should I stay at a job I don’t like if it could lead to a big pay-off in a few years?

by Alison Green on August 31, 2021

A reader writes:

I’m facing a major decision that I thought I was solid about but now I’m not so sure. I went to school later in life and graduated in 2014 as an accountant at the age of 32. I’ve been working in my field ever since progressing from bookkeeping at a small manufacturing company to my current job as an assistant controller for a small tech start-up developing what could be a really huge platform. To put it into context, we hold 20% of the patents in our market and are ahead of the big guys like Amazon and Dell in terms of development and deployment.

When I joined this company almost two years ago, my job description was for full cycle accounting but in reality I am more HR, payroll, office manager, and executive assistant than I am accountant. I spend roughly 2-4 days a month on actual accounting (which I love) and the bulk of my time is spent on these other tasks. I understand that we’re small (less than 30 employees, most of whom are software developers) but that wasn’t what I signed up for. In the past year, I’ve come to dread hearing my computer or phone go off with messages from my boss because it’s always for some task that I dislike.

This led me to start job searching, and since I live in a large metro area I was able to find an accounting role fairly easily that should be 90% accounting. It is in a more stable industry and comes with a $12,000/year salary bump, 401K, and cheaper health insurance (for better coverage). I told my boss I was leaving when I accepted the offer from the other company, and while he wasn’t happy I thought he took it pretty well.

However, he asked me to stay on part time for 4-5 hours a week at half my salary while he finds my replacement and I train them, which is fine since he’s the only other finance person and I know he has a lot on his plate already. Since then, he’s been making sideways comments about me leaving and how difficult everything will be on him with me gone. Culminating in today, when he offered to increase my salary by $10,000/year immediately with another $10,000/year when we close our next funding round (before year end) and shares in the company that could conceivably be worth a life changing amount of money in 2-5 years if this tech is as massive as it looks like it will be.

This leads to my question as I’m now unsure what to do. I was fully set on leaving immediately and no amount of money would change that because I’m miserable, but when I say life changing I’m talking upwards of $300,000 minimum, depending on when I exercised my options in the company.

What I am currently doing isn’t difficult, just soul draining for me because it’s not what I love to do. There could conceivably be more accounting functions within the next year or two as we have some big contracts being worked on right now that will grow our revenue immensely when they kick in. I just don’t know if my executive assistant type duties would ever go away (my boss is not very tech savvy and needs a lot of basic help with things like creating PDFs or excel tables, etc.) and whether to prioritize my happiness with what I do every day or the possibility of a big payout with my current company.

I grew up extremely poor, so that may be why I’m so conflicted. Since I’ve been with this company (less than two years) I’ve increased my salary by almost $30,000/year over my last job. However, my fiancé and I are solidly middle class with our combined incomes, and we’re not hurting for money although we don’t have anything substantial saved for retirement yet. But this kind of money would help us move from renters in a high cost-of-living city to home owners, save/invest for retirement, pay for our wedding, and help my teenagers with college expenses. Please help. What do I do?

First and foremost, see that what you’re contemplating is a gamble. A really big gamble.

You could stay at this job but never see that life-changing money. There’s no guarantee that your company’s tech will end up being as huge as they’re hoping it will. The last two decades are littered with companies that were once believed to have enormous promise (especially by the people running them) that never came to fruition. Those shares could end up worth very little. It’s not uncommon for it to go that way.

So the first question I’d ask yourself is: If you stay for several years and the life-changing money never appears, how will you feel? Will you still think taking the risk was worth it, or will you regret that you did? If you knew right now that this was the most likely scenario, how would it affect your decision-making?

The second thing is, it’s okay to turn down money because you don’t like the price it comes at. So often we’ve been socialized to believe we must go after more money when it’s possible (part of that is what happens in a society where people don’t have a secure safety net), but it helps to step back and ask whether what you would need to do to get that money is worth it to you. Some people calculate that doing work they don’t like in exchange for more money than they could earn otherwise is a trade-off they’re willing to accept. For some people it’s not. Other people are willing to work 60-hour weeks, or put up with a boss who makes them miserable, or deal with soul-crushing clients if the price is right. Other people aren’t. (Of course, for all of these, it often depends on how much money we’re talking about. I’m not going to deal with most of those things for a typical middle-class salary, but offer me enough and at some point I do have a price tag for most of it. My price tag is probably unreasonably high, but it’s there. On the other hand, there are things most of us wouldn’t sign on for regardless of price, which is why there aren’t more hit men walking around.)

