there’s nothing I can do about my nightmare workload … right?

by Alison Green on March 13, 2024

A reader writes:

I’m in a rough spot at work. When I started nearly two years ago, this was a six-person company: two owners and four staff. One staff member, who split a workload with me, moved away a few months later. They posted his position immediately, but nobody from the first wave of applicants worked out, things got hectic, and by the time the dust settled I had been handling the full workload for so long that they never replaced him.

A few months ago, my de facto supervisor took a job elsewhere. Three weeks later, my last remaining coworker did the same. (The timing was coincidental even if the root causes were similar.) During her notice period, one of the two owners went on maternity leave. The remaining owner is a few years from retirement and largely focused on client relationships and big-picture decisions. This left me as the only person around with any operational know-how, in an industry where regulations require us to stay in operation. We hired someone who’s been fantastic, but training is another thing on my plate and there’s only so fast I can do it, particularly since we have no written procedures. It’s slow going and hugely time-consuming to create them, but I know in the long run it saves me time over the “figure it out, and then I’ll look it over and tell you all the things you couldn’t have known you were missing” way of doing things.

We’re slowly easing down from having 100% of all tasks involve me in some way, but we’re still upwards of 90%. (There’s client-specific variation even between comparable work items, so it takes a while for someone new to be able to fly solo.) We’re supposed to get another new hire after the maternity leave is over, but that’ll be another situation where it’ll mean more work for me in the beginning. Having the other owner back will be helpful in some sorely-needed ways, but it’ll also be a net negative because the business will start ramping up for a busy spring.

We’re probably 4-5 months out from my job not being a complete nightmare, and a month and a half out from me being able to take a week off without this place collapsing. I have a retention bonus coming in April, and my plan is to quit if things aren’t really and truly good by July. The remaining owner means well and panics at any sign of me being unhappy, but I can’t think of anything they can do to meaningfully improve my situation that wouldn’t involve them going back in time and making better decisions about staffing, compensation, cross-training, and documentation.

Here’s my question: Am I right that in situations like this, there’s not really anything to be done except power through it while new hires are trained up? My outlook is basically, “This is miserable, but they’re throwing money at me to get them through it, so it is what it is.”

Yes and no.

When the only solution is “go back in time and hire more people months ago” and hiring them now will mean more work for you because you’ll have to train them, you don’t have a ton of options. Depending on the role, you can push to hire people who will need less training … or for someone else to help with the training (although that doesn’t sound possible in your situation) … or for the training to be structured in a way that minimizes the burden on you (for example, the new hires master X first so they can take X fully off your plate and you get a month to focus on Y before you do more training). But when those aren’t feasible or wouldn’t make enough of a difference, then yeah, it is what it is.

On the other hand, you have a lot of leverage in this situation. You can say, “I’m available for X hours a week and no more” and hold firm on that, or “I only have room for three of these six projects” or “there’s no way I cover all this work in the time I have; let me know how you want to prioritize but some of this is going to get dropped because there’s only one of me,” or whatever other boundary you want to set. Sometimes doing that can shift some of the burden off you and back to the business, where it belongs (meaning, for example, that maybe they don’t get to do every single project they want to do, if they haven’t staffed for it).

You can also ask for money! Point to how much extra work you’re doing and the increase in your responsibility level/hours/etc. and tell them what number it would take for you to do it happily. You mentioned a retention bonus and maybe it’s big enough to achieve that … but you’re also still planning to leave in July if things aren’t fixed, so there might be room to think about what number would make you want to stay (if any) and ask for that. Or maybe there are other things you want — more time off, a better title, a promotion. If so, now is the time to ask.

Your employer sounds very, very dependent on you right now, and they’re also making you miserable. You’ve got leverage. Think about how you might use it.

Read updates to this letter here and here.

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{ 182 comments }

{ 182 comments… read them below }

  1. ZSD*

    What does it mean that regulations require the company to stay in operation? Does it mean that if they want to stay in business long-term, they’re not allowed to shut down for a couple months while they hire new people? Or would it somehow be illegal for the company to close? Part of me can imagine that applying to companies that provide entitlement human services, but part of me thinks those are supposed to be provided by government agencies. I’d appreciate insight from the commentariat!

    1. Ipsissima*

      I work in a medical lab, and if we shut down we would face massive fines, and also would have to get *everything* re-inspected and re-validated before picking back up, so maybe something of that nature? I hope OP responds; I’m very curious.

      1. ZSD*

        Interesting! What would be the grounds for the massive fines? Do you receive NIH funding, so shutting down would be a violation of the contract/grant?

        1. Ipsissima*

          The fines would come from insurance companies for breaking contracts, and possibly also from the federal government for failing to provide medicare/medicaid services, although I’m not entirely sure how that would play out. We would probably also face fines for breaching contracts with our suppliers, and maybe from smaller labs that send us work.

          As Antilles noted below, the fines plus not being able to start working again until everything was validated (which can take weeks) would basically mean that closing for a few months would be the same as declaring bankruptcy.

          1. LCH*

            does this mean the company can never close and must continue in perpetuity or does it mean that the closure process for when it does finally need to shut down would just be very long? because the first one sounds insane.

            1. Harper the Other One*

              From a friend involved in a similar business winding down, a very long process when planned – I think her org announced its plan almost 2 full years before closure and very slowly reduced their intake as other organizations picked up more.

      2. Antilles*

        if we shut down we would face massive fines, and also would have to get *everything* re-inspected and re-validated before picking back up
        AND you’d be unable to perform work for any of your current clients until that re-inspection/re-validation process concluded, leading to all your clients immediately pulling their contracts because you’re not a certified laboratory.

        There’s a solid chance that even a brief “pause” for a couple months would effectively be declaring bankruptcy.

        1. MassMatt*

          Maybe, but the fact remains the owners of the company have allowed it to come perilously close to exactly this outcome. One is close to retirement and checked out of much of the work, and the other is out on maternity leave. And between the two of them, they have allowed the work of four people to fall to a single person!

          The saying “you can’t care more about a company’s success than the owners do” definitely applies here. Why aren’t the owners running around on roller skates dealing with these issues?

          LW unfortunately seems to have drunk the Kool Aid that all this is their problem and there’s just nothing that can be done about it. I hope the owners are indeed paying them well–as in well over the total of all four salaries they WERE paying before everyone else left, not an extra 10 or even 20%.

          If not, and all this really depends on the LW doing everything, they should go to a better-run competitor, or open up their own company. At least they would actually get the benefit of working 100 hour weeks.

          1. Knope Knope Knope*

            I agree with you on principle, but if the company is this close to shutting down without her, and her time off would equal a shutdown of sorts, and that would force the company out of business, the owners have unfortunately made it OP’s problem if she is reliant on this job to survive from a paycheck or insurance. It’s hard to interview or even apply for jobs in a situation like this.

          2. respect the dead*

            Off topic, but..
            Please don’t say “drank the koolaid”. That’s referring to the mass murder suicide perpetrated by Jim jones. It was horrific.

            1. Evan Þ*

              I’ve heard it’s also historically inaccurate, in that Jones and his cronies forced a lot of people to drink the poison who weren’t willing to.

              1. sparkle emoji*

                It also wasn’t Kool aid, it was flavor-aid, so there are multiple levels of inaccuracy in the popular joke.

    2. Lady_Lessa*

      My interpretation about the regulations are: to run the place so that you can legally sell items, these are the regulations that you must abide by.

      Example, candle making-sell to average user-use any wax at any concentration and molds can be made of any suitable material
      Candle making-sell to historical society for use at living museums. Recipe must be exactly what was used at the time, with the correct material wicks, and molds same material and design as used at the time the living museum is portraying.

