that client – and we very specifically don’t even test for marijuana.

    1. Engineer Girl*

      And of course business needs could dictate that you move personnel around to support that client. Which means you can utilize anyone in your company, not just certain people.

  15. I Herd the Cats*

    My oldjob sprang a drug test on me as well, at the last minute in the hiring process after I’d accepted their offer. I did it, because at that point I really needed the job. But I object to it as an invasion of privacy, except in cases where you’re engaged in some sort of work where it’s a critical safety issue. I don’t use drugs and I knew I would pass the test, and I did, but it rankled. For folks who say, well, you know you’re going to pass so what difference does it make, my answer is: that’s an argument used for all sorts of invasions of privacy. In hindsight, that random drug test was an indicator of what the company was going to be like in terms of paranoia and lack of boundaries. I left.

    1. AndersonDarling*

      My company just made a policy about random drug testing, but it wasn’t really their decision. It was part of an insurance overhaul and it was the only way to keep our liability insurance.

    2. Princess Consuela Banana Hammock*

      I’m sorry that you had that experience, I Herd the Cats. That’s a shady thing to spring on someone after they’ve accepted an offer, and I agree with you that for most jobs/fields, random drug testing is bad policy.

  16. rubyrose*

    #5 – the approach I’ve taken which has been mostly successful is that when they ask you (typically in the first interview) when you will be able to start, you say “I’ll give my current employer 2 weeks notice when I’ve passed the background check and drug screen. How long does it take for those to clear after I’ve accepted the offer?” Or you can ask that question yourself, if they don’t. Most companies will tell you right then if there is a drug screen.

    Alas, I said mostly successful. At a large urban hospital I was told I would need to visit the employee health center 3 times to be cleared for work. I assumed they would be drug testing. It turns out there was no drug screen (“they didn’t have the facilities for it”) and they were more interested in whether I had TB and if I could prove my chicken pox vaccination from 50 (yes, fifty) years ago.

    1. Gaara*

      This would sound really odd if I did it, because in my industry drug testing is practically unheard of (law practice). But if drug testing is common in your field it could work without raising eyebrows.

      1. KellyK*

        You could phrase it more neutrally as “any checks you run after an offer, like background and reference checks.” That gives them an option to bring up drug testing if they’re the one oddball employer in your field who does it, but it doesn’t make it sound like you’re worried about failing a drug test.

        1. AndersonDarling*

          You could always ask, “Can you tell me what your hiring process looks like? What steps are there and how long does it usually take?” You will usually get answers about drug, background, and credit checks. You can also check on glassdoor.

      2. Princess Consuela Banana Hammock*

        OMG if most lawyers (excluding those who work for local/state/fed gov’t) were subject to drug tests, there would be no lawyers.

    2. Working Mom*

      What I think is frustrating about OP #5’s position is that the recreational use is legal in his/her state. I wish there was a better way for companies who operate in a state like that to better align with the state laws. I’m not saying that all employers should allow recreational pot usage, as I do agree it can depend on the nature of the work. In some environments and roles it’s a non-issue, and in others it could pose significant safety risks. I just wish there was a better way to tackle that – so that a person applying for a job where it would be a non-issue could effectively raise their hand and say “I’m using legally per state laws” and not be labeled “drug user” in that negative way.

      1. Emilia Bedelia*

        That is somewhat how it is done currently, in my experience. When I took a drug test for my current job, the testing facility told me that if anything came up in the results, they would contact me first and I would have the opportunity to respond/explain myself to the testing center. THEN they would contact the employer to tell them the results (at the time I was on opioid painkillers for an operation, so I was worried about that showing up). I’m assuming if marijuana had showed up and I could demonstrate that I was legally allowed to use it in my state, I would be able to make this argument at that time.

        1. Working Mom*

          Ahh, yes I like that approach. It could become challenging if an employer operates in multiple states, but I imagine it would evolve into just another thing that varies by state. (So many labor laws, etc already vary by state.)

        2. Noah*

          Yes, that’s how it works. I take Adderall and it shows up as amphetamines. So I get a call asking me about it, and I have to provide the name/phone # of the prescribing physician. I assume they do something to verify it from there, and then it is reported to my employer as a negative result. My employer doesn’t even know there was a positive initial result.

          I have random tests a few times a year because I work in the airline industry, and have since I was 18. I’ve always been under a DOT drug testing program, and marijuana use is illegal because the DOT is a federal agency. They don’t care if it is legal in your state (medically or recreationally). However, I can certainly see how non-DOT drug testing would allow marijuana use depending on the state you are in.

        3. OP #5*

          Being able to legally use it the state doesn’t mean the employer can consider it illegal. The courts have found that because the federal government still considers it illegal (and simply looks the other way in regards to legalized states), the employer can choose to consider it illegal as well. This goes for medical marijuana as well, per the courts.

      2. Michele*

        Yeah, it gets tricky with companies that have facilities in multiple states. Because we work with federally regulated controlled substances, we have to be drug tested where I work. We also, again because of federal regulations, have to have policies for how we deal with employees who fail the drug tests. In addition, we have a company policy that states that within a country, everyone has the same benefits and rules. That was great for gay employees before gay marriage became the law of the land because it meant that their live-in partners were given the same access to health insurance as married people–we had a facility in Vermont, so benefits given to employees in Vermont were given to everyone. However, if you work in a state where marijuana is legal, you can still face the federally required disciplinary actions if you test positive for drugs.

        1. OP #5*

          That’s really interesting. Before marijuana was legalized, I worked for a Fortune 100 company with offices in every state, and they had state-by-state regulations for drug testing. All the offices in our state did NOT drug test, but some other states did.

