what do I owe my long-time employer when I quit?

A reader writes:

I have been working for the same small law firm for almost 10 years. It once consisted of me, a billing assistant, a paralegal, a receptionist, and the attorney. Over the last three years, all of the other employees have quit and my boss has failed to replace them. He did attempt to replace our accounting and billing person – first with his wife, then with his former babysitter, then a friend, all of whom had zero experience and worked just long enough to screw up our records and quit. This took place over the course of about a year and half, during which time none of them ever truly took on all of the work that they should have and I was expected to train and assist each new hire, while also making sure what they never got to was completed. When they failed, he allowed me to hire an administrative assistant who was an unmitigated disaster. She lied on her application and in her interview and refused to accept that she made mistakes or correct them. It’s been been seven months since we fired her, and he has only attempted once to hire someone to replace this person – another friend with zero experience!

Part of the reason that I’ve tolerated this is because we’ve been together for so many years. I know his family, have seen his kids grow, was there when his father passed away, etc. On his side, he was there when I was diagnosed with cervical cancer, when my fiance was hurt and out of work and I had to leave work early to take him to four doctors a week and when I got the call that my grandmother had passed and was so upset I couldn’t drive – again, the list goes on.

The other reason that I haven’t left, despite my ever increasing unhappiness, is that I am getting married in two weeks and will be taking half of the month off for my wedding and honeymoon. I took a lot of personal time this year, knowing that no new company would have allowed this, and basically sucked it up so that I could have everything I wanted for my wedding and keep a stable job.

When I come back I know what I will face: he’s already decided against temp help so mail will be unopened, checks written without using the system, deadlines missed, and emails unanswered. I gave him a list of things that need to be done while I’m gone and asked him if he wanted to go over what we need to get done before I leave – he said no. He has all but said he’s going to try to wait it out and do nothing until I get back. I am simply trying not to think too much about it so I don’t stress out during my whole trip.

I know him well enough to know what will happen when I get back and when he waves his arm at the disaster that he’s left me and laughs, there is nothing that can stop me from quitting.

So my question is twofold: 1. As an employee of 10 years, what do I owe my employer as far as notice? I do literally everything in the office and I don’t think he could learn what I do in two weeks and there is definitely no way that he could hire someone within that time frame and train them to do everything that I do. At the same time, I feel like if I give him too much notice he will assume that he can just put it off and I won’t leave. 2. Should I tell him all of the reasons why I am leaving, or just leave it with a general “I don’t believe there is any further opportunity for me with the firm and it’s time for me to leave”? If I listed all of the reasons that I feel I am being taken advantage of it would be just as long as this letter is now, if not longer, but I don’t want to sound like a psycho either. Help!

You can read my answer to this letter at New York Magazine today. Head over there to read it.

{ 85 comments… read them below }

  1. Whats In A Name

    I think one of these two is your best bet: “It’s been tough for me to juggle everything in the last few years with what’s happened with the billing, paralegal, and receptionist positions, and I can tell I’m burning out.” Hell, you can even say, “When I realized I was spending my honeymoon dreading the chaos I’d be coming back to because there was no one to cover for me, I realized it was time for me to move on.”

    I don’t see a reason to give a long list of all the issues, but I do think one of the above statements will give an honest summation of why you are quitting and maybe will open the door to more conversation. The way he laughs you off sounds almost brother-sisterly and maybe there is a line that has been crossed that he can’t go back over. Or maybe he hasn’t realized how unprofessional his behavior and the office dynamic have become and there’s room for change to happen.

    It’s not going to be an easy conversation by any means but I think you should at least open the door with one of the above. I definitely do think you should NOT let him guilt you into staying any longer than a notice that you are comfortable giving. I definitely don’t think you “owe” him anything. But you do need to speak up to some extent.

    1. Princess Consuela Banana Hammock

      Ditto, and I definitely would not provide a list of reasons for why you’re leaving. OP, if he asks for feedback, and you think he can hear it without it negatively affecting a future reference, then I would do an exit interview with him instead of putting it all down on paper. But it sounds like conveying your reasons won’t necessarily help you or him (assuming he’s non-receptive, which sounds like the case).

  2. Sarah

    Personally I would not bother about listing the reasons you’re leaving — either your boss knows and does not care (because it’s really obvious based on all the issues you describe!) or he is willfully blind to the situation — with all the evidence of dysfunction before him, I don’t think one more conversation is going to change his mind!

    I can’t tell from your letter whether you are planning to look for another job after you get married and quit or whether you’re planning to take a break from working for a while. Depending on which one, I think you can easily use either as an excuse here. So, either “I’ve accepted a position at Place X and I start on February 1” or “My new spouse and I have decided it makes sense for our family for me to stay home right now.”

    1. Jersey's mom

      Boss already knows all the reasons why you’re leaving.
      “I gave him a list of things that need to be done while I’m gone and asked him if he wanted to go over what we need to get done before I leave – he said no. He has all but said he’s going to try to wait it out and do nothing until I get back.”

      If you give him a list, he will nit pick it, and you, to pieces. He already knows the problems and has not seriously tried to fix them since you are there, bending over backwards to fix the problems.