      1. Juicebox Hero*

        The candlemaking example wouldn’t explain why the business had to stay open, though. The historical society would have to find a new candlemaker who could make period correct candles, which would be a PITA, but as long as they were made right it wouldn’t matter who made them.

        1. ThatOtherClare*

          Payments for breach of candle supply contract could be enough to bury the company, perhaps? Sometimes people bite off bigger projects than they can afford to fail on.

      2. Kuddel Daddeldu*

        Often it’s grandfather clauses. For example, zoning laws can change, rezoning an area to residential. Existing businesses can stay as long as they stay in operation; when you shut down (for longer than e.g. a week) you are not considered an ongoing business and have to move.
        Same for many other regulatory items; when rules change, existing businesses are often permitted to carry on but when you do a substantial change (such as moving or shutting down), you have to fully abide by the new rules which can be costly to impossible.

    3. PotsPansTeapots*

      My first thought was that the business has a government contract that’s a significant chunk of the revenue, but also has some preconditions.

      1. Coverage Associate*

        Yes, a lot of the government funded social safety net is actually run by private organizations. For example, here in San Francisco, very little low income housing, and I think 0 supportive housing, is actually public. Outside organizations actually own the buildings and pay the social workers, etc.

    4. Captain dddd-cccc-ddWdd*

      I think it means their clients need to meet some kind of regulatory requirement, which OP’s company is providing for them. So the clients need this company to stay in business, because OP’s company’s services are how they are staying compliant with that requirement.

      1. RIP Pillowfort*

        That’s what I was thinking. Environmental monitoring is what this reads to me. And you can get into some trouble if you default without continuity of operations depending on what you’re doing.

        1. actual cat herder*

          my last job was in environmental monitoring & this whole post is setting off alarm bells. we were a startup but had a government contract that was (barely) keeping the lights on. if we were to shut down, the company would just declare bankruptcy.

    6. Brain the Brian*

      Awfully close to the line here about not speculating where LWs work. The LW says their company cannot close; let’s take them at their word.

      1. Dinwar*

        To a certain extent, though, this will determine the answers we can provide.

        For example, I’m in environmental monitoring/remediation, and if I told my boss “I’m only working 40 hours a week, what gets done gets done” they’d laugh at me. The industry standard is 10 hour days, 5 days a week (or 10/4s, working 10 hours a day for 10 days than having 4 off), and it’s extremely common to work beyond that (there are tests that take 24 hours, and spills always seem to happen at the end of the day). My best is a 78 hour work week, and I think my longest shift was 36 days straight, and I’m considered a lightweight. There’s also night work, and weekend work, and a bunch of other issues that mean you never have a “normal” schedule.

        In contrast, some jobs NEED to be done in 8 hours. I know some chemistry issues where that’s the case. You can have 20 0r more of these running and it’s insane amount of work, but it’s all done by 5 pm or you’ve failed. In such conditions telling your boss “I’m only working 40 hours” is going to cause laughter because of course you will, it’s a question of what happens in those 8 hours.

        So while speculation isn’t ideal, to a certain extent it’s necessary.

        1. Kyrielle*

          I think that the key is linking it to the advice. So you might, for example, say “I’m in X and what that would look like here is…. and I’d recommend Y, and Z wouldn’t work because of Q.”

          And if OP is in that field or something similar to it they will be able to apply the advice, and if not they’ll know to skip it.

          But me – who works in a field where that’s just not the case – being curious about it doesn’t really call for any speculation, because I don’t have a potential answer change with the knowledge.

        2. Brain the Brian*

          Plenty of other industries have required long hours. That doesn’t change the boss / employee dynamic of asking for more help / money / whatever when you have a lot of leverage to do so.

    7. Annony*

      My guess is that it is not illegal for the company to close, but more that if they do close they can’t easily reopen. For example, a nursing home can’t simply say they are short staffed and close for two months to train new employees. They can stop accepting new patients. They can try to transfer some to other institutions. But if they completely close they are probably not reopening.

    8. OP*

      I mainly wanted to establish for Alison that temporarily closing the business wasn’t an option, in case that was going to be part of her advice. I imagine in a lot of fields, the “break glass in case of emergency” option in this situation would be to wind down operations temporarily – telling clients we were unavailable, reducing operating hours, whatever. None of that would be an option here, and there’s nothing that allows the business to temporarily suspend service. The business keeps providing a client with service or it needs to sever the obligation by dropping them entirely.

      2. a thought*

        Given those options, it does sound like the business may need to consider dropping some clients!

        Not that it’s in the OP’s control, but sounds like the owners COULD reduce the workload here (yes, huge hit to the business but sometimes that happens!)

      3. AnonInWiscosin*

        I think what we want to know is, could the business drop clients without going out of business completely? Is this a case where breaking even one contract would come with enough penalties to sink the company?

        I know it’s not ideal to drop clients, but any company that is one bad cold from going under should be looking at any and all options (including deciding to close).

      4. anonymous anteater*

        I am trying to square this with your comment that business will ramp back up when one owner comes back from leave. That sounds like there was flexibility to ramp down business for a predictable event. Perhaps fewer clients were taken on on anticipation, or whatever makes sense in your context. Maybe there is an option to have the returning owner contribute to training for some time, and delay the ramping back up so you don’t go insane.

        1. MCMonkeyBean*

          I think they are saying that the business owner returning happens to coincide with a busy season so the benefit of the owner’s return will be cancelled out by the natural increase in workflow. I don’t think it was going to ramp up *because* the owner returned.

  2. FlynnProvenza*

    I’d also tell them you can’t proceed at this pace without a temp. If you could get a temporary worker in there, even to shadow you for any busy item you can pass over (including translating your notes to edited SOP’s), that may free up some of your time. And who knows? You may find a temp that is suitable to hire on permanently.

    1. Juicebox Hero*

      This. Even if the temp couldn’t deal with clients, someone to do the day-to-day work of sorting the mail, filing, and other tasks would be that many less things you have to do.

    2. Spicy Tuna*

      100%. I had a role years ago in a heavily regulated industry. Every other company in our industry had an entire department handling the work that I did, but my company had me and an assistant. My assistant was…. subpar. However, I would never, ever let her go because while she was generally not very helpful at anything substantive, she handled a LOT of admin type tasks for me, such as filing, mailing, etc. It seriously freed up a good 2-3 hours of my day, when a typical work day for me was 5AM – 7PM

      1. hypoglycemic rage*

        as someone who is in an admin-type role, can i ask what made her subpar? i want to make sure i am NOT subpar in my role….. (which i realize the answer to this might be job/industry-dependent.)

        1. Your Mate in Oz*

          I read that more as “my assistant is not very good as a teapot painter, but they do a lot of admin which frees me up to paint teapots”.

          And sometimes that’s as good as it gets. I’ve been “the one employee who is essential” before and had the boss’s whole family in the office helping for the weekend… “you write code. Anything we can do, we will do”. But that was a weekend, not a year.

          1. Grumpy Elder Millennial*

            That’s how I read it, too. The assistant isn’t very good at grooming the llamas, but was invaluable because she kept things organized and moving. By doing that, it gave Spicy Tuna a lot more time to groom the llamas.

          2. Bear Expert*

            I’ve been involved in these kinds of call to arms. I don’t have the specialized knowledge in X, but I can write process and procedure docs.

            Shadow the teapot painter, write down what I see, ask clarifying questions when they aren’t racing paint drying to get to a pause point, write a draft of process, figure out where obvious gaps or clarifications are needed, ask more questions, give draft over to get reviewed/redlined/laughed at (Oh this is an acronym, and you spelled it wrong every time!)