          It’s worth noting that personal use of marijuana isn’t technically against federal law, as that isn’t within the scope of federal law. Federal law is concerned with larger-scale crimes, such as drug trafficking or distribution. So, there isn’t a federal punishment/disciplinary action to be had, really.

      1. Engineer Girl*

        Maybe polio?
        Screening for TB and chicken pox would be important if you are around immune compromised individuals.
        Screening for contolled drugs would be important if you were around those drugs.

  17. Sas*

    # 1- The luxury to be able to answer this question without getting upset or say something mean like, “humble bragging” (which would not be appropriate) would get to me. I was in business with my ex. He owned houses downtown in a city where he and I lived, and his fam owned part of the houses also. Fixer-upper type of thing. He asked me to help for almost a year. He said he would pay toward the end, he refused. I lost months of pay. Ex-sh (sh-thead) took my card to pay for some of the supplies (Think $$$) and then did not pay me back. Upon me asking to meet him at his place and pick up checks for my payment after asking for months, his mother met me at his door when I got there (scare of all scares), screamed at the top of her lungs at me, called me all kinds of names, I sat out in the pouring rain for a long time that evening and cried on the sidewalk in front of their house (much to their confusion) as they tried to report me, and his mother said that her precious son (think 30 years old at this point) wouldn’t ever have to pay me back. My ex hid behind a wall in his hallway/ kitchen the whole time that this was happening (until when I was sitting out on the sidewalk and he went to window and started to yell). He didn’t pay me back. Any who, I barely made it out of that situation . Next day, they were both (behind my back) telling everyone we knew that what happened was I came over there to threaten this woman (beast) and what would you do if she (I) came over to your house, what would you do in this situation kind of thing. My life was almost ruined. I came from an abusive situation growing up and had little place to turn. Horror story is mine, but long story short, Artemesia’s advice from above “Carolyn Hax’s advice to think about how your future partner would be likely to behave if you divorced; some people behave very badly and viciously and they are generally the people you always knew would be jerks in those circumstances.” Probably true. As well as others advice. You are fortunate and in a good relationship. AAM would probably not be happy with me writing people’s real names on this site, but if I could, they would probably deserve that.

  18. Zahra*

    OP1: One more thing: what happens if the business suddenly goes south and you both lose your livelihood? Having all your (financial) eggs in the same basket may not be the best idea.

    1. J.B.*

      Good point. I kind of like a middle ground. OP1 could certainly consult for the business and give them advice on how to set up the website. But as a contractor, not as a partner. Give them a great template so they can go out and hire someone else to do the work. But keep (or transition quickly into) a different day job.

      Layoffs, business declines, health scares happen. I was incredibly lucky to have stable employment when my husband was laid off.

      1. Artemesia*

        Both my husband and I have been unemployed; both my daughter and SIL have been unemployed and the saving grace was that the spouse could keep the ship afloat until the unemployed person found work again. Losing my job when the company failed was devastating to me as it was to my daughter when it happened to her — but neither of us had to lose a night’s sleep over whether the mortgage would get paid. Living well within your means and not having all the employment eggs in one basket is very reassuring in a tumultuous economy.

      2. AnonAnalyst*

        But the flip side is that only being a contractor also means that she can be cut out of the business at any time. If the OP envisions this as a side gig or is otherwise fine with having her role minimized in the future, I think that’s a reasonable option, but she should be clear that being a contractor means that that relationship can be severed easily by either side.

        I know that I personally wouldn’t be happy with that arrangement, especially if I had been involved in helping to start the company and building the business. I would want an equity stake in the business, but I would absolutely make sure that was clearly spelled out at the outset (as well as a succession plan for what would happen if I were to exit the business). Frankly, it would be good for each family member’s stake in the business to be spelled out clearly as well, since it’s not unheard of for these things to cause issues down the line with family relationships.

        1. AnonAnalyst*

          Ack, hit “submit” too quickly. I meant to add that this is only relevant if OP wants to stay involved in the business – if she just wants to help set it up and transition to keep her main source of income separate from the business, J.B.’s suggestion is right on.

  19. Anon 2*

    OP1…. get things I’m writing. While I have no doubt you are committed and your family loves you, if you were to break up things can change radically.

    I have been involved with more than one person where we had all these rational plans for how we’d handle a break-up went down the toilet when we actually broke-up. It’s easy to talk about things in theory, but once you start mixing emotions in things get messy. For example, I liked my step-brothers ex-girlfriend, and she was very close with my parents (she lived with them for six months), but when they broke up we didn’t see her again. We didn’t want to hurt her by cutting her out, but family comes first, and my step-brother found it painful to see her and hear about her. Now a few years later she’s like a stranger. And, I am sure she never thought that would be the case.

  20. LQ*

    OP #1
    I apparently have a weird family in that we have relationships with ex’s without the family. One of my cousins had an amazing girlfriend, she comes over and hangs out with the family often even though they are no longer together. She and his mom had a small business for a while after they’d broken up. My mom had a little business with my dad’s sisters after they’d split. (And a couple other examples! We are weird.)
    If the conversation around “Let’s make sure we are legally ok even if something happens” had come up they would have been 100% on board with making sure it was a good idea and that there was documentation around it. If they aren’t willing to have that conversation, don’t do it.
    I don’t think it is 100% a bad idea, but I do think you need to at least have that conversation. It will tell you a lot.

  21. Gaia*

    My company is now combating the issue of drug testing as 3 of our 4 sites in the US have legalized marijuana use for recreational purposes. We do pre employment drug tests for certain positions (they involve safety and work that could possibly endanger the public) and historically the company has screened for any drug use.