I don’t know where you fall on that spectrum, but I urge you to really think about it and figure it out. Don’t just reflexively fall into “it’s a lot more money so I should do it.” (I know that advice is especially hard to take when you grew up poor; that financial insecurity can stay with you in really fundamental ways even after your circumstances have changed.) But it’s also okay if you decide, “You know what, I am totally up for doing this for three years in exchange for a guarantee of $X, and I will have a clear ending point for when I’ll move on.” Just make sure X is real, not a maybe/might happen.

Also, is there an option here where you negotiate with your boss not just about the money but about your job duties as well? Have you told him straight-up that you want to be doing mostly accounting and the rest of the work is what drove you to look at other jobs? In exchange for getting to keep you, would he be willing to hire someone else to do the payroll/HR/office manager/executive assistant parts of what you’re doing now? (And if he did that, would there be enough accounting work left over to fill your time?) Even just moving some of that off your plate — like by getting him an assistant — might be enough to change your job in ways that would make you happy to stay. But there’s a big caveat: you have to trust him to make it happen. You don’t want to turn down this new job, only for him to drag his feet for months and not actually change anything.

But if the money is the root of this, make sure you’re basing your thinking on the hard numbers in play right now — not what could maybe/maybe not be in play in three years. And if you look at the money, the $10,000 bump your boss just offered you still puts you $2,000 below what the new job offered, plus they have cheaper health insurance so calculate that cost in too. And if he comes through on that additional $10,000 bump later this year (which is not guaranteed), that puts you $8,000 ahead of the other offer. Subtract the health insurance difference and let’s call it $6,000. That’s $500 extra per month — or maybe more like $375/month after taxes. Is $375/month enough to do work you don’t like all day? It might be! Just make sure you’re looking at the real numbers.

Good luck.

Read an update to this letter. 

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{ 372 comments }

{ 372 comments… read them below }

  1. Aunt Vixen*

    Don’t do it, friend. $10k now and $10k “when” is actually $10k now and $10k IF. The plan is to complete the next funding round in the next quarter but even that isn’t a guarantee – still less is it a guarantee that you’ll get a life-changing windfall two to five years from now. By which time the job doing what you actually want to do for more money and better benefits will of course be long gone.

    Go now while you still have a chance to be happy.

    1. Mona-Lisa Saperstein*

      Yes! I commented below, but all I could think of when I was reading this letter were the people who stayed at Theranos because it was just! on! the! cusp! of! greatness! The funding kept on coming in, but then it didn’t, and it all came crashing down. Of course this company is more stable than that (because it’s impossible not to be), and of course most of the Theranos employees have gone on to find other jobs, but it’s just a reminder that sometimes future greatness doesn’t actually materialize.

      2. Christina*

        Yes! The first thing I thought of was all of the companies who used and abused their employees with the looming promise of a great pay off (Theranos, WeWork, etc.) that never actually pays off. I work in research and development and having some patents and promising technology doesn’t mean anything until those majors deals are signed. Don’t bank on those “maybes” unless you have a reliable confirmation that 1. it will be happening 2. the realities of how you will benefit are made crystal clear to be.

        1. Cassie*

          I’m a bit late to the thread but I met with a guy earlier today who was given a bunch of stock shares as part of his compensation and to make up for a slightly lower than market salary. It seemed like a fair trade off until the firm went bust.

      3. Barbara Eyiuche*

        I was all ‘stay for the possibility of the life-changing money’ until I read that it was $300,000. That’s not enough. Three million? Sure, stay for a few years and see if it pans out. You can presumably get another job in three to five years if it doesn’t work out.

        1. Perspective*

          Just for some perspective: $300k is A LOT of money to most people. As the letter writer said, “But this kind of money would help us move from renters in a high cost-of-living city to home owners, save/invest for retirement, pay for our wedding, and help my teenagers with college expenses.” Any ONE of these thing is a life changing thing- let alone if the LW is able to parlay $300k into all four of these. And if a person has any sort of debt- student, medical, car/house loans- boy howdy, $300k would change that person’s whole life. And not just the actual elimination of the debt- the stress of how to pay that off, planning future payments, etc.