            Polish document for appropriate audience (is this to give to a newbie who needs to follow the physical steps at a high level of detail? Is this to have on hand to remind/govern ongoing work for people who basically know what they’re doing but should have a checklist? Or is it for an outside party/auditor/accessor to use as evidence that the procedure is documented and needs to contain purpose, pointers to the governing policy, pointers to the evidence the procedure has been followed?)

            Specialist focuses on doing X and shoring up my understanding of what is material. I do all the non specialist bits. With a handful of people who can do the doc writing, you can get a pretty solid collection of training or auditor docs in a shockingly short timeframe.

            Which could be helpful for LW as well – have the owner hire temps to develop process/training materials, and decrease the load of training and oversight on every bit of work handed off to someone new. Even if projects look like LW identifies which bits can be done according to the “standard” process for this client, Newbie does those, LW does the “custom” bits. Anything that can hand off repetitive, non specialist work.

    3. Sloanicota*

      This “ramp up for Spring” sounds optional. The organization can’t ramp up right now unless they get their hiring under control. Be clear about that and maybe it will kick them into gear. It’s costing them money not to add capacity.

      1. Spargle*

        Agreed! If they are truly going to ramp up without additional help or whatever you need, then you can ramp out.

      2. Grumpy Elder Millennial*

        Though the added challenge is that the OP will have to train anyone new, since the one owner who’s around won’t be able to. So it means even more work for the OP in the short term if they hire now for substantive roles. Though it’s certainly worth considering whether a temp handling admin stuff could take some of the load off.

    4. Ama*

      This is what my current employer did when I was completely overloaded (although not as small as OP’s employer, I was supposed to be a team of three, got down to just me, hired a second and planned a workload for a team of three to kick off in a few months and the second person quit after only five months). We hired a consultant with specific expertise in the tasks we had planned and a general office temp to help cover some of the basic clerical and data entry and although it was still hard (you do still have to train even an experienced consultant in how your employer does things), it was the only way I made it through the next nine months.

      The general office temp ended up being a gem who we hired permanently and worked for us for three years (she’s leaving next week to go on to bigger and better things and I couldn’t be happier for her).

    5. Tio*

      I was thinking contractor or consultant, but yeah. I think OP thinks that training someone who’s not staying long term would be a waste of their already strained time, but consultants and contractors tend to be higher level and usually more autonomous. It may be worth looking into if there’s anything available, and if they’re steeped in government regulations, there’s almost ALWAYS someone willing to take your money to tell you how to do things. Or train the new person on some of the regulations so you can have that time back!

    6. ferrina*

      Yep. OP, think about what little things you can take off your plate. Can the documentation be drafted by a freelance writer (recommend an actual writer vs a temp)- maybe you leave voice recordings then have someone else write/format it for your review? Can you have a temp in for a half day to do some of the repetitive parts of your work while you train the temp on the more complex stuff? Are there contractors who work in your field that you can outsource some of the projects to? At this point it doesn’t matter if hiring a contractor means you lose money- the owner is about to lose you if they don’t do this, and if they lose you it sounds like they will lose the business.

      Also think about what deadlines can be pushed- anything that can be pushed, should be pushed. Flag some things for your owner, and let them have that conversation with the clients.

    7. ariel*

      I like this idea a lot – even dictating procedures would be a relief, I promise OP (been there, been shocked at how great it was to talk and know the notes would be good enough).

    8. Beth*

      This is a good idea. But OP, you should also consider just telling them that you can’t keep up with this pace. They do have options! The owner that’s still present could pick up more of the day to day workload. The owner who’s on maternity leave could return part-time. They could hire a temp or three to help with lower-level tasks. They could hire an experienced, skilled worker who can jump in and only need training on the company-specific details. They could put some projects on pause so you can focus on a reasonable workload.

      They’re choosing to let you take all the work instead. That’s a choice they’re making, and it does give you leverage. You can just refuse to do more than you’re actually happy to do. What are they going to do, fire you?

      1. Reluctant Mezzo*

        What if OP is hit by a bus? Then the business is totally screwed anyway. If OP has a physical breakdown from this work, the same result.

        1. Dog momma*

          ^^^. I’ve always said this, no one is irreplaceable. If the business feels they can’t do business w/ o the OP, get them some help or they won’t have a business!

      2. Grumpy Elder Millennial*

        Certainly worth considering if the owners can pitch in on stuff. Just because one owner is currently focused on big picture and client relationship stuff doesn’t necessarily mean that they can’t jump back into some of the operational stuff.

        Normally, I’d be pretty resistant to asking someone to come back from maternity leave early, but this is a business owner. A business owner who, with her co-owner, dropped the ball. If she’s physically able to do even part time, that could be a huge help. Maybe she focuses on hiring and training so the OP can focus on getting stuff done.

    9. Gumby*

      If hiring a temp to do your work work isn’t helpful because the work is so specialized that no general temps exist pre-trained, can you have work hire a “temp” to take life tasks off your plate? Cooking, cleaning, laundry, car maintenance, etc. (My sister worked in building management for a high-rise in LA – it was possible to pay through the nose for a service that washed your car and refilled the gas tank while you were at work. I, personally, would pay through the nose for someone to schedule and take my car to regular oil changes during the workday because I am terrible at remembering to do that on time.) Or pay you enough to hire your own housekeeper / private personal assistant until the workload abates. Basically, make it so you can do *only* the work things that are necessary and personal things that you actually want to do.

      1. Grumpy Elder Millennial*

        This is a super interesting idea! I couple years ago, I ended up having to do a massive task at work, with only one other person, and an unmovable deadline. I ended up bribing my neighbour to make me lunch several times because I just didn’t have time. It was super helpful. So I totally get how that could make a real difference for the OP. It’s not a long-term solution, but could be super helpful in the short-term.

    10. Artemesia*

      I’d be in overdrive on my job search in this situation. Businesses are happy to use up employees and not provide proper staffing as long as they can get away with it.

  3. Juicebox Hero*

    What sort of privately-owned company that’s that small would be required to stay in operation, and by whom? I get that the LW doesn’t want to reveal too much, but that doesn’t make a lot of sense to me. What if LW does quit and leaves just the owners by themselves? What if the owners want to sell the business or retire or otherwise decide to close up shop?

    1. Falling Diphthong*

      Meteor strike. Bus hit. Two or three unrelated medical emergencies that happen to align.

        1. OP*

          Oh, no worries, I have my instructions for who to contact to initiate emergency continuity measures if I get to work one day and find out both my bosses have been set upon by zombies.

    2. Peanut Hamper*

      They are probably in a highly regulated industry and it means that they can’t shut down for even a short amount of time because they have government contracts they need to fulfill. An inspection service that goes in and calibrates or validates equipment for drug-manufacturing operations comes to mind as an example.

      1. WellRed*

        If they are that highly regulated I’m wondering how they manage to meet certain requirements like staffing levels. That doesn’t help the OP but OP, this isn’t on you. You can’t care more than the owner.

  4. Falling Diphthong*

    Another new hire after the maternity leave is over.

    This stood out to me as very strange timing, unless the idea is that the returning owner could and would handle all of the training for the new hire.

    I like the advice to just flat out ask for more money. And before you do, think about a number that would cause you to be relatively happy with the situation–it sounds like the retention bonus is enough to keep you around up until that deadline, but not a moment longer. (To be clear, I mean that your workload gets better over the next few months AND you feel, retroactively, that the large amount of additional money they gave you made the hellish months worthwhile. Not OR.)

    1. Captain dddd-cccc-ddWdd*

      Probably the co-owner (currently on maternity leave) needs to have input on the hiring process?

      1. Person from the Resume*

        Or quite possibly she does all the work needed to hire someone because the other owner can’t or won’t.