      And yeah, I understand that with the ‘personal’ relationship, it seems to make it harder for you to quit with two weeks notice. But think about this; has he bent over backwards to try to fix things? Hell, you’re leaving on your honeymoon and he’s already made it clear that he won’t do a damn thing – leaving a huge urgent mess for you to clean up when you get back. A real friend does not do that to a friend. He’s not your friend. You’re “closeworkers” who are tangentially involved in each others personal lives. Trust me, 6 months after you’ve quit, you will not hear from him or his family, get any cards or calls…….

      It feels like there is an emotional friendship bond here, but there isn’t.

  3. Q

    You owe him nothing except two weeks notice. What if you decided to just stay at your honeymoon location forever? He’d make do.

    However, if you’d be willing to stay with more help perhaps an ultimatum would work. Tell him if he does not have a competent admin assistant and other position (or whatever you need) by a certain date, then you will be submitting your notice. It lets him know you are unhappy and seriously considering leaving but it also gives him last last chance to make it right and hold on to you.

    1. Morning Glory

      “What if you decided to just stay at your honeymoon location forever? He’d make do.”

      Well sure, but if she’s been there 10 years, he’s probably going to be a really important reference for her. It can be as much about burning bridges as whether he would make do.

    2. Princess Consuela Banana Hammock

      I’m not sure an ultimatum is a great idea. So far, neither common sense nor personal loyalty has moved this attorney to hire adequate (or even qualified) support. Issuing an ultimatum immediately makes the relationship adversarial, and as MG noted, the reference of a 10-year employer matters. But more importantly, it sounds like OP wouldn’t want to stay even if he met the terms of her hypothetical ultimatum (hiring additional support) because he’s not focused on hiring for quality/competency. The fact that she has a letter-length list of reasons to leave is also not a great sign—it doesn’t sound like her boss can turn things around with/for her.

      But you’re right that she should evaluate if she would stay if he made significant changes. It might impact how she frames her decision in terms of the amount of notice she gives, etc.

      1. HYDR

        Does he realize that he is sinking his own business, the one that he has worked his entire career to build? Does he want to retire but does not see a way out, so he is just ignoring everything? It seems like there are underlying issues there.

        It’s tough to just leave your work/job behind, but you need to rip the band-aid off. Hopefully by you leaving, he will realize that he needs experienced help to get back on track.

        1. RD

          So often attorneys see their businesses as a calling instead of a business. They don’t see themselves as businessmen, and therefore do not cultivate the skill set to run it as a business.

          Obviously that’s a broad generalization. I’m sure there are many attorneys who run a tight ship, but I have seen it happen where private practice attorneys get so caught up in the legal work that they forget to bill or collect or market.

          1. SpaceySteph

            My dad is a Dr and has a whole soap box speech about how they should teach more business classes in med school. So many Drs just want to practice medicine, but fail to realize that they need to run a small business to do so. Even if they truly don’t want to profit, you can’t provide an acceptable standard of care if you can’t pay for rent and electricity and equipment and staff.
            It seems the same goes for law school and lawyers like this guy.

            1. Teclatrans

              Yup. Ditto for the massage therapists and family therapists and occupational therapists I have known. I imagine this can extend to plumbers and carpenters and etc. You study to do the thing you love, and then you have to build a practice (unless you want to work as an employee, which is sometimes not possible and often less desirable), and business acumen is hard to come by, and running a business often feels antithetical to the service you provide. If these folks wanted to be entepreneurs, they probably would have started other sorts of businesses.

            2. Mrs. Fenris

              Veterinarians too. Animal hospitals are incredibly complicated businesses, and unless they got their business knowledge elsewhere, vets have zero training in how to run them. And boy, does it show sometimes.

          2. Cafe au Lait

            My Mom’s a photographer and started her own photography business a couple years ago. She loves the photography side and hates hates hates the business side. I feel that there’s a market for a general small business managing company. Much like a temp agency but perhaps a bit more involved in the weekly operations of a small business.

            1. Crazy Canuck

              Yes, there is a market, but I wouldn’t recommend chasing it. I started up a bookkeeping business about ten years ago aimed at helping entrepreneurs and other small businesses. It lasted a little over a year. As a group, they didn’t understand how many hours it takes to run a business properly, and I had nothing but headaches collecting on my invoices. They were getting the 25+ years experience the two of us had at about a tenth of the salary for just one of us, and they still bitched and moaned about how we were personally bankrupting them. Never again.

  4. Emily

    You don’t “owe” him anything. Sure, you’ve been employed by someone who by your account has been a decent boss and human being (even if he wasn’t very skilled at managing the business of maintaining his staff). But in exchange, you’ve performed your job well and in the face of adversity, correct? So, you guys are even in that regard! No owing/guilt necessary.

    A standard 2-4 weeks notice is fine. No need to try to make him understand, acknowledge, or accept your reasons. If he were the kind of person who would respond to and change because of them, he would have already done so, as these aren’t guarded secrets you’re holding on to, right? “I’m ready to move on,” is a good enough reason.