          I recently changed from a job that paid $15.50 an hour to one that is about $20.50 an hour. I have no debt and, because of circumstances, could reasonably afford anything I wanted, within reason. (IE: I didn’t have to worry about affording my bills or if my car broke down, paying for repairs.) The shift in my pay allowed me to start feeling like maybe I could afford some stuff I wasn’t sure I could before- if I had big medical bills, a vacation, a better car if I need to replace it, etc. I had savings before, but now I feel more confident in setting aside a little more or maybe even tying up some money in some longer term CD’s, whereas I wouldn’t have been comfortable with that before. If someone where to say, “Stay in your job for three years for the potential to make an extra $300k,” I’d have to take a good hard look at it because then I could think about buying a house or stop worrying about what happens to my parents when they’re elderly and need care.

          1. Barbara Eyiuche*

            I think it depends more on how you were raised. I don’t make much money, but to me, when I was reading ‘life-changing’ I was expecting a lot more. For the OP, I don’t think it is enough to stay in the current job.

            1. Smh rn*

              Yeah 300000 is a lot but it’s not retire a never worry a gain money. And it’s not a big enough payoff laid against the risks of it never materializing. Go with the sure thing.

          2. KK*

            I live in California, and don’t make that much to begin with, so I’d be in the same boat. After finally having a year’s worth of emergency cash, maxing out my retirement account, paying off student debt, and getting some PT that insurance won’t pay for, I really wouldn’t have that much left. It would be nice for a little while, but I’d still be making it budget and last as long as I possibly could since it wouldn’t last me that long. And even if I took all of it & tried to, I wouldn’t have enough to buy house right now, I’d likely end up losing every bidding war.

        3. NYC Taxi*

          Agree it’s a big gamble. 300K is not life changing, regardless of what people here are saying. It really isn’t. It’s a great start on an IRA or other retirement account for a person in their 30s that will have big pay off in their 60s-70s. $3M, then we can start talking life changing.

          1. louvella*

            But like…how is having enough money to easily retire not life-changing? That is HUGE. I am 34 and have $12k saved for retirement, how would adding $300,000 to that not change my life?

            If I had $300,000 I could pay off my student loan debt. I could buy a car. I could buy a house. That would be MASSIVELY life-changing.

            1. NYC Taxi*

              Pay off your student loans and put the rest in savings. Homes are expensive. You’re always paying for some maintenance thing. New roof, Repair to roof. The boiler needs repair. Insurance, taxes, And you just spent all your money on a house and car. How are you paying for all of that?

              1. louvella*

                I mean, don’t worry, I will likely be renting for the rest of my life, if that makes you feel better. But renting is pretty damn expensive too. Yes, repairs are expensive, but everyone I know who owns pays less on their mortgage than it costs to rent an apartment.

                Even if it was just all in savings…if your argument is that having $300,000 in savings is the same as not having $300,000 in savings…I really don’t think that’s true. But I mean, if having $300,000 in savings really doesn’t matter at all, guess it’s fine that I never will.

                1. No Longer Looking*

                  NYC Taxi is saying it isn’t always less than rent once you factor in costs for repairs, upkeep, taxes, and insurance. You have to do a deep budget dive, you can’t just compare the rent vs mortgage numbers.

              2. louvella*

                Also just want to point out that a lot of jobs require cars, so if I owned one that could actually increase my earning potential.

            2. Nanani*

              Could you do all of those though? I don’t know anything about cars but the other two could eat 300k all by themselves in a lot of places

              1. louvella*

                I couldn’t buy a house outright but I could easily afford a down payment, and the down payment is what is preventing me from being able to buy a house.

                1. Nanani*

                  So it’s life changing, but not for very long, I guess you could say.
                  Once you have the house, your one time 300k is not paying the bills on the house’s utilities, and everything else in your life is still there. Maybe more expensive, if the house is farther from where you work and shop and all that.

                  Point is –
                  When I hear “life changing money” I think along the lines of “don’t have to work unless I want to” more than “achieve one of many financial goals, which means when we’re talking about a one time sum (as opposed to an ongoing thing like a pay bump) it needs to be really really REALLY big.
                  Perhaps this is what’s fueling the conversation in here about what is and is not life changing?