        Which is “not cool” for the LW that things are being dropped because of one person’s maternity leave (which they deserve). I guess this is a small business problem that they just don’t backfill a planned leave.

        1. Artemesia*

          The maternity leave was not a surprise; the boss just chose not to make sure they were staffed properly because she knew she could count on abusing the OP. I’d be so gone the first moment I could do so.

          1. WellRed*

            I totally agree with this, it wasn’t a surprise, they chose not to make arrangements and current boss is wringing her hands hoping OP doesn’t look up from her work long to see thus. I hope that bonus is into the five figures.

    2. Get after it, OP*

      This is exactly what I’d do. The owner knows how precarious the situation is, OP knows what they’re getting into and how to solve it, the only sticking point is that OP is being worked to the bone.

      The owner is focused on strategic stuff, so I’d lay out the operational plan exactly for them with timelines, responsibilities, expectations, deadlines, risks, etc. And since I’d be orchestrating this and ensuring it’s success, here’s the promotion/raise/bonus/benefits I’d expect for this role.

      OP sounds like someone I’d want to work with: cares about shared success, sees the problems and wants to solve them, and respects themselves enough to do it in a sustainable way. I look forward to an update on this one in 6-12 months.

    3. Kuddel Daddeldu*

      I think this is due to the co-boss will bring in more business once back from maternity leave, so there needs to be more back-end capacity.
      Still shortsighted as any new hire needs to be trained and it looks like a rather steep learning curve.

  5. mango chiffon*

    Confused by the other owner coming back meaning that the business will become busier…Are they unable to slow down the pace of new business while they are trying to recover their staffing?

    1. Juicebox Hero*

      It sounds like it’s a business with seasonal fluctuations, and the other owner is coming back because she knows things are going to ramp up rather than her doing anything to make it busier.

  6. BMac*

    Ugh I totally feel OP’s pain! I also am the sole operational employee at a business where sometimes that’s fine and sometimes I am absolutely drowning. I have no suggestions (aside from YOU ARE VITAL, MAKE THEM PAY YOU FOR YOUR VITAL WORK) only sympathy.

    1. Your former password resetter*

      it sounds like they could shut down, but it needs to be a slow and planned winddown over time.

      finishing up contracts, slowly shedding suppliers, working with other agencies/companies to transfer ongoing work, etc.

    1. OP*

      I’ll probably send a formal one in once I’m on the other side of my self-imposed “if it’s not ACTUALLY GOOD by now, quit” July deadline, but since I actually submitted this question back in January: I’m happy to report things have gotten a lot better! My boss coming back from maternity leave was an even bigger help than I could have hoped for, and her #1 focus has been helping me out. We’ll see what that looks like a few months down the road, but I’m hopeful.

      1. Hastily Blessed Fritos*

        If it does work out and you stay, I hope you’re able to negotiate for a lengthy paid vacation when the dust settles!

      2. Another username forgotten*

        Have you worked out what your hourly rate is? You are working your socks off and the owners are reaping the benefits. They’ve kept the salaries of the 3? people they’ve not replaced. Heck they could double your salary and they’d still be ahead. As other people have said – this isn’t your business and you can’t care more about it than the owners. You’re insulating them from their mistakes of not doing the hard work of hiring new staff – cause really why would they when you’re doing all the work. Unless there’s no other job options around I’d take the bonus and run. You only get one life and one body and you seem to be currently working it to the bone and taking on stress and doing damage to yourself to benefit someone else’s peace of mind and bank balance a heck of a lot more than yours.

  8. Bee*

    It sounds to me like they can afford to double your salary until the new hire is up to speed enough that you can hire a third person, tbh. (And backdate it to when you became the sole employee.) Maybe that would make it tolerable, knowing it’s a temporary situation? Maybe not, but it’s worth considering!

    1. Cabbagepants*

      I also want to know what happened to the money that was supposed to pay all these people.

      OP, you sound conscientious, but the company is hugely taking advantage of you.

    2. Sloanicota*

      This was what I was thinking with the comment that they could choose to hire senior-level people who can get on-ramped quicker. If they want to pay enough money to lure someone good away from a comparable role, it sounds like that should be an option on the table, and the money should be there. Don’t let them try to hire junior people and make it your problem to train them.

    3. Beth*

      Agreed! I understand wanting to keep your workplace afloat, but OP, it sounds like you’re currently doing way more work than either of the actual owners. They’re the ones who benefit most from the profits (and therefore the savings from all the people they aren’t employing anymore), but you’re the one putting in all the stress and hours!

      You should figure out what would make this feel actually worth the suffering you’re going through–knowing that you’re currently doing the work of at least 5 people and borderline solo running the entire business, so, don’t let yourself be limited by “that’s too much to ask”–and ask for it. If you’re refused, you should leave now, not in July. It would probably mean the company fails, yes…but that’s not really your problem at that point. They don’t get to sustain their company at your expense and not even compensate you fairly for it!

      1. Falling Diphthong*

        As an employee, you can’t care more about the business staying in continuous operation than the owners of the business do.

    4. Linda*

      OP should be getting quadruple the salary, since OP is doing the work of 4 or 5 people. The owners would be up a very unpleasant creek without OP. A while back there was an ask-the-readers from a woman who got promoted to a high-stress position with appropriate salary, and she wanted advice on how she could use that money to take stress out of her home life. Things like meal delivery and laundry service. OP could keep that in mind while considering how much money would make the situation worth it (and motivate the owners to actually fix the problem instead of letting OP work themself into an early grave)

    5. Generic Name*

      I’m really wondering what kind of money the OP makes versus what the owners make. I sincerely hope OP is making at least 6 figures, but something tells me they are getting substantially less. Something is amiss. The owners are running the entire company on your back. I have no idea what the margins are in your line of work, but I assume that the extra profit of one person doing five people’s jobs goes to the owners. I wonder how your bonuses stack up against profits.

  9. Show me the money!*

    Very tough situation, but regardless of what you do, you may as well get as much money for your misery to date as possible.

    Perhaps that retention bonus could triple or quadruple?

    You hold almost all the cards now, but that won’t always be the case…so play them!

    1. Sloanicota*

      Yep, you’re going to be miserable anyway, so you’ve got very little to lose by asking for roughly double your current salary so at least you can outsource more things in your daily life / start putting together a cushion for when you flame out.

    2. Double A*

      Yeah I’m sorry, a one time bonus? No, sounds like you get the bonus and also double or triple your salary, which is still a bargain because you’re doing the work of 4 people right now. Plus they’re only paying benefits for 1.

  10. Colette*

    One point I think the OP is missing – regardless of whether the company is required to stay in business, that is a problem for the business, not for you. You can quit today if you don’t want to do this anymore.

    And if you’re working ridiculous hours, you can stop. Sometimes the pain has to hit home for change to happen; if you are burning yourself out, that’s only painful to you.

    1. Twix*

      I came here to make the same point. It’s easy in a small business for employees to feel personal ownership of the success of the business, but any regulations that require the business to operate a certain way are ultimately the owners’ responsibility, not yours. Given both the situation and the amount of leverage you have, one option (which Alison touched on) is to just… not let it be your problem. If you are not willing to solve all of the business’s staffing problems for them, you are allowed to refuse without figuring out how to make that work for the business first. Figuring out a different solution is the owners’ problem, not yours. (And that solution might be “Pay LW enough money to be willing to make it their problem”, but that’s also something you’re not obligated to agree to.)