    We’ve now decided that beginning next year we will still screen for drugs but exclude marijuana results. I just finished work on a committee to rewrite our drug use policy to make it clear we don’t prohibit the use of marijuana in employees so long as they are not effected during work hours (including on call time) which is the same as our alcohol policy.

    I’d like to see us go a step further and stop drug testing entirely but the company is HQ’d in a very conservative country and so even this was a major battle (and was only ‘won’ when CA and MA legalized recreational use this year).

  22. M from NY*

    OP1 In case you are reading previous posts and telling yourself that would never happen let’s look at this another way (that I only saw one person touch above). What happens if business is successful beyond belief? How will assets be alloted? What if a partner wants to sell but can’t afford to buy another out who wants to keep it in the family?

    I see many posters referring to fact that this is boyfriends family but even if he was your husband an agreement needs to be written out. I wouldn’t presume that it’s ok to just say you’re a contractor. Why should family financially profit off of your partnership level input? It’s fine to come together to form this venture but keep the business side business like. As with insurance, it’s better to have and not need than to find yourself needing it and not have.

    1. nonymous*

      Yes, there should be a written plan in place to protect the *company’s* interest in the case that anyone leaves. I’m thinking of situations where one of the three couples get divorced, hit by a bus, or simply wants to move on to another career/investment.

      Even if this company never gets past the point of providing salaries for everyone involved it isn’t fair to the rest of the team (plus any hourly workers) to have to scramble for a new job when a life event happens to one party. And if the company is wildly successful, there might not be enough capital to buy a departing partner out (assuming the remaining partners want to stay and keep growing the business).

      It may be a reasonable structure to have senior partners with primary ownership and grant junior partners (e.g. OP, OP’s bf, otherson) ownership with a vesting scale & profit sharing. The more work is performed at under-market rates (e.g. partner-quality work paid as contractor), the more generous that vesting and profit sharing should be. One other consideration that OP needs to take into account is her expectations of how the company will be managed. There are different balances between growth and income that a company can choose, and while it may make sense to prioritize income for the closer-to-retirement age set, it may mean that any ownership OP gains will have limited value.

  23. Important Moi*

    I would just like to thank Alison for providing a heads ups for deleting off-topic threads, given how derailing and unwieldy some off-topic threads have been. You’ve been very gracious in handling the questions and criticisms (sometimes you didn’t have to be).

    I say this as someone who’s been reprimanded.

  24. Manic Pixie HR Girl*

    OP4: Last year, I had someone leave right before Thanksgiving. By the time I had permission to backfill and had a preliminary list of candidates, it was mid-December. I was taking off time at Christmas (and I imagined many of my potential interviewees were as well), so I got permission to schedule interviews for after the first of the year. (I had also JUST hired a new person and was in the midst of training her as well – it was a bit cray!) My new person didn’t end up starting until the end of January. Honestly, if I hadn’t had one standout candidate that really wowed me (and whose work I was familiar with, which was really just a lucky coincidence), it would have been even longer.

    Regarding your current predicament: If you can, work with your counterpart to get some good procedures in place – step by step instructions for critical tasks, and a standardized organization system for files (naming conventions for share drives, a certain way a folder is organized for hard copy). Honestly, this is a good idea to do regardless – you never know when something could happen and people have to be out unexpectedly for an extended period of time. This will also help you in training your new hire. Also, this way, if someone calls you off hours, you can tell them to “refer to the procedure on the X drive” if the need something.

  25. BetsyTacy*

    #3 and #4: If HR and management is telling you to let some things/coverage may slip through the cracks because of staffing issues and they know that, try not to stress over it. Trust that your management has faith in you and is not setting you up to fail (provided that they haven’t given you cause to doubt this in the past).

    I say this as a manager who has basically had to demonstrate that there was a need for a replacement staffer. After a great employee moved on, we were all working 20+ extra hours a week to ensure that x, y, and z would get done. Our management didn’t realize just how many hours were being worked and hadn’t re-hired because in their eyes, everything was getting done and the additional staffer didn’t seem necessary. Once we started working a normal amount of hours, our management started to realize that this was a necessary thing. The same happened with a receptionist. Once management had to start scheduling their own meetings (basically herding extremely well-heeled cats with massive Napoleon complexes) and dealing with absurdly time consuming issues like making sure the copier got repaired, we had a new receptionist hired within the month.

    1. AnonAnalyst*

      Yeah, I wondered if this might be part of what was going on. I can relate to the OP because I hate leaving things on my to-do list and feeling like I’m constantly behind, but unfortunately, in some places people need to actually see things start falling through the cracks to believe there is a problem.

      This happened to me in a past company. My position had a highly variable workload, which was very light during certain times of the year but extremely heavy at others (to the point where I would routinely work 10-12 hours a day for a couple of months, and that was after bringing on part-time assistance). The organization went through a restructuring and my position was merged with another job with a steadier workload. This was fine during the slower periods from my original job, but untenable during the heavier periods. I also got a new manager as part of the restructuring who didn’t understand what was required for my original job, and he didn’t believe me when I kept raising concerns as we got closer to the busy period that I would either need to skip some tasks for that period or get some help in order to get everything done.

      I’ll just say that it didn’t go well since there weren’t enough hours in the day to get everything done for both of those jobs, but he had to see it for himself before he was convinced that I actually did need more resources. It could be a similar situation in OP’s company, where her manager realizes they need more help but the higher ups don’t see the problem.