  5. F.

    “Working at a very small, very dysfunctional business can limit you if you stay there too long, because you tend not to get the sort of feedback, opportunities for growth, and reputation-building that you can get if you’re working somewhere more functional … and sometimes the experience you get is so steeped in the dysfunction of the place that it’s hard to make it translate to other settings.”

    Take it from someone who has let it go on for so long that they are too old and have too much experience to find another job: GET OUT and DON”T LOOK BACK! I will be at my dysfunctional, small company for 10 years this year. When I took the HR manager position for two years, we went through four failed replacements for me at the office manager position, so I ended up doing both positions (plus most of the unfilled safety manager position) for the better part of the two years, and it nearly killed me. They finally replaced me at HR manager, and I returned to being only the office manager.

    Your current boss is going to try to contact you and beg you to help him out. He will want you to train the new hire and be on call for questions after you are gone. I strongly suggest that you do not do it. This was a professional relationship, even though it did cross over into a personal one. Be prepared to walk out the door on both aspects of the relationship.

    1. the_scientist

      I fully agree with this. My first post-graduate school job was in a small organization. It’s so tough when you have that kind of personal rapport with your boss and feel some loyalty/responsibility, especially if you’ve supported one another through various challenges (my boss at this organization had a number of difficult personal circumstances crop up during the time I worked there, and relied heavily on our small team for logistical and emotional support). But at a certain point you need to prioritize your own mental and physical health, as well as your career trajectory. As Alison mentioned, there are a number of pitfalls to working in a small organization; having moved to a much larger organization was, I can say, a really smart move for me career-wise: I have access to mentorship, training opportunities, professional development support, promotions and internal job opportunities. I didn’t have any of these things at that smaller organization. Plus, there are clearly defined organizational structures and hierarchies in place to mitigate the chaos.

    2. ST

      “He will want you to train the new hire and be on call for questions after you are gone.”

      Consultants hourly fee much higher than regular salary!

      1. Elizabeth West

        Yes–but if OP doesn’t want to do this, I would sit down and make a really good SOP document for the incoming person. I normally like to do that anyway, but if I worked here, I would consider it vital. The poor next person will need it.

      2. periwinkle

        Based on what the OP has told us, I wouldn’t expect the boss to know how to process a consultancy payment, let alone get around to doing it.

    3. Bwmn

      I could not agree with this more.

      I was at a nonprofit where I was the only fundraiser and felt hugely hung up about not being able to “just leave”. So I gave 3 months notice. Honestly, giving that much time almost seemed to lull them into a sense of “this isn’t happening” and when my final two weeks rolled around everything was still as hectic if I’d only given 2 weeks.

      When I left, I was also returning to live in the US from overseas – so the extra time ultimately helped me out. And similarly when they hadn’t found a replacement, being able to stay on as a consultant also helped me out – but by the time I had a new job, they were still deeply dependent on me.

      When you work somewhere that has blurred professional boundaries and that level of dependence – you just need to set firmer boundaries.

      1. Not So NewReader

        Similar story here. A friend had been at her job for decades. She knew it like breathing. She gave six months notice. They hired someone to start a week or two before the date. TPTB sincerely believed there was nothing to the job. The first person lasted maybe 5 months. My friend agreed to come back and train for an hourly rate. When they had to hire another new person my friend was tired of training. Oh well.

        Lack of planning and forethought on one party’s part, does not constitute an emergency on your part, OP. If you wanted to you could spend the rest of your life bailing this lawyer out. Honestly, I would be done with the job when he showed lack of concern for your staggering workload. Crap happens and sometimes workloads get overwhelming. The proper response is to say thank you, not laugh at the employee/situation. In that moment he told you everything you need to know.

    1. Adam V

      Yeah, if there’s two weeks left, you could do that – just tell him “I’ve decided not to come back after my honeymoon, so this is my two weeks’ notice.”

      But then, you might remove the “I have to go back to that crazy business” stress from your life, but you’d add the “I have to find a new job as soon as I get home” stress. I personally would probably keep the paycheck and just go in every day saying “not my problem, not my problem” to myself.

    2. Ann O'Nemity

      Financially that may be hard, especially if quitting negates the PTO. And this isn’t the ideal time for the OP to be aggressively job searching.

  6. AnonForThisOne

    I know these feels.

    You need to accept that, whatever happens when you’ve left or even when you’re on vacation, it’s not your responsibility to worry about the state of things in the office. Much easier said than done, especially when it’s almost guaranteed you’d be coming back to a mess after your honeymoon, but it sounds like you’re using that fact to fuel your departure from the company anyway, which is probably a good move, all things considered.

    I’ve spent more energy and time than I can tell trying to train people for my department who just don’t end up working out, and whenever I think “Hey, maybe I can start job-hunting now, safe in the knowledge that my department will be left in good hands!”, wham! Something happens and that person is fired or quits. I’ve had to come to the realization that there will never be a perfect time to leave, and that it probably will cause quite a gap to be filled and hassle for others, but to the extent that I’m not increasing said hassle (letting work pile up before I leave, not bothering to document anything, etc.), that’s just Too Bad, and they’ll find a way to cope.