      1. Not Tom, Just Petty*

        “It’s easy in a small business for employees to feel personal ownership of the success of the business”
        It’s like being the kid brother who gets to take the sled back UP the hill.
        Only exponential.
        It’s not your sled, you don’t get to ride it. You get to bring it back up the hill. Oh boy! You are best!
        You get some satisfaction from seeing people happily ride down hill. But at the end of the day, OP is doing all the work. The active owner is giving sled rides to clients while OP runs around building, patching and setting up sleds.

    2. Juicebox Hero*

      Plus a zillion. It’s like everything else – you can’t care more than the owners do so please don’t burn yourself out trying to save them from their… not especially great decisions.

      1. RVA Cat*

        This. I immediately thought of pharmacist who died from a heart attack trying to do everything at her understaffed store.

        You are more important that this job.

      2. BlueSwimmer*

        And… they can shut down the business or fire you at will, even if you have run things for them for years. My husband was in this situation. He was pretty well paid for the job but ran the entire business that made the owner wealthy, dealt with all the stress, had to fight to follow regulations that the owner decided he didn’t want to follow, etc. It was extremely stressful. He even figured out that his predecessor had embezzled hundreds of thousands of dollars (predecessor went to jail and they recovered a lot of the money; my husband’s reward was a used Xbox the owner didn’t want anymore).

        After years of being a loyal employee and making the business a success, he was told that the owner wasn’t making enough money so he could either take a 50% pay cut (to well below market norms for the job) or the owner would just shut down the business. I think the owner really thought my husband was so loyal he would take the 50% pay cut so the owner could maintain his three homes.

        Instead, he said goodbye and walked away. He has never been happier, he has lost 50 pounds because he isn’t stress eating, he is sleeping all night, and life has improved a million-fold. I only wish he had decided to walk away earlier but he struggled to know his own value.

    3. ferrina*

      100%

      I’m glad OP has a deadline in their head for when they are going to walk away. That is absolutely the right thing. The owner needs to be solving this or empowering OP so they can solve this. If they won’t do either of those things, walk away.

      And OP, it will take a lot of time to recover from this. There might be a delay before it hits you, but it will hit. Speaking from personal experience.

      1. Cold Snap*

        “And OP, it will take a lot of time to recover from this. There might be a delay before it hits you, but it will hit. Speaking from personal experience.”

        ^ YES. This is super duper true. I’m in it right now…give yourself at least four times more time than you think you’ll need to recover.

    4. Cold Snap*

      I agree, OP is taking on WAY too much personal responsibility for the success of the company. OP: If you establish healthy boundaries, and the company drowns, that’s on the owners refusing to properly staff, not because you weren’t willing to sacrifice your entire life for their gain. And they ARE gaining! I agree with all the commenters saying you’re being taken advantage of; they know exactly what they’re doing.

      I’m skeptical whether you can get more money, and I’m VERY skeptical that you can get more money plus revert to a reasonable workload, since they’re so used to you carrying all the weight. Good luck!

    5. Massive Dynamic*

      This – you can’t care more about the business’ ability to stay alive than the owners do.

      1. Not Tom, Just Petty*

        Question: how does OP say, “no matter how much money you give me, I cannot put more hours in the day. I cannot be in two places at once,” without sounding like s/he is turning down money?
        Take the money. You deserve the money. You deserve the salaries of three people, but paying you the salaries of three people should give them the expectation that you are going to do three full time jobs.

        1. Twix*

          By being explicit about it. “You are currently paying me $X, and I am willing to put in Y hours per week at that salary. I would be open to working up to Z hours per week if that’s what’s needed to run the business, but I would need to be compensated appropriately. Working more than Z hours per week is not an option for me.”

    6. Dust Bunny*

      Thiiiiiis.

      OP, your responsibility is to do your job, not yours plus four others that the owner hasn’t felt pinched enough to fill yet. Let him feel pinched. He should be a lot more worried about filling these positions than he seems to be.

    7. Person from the Resume*

      Well, the LW is staying for their April bonus and does plan to leave in July if things aren’t really and truly good by then.

      This does sound like just trying to hang on to a job in hand that they like and looking for advice if they were missing anything … which it doesn’t really sound like they are not.

    8. Falling Diphthong*

      Sometimes the pain has to hit home for change to happen.
      It’s amazing how fast solutions are found when employees figure out how to make sure managers are the ones inconvenienced by the problem.

      1. Hamster Manager*

        I once ran an entire charity event SOLO for multiple years that just HAD to get done, magically after I quit, they didn’t need to do the event anymore. Cool.

        1. FlatWhiteWalker*

          I had the same thing happen! When I was minute-taker for leadership meetings, a manager (male, engineering) asked me (female, admin) to do the same for his DEI meetings.
          I politely deferred, citing my existing workload and that I wasn’t part of the DEI team. He pushed. My manager backed me up and suggested he take the minutes himself.
          Surprise, he then decided those meetings didn’t need to be minuted anymore.

  11. Yup*

    Look, no company worries if they need to fire people. They just fire them. The amount of worry individual employees have for a company, and the overwhelming work input they generate like this, should not be normalized. You getting sick and stressed and compromising your health and mental well-being should not be normalized. You don’t own or profit from this company. You owe them the work as set out in your contract or agreement. If you end up too sick to work they will replace you. This is not your life—this is the work that allows you to live your life. Don’t let them dictate your life like this. Put down your limits or just get out. Good luck to you.

  12. Respectfully, Pumat Sol*

    This stuck out at me “Having the other owner back will be helpful in some sorely-needed ways, but it’ll also be a net negative because the business will start ramping up for a busy spring.”

    What if you just….don’t ramp up? Have the owner actively work to keep levels of operation/sales where they are. Say no to additional work this spring. You don’t have the bandwidth for more work and ramping up for MORE WORK is just going to make the issues worse.

    1. Yup*

      Just to add: No amount of money in the world is worth a burnout. It deeply affects your life and you end up prone to more in future. I don’t think leveraging this situation is the answer. You need to protect your health at all costs.

      2. Hamster Manager*

        I agree with this. I just dropped out of a severe burnout job to make literally 50% of my previous salary (thanks, past me, for aggressively saving!), and despite some financial fears, it was the obvious, only choice to make. Now that I’m out, I’m noticing how bad I feel, how bad my body feels, how much my face has aged in just a few years at that job. It’s getting better, but sooooo slowly.

    2. E*

      Agree! I worked at a place where the owners took every little job when we weren’t staffed properly. After a couple years, the house of cards collapsed. As a result their reputation is toast with multiple clients and they can no longer get work in that particular industry and lost an entire division of the company. It would have been so much better to focus on what they already had.

      1. Kelly*

        I also worked for a vet practice like that. The vets were getting overwhelmed being expected to see literally anyone who called with an emergency overnight plus work a bare minimum 50 hour week AND the owner kept taking on more high maintenance clients and services and just expected us to be excited to work 12 hours a day like he did. We weren’t even being compensated very well so half the vets quit within a week of each other.

        Owner threw a tantrum, but the business survived and has cycled through a bunch of vets in the last few years. The only original ones remaining are stuck with a terrible non-compete clause that would require them to uproot their whole lives to change jobs.

        1. Galentine*

          If you’re still in touch with the remaining vets, encourage them to take their non-competes to an employment attorney! It may be overly broad and partially/entirely unenforceable.

      2. ferrina*

        I worked somewhere where the philosophy was “Every Sale is a Good Sale.” Um, no, not when you don’t have the staff or tech to do the work.

        I finally got some traction when I met with my Grandboss and Head of Sales and said “Gee, thanks for the new project- I can start it next month. Unless you want me to not deliver the results for Big Client A?”
        Said pleasantly and calmly. They both immediately started asking why I couldn’t possibly do both, and I just quietly confirmed that unless they could get me a time machine or a clone, it was against the laws of the space-time continuum. But I was happy to get started next month (I was very pleasant in this conversation, and my tone was of course I can’t get a unicorn by next week, as you know).