      1. StressBalls*

        OP#3 here!
        Hmm I think my manager is playing the long game on this one. Rather than filling the mat leave position, she’s adjusting the organizational expectations for a few months. Once the mat leave staff member comes back things should normalize (hopefully)!

    2. Marillenbaum*

      Now I’m imagining cats in an office wearing two pairs of tiny high heels and tiny Napoleon hats. It’s perfect.

  26. Sunshine Brite*

    Ugh, drug tests. It was really awkward to meet the HR person at my previous job and have him be the one to monitor the drug test completed in the bathroom off the office of the managers. Companies thinking about them should really do it off-site.

    1. AndersonDarling*

      My husband interviewed at a weird little staffing firm where they put the cup in front of him and said they needed to do the drug test. He asked where the bathroom was. There was no bathroom, it was for employees only.
      He looked at the cup, and looked at the interviewer, and then walked out.

      1. Observer*

        How on earth do they get any decent staff? I mean, who with ANY options is going to go along with that?!

      2. Zombeyonce*

        I…I just don’t understand how someone could think this was reasonable. And what if it was a woman? As horrible as it is, at least a man could turn the other way and not have anything seen, but would they expect a woman to just squat there in front of them?

        It’s all so incredibly terrible. I’m glad he walked out.

        1. Observer*

          Maybe it’s not a “woman’s job”. (What’s the emoticon for “rolling my eyes”?)

          More likely they didn’t think.

    2. Leatherwings*

      Ewww. Yeah, I don’t want anyone I work with or near to ever be that up close and personal with my pee.

    3. Princess Consuela Banana Hammock*

      Ugh, that is not an appropriate way to do a drug test—I’m so sorry, Sunshine Brite!

      And AndersonDarling, WOW. Just wow.

  27. Jubilance*

    Re: OP#5 – with the labor market tightening up, more companies are seeing less candidates because of drug testing requirements. Some of it is mandated by law, like trucking. For other industries where it’s not mandated, I wonder what the rationale is. Perhaps the continued lack of applicants will get some of these companies to rethink these policies, at least for appropriate positions, like office work. And of course, companies should continue to test those who they feel are under the influence in the workplace.

    The NYTimes did an article earlier this year about this issue – I’ll post in comments.

    1. Noah*

      The ground handling contractor in Denver for the airline I work for has had a very difficult time maintaining staffing levels because it is hard to find people who can pass a drug test. It is not optional because it is required by federal regulation. I’m sure it also surrounds the fact that the airport is kind of out of the way in Denver and the pay isn’t great by any means.

    2. Engineer Girl*

      There are several issues in drug testing (not just illegal drugs).
      First is safety and high value equipment. This occurs mostly in transportation, warehouses and manufacturing facilities.
      Second is a need for quick response times. Tests show that people under the influence respond more slowly (even though the subjects think there is no change). In certain jobs those 2 seconds make a difference.
      Third is critical thinking. Tests show that this is one of the first areas affected by drugs. And again, the subjects don’t realize how badly they are affected. Certain jobs need you on point.
      Fourth is fine motor control.
      I want to point out that it isn’t just illegal drugs that can do this. Alcohol, migraine and pain meds can also cause an issue. The reasonable employer isn’t looking for illegal drugs – they are looking for drugs that impact performance.
      Fifth usually is about security, handling money or confidential info.
      Sixth is that certain contracts require drug free employees, usually due to the first five reasons.
      A smart HR department would advertise the requirement ahead of time so no one wastes their time applying.

      1. a different Vicki*

        A really smart employer would be looking for a way to test response time and fine motor control directly, if they were relevant: those can also be affected by fatigue and neurological issues, neither of which will show up on a drug test. If someone is going to drop the expensive blown glass teapots whether or not they’ve had any relevant drugs in the last year, a drug test doesn’t tell the employer what they need to know.

        1. Engineer Girl*

          Actually my employer used to have huddles prior to highly coordinated activities where they would check in about medicine, hunger, stress, exhaustion. That was on top of the other tests.
          And yes, it came about because someone dropped the teapots.

  28. overcaffeinatedandqueer*

    I also dislike drug testing, not because I’m pro-drugs for myself (for others, I don’t care what you use so long as you don’t make secondhand smoke- my meighbor uses pot, and the issue I have with him is that the smoke/fumes under his apartment door irritate my asthma when I go in the hall, not that he uses it), but because drug testing can reveal sensitive medical conditions and/or chronic problems.

    Then, if you fail because of medications needed for a chronic problem, or mental health, it’s easy to figure “this medication is likely for this, and I don’t want to hire a crazy/chronically ill person.”

    When I was temping, I did ask about tests, explaining I might fail due to medicines, but didn’t say what ones. Fortunately, the company did not test, because I might have failed, and then had to show my prescription; and the thing causing me to fail would have been anxiety meds, which are clearly only for a mental health condition. Could lead to discrimination.

    Maybe OP could get a medical card, and then explain that he will fail the test for medicinal drug use? Medical use is protected in a lot of jurisdictions.

    1. OhNo*

      Well, whether medical use would be safe depends a lot on the company’s feelings on the topic of marijuana. As the OP noted in the letter, since it’s still illegal on a federal level, companies are legally able to refuse employment based on marijuana use, regardless of local laws on the subject.

      That glitch aside, I’m absolutely with you on drug tests leading to other forms of discrimination. I’ve only had one job that required a drug screen, and I made sure to mention to the nurse ahead of time that I was on quite a few medications, and wanted to know what would be caught by the screen. She was kind enough to give me a list of the tests that would be done, and the types of drugs/medications that would be caught by the tests.