    Perhaps three weeks, or whatever little extra might show goodwill, would be appropriate here given your long history. But beyond that, hold firm, because it sounds like there might be a fair bit of flailing around at the thought of you not being there anymore. Breathe, keep calm and repeat: It’s no longer my problem!

  7. AndersonDarling

    Two weeks, four weeks, or two months notice, I doubt the boss will do anything productive with the notice period. He will wait for the last day and ask all pertinent questions, or will just expect the OPs replacement to figure out everything when they start.

    1. SpaceySteph

      Depending on the nature of your workload, you might consider taking some of the notice period to document how you do your job.
      It isn’t required or owed, but it might help the next person figure it out and would probably be a kindness to both the new person and the boss.

    2. BRR

      I agree with all of this plus I think no matter how the LW prepares, it’s likely the boss will keep calling them with questions. I would read through the letters on that topic.

  8. NK

    If he asks you to give a longer notice period, weigh very carefully the pros and cons for you. My husband left his job, which included turning down a counteroffer. His boss pressured him to increase his notice to 4 weeks to give him time to get someone else in. Luckily his new company was fine with it, so he agreed to it. Sure enough, boss dragged his feet on hiring anyone, so the extra time really just felt like a power move on his part. It might have been worth it if he thought he could get a good reference out of it, but his boss repeatedly stated that per company policy he’d never be able to give a reference beyond confirming dates of employment (which is total BS). So in short, he spent an extra two weeks at a job he hated which didn’t even come close to accomplishing its stated purpose, and got nothing in return. A couple years later he’s still annoyed that he did it when the subject comes up.

  9. Captain Radish

    This sounds very similar to the disfunctional business I recently left. I worked for the same guy for almost seven years and he generally treated me pretty well. The problem was ultimately I ended up doing pretty much everything. I was the IT head, I covered service calls, I did all installs (for however many there were), I managed the warehouse, I did everything. It got to the point where I was so burned out I wouldn’t show up to work until 8:30 or 9 because there wasn’t any real point in doing so and I stopped caring about the probably failing business.

    I quit (and gave three weeks notice because I dredged up feelings about my boss) and haven’t felt bad about it since.

    1. Captain Radish

      I forgot to mention he later became such a pest I had to change my cell number. Fortunately for me I got service through my new company.

      1. AndersonDarling

        That’s what I fear for the OP. No matter how much notice she gives, the boss won’t use the time and will call her constantly once she leaves.

        1. Anon for this

          This exactly. This is my fear leaving my current job.
          I expect I’m going to have to seem like a jerk at some point, and just stop responding. But I don’t want to burn the reference since I’ve been here pretty much my whole adult life. Wish me luck.

          1. Captain Radish

            Very fortunately for me my current job didn’t check references as of the two places I’d worked up to this point one was bought out and one was disfunctional.

  10. Parenthetically

    My thought throughout this was that it isn’t doing him any favors for you to stick around. Better for him to experience the consequences of his actions without you there to be a buffer. Document your tasks, and walk out the door knowing that he’s ultimately going to have to stand or fall on his own two feet.

    My dirty lens is this: a good friend of mine worked in a similar situation where she was admin, accountant, PA, errand girl, office manage, supply organizer, cigar-end-picker-upper and general nose-wiper for the three men in the office. It took her giving notice and then leaving the job for them to get their crap together. Now the office is much larger, and MUCH more professionally-run, because they realized that they had been taking advantage of their long and close association with her, and asking this extremely competent woman to do things no other employee would agree to do. It’s better now BECAUSE she left. Maybe it won’t be a wakeup call for this guy (I don’t have the highest hopes given his track record of not replacing employees), but maybe it will. Fingers crossed.

    1. k

      That is the outcome I would hope for. Boss has been using OP as a crutch; why hire 3 more people if OP will just do everything? When she leaves perhaps he’ll finally be able to see why he needs to hire multiple, competent, qualified employees.

  11. BRR

    I feel resignations have been poorly portrayed by the media. Your resignation only needs to include that you’re resigning and when your last day is. It might feel like you’re leaving a business in a lurch but people coming and going is natural. You also don’t have to do some sort of confessional. You don’t have to say anything at all although if you need this person as a reference you’d likely be burning a bridge. A simple, “I’ve been here for ten years and want to pursue other opportunities” is enough.

    For you specifically, don’t feel bad about leaving him with no help. It sounds like he’s made his bed and now has to lie in it. Are you sure you want to quit with nothing lined up? It’s much harder to get a job without currently being employed (even though it shouldn’t be). I’m going to bet he won’t act on hiring a replacement and will try and get you to stay longer. Do not let him guilt you. It will never be “just one more week.”

  12. Barney Barnaby

    Am I misreading this, or does the OP intend on leaving without another job lined up?

    I would think that the better solution would be to job-hunt after her honeymoon, and then give two or three weeks notice. She benefits in several ways: job hunting is easier when you have a job; she won’t have to explain to potential employers that she quit her long-term job right after her wedding (which, since sexism exists, could make people think she’s not committed to her job); and there won’t be an issue of “I feel like if I give him too much notice he will assume that he can just put it off and I won’t leave,” because there’s that shiny new job lined up.