        The next day I was magically approved to hire on two new staff.

    3. Peanut Hamper*

      This is not practical if they are in an industry with seasonal variations, but yep, if they have control over this, then they should exert that control.

      The way it is worded does sound like a seasonal fluctuation, though.

  13. CityMouse*

    Honestly, I’d consider another job. There’s a very good chance this will happen again and again. What if your new hire quits? The boss here isn’t managing people appropriately and is leaning on you. This is not how a business is run and I’ll bet anything you are not being compensated sufficiently for just how much they’ve done to you.

    1. Ama*

      Yeah, I commented upthread about a specific emergency coverage when things were at their worst in my department, but that whole experience made me look around at how often various departments at my employer go into crisis mode when even one position is vacant or someone is on leave, because the senior staff refuse to staff for any emergency coverage situations and have a terrible habit of committing to new projects and THEN hiring staff (and we are slow at hiring so the new staff never seem to be onboard before the project kicks off). So I am leaving myself soon — I gave them an enormous amount of notice because I’m going freelance so I can set my own start date, but I just got so tired of constantly cycling in and out of crisis mode for normal staff departures, maternity leave, etc.

      1. Tracy*

        I work for a very small business that has trouble attracting qualified employees due to the nature of the job sounding really awful. Our last hire made it a few years before quitting, leaving me the only employee qualified to do about half of the business’ income-generating work. I could step up and take on more work/days/hours and get a bump in pay, but it’s not worth it to me to sacrifice my mental health for someone else’s business so I have refused their gentle prodding about the possibility. I don’t have any decision making responsibilities or pay so I consider it not my circus or my monkeys. Honestly it’s a great position to be in to get what I want.

        1. Grumpy Elder Millennial*

          Very sensible! If you don’t want to have more work and responsibility with higher pay, that’s entirely reasonable. I’m glad you’re doing what’s best for you.

    2. Expelliarmus*

      The OP commented above that they’re holding out until July to see if things get better.

  14. MollyGodiva*

    Poor decisions by management is not your problem. You can only do so much. It is their business, they need to run it properly.

    1. Sloanicota*

      This is a great point too. OP is not an owner. Why run yourself ragged for their business that they’re not having much urgency staffing? What would it look like to do a bit more quiet quitting* and only delivering a reasonable amount of work for your current salary?

      *such a misleading term because it’s … not quitting!

    2. Busy Middle Manager*

      Unfortunately yes. I would “boostrap” and work extra up to a point but not go overboard. A good measure could be “up to the point its adding meaningful line items to my resume” or “prevent important customer from leaving.”

      I lean towards management on these cases but I feel like management is doing something wrong with his much turnover. And whole maternity is important, you need to plan for when you’re out. Same with checked-out-almost-retired one. Not “woops this predictable thing happened, can’t help bye” nonsense.

      Also to be practical, I’d “bookend” the day and weekend with activities so you 1) don’t feel the urge to stay late every night and have concrete reasons to leave by 7PM, and 2) you have a concrete thing to say if management decides to be unreasonable when asking why stuff wasn’t done. And 3) keep some sort of log of activities to CYA. “I skipped doing work for Columbia this week because our Harvard account took 30 hours of my time + I had to do all of the bills that took another 20” sounds better than “I was busy”

    3. Seahorse*

      That’s definitely true, but I have sympathy for the LW too.

      It’s much easier see the poor management decisions as outsider with no involvement. That’s harder to acknowledge when you like the business owners as people, care about your clients, and don’t want to walk away from a job you’ve poured so much time & effort into.

      I hope LW is able to look at Alison’s response and these comments and take a step back to evaluate their next steps without feeling guilty!

  15. Sloanicota*

    I recognize myself in this situation. When I started, my org had seven people; for most of last year, we were down to two, of which I was one. The main thing is that I pushed, and was heard, and received, a reduction in the overall workload. We walked away from some things that didn’t make sense for two people. We hired contractors for some things. I also pushed for big raise and promotion, and got it, although in retrospect I should have asked for more. We’ve since hired one senior level position back and are working on another midlevel, so we’ll be at four soon, hopefully – but I don’t trust it, as we have chronic turnover that will probably continue to plague us for a while until the person in charge gets a clue.

  16. caseykay68*

    I sympathize with the sentiment/feeling that because you have been doing it for so long, that you need to be involved in all the tasks. And yes as you get someone trained it can take some of your time, as can documentation. But, does it really need to be 90-100% of tasks you need to be involved in? That feels like a big bottleneck that could also be causing some of the issue.

    Aside from the other good advice what about hiring a consultant who could do you documentation? They don’t need to know the job, just need to be good at documenting the steps/process.

    1. Sloanicota*

      Yes, there’s not a good way to phase this, but I find that when you have an employee in a position like OP’s, it becomes very un-fun for the new staff people, and they often struggle to get ownership of their tasks because you’re there and you know it so much better and you’ve been doing it alone for so long. It’s an artifact of Founder’s Syndrome in organizational theory. Also, when you’ve been operating in crisis mode for so long as the key decisionmaker, you generally come up with unfriendly/unwelcoming processes that ice people out. OP will have to be very conscious of forcing the handoff to happen and actually taking a big step back. I suggest a sabbatical, a long vacation after the new person is reasonably in position to give them a true sense of ownership. Especially if you start thinking things like “nobody we hire has the right kind of passion or the commitment that I have.” Even for well meaning people this gets addictive.

  17. Parenthesis Guy*

    I like the advice for this person to say that they can only work a certain number of hours a week. I’m not sure how practical it is though. If they have more than 40 hours of critical work a week, then maybe there’s nothing to be done.

    It may be worthwhile to ask for ownership in the company. They need your expertise and without you they won’t be able to function. You may be happier working long hours for something that you have part ownership in.

    1. Mark This Confidential And Leave It Laying Around*

      I wouldn’t want to own this! As for being unable to run a business on one person’s back in 40 hours a week: of course that’s true. The solution is to let the failures happen. “Why didn’t you do x? We missed the deadline!” Answer: we don’t have enough staff to meet the deadline. As long as OP keeps all the balls in the air, no change is coming.

  19. bamcheeks*

    It seems like the obvious solution from a business point of view is to say no to more clients and ramp down the amount of business you are currently able to do. “We aren’t taking on new clients at the moment” “We wouldn’t be able to schedule another project before August 2024” are complete sentences that your owner is refusing to say. As is, “I’m very sorry, we are going to need to push back the deadline on this project” or “I can recommend other agencies who might be able to pick up some of this work.”

    LW, you seem to be seeing the pipeline of business as a fixed point, and the only variables as how many people are available to fulfil it. I would submit that this is not how the majority of business operates, and that your owner is making a conscious choice to keep the same level of business coming in whilst not adequately staffing the company to respond to it. Obviously these kind of bottlenecks happen sometimes (in both directions), but given this seems to be getting towards 12 months of crisis, I think that’s bad management!

    What would happen if you had a frank conversation with your owner about about decreasing the number of clients or the amount of business coming from them? I get that every business is worried about doing that and whether or not they’d be able to ramp back up, but losing your sole remaining employee is not a sustainable business plan either.

    1. Twix*

      I’m wondering based on the comment about regulations whether this is something like a healthcare or emergency service or utility provider that’s legally obligated to handle certain kinds of requests. But if that’s not the case and the owners can choose whether or not to take on new clients, then I completely agree. If the company can’t supply enough of the service to meet demand, it’s not fair or reasonable for the owners to keep accepting new work and expecting the staff to make it happen.