      I wish employers were willing to provide this kind of information before the screen as well. It would be really nice to know exactly what they’re looking for in advance, so applicants could make an informed decision about whether they want to put up with testing.

    2. Artemesia*

      Really good point. Just as blood tests by insurance companies can be used to discriminate based on genetic markers (whether legal or not), drug tests can surface anti -depressants, anti psychotics, and assorted medications for chronic conditions and be used to weed out people with on-going health issues.

    3. Emi.*

      I’ve never had to do a drug test (although I think I will for my EMT application). If it’s done by a third party, does the third party typically tell the employer “Here are Applicant’s results” or just “Applicant did not show signs of any drugs on XYZ list”?

      1. Noah*

        In my experience, it is either positive for X or negative. If you test positive and can explain it as the result of prescription drug use, it is just reported to the employer is negative. They don’t even tell them about the initial positive.

        When I was a paramedic, we usually had to take a 9-panel drug screen instead of the more typical 5-panel. I assume they were looking for narcotic diversion because we have access to them.

      2. Stardust*

        Typically third party just says “no results of drugs” back to the employer (prescription info provided to the third party lab only and then they mark as passed instead of failed). Unless a prescription cannot verify why Meth or Cocaine is in the system, then the test will say failed because of “x” drug.

    4. Stardust*

      I’ve had to take a preemployment drug test (where the job offer was conditional on passing the background and drug tests) probably for about 7+ previous jobs. It’s been very common (more often than not!) Maybe once or twice it was a urine test, but most the preemployment drug tests have just been a mouth swab (I was instructed to not eat or drink or smoke or chew gum for 30 minutes prior). In my last job, the drug test with the swab of the mouth was never touched by HR. The new hire opened the packet, opened the swab packet, was instructed to put the swab in between the cheek for so many minutes and put the swab into the container and add a stickers seal over the lid. Then the form with their name and phone number was put into a plastic bag along with the container specimen and both were sealed in another plastic bag. The kit was sent to a Lab and then the medical reviewer at the lab would call the directly to ask for prescription info. None of the prescription info ever went back to HR (just a pass-clean or a fail-for X drug). If the medical reviewer had left a message to clarify a prescription based on the results they had something like 48 hours to respond. Having a third party lab do the testing and checking on any possible prescription kept the private info out of the employers hands (unless they failed and didn’t provide a prescription for meth!) Anyway, I guess what I’m saying is if done right, the employer will never find out about anxiety meds or any meds for that matter.

      1. Stardust*

        If I didn’t say it very well, the results of any substance (prescription drugs backed up by a prescription) came back as “clean” (just passed, not details of any prescriptions).

  29. eplawyer*

    LW1 — think of it as life insurance. You sure hope you never need it, but its great to have if you do. It sounds like you and your boyfriend have some very practical conversations, which is good. Too many couples get caught up in the “but it’s twu wuv” and don’t think about what the “happily ever after” really means.

    Get a detailed agreement that lays out what each person is contributing to the new business and what happens if someone leaves the business, how profits are shared etc. Consult a lawyer. You, especially, get one of your own. Don’t just trust them to do right by you. Don’t use a form you found on the internet. The money you spend now to do it right will be worth it.

    If all goes swimmingly, you will be a millionaire and can retire at 35. If it should not, you are still protected. A business agreement can ensure that even if you do break up, you will be more likely to have a drama free break up because the agreement addresses some potential flash points (no guarantee, I do family law even with agreements people fight over stupid stuff because … emotions).

    1. myswtghst*

      I think life insurance is a great analogy. You can love someone and be in it for the long haul but still realize that sometimes things go wrong, and being practical about it when things are good is a heckuva lot easier than trying to sort it out when hurt feelings are in the mix.

  30. Linda*

    #5 I don’t feel that doing a drug screen is an invasion of privacy. If you work for a company that requires good thinking skills, I don’t want to have to work with someone who gets high each night. The test is to protect not only business owners, but customers and patients. Lawsuits are time consuming and expensive. And it won’t be the drug user that pays.

    1. Leatherwings*

      This was covered pretty in-depth above, and Alison asked us not to go into our own personal preferences on drug testing. OP is allowed to have this belief and we should leave it at that.

      1. Ask a Manager* Post author

        Thank you. This is like responding to a letter-writer who doesn’t want to accept a job with prayer breakfasts with “you shouldn’t object to prayer breakfasts.” She does object, and that’s her call.

    2. overcaffeinatedandqueer*

      But it does invade privacy for people who need tested substances for medical conditions (opiates, benzodiazepines, and steroids are commonly needed meds for chronic problems or mental health). And it’s easy enough to figure out what they’re for. So you have a choice of disclosing a stigmatizing medical condition, in effect, or failing or refusing to take it, and not getting the job. That’s my issue with the testing.

      I would have failed the tests recently; I needed steroids. But I needed to make my face stop swelling, not “get high” or dope to win the Tour De France!

      1. paul*

        I’m fairly sure most UA’s don’t even check for steroids (and your standard steroid used for swelling is corticosteroid, not anabolic and I don’t think they’d trigger the same drug test as each other).

        1. overcaffeinatedandqueer*

          That’s interesting, I didn’t understand that difference. I understood that steroids used for allergies or autoimmune are older and more widely used than anabolic steroids (I am a James Herriot fan- he was an English vet from the 1930s on- and he was using basic steroids on animals since the 50s.) But I didn’t know they were so different that one wouldn’t flag the other. Thanks!

          1. paul*

            I’m not 100% sure on how it goes, but both my brother and I are former athletes (not professional, but did compete in tested competitions) and had to clarify that ourselves since we’ve had to take steroids for skin infections ourselves.