    It’s not clear from this letter if the OP is an attorney, a paralegal, or what-have-you. If she is an attorney, she can also explain that a dysfunctional office environment puts her at risk of professional malpractice issues (missed deadlines, etc.). If her boss wants to take that risk, that’s on him, but it’s completely reasonable for her to not do so.

    1. Partly Cloudy

      “…job hunting is easier when you have a job…”

      Not necessarily. As long as you maintain your network of contacts, job-hunting without a job is easier in terms of scheduling interviews and the time and effort of filling out applications, writing/tweaking cover letters, etc. Job-hunting itself can be a full-time job.

      1. Natalie

        And a draining job can often be more than full time – outside of work, you aren’t left with much energy for job hunting.

    2. Natalie

      “she won’t have to explain to potential employers that she quit her long-term job right after her wedding (which, since sexism exists, could make people think she’s not committed to her job);”

      I’m not sure how future employers would ever know about this?

      1. Not So NewReader

        I think when her resume shows all the different responsibilities she had the new employer will be able to figure it out.

    3. CanCan

      +100

      (Assuming you’re a lawyer. I was a junior attorney in a small firm, with one partner and one other associate, so I can imagine your situation, – except that we had about 15 support staff!)

      Except that I wouldn’t be so explicit about a “dysfunctional office environment.” This may not be true everywhere, but where I’ve worked, badmouthing another lawyer is frowned-upon. Regardless of his bad organizational skills, he’s a “senior partner” in the eyes of others. The same message can be given as a hint: no administrative support; having to perform the duties of a legal assistant, receptionist, billing clerk, etc. means there is little opportunity to grow your own business in the firm.

      However, unless this situation really is putting you at risk of professional malpractice, I would stick with it until you’ve found a job. Figure out a way to balance your workload – i.e. tell your boss that you won’t be able to do reception, bookkeeping, etc. any more, because you don’t have enough time to manage your own client load. If he insists that you prioritize that other work, tell him that you’re going to have to reduce your legal work. Have a discussion about which files/clients you’re dumping onto him / declining to serve as a firm, etc.

      1. Barney Barnaby

        I should have been more clear: that’s something she can explain to both prospective employers and her current boss.

    4. SarahTheEntwife

      Why would she mention her wedding to employers? I mean, yes, that would absolutely be an unfair red-flag in many interviewers’ minds, but only if she told them rather than just giving the not-particularly-noteworthy explanation that it was time to move on, plus maybe something neutral about staffing changes no longer makin the job a good fit.

  13. Workfromhome

    I think the OP has already repaid any good will the owner might have earned by being a decent human being. Doing the work of 2-3 people for so long more than “pays” for anything that might have been given (time off).

    If you plan to job hunt after you return than job hunt and give 2 weeks once you land a new job. If you don’t care about/need immediate employment after the wedding then I say write you two line resignation letter now and put it in a drawer at him. Your wedding and honeymoon will be so much more enjoyable if you know that the day you come back you will be giving notice and only have 2 more weeks of hell. You can spend that notice period catching up on all the work that piled up without worrying about the future work piling up while you catch up..you wont be there when it does!.
    Its really perfect timing for the OP. A big life change in marriage, two weeks off to think about the future and discuss the future with your new partner. Its perfectly logical that this might be the time you choose to leave .

    You owe nothing more than 2 weeks notice and to be at least respectful in your resignation. “I have decided that now is an appropriate time in my life and career to move on. My last day will be two weeks from X. I appreciate the opportunity over the last 10 years” DONE

    Unless you are desperate for $ I’d be sure to only respond to brief critical questions for the first week after your notice (IE You changed the password for the accounting system last week and no one else knows it). After that I’d just ignore any attempt to draw you back in.

    I really don’t see a path for you to work for this person again you will always be seen as the person who will make sure things get done no matter how much effort it requires. There is a good chance that the place just completely falls apart once you leave.

    1. Not So NewReader

      Depending on the boss, it could be that no matter how much OP explains all she has done for him, he still fails to understand. OP, remember your goal is to get out of there, not to make him understand. If he has not figured it out by now, then he will be quite a while longer sorting things. Build yourself a new life with your new spouse.

  14. Seal

    Alison’s advice with regard to part 1 of the OP’s question is great. People really don’t seem to understand what they should do once they give notice. Those last few weeks on the job are your last chance to make an impression on your soon-to-be-former colleagues. Do you want to be remembered as someone who worked hard to make as smooth a transition as possible or the asshole who slacked off once they gave notice?

    For that matter, make sure you clean out your desk and take ALL of your personal stuff with you; if you don’t want it, toss it, recycle it or give it to someone else. I am regularly irritated and astonished by what people leave behind when they quit their jobs. Your former coworkers shouldn’t have to dispose of your porn. Not that I’m implying that the OP has porn stashed in her desk! But a former coworker of mine did. I truly did not want to know why.