      1. bamcheeks*

        But surely nobody would be so wedded to the free market that they would outsource an essential service to a tiny agency of 2-3 people with no operational redundancy or continuity plan?

        OK, that was sarcasm. But if that is the case, it’s either Not LW’s Problem or they need to be paid much, much more to make it their problem.

        1. Twix*

          Of course not. That would be crazy. What kind of society would choose to function like that? /s

          But yeah, I 100% agree. It’s not LW’s problem either way unless they want it to be. However, it does impact what options are available to LW. If accepting new work is optional, it would be totally reasonable to say “If you want me to stay, stop accepting new clients/figure out which clients you can let go until you’ve resolved the staffing issues.” If it’s mandatory, the workload is still a problem but it’s one the owners don’t have as much immediate control over. (Although if that’s the case, the failure to staff the business appropriately is even more egregious!)

        2. Kendra Logan*

          No kidding. After Hurricane Katrina, two care homes in New Orleans came up with evacuation plans for their residents for future disasters.

          Then they discovered they’d both hired the same low-bid contractor to carry out the plans. In a real situation, the contractor was equipped to evacuate only one of the homes.

    2. Dog momma*

      Somehow I think the big client is the Feds…and you don’t tell them ” no”….ever.

  20. PotsPansTeapots*

    “The remaining owner means well and panics at any sign of me being unhappy…”

    This is good! There are so many AAM letters about your situation, but most of those have a boss who doesn’t care.

    You have a boss who cares about your job satisfaction – tell her what it would take for you to be satisfied. An extra 3 weeks of vacation after busy season? A temp? 2 temps? Unlimited bags of dried figs? Alison is right – you hold most of the cards here, don’t be afraid to ask for what would really make it easier for you, even if it seems like a big change or a lot of money. View it as giving your bosses a chance to keep you on, if that helps.

  21. Dinwar*

    I don’t remember writing this letter, but it sounds eerily familiar…..

    For me, money wasn’t an issue. I’m well-compensated, and more money simply wouldn’t change the equation any. Money doesn’t help if you never have time to spend it (and in the environmental world the company pays for your hotels and food on the road). And the schedule is what it is, based on chemistry, physics, and legal requirements–I couldn’t change that (much) without someone being hurt or going to jail. What I did was leverage the experience to moving up the chain-o’-command–getting more experience in management and moving into a PM role. For me, having that timeline (and aggressively working towards it) helped. I can endure anything for a few months, as long as there’s an end.

    If you take that route, one thing I would emphasize is figuring out how to prevent it happening to the next person. In my discussions about my successor in my previous role I made it very clear that we need at least three people to take my place, including a clear delineation of the roles and responsibilities for each person (with references to specific plans and company policies). The idea “I endured it, so you must” merely continues the cycle of abuse. Carefully thought-out documentation is important to this, because if it’s just you saying “This is too much” it can be dismissed, but if it’s “Here’s how this will get you put in jail” you will at least get a fair hearing.

    1. Charlotte*

      I think this is a great point — not only figuring out how to prevent it happening to the next person, but preventing it from happening to OP again. What if both new hires quit within weeks of each other? Writing the documentation now sounds like a good plan, but if possible it’d be great to train all the new hires to create documentation as they go and also make sure that all new hires need to be cross-trained at least a little. In such a small org, that only makes sense.

  22. AnonInCanada*

    No amount of money on the planet is going to help you when you die of Karoshi. How helpful the Japanese came up with a word.

    You call the shots, OP. You have leverage with these bosses. Start using it: demand a sustainable work-life balance so you don’t end up burning yourself out, and let them figure out what to do about it. You leave at precisely what time you feel you can in order to maintain your life. You’re not paid enough to deal with this crap. Best of luck!

    1. LTR, FTP*

      Agreed. I would be having a serious conversation with my boss: “I’m burnt out, and starting tomorrow I’m only working 40 hours a week, full stop.” What are they gonna do, fire you?

      If the business is literally going to fail if more work needs to be done, there are two answers. Find someone else to do that work besides you, or pay you a ridiculous (and I mean ridiculous) amount of money to do it yourself. And it’s not your job to find the other workers or the additional salary.

      You have all the power here. Push back. HARD. Make us proud!

  23. Astronaut Barbie*

    Yeah leverage this situation NOW for more money, a new title (which would help if you still do decide to leave) and whatever else you want. Because once they do hire, your leverage will dwindle as they get experience.

  24. Dawn*

    If you’re doing 100% of the work anyway, why not go into business doing this for yourself instead and stop doing all of the work while the owners of this business collect on it?

  25. Person from the Resume*

    I think what can be done is for the company to throw money at the problem. The company is getting by with a lot less payroll to pay now.

    (1) Pay you more to make this terrible period worth your while. Perhaps even temporarily until new hires are doing work. Or regular bonus until things are better in July

    (2) Hire temps to do basic admin/office work.

    (3) Contract some things out like hiring a new person so it doesn’t wait until the owner returns from maternity leave or tech writing to get the SOPs and training materials completed by someone other than you if you provide content.

    (4) Hire above entry level (they’ll have to pay more than entry level salary) so new hires come in with experience and maybe learn the job faster.

    (5) If at all possible do not ramp up. If it’s seasonal (like tax season), there’s nothing you can do, but if any of the busy season is generated by new clients do not take any new clients.

    It does sound like the company hasn’t gotten creative about trying to solve the problem and they plan to continue with business exactly as usual but with having you try to do the work of 4 people while the normal processes (including maternity leave) continue.

    1. kiki*

      Yes! It sounds like the company has been saving an amount equal to the payroll of 3-4 people while still completing most/all of their projects and work (so still making the same). LW should be seeing some of that. The business may balk at increasing his salary a lot since the goal is (hopefully) to restaff to capacity ASAP, but in the meantime, LW should be making pretty insane quarterly bonuses.

      It sounds like the company right now is profiting off of LW’s extra work and had delayed making necessary changes that would allow them to stay staffed appropriately. I think they need some sort of financial incentive to push them to make the needed changes fast.

  26. Admin Lackey*

    I also wonder, OP, if you can think of some services that would make your life easier outside of work and factor that into whatever salary that your ask for.

    Cleaning service, some sort of meal service, a nanny or babysitter, hell I don’t know, a dog walker, someone who will do your laundry. Any menial task that you can outsource is personal time you can reclaim and use to rest.

    And it really sounds like you need rest! They’re completely dependent on you and working you to the bone – you need to ask for a bunch more money

  27. Glazed Donut*

    If there’s anything I’ve learned about job vacancies, it’s this: if a person leaves and there’s a gaping hole that’s going to negatively impact your workload/workplace well being, become a squeaky wheel about getting that position filled ASAP. Don’t assume someone else is on it or realizes the impact or cares – make that a weekly priority to ask for updates, how you can help create a plan to fill it, enact the plan, etc. Not always possible, but it needs to be as important to others as it is to you or else many people end up in this burnout, angsty land.

  28. Glowworm*

    Op this isn’t an or, it’s an and/and/and. You can and should stand firm in demanding more pay, fewer hours, and some kind of temp help/ task restructuring / reduction in projects.

  29. François Caron*

    Get out.

    If a company dumps extra work on you with no adequate compensation and can’t — or won’t — find replacement personnel in a timely manner, that business is already in very serious trouble.

    You might also discover during your job search that you were seriously underpaid for years.

    Don’t make the company’s problems your personal problems. This company IS your immediate problem!

    1. Laser99*

      The LW is being exploited, pure and simple. They’re hoping she won’t notice, or will be too nervous about pushing back.