      2. Mononymous*

        Wait, corticosteroids can cause a failed drug test? OMG. I had no idea. Guess I better be doing some research, because autoimmune disease. Ugh.

        1. Natalie*

          No comment on corticosteroids specifically, but every pre-employment drug test I’ve taken has had a space for me to identify any prescription or OTC medications I take regularly. Presumably they would want documentation of certain prescriptions, like opiates. If you are taking a medication you need that won’t actually affect your ability to do the job, I would think the ADA would protect you.

          1. Artemesia*

            Having to share the details of your chronic medical condition is hardly preferable to it being outed by the drug test. People discriminate based on health conditions when they can; this makes it easy. As long as they don’t SAY this is the reason i.e.’ Josh is diabetic and uses an anti-depressent so we don’t want the risk to our health insurance or his possible absenteeism due to depression’ they can discriminate with impunity.

            1. Natalie*

              Yes, absolutely. I’m not in favor of pre-employment drug testing for a whole host of reasons, and that’s one of them. I just wanted to mention that you have an opportunity to disclose medication, so it’s not like you have to, say, stop taking your meds to pass a drug test.

          2. OP #5*

            In my state, the ADA doesn’t protect someone with an Rx for medical use of marijuana – the courts have ruled on that previously. But, their ruling(s) was specifically about weed and didn’t cover any other kinds of Rx medications.

    3. Temperance*

      This is pretty insulting, actually, and the law disagrees with you. There needs to be a rational business purpose for the testing requirement.

    4. Ask a Manager* Post author

      If you work for a company that requires good thinking skills, I don’t want to have to work with someone who gets high each night.

      You already do work with people who get high in the privacy of their own homes in off hours. You also work people who drink every night, and people who don’t get enough sleep and are impaired the next day as a result, and so many other things that could impact someone’s work.

      Keep your focus on how people perform at work and you’ll be focusing on the right thing, not what goes on in the privacy of someone’s home.

    5. dawbs*

      Funny about not wanting to work with the person who ‘gets high each night’.
      I have chronic migraine (which is it’s own category in the world of migraines).

      There have been extended periods of time where I take some HEFTY pain drugs daily. Apparently no one cares that I take a cocktail of vicoden and barbiturates both day and night (while at home and while on the clock)…but I can’t take THC (which would likely cause less mental and physical side effects–but I don’t know, because pot is still illegal federally and I want to be employable so I’ve never tried)for that on my own time.

      If the true interest was protecting people, then I think they’d be begging me to try pot.

      1. Bonnie Fide*

        Your point still stands, but FYI you would be considered unfit for duty in my department at my company on the medications you mention (production).

        After your condition required you to be absent enough times, you would likely be transitioned into a role where being on painkillers would not pose a threat to your safety.

        If that makes you feel any better.

        1. dawbs*

          I think that might further highlight part of the drug-test problem.

          I currently have things medically under control–infrequent migraines and meds (relatively). But if I get a test (I get hair tests in my field), I have to put down any drug they might find in my system–in my field I get a hair drug test, and chances are, I’ve taken treatment meds in the last few months–not on the clock, but the test doesn’t tell anyone that.

          So I have to dump my ENTIRE medical info/drug list (and my drug list is long, because we work with a variety of meds so I can take partial dosages in order to not be as affected by meds and to avoid dependence–talk about a place where it backfires!) onto paperwork for all and sundry before I can get a job.

  31. ilikeaskamanager*

    the “legal at the state level but illegal at the federal level” makes things confusing, but the real issue is if someone is impaired at work. For this reason we do pre employment drug and alcohol screening and reasonable suspicion testing at any time. its not a perfect system, but it’s the best we have. I understand the issues with privacy, but we are up front on all our recruiting materials that you have to pass this test to work here, and we state this in every interview as well to avoid any last minute surprises. I am sure we have had candidates withdraw from the process for this reason, but at least they do it before they compromise their current jobs.

    1. Natalie*

      But pre-employment screening doesn’t tell you anything about whether or not someone will be impaired at work. You’re not checking for the most commonly used drug (alcohol) and the second most commonly used drug (marijuana) will show up even if someone has used it over the past couple of weeks, no matter what time of day it was.

    2. Jessie*

      “the real issue is if someone is impaired at work. For this reason we do pre employment drug and alcohol screening and reasonable suspicion testing at any time.”

      I had two glasses of wine last night. And yet here I am at work, functioning, not impaired in any way. Got a nice sleep, woke up on time, and here and working.

      Companies with blanket drug tests misunderstand in a really fundamental way what it is they are actually testing. The results don’t tell them what they usually think the results are telling them.

      Now, I *am* impaired by AAM. I’m commenting instead of writing a thing I need to write – but a random drug and alcohol test wouldn’t cover that. ;-)

    3. Princess Consuela Banana Hammock*

      As others have noted, pre-employment (and even during employment) drug testing does nothing to determine if someone is “impaired” (and what even is your threshold for “impairment”?). And if impairment is your concern, why does it matter whether a substance is “legal” or “controlled”?

      Unless testing is required because of the specific job—e.g., air traffic control, pilot, truck driver, national security, government contractor, law enforcement, person working with controlled substances—then it contributes nothing to the quality of your employees/applicant pool, and it discourages a lot of effective, highly-qualified folks from applying.

    4. Brogrammer*

      I’m gonna relate this to Alison’s sleep post today – medical marijuana is the only reason why I get as much sleep as I do (which still isn’t enough, but it’s the best solution I’ve found yet). I’m way more impaired after a sleepless night than I am after a night where I took a few puffs and got a halfway decent night’s sleep. But you can’t test for sleep deprivation.