  15. Stellaaaaa

    Plan any other trips or time off now and then see where the best buffer period seems to fall. Your boss is basically your only relevant reference and he allows you more time off than you’re bound to get from a company that’s better in other regards. So enjoy your benefits now but I’d say commit to a four week notice period.

  16. Chriama

    One thing I’m wondering about is it sounds like the boss was responsible for doing the hiring and he did it wrong. What if you did it? Are you comfortable with presenting an ultimatum where he gives you a budget for hiring help and leaves it to your discretion or you leave?

    I know that Alison says you’ve been there for a long time and it’s time to move on in order to make yourself more marketable overall, and I somewhat agree with that. But I also know that depending on where you are in your career, and how close you are to retirement (financially, not just physically/mentally), you might just want to stay here forever. If that’s the case then maybe you can get a little more proactive with your boss to make this a place you want to work at forever.

    Another option if you want to leave but aren’t sure when and don’t want to leave him in the lurch is to get proactive about your succession plan. Maybe the next 2-3 months are you finding replacements and training them for you to leave. I know it’s a huge commitment and not one that you should feel obligated to take on. And if you just want to make a clean break and are worried about making well intentioned but ultimately unfeasible promises then you should just go.

    I’m just trying to point out that there’s a middle ground between giving 2 weeks notice and continuing to suffer at job that’s burning you out.

    1. TootsNYC

      As I mentioned below, I’d try to wrest the hiring initiative from him, get him to approve it, and hire at least one person.

      And I’d still leave.

      I wouldn’t make it an ultimatum; I’d just make it that we were getting another person for the good of the business. And then I’d meanwhile be looking. Then when I do leave, he’d have at least one person already on hand (or nearly so) to help him out.

  17. Person of Interest

    Sounds like the most important thing would to be give enough notice that you feel like you have enough time to fully document everything for the next person (or so that your boss to pick up key tasks). Take it from someone who left an 8-year job under a ton of stress – it helped a lot to know that at least I had written everything down for them and didn’t just take all that institutional knowledge with me. Even if your boss lets some things fall apart after you leave, you’ll rest a lot easier knowing that you did everything that you could reasonably do to prevent that.

    1. TootsNYC

      You can also start documenting as you go, even now. Doing it while you’re working is usually a good way to not miss something.

  18. SadieMae

    In general, with a boss and a situation like this, I wouldn’t go into detail about why you’re leaving. He doesn’t sound like a very self-aware person, and I doubt he’d take in much of what you said anyway. Generally, I’d just say, “I’m ready to move on.”

    BUT. I wouldn’t do that in this particular situation, and here’s why: A lot of men assume female employees will quit the moment they get married, and you don’t want him to think that’s the reason you’re leaving just because of the timing of your departure. You’re going to want him as a reference, and the way you’ve described his dismissive behavior, I’m imagining him talking to a potential employer: “Women, amiright? What are you gonna do?” Grrrr.

    I think I would tweak the truth a little (he doesn’t have to know how long you’ve been considering this move) by saying, “Boss, when I came back from my honeymoon and realized nothing had been done in the office for two weeks, I realized I no longer want to be in this job, where responsibility falls disproportionately on me. The turnover we’ve experienced these past few years, and the fact that many new hires haven’t been qualified for their positions, has put a lot of pressure and extra work on me, outside of my regular job duties. So I’m going to move on to a position with more clearly defined duties. My last day will be (date).”

    And then stick to your guns – no response if he tries to guilt-trip you into staying in general, or staying another week, or coming back after he finally gets around to hiring someone, so you can train him/her. If it were me, especially since you don’t yet have a job lined up, I’d give him a full month’s notice, during which time you can be getting your resume in order, brushing off the old power suit, and job-hunting in your spare time. And then if he hasn’t hired someone by the time you leave, you know you gave him more than enough time, and you can leave with a very clear conscience. Good luck!

    1. Parenthetically

      I loved someone’s idea upthread of responding to, “Come back and train your replacement!” with, “Sure thing, my hourly consultancy rate is $XX.”

    2. TootsNYC

      I’d start right now by just making comments frequently. “Are we going to hire someone?”
      “This would be so much more streamlined if we had an office manager.”

      Just constantly make it hard to hide from, that you’re overworked.

      Then when you leave, he won’t be surprised. And maybe he’ll take a hint.

      1. Zombii

        Don’t hint. Don’t “if..”. Don’t ask. Passive-aggressive tactics in the workplace are a pet hate of mine and I’d like it if anyone who expects to be taken seriously as a professional would stop it.

        Tell him directly that someone else—someone qualified and competent—needs to be hired. Yes, that means checking references. Yes, that means a longer search than calling up a random friend or family member or a previous babysitter, but the quality of your support staff should never depend on blind luck.

  19. Chickaletta

    I’m curious what happened to make most the employees quit within three years of each other, and how the boss isn’t able to replicate his hiring of them, assuming he was the one to hire nearly half a dozen competent people in the first place.

    There’s more the the story, I bet.

    1. Chaordic One

      Exactly? It sort of sounds like the employer’s practice might be having financial problems and he is afraid to (or unable to) hire competent professionals (or even trainable people) to replace the ones who have left. Yes, I’m speculating, I know.