    2. Generic Name*

      Honestly, I’m dying to know what OP is making. I sincerely hope at least 6 figures, but something tells me they are probably making $50 or 60k, but maybe that’s me being cynical.

    3. Garblesnark*

      As someone who has multiple permanent disabilities from letting companies be my problem… yeah, this.

  30. Burnt out*

    I was in a similar position a couple of years ago. Explore doing the bare minimum required to keep things afloat, and training. Take a hard look at your workload – if you quit, what would the owner need to find a way to get done? Do those, and not anything that can be skipped or postponed. Also consider hiring a contractor to assist – they may not get things done as well as you would, but at least the things will get done. Above all, remember that this is the owner’s problem, and if they don’t care enough to find a solution besides you working yourself into the grave, you shouldn’t care more than they do.

  31. MistOrMister*

    Besides asking for more money, it sounds like this would be a fabulous time to ask for a change of title, if you are so inclined. It could be helpful when looking for another job.

  32. Ms. Murchison*

    I wonder if the LW can negotiate some steep increase in vacation leave accrual, with the understanding that they’ll need to take a 3-week vacation to recover once they get restaffed. At the very least, LW should negotiate to be paid over and above the salary of the highest person they’ve been covering for (sounds like the supervisor for their position?). I hope they’re factoring in how much and what kind of recovery they will need after enduring months of this.

    LW, don’t put off any medical appointments during this push time. Going this hard will take a significant toll on your body and ignoring it will only make things worse. And consider taking peak-COVID precautions regarding exposing yourself to any viruses going around. You’re more likely to get sick because working this hard is going to wear down your immune system, and you’re going to feel compelled to still work if/when you do get sick.

    1. Ms. Murchison*

      LW, you mentioned getting another new hire after maternity leave is over. Can you push for the big-picture owner who’s still in the office to hire someone sooner?

  33. Alex*

    Are there specific tasks that the owner on maternity leave could do from home that would relieve some of the pressure or tasks that she could train the new hire on whilst looking after the baby? Or even could they spend company money on a nanny to allow her to return to work sooner?
    Whilst maternity leave should be a universal benefit when you own the company it sometimes isn’t possible to take a leave if you want the business to survive and it’s not reasonable to put the level of pressure on an employee that the OP is currently facing in order to take leave.

  34. wine dude*

    Whenever I hire a new person I have the next newest person train the new person initially. This helps reinforce the next newest person’s training and takes it off my plate. Then I come back and make sure the new person has learned everything. Hopefully OP’s business would allow for this sort of thing.

  35. Not an expert*

    I think there is one more thing that can possibly be done, and that’s urging the owners to scale the business back until you’re fully staffed and the new staff is trained. They should have done this when they were down to one employee and one owner, but it’s sound like they didn’t (or not to the degree that they should have). This may or may not be possible, but at a minimum, they should not be taking on new clients at this time!

  36. I went to school with only 1 Jennifer*

    LW, I’ve done job training and this change may help you quite a lot: instead of writing up training materials ahead of time, *show* your fantastic new person how to do the thing, while they take extensive notes. Then have *them* write up the how-to document, and give it to you for editing. You can then add info they missed (or you missed at the time), or background info that is helpful, or what have you.

    You get these results: (1) you get a good idea of how much your colleague understands; (2) they learn more thoroughly as a result of doing the write-up; (3) you get to edit instead of write; (4) you’ll have the written procedures in place for the next new hire. Number 3 is probably the biggest deal for you right now, because for most people, editing is MUCH easier than writing.

    And yes to asking for more money, because if you can afford to outsource any daily tasks, you’ll feel much less harried right now. What to outsource? Cooking dinner (restaurant take-out) and doing laundry (wash-and-fold services) are two good places to start.

    2. nnn*

      Yes, this is what I came to suggest.

      The whole reason why my workplace now has very robust written procedures is because one trainee was taking a lot of notes, and when there was some downtime she and her trainer adapted them into general procedures for future employees.

  37. kiki*

    This isn’t for LW as much as for any business owners/ managers/ directors who. may read the comments– this is why you need to staff higher than the minimum based on your capacity and make sure you’re backfilling roles quickly. Allowing a team to atrophy may work for a while but that risks total collapse.

    1. Grumpy Elder Millennial*

      This. When there’s no slack in the system, you’re going to have problems. People are going to take vacation, have health stuff come up, have family obligations, etc. The minimum staffing level should be however many people are needed to manage the work under non-ideal circumstances.

  38. Kelly*

    Try out Scribe is an add on for google chrome. It records what you do and creates an SOP with step by step instructions and pictures. You may even be able to have the co-owner on maternity leave use this to create some guides for new hires.

  39. WhyIsEverythingBananas*

    What concerns me most about this whole scenario is “and then the other owner will come back and we will ramp up for spring”. I don’t know how flexible this is but…under the current circumstances? There simply cannot be “ramping up” happening. I think OP needs to be clear about how they simply cannot do ANY additional work unless it is directly oriented towards ultimately alleviating the workload. That may mean some short term business sacrifices, but no amount of money can compensate for running at burnout levels of work. If you burn out, OP – your business will be in MUCH worse trouble than if they lose out on a few client contracts or burn a couple bridges, since then they WILL cease operations!

  40. Michelle Smith*

    I worked in a job where my team dwindled down very similarly to what you’re describing and then my boss left to go work somewhere else and the person who took over was not as good. While we eventually did get new staff in to ease the burden, it actually never got back to the point where I was happy. I’m still dealing with the physical and psychological repercussions of that burnout over 2 years later. Even if they hire new people, if you find that the job is negatively impacting your mental or physical health, still leave.

  41. Garblesnark*

    LW, I don’t know you, and I don’t know your choices.

    At this point in my life, in a situation like yours (and I have been in situations that felt like this), I would make choices I would have found unthinkable ten or even five years ago.

    I would sit down with the owner and I would say, “listen, all I have to gain here is my paycheck and all I have to lose is a lot of stress. That is changing. I will accept this arrangement in exchange for a permanent doubling of my salary, an immediate bonus of X, a retention bonus of Y when your partner gets back, and three temps who start by next Friday. And I’m taking PTO for all of July which won’t count against my balance and expensing all my meals while I’m in the office.”

    Because that’s the minimum where this amount of stress could possibly be worth it.

  42. ThatOtherClare*

    Letter Writer, you mention that you’re spending a lot of time creating training documents. A lot of people are suggesting above that you should request a bigger bonus, but that doesn’t ease your workload at all.

    Is there any chance your company might instead be able to offer a big enough wad of cash to entice one of your recently departed co-workers to take a short term contract to write up some of the needed documentation? They might be willing to spend a one-off month of Saturdays creating 20 process/procedure training documents – if they left on decent terms and your company offered them a large enough financial incentive to do so. It would be worthwhile asking them. The worst thing that can happen is they say no and your situation doesn’t change at all.

  43. Mangofan*

    One idea: can you take the “figure it out, and then I’ll look it over and tell you all the things you couldn’t have known you were missing” approach and then have the new hire write up the training documentation themselves based on that experience, and you just review and edit it?

  44. Semi-retired admin*

    OK, I know we all need and deserve maternity leave and I would fight for that in most cases, but one of the owners is taking leave, and leaving her company in the hands of a soon-to-be-retired partner who is basically checked out, and one employee doing the work of four? That would definitely not fly with me. As long as there are no medical complications that we don’t know about, the owner needs to find a way to get back in there and work on figuring this out, even if it’s part time or remotely. The self-employed don’t have the luxury of the benefits that an employee has.

  45. El*

    Ooh, I’ve got one. In addition to better pay, negotiate a VERY long (3-4 week) additional paid vacation at the end of the busy period (a specific date so it doesn’t get eternally pushed back).

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