  32. anonderella*

    “But life can throw curveballs that you can’t predict”

    My SO and I have been together for seven years or so, and we love each other very much.

    But last night we lost the tv remote in bed, and His Genius decides to leap out of bed and toss all the blankets I’m under high into the air – immediately the air under the blanket becomes an icy space vacuum.
    And there was an unholy volume that escaped from my mouth.

    We are lovely people, most of the time, but we accept that we’re both pretty volatile and stubborn, and we also do as the OP does, to try as best we can to pre-nup large joint decisions, or ones that impact us both.

  33. Tasha*

    I was once offered a job contingent on a favorable drug test, and was told that if I didn’t test, I could never be hired by them. I actually wanted to turn down the job for reasons unrelated to the test, but because they were a big employer in the area, took the drug test. (To be fair, it was a hospital system; on the other hand, mine was a job with absolutely no patient contact.)

  34. Lady Blerd*

    OP3: My direct report has done and is still doing overtime this year because she wanted extra days off to make extra income and to travel. I told her for 2017 and beyond, I would not be so quick to approve her doing so because I don’t want her to literally get sick becase she’s working so much or that she she’d hate her job and would resent having to come in knowing how long she’d be in the office. Unless you have some time sensitive items on your to-do list, keep you regular hours, you will eventually catch up. In fact, you could make a plan on you split your work hours to work on current items and some of the work that is held over from before you were sick. Your boss has your quality of life at heart, it will not always be the case so I say enjoy that.

  35. Justin*

    Letter 1: they’re his family first and foremost and probably won’t have any loyalty or kind feelings towards you if you ever broke up with him. And even if they were totally fine with you staying on as en employee in that case, you might not want to stay because of the inevitable awkwardness. Also maybe this is a weird bias of mine but I’d trust siblings far less than I’d trust parents, especially when family money and resources are involved. And maybe think about getting married first, I know marriages can and do end all the time but at least you might get some more legal protections for any money related to the business and they’d probably take your commitment to the business a little more seriously, you’d be “family” at least in some sense.

  36. animaniactoo*

    Late to the table here, but I think one of the best pieces I ever heard was from a divorce lawyer talking about why pre-nups are a good thing and do NOT indicate a lack of faith.

    Faith is impractical, and it’s a bad risk to take when you can ameliorate it simply be being as practical as you can about your faith. So getting married – going into business together – those are your impractical acts of faith. That you backstop by figuring out what happens if the *currently* unthinkable happens.

    And the time to do that – to decide how it all gets split up and dealt with, etc. is to do it while you both still like each other and are willing to be fair and generous to each other. So think up all the scenarios that you can now, and plan around them.

    If you ever have to use it, you’ll already have it setup and won’t be running on (negative) emotions while you try to make those decisions. If you never have to use it… mazel tov!

    1. Emi.*

      Are pre-nups a normal thing to do? I thought they were mostly for Fancy People with massive inheritances.

      1. Katie the Fed*

        they’re a good idea in a situation where you have unequal assets or earnings potential.

        We didn’t do one because we had very similar assets and our jobs are very similar, so if we split up we’ll just do a simple 50/50 split.

        1. animaniactoo*

          Actually, part of the point was that it’s smart to do one even in that case – because while that’s true *now*, it may not always be (life happens, priorities change, etc).

          Emi – So my husband and I have not alot of assets, but what we have therefore becomes even more important to each of us as all we have. He was of the “trust or don’t get married” variety, while I am significantly in the “I can trust you until the cows come home, but life changes and I’d rather be pre-pared” camp. Figuring out how to negotiate this was one of our pre-marriage hurdles. In the end, we have a marital agreement/pre-nup which gets e-mailed back and forth every few years (just reviewed, need to update with current changes), but is not an official legally drawn up document. We couldn’t afford it at the time, but I figure that it’s strong enough to show the agreement and the intent of the agreement if we ever end up at odds.

        2. Triangle Pose*

          They’re a good idea in any situation. Even if you both have similar assets and similar jobs now, things can change – one of you could incur a lot of debt, get fired, have a ton of medical expenses, etc.

      2. LBK*

        I think that’s what animaniactoo is saying – that everyone should have one, not just people with a lot of assets to protect. That seems like sound advice to me, because even in an amicable divorce the process of divvying up assets can be long and stressful when you just want to get it over with.

    2. Kai*

      This was exactly my thinking on the matter when I got married! I wanted to set something up that would be fair to both of us, while in a mindset where I’m feeling loving and generous, just in case things went horribly wrong one day. It’s rather romantic in that sense.

      (In the end we didn’t need a pre-nup, based on the laws in our state and the fact that neither of us have major assets, but still.)

    3. Jules*

      Remember Jessica Simpson and Nick Lachey. They went into the marriage where he was the successful one and her dad thought she didn’t need one. When they divorced, he gained a nice alimony because she was out earning him.

  37. Jules*

    #5 AAM, does it matter if he/she works in a conservative environment/small town/city/limited geographic area? Because of where I am, we might not meet each other professionally daily but word gets around. Should someone be concerned about their professional reputation if they say, “I object to drug testing on privacy grounds, so I’ll need to decline the offer.” I am not a user but both my spouse and I agree that for office worker, really non of anyone’s business unless they do it on premise. And yes, we are in a state where marijuana is legalize for medicinal use.

    1. Ask a Manager* Post author

      It depends on how comfortable you are owning your opinions and values. In my experience, supporting privacy rights and civil liberties hasn’t been hugely controversial, but if it is in your area, you’d want to factor that in.