    2. Zombii

      Where does it say any of them were competent? I read that he hired LW, a billing assistant, a receptionist, and a paralegal. It was my impression that a lot of paralegals go on to become lawyers, so not necessarily anything wrong with the business to explain that one. If the paralegal left first, I could see a chain reaction where the receptionist, LW and billing assistant then became responsible for the paralegal’s work. Then either the receptionist or billing assistant got fed up and found another job, repeat process until it’s just LW.

      It mostly sounds like the attorney just hired.. whoever, and got really lucky with the batch the LW was hired into. Then he couldn’t replicate the good luck, and quit trying.

  20. Mobuy

    I wasn’t sure if the OP has a new job, wants to look for a new job, or wants to stay home. If she has a new offer, two weeks is fine, as everyone else has said. If she wants to look for a new job and she has a good relationship with her boss, she could let him know she’s looking, ask for some time off for interviews, and promise to give him two weeks when she has an offer. Meanwhile, of course, she would be happy to train a new hire, wrap things up, etc.

    The advantage here is that she doesn’t feel like she is leaving her long-time boss in the lurch but also has income until she finds a new job. The disadvantages, though, are that he could be resentful, push her out (doesn’t seem likely since she’s the only employee!), or give her a poor reference. It would really depend on the boss and her relationship with him.

    1. AcademiaNut

      Reading over the letter closely it sounds like the OP doesn’t have a new job yet, and probably wants to look for a new one, but is reasonably sure that

      “I know him well enough to know what will happen when I get back and when he waves his arm at the disaster that he’s left me and laughs, there is nothing that can stop me from quitting.”

      ie, it will be a breaking point, and she will have reached a point where she can’t take it any more.

      If that’s the case, I think writing out a resignation before the wedding and sticking it in a drawer at home, for peace of mind, and then when she gets back telling him that when she was on a break she realized just how burnt out she was getting doing everything and that she needs to quit for her own health.

      Otherwise, if she can stick it out for a while I’d start job searching the moment I got back, concentrate on documenting the most important stuff and making sure the finances are up to date, and give two weeks notice as soon as I got a new job.

      My guess would be that the boss doesn’t see all this as being a problem, because everything gets done. The only thing that will drive it home is the OP actually permanently leaving the job, not being willing to rush back to fix things as they break, and having things fall apart on him completely. With a few intervals for hiring untrained and incompetent people that make things worse.

      1. Trillian

        Breaking point … That’s what happened to a friend of mine. Came back from vacation, walked into the office, boss screamed at them again, they handed in their notice and walked out. A couple of weeks later, they had a new job, more pay, and a decent boss.

  21. animaniactoo

    “Jack, we’re too familiar and comfortable with each other. I keep trying to fulfill and support the roles of the people you have been trying to replace with people you know rather than go through a formal hiring process. I know that the admin was a disaster and maybe if we’d handled it better we could have replaced her as soon as it became obvious that she didn’t know what she was doing, but I still think that’s what your business needs. I appreciate everything you’ve done for me, but I can’t handle knowing that if I’m out of the office I’m coming back to this AND that even if you hired competent people tomorrow who only needed to be trained in how to their jobs HERE, that it wouldn’t change fast enough for me because I’m just so burnt out now.”

  22. rubyrose

    I think I would give him a maximum of 3 weeks notice, but 2 would be better. Maybe tell him that you will stay 3 only if you get to take a week to document everything and he needs to make that decision immediately. I would not offer up why, but when the topic comes up, comments above have already given you some great ideas. Just keep it short and sweet and non-negotiable.

    I’m assuming that with all that you cover you have been putting in overtime to get it done. Stop that immediately. Let him feel some pain around things not getting done.

  23. Chaordic One

    One thing about this letter. The OP told of how her employer brought in his wife to fill in and how it didn’t work out.

    I hope we won’t dismiss all spouses of professionals working with their SOs out-of-hand. I’m aware of many professionals and business people who have their spouses running their back offices and it usually works out fine. Often the spouse working in the back office will get a bad reputation because they end up making the “collection” calls.

    1. TootsNYC

      The one worry I had about that was that he was looking to avoid something–avoid paying a salary, or avoid the work of hiring someone.

      How is the business doing? Is it that he can’t afford to pay a reasonable salary for those jobs? Or is he overwhelmed by hiring?

      if the OP can identify one of those, she might be able to nudge him past it, or blow past it herself, and then she might feel better about leaving.

      But she should leave.

  24. TootsNYC

    Here’s what you do:

    Either before or after you come back, say to him: “Boss, I’m going to put an ad in the paper for [an office manager / an accountant / an extra set of hands]. As I’m getting ready for being away on my honeymoon, I’m realizing–this is horrible for the business to have only me able to handle some of this crucial stuff. You could go out of business or end up in legal trouble if you don’t have someone besides me to take care of stuff. And I’m going to be away–what if I suddenly got sick? So I’m going to set up interviews for a job at $X salary, and I’ll bring you the top 3 candidates.”

    and in the meanwhile you ALSO get your resume out there.

    Then, whichever comes first. Hopefully you’ll find someone good enough quickly (but go for good, not “available soon”), and then when your own new job comes through, he’ll have SOMEone on hand.

    And if he doesn’t, well, he’s got hopefully a decent crop of resumés coming in.

  25. Not So NewReader

    Remember OP, if he says “You owe me!” does not mean that is true just because he said that.

    You could bargain to give him one more week of work in exchange for him signing a letter of recommendation that you have typed up for yourself.

    1. cncx

      i like what someone upthread said- whatever goodwill OP’s boss has shown has been paid back in spades by the fact that OP has done the jobs of 3+ people. I don’t think OP should feel guilty about anything, bossperson is not feeling guilty about burning OP out.

  26. Kate

    This is probably my first time commenting, because this situation sounds so familiar. Also a small law firm, and I’ve been taking on more and more as people have quit. (But I’m very lucky – although one of the partners has his head in the sand and expects me to do all his work first, always, the other partner is much more reasonable and understanding of what’s actually going on.)

    I’ve had to realize that this is not my problem to solve. The latest person to leave did so six months after going part-time due to family health issues. The reasonable partner said that she saw the resignation coming and wasn’t surprised, but we still haven’t hired the replacement. That was not my decision. I refuse to make myself crazy with stress and long hours. I did not cause this problem, so I will do everything I can in the eight hours a day I’m at work, but if things go undone, so be it.

    Today I actually called in sick – low-grade fever, and reasonable partner told me to stay home. No idea how things went, the day after a long weekend with no one to answer the phones or greet clients. I’m sure tomorrow won’t be much fun, but I’ll still be leaving at 4:30.

    1. MsProfessional

      Situations like this are far too common. The fact is that a law degree does not in any way make you a business expert. Even if you’ve taken business law, law schools they don’t teach you about Six Sigma or human resources. I understand why the ethics rules dictate that only attorneys can be partners in a firm. But given that only BigLaw firms would even *consider* hiring a business consultant to make sure the firm is both efficient and productive, you get a lot of terribly run firms and lawyer burnout.

  27. specialist

    You should give the boss a list of people. Tell him that he needs to hire someone for these positions–actually competent people, not fill ins who don’t know what they are doing. Give him a list of people, information from a temporary service, or whatever it takes to get a competent person in your office. You know you’ll have issues when you come back. This way it will be very clear that your resignation is a direct result of the lack of support. Or maybe things get much better and you want to stay.

  28. ilikeaskamanager

    You are thinking a lot more about his company’s well being than he is, as evidenced by the fact that he has been perfectly willing to run his business in this fashion for a long time. Give a professional notice, but don’t be surprised if he pushes back at you. Stick to your guns, don’t get into details, and look ahead, not back.

  29. Lynne879

    This sounds like the future of one of my jobs. It’s a family owned store where none of my boss’s family are employed anymore because of multiple fallouts, I know of multiple people that are retiring or are about to quit & I know he has no plans to replace them. How do I know this? Because one person put in her last day for the end of December, and she put in her notice months beforehand. She is still working at the store because the owner has convinced her to stay a few extra months because he wants to keep her and is not hire interested in hiring anyone else.

    I agree with everyone else here: give him 2 weeks notice and no more. If he pushes back and requests for more notice, stand your ground and don’t give in.

  30. Graflex

    “It once consisted of me, a billing assistant, a paralegal, a receptionist, and the attorney. Over the last three years, all of the other employees have quit and my boss has failed to replace them.”

    OP, if I’m reading this right, then the only people left at the company are you and the attorney?

    That’s. . .not really a law firm. It sounds like you’ve done everything you can for him, but unless he hires additional people, that’s it. I wonder if he’s trying to get out of his business, but he can’t quite let go of it – so he’s still slowly plodding along, until someone “pulls the plug” for him. The others left on their own, but you’re still there, and that’s enough of an excuse in his mind to keep going.

  31. MsProfessional

    Up until the third paragraph I was convinced you worked at the firm I just left. I was in almost your exact same situation, except I was the junior attorney. From there, the situation was the exact same. I had enough cases to sustain at least 3 associates when I got hired. Then the paralegal quit, and his wife claimed to be too stressed out to fill in, so I became the paralegal and his personal assistant also (he refused to read our calendar and insisted I give him a verbal rundown of all deadlines and appointments every day). I was actually having panic attacks because I felt so overwhelmed and was sure we were going to get a malpractice suit. Then I found out he was already fighting a malpractice case from before I got there! It was awful. My take: You can’t put a price on peace of mind. However, since this is your sole employment in 10 years do everything you can to leave on cordial terms. I assume you’ve already done the financial calculations and know whether or not you can survive on your fiance’s salary alone for more than a month or so. If you can afford to leave, then do it!

  32. Cheryl

    Alison, I just wanted to thank you for everything that you do!

    Your articles have gotten me through some very tough times in the work place and helped me push forward. I am hoping to end my tenure of 9.8 years in the next couple of weeks and the human side of me is feeling guilty even though I shouldn’t and it isn’t my company.

    This article really resonated with me and helped affirm what I knew deep down.

    Thanks again!

Comments are closed.