  38. kittycritter*

    OP – why don’t you just use that synthetic urine they sell in head shops? Hasn’t failed me yet!!

  39. Long Time Reader First Time Poster*

    #5 I work in an industry where drug testing is not the norm. In fact, I sometimes joke that smoking weed is generally a requirement of the job. I live in a state where recreational marijuana is legal, FWIW.

    I’ve only been tested once in my entire career (and it was for a summer job at my dad’s company when I was in college, so I kind of had to take it), but if a potential employer asked me to pee in a cup I’d say no.

    The kind of company that is up for that kind of invasion of privacy is not a company I would want to work for.

  40. Jane D'oh!*

    Thanks to a bad experience, I now ask about the TYPE of drug testing being done when applying for jobs. Years ago I was looking for work about 8 months before my wedding, and ended up having to submit a hair sample. The employee processing me was an incompetent moron, and she cut an inch-wide chunk of hair from the base of my neck! My hair was halfway down my back at the time. I went home and cried, and ended up with a stub that was nearly impossible to hide in my up-do. It’s been 15 years, and I’m still angry about it.

  41. jaxon*

    I’ve been thinking a lot about the topic of #3’s question – how do you get all the work done when there’s a backlog you aren’t responsible for? I was promoted into a role where I’m doing the jobs of 2.5 former employees, and I have been actively pushing back against all new assignments. It’s really, really hard to figure out how to actively manage the workflow, and that process of actively managing workflow effectively becomes 20% of my job, which is 20% LESS of my time I can devote to actually doing the work that’s continually backing up. It’s a paradox that I am really stuck in at the moment.

  42. sarah*

    For OP#1 – Alison’s advice is great, and I would also add – try to be as practical as possible about what the “worst case scenario” really is. I will never forget the massive eye roll I had (privately, not to her face) over a friend who decided to start dating her roommate, and then later after they broke up, he immediately started bringing home a different woman every night of the week. She — in all seriousness! — told me “I thought the worst case scenario of dating my roommate would be that we’d have a friendly breakup and then one of us would move out when the lease was up! How could this have happened!” Meanwhile, I’m privately thinking “Hm, that sort of sounds like the best case scenario here?” Obviously you don’t want to think about the fact that your boyfriend (or you!) could cheat or that something else could happen to lead to an extra hostile breakup, but the reality is that most people never see those things coming (or else they wouldn’t get in the relationship in the first place). And yet, they do happen to some people. So, better to be prepared and not need the preparation than the other way around, especially since presumably there is some reason you guys have decided not to get married despite a very long period of dating.

  43. The Strand*

    #1, Please work with them as a contractor only. Somebody told me many moons ago, when I first considered opening a small business, that you always need to consider that business partnerships almost always end, and that figuring out how you’ll part is as important as how you’ll start. It doesn’t mean you don’t still like each other, but your interests change. Maybe one of you wants to retire, or just sell out your share. When you’re family or close friends, this becomes even more difficult.

    Even if you are an experienced professional, very comfortable being straightforward, direct, and kind with business matters… that doesn’t guarantee the family member or close friend will be. It’s just business, except it’s not – your friend or family member may not be able to separate the business needs from their ego, or self-worth. Less mature people may even threaten your personal relationship continuing if they don’t get their way in the business. It seems like half the episodes of Marcus Lemonis’ “The Profit” revolve around family or friend businesses that can’t work because of the relationship, not the business plan.

    #5, You mentioned professions where you agree it’s OK. If a particular profession is central to an organization’s bottom line, my experience is that you can’t ask them to budge one inch, fair or not. Every time I have ever been drug-tested, it was for a position at a hospital. I never got near a patient, never treated a patient, nothing to do with my job. But I was held to the same standards as a doctor, nurse, or other provider. I’m guessing a place like a railroad or a trucking firm would be likely to have unyielding standards.

    1. dawbs*

      FWIW, some of the things like trucking firms and bus drivers have federal rules on drug testing.
      If you want to make your head hurt, you can see what the DOT says in “49 CFR Part 40” (IANAL, nor any sort of expert–but that’s what it’s called on the DOT’s website, so I assume that’s the real info)

    2. kittycritter*

      I’m an IT worker – Peoplesoft business analyst – and every IT position I’ve ever held has drug tested as part of the onboarding process, which I think is ridiculous. If I want to smoke a bowl a few nights a week before I go to bed, that’s nobody’s business. As long as I don’t get high before I go to work (which I would never do, that would be extremely unpleasant, not to mention a waste of good chronic!), then I don’t feel I have wronged my employer. I can’t believe it’s 2016 and we still have this outdated, exaggerated fear of marijuana – placing it in schedule 1 with heroin, LSD, and the like.

  44. One Handed Typist*

    #1 – ANY business – especially family businesses!! – should protect against the 5 Ds (as Dave Ramsey calls them). Default, Death, Debt, Disability, and Destruction. There’s other “D”s that can pop up – drug use, disinterest, divorce. What if boyfriend’s sister gets a divorce and her ex is insisting on claiming half of her portion of the business as community property? What if his brother is married and the wife goes on a shopping spree, sinking them into debt? Or sister’s husband gets caught up on prescription pain killers or alcohol? Or if sister is in a horrible car accident that prevents her from working? The family could easily lose everything if just one thing happens. That’s why you take the time to talk it out, make decisions when those situations and the stress aren’t pounding you down. Put it all down, have an attorney review it, then start the business.

    #4 – I feel for you, OP! Is it possible to temporarily train an existing employee or two as backup to just a few of the job duties?

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