              2. louvella*

                For whatever reason I can’t reply to your most recent comment, but I ​would say for me life-changing is:
                Knowing I can retire at some point, perhaps at 65 or so
                Having savings for an emergency
                Not being in debt
                Being able to afford a car, which opens up a lot of jobs and also where I can live

                I mean, the idea that $300,000 couldn’t help me buy a house is pretty extraordinarily depressing, but maybe it’s true. Maybe even if I were able to save $300,000 it just won’t be possible for me. I could certainly easily afford a mortgage but maybe the repairs will just always be out of reach. But I am very curious if most home owners have $300,000 in the bank! Because I don’t think most of my friends who own do. Most of them got help with the down payment from family, or got an inheritance, often much less than $300,000. (Neither option is available to me.) Maybe they all made really terrible money decisions, I’m not sure.

                1. louvella*

                  Though I’m not sure why you think I can’t pay for utilities, I pay a lot for utilities now…

                2. louvella*

                  Ok sorry but I just reread your comment, you said “everything else in your life is still there.”

                  It’s not, the cost of renting is no longer there. The monthly cost of renting is higher than what I would be paying for a mortage. The utilities would be similar. Repairs are the big concern. Maybe you need more than $300,000 to cover repairs. I’ve taken some classes on home buying and numbers like that were never thrown around but maybe they should have been.

                3. Amaranth*

                  I would find it life changing because its a huge relief to know you have enough money not to have to keep a toxic job, you can afford it if your car breaks down, buy a condo or house (if COL isn’t incredibly high), or you could cover any health issues that might crop up, etc. Just having enough money put aside so you know that your kids won’t go broke caring for you when you get older – that’s another good thing. it doesn’t have to do ALL of those things to change your life.

                4. Anon2*

                  Whether 300k would significantly improve your likelihood of buying a house probably depends on where you live. Whether rent is more or less than a mortgage is also location-dependent. Maintaining a house is a huge expense, as are taxes. In some areas, the taxes are in effect passed on to renters but again, it depends on the housing market where you live. Insurance is also a factor depending on location.

                5. Maid Dombegh*

                  This is more a reply to Nanani above, but there’s no nesting left on that comment. I think what’s being discussed here is the difference between “life-changing” and “lifestyle-changing”. For me, $300k would be life-changing, in that I would stick it straight into my retirement savings and pretend I never saw it until I’m actually ready to retire. It would mean there’s a chance I actually could retire someday, so that’s life-changing. It wouldn’t be lifestyle-changing because I would still have to keep working for now. In OP’s case, if they could use that money for their kids’ college, that would certainly be life-changing for the kids.

                  But I would also find an extra $12k a year life-changing. I could spend a bit more on my fun hobbies, and yes, put more towards retirement. Having better health insurance could turn out to be life-changing too, since you never know when you might need it. So for OP, since the $300k might not be real but the $12k/year plus better health insurance definitely is real, that’s what I would choose. I see below that they did accept the new job, and I think that’s the right decision.

                6. Britt*

                  Louvella– have you tried lending options that don’t require a large down payment? My understanding is that in many cases you can get a mortgage with 3 or 5% down, and sometimes even zero down.

                  If you’ve run the numbers in your area and a mortgage payment (including taxes and insurance) really is significantly lower than the cost of renting, then finding enough money to scrape together a small down payment seems really worthwhile if possible. (Not to downplay how hard it can be to save…)

                7. EchoGirl*

                  @Britt: The problem is, a lower down payment means higher monthly payments. So a really low down payment might mean a mortgage that isn’t that much cheaper than local rents, depending on the actual numbers involved.

          2. louvella*

            I should add I don’t think the OP should stay because it’s not in any way guaranteed, but if it were guaranteed…different ballgame.

          3. DrunkAtAWedding*

            Whether an amount of money is “life changing” really depends on where you are in life, doesn’t it? The letter writer listed exactly how it would change her life, and since that’s the life in question, I’m happy to accept her assessment on that.

            1. NaN*

              +1 to this. I don’t know why this point is worth arguing. Life-changing doesn’t mean “set for life,” it just means that it would drastically change a person’s financial situation. Life-changing for one person isn’t necessarily life-changing for everyone.

              The bigger problem here is that it’s promises of potential money, life-changing or not, that have no guarantees of materializing.

          4. Koalafied*

            Yeah I think different people define that phrase differently. The overdue repairs and improvements I could make on my house with $300k lump sum would change my life, in that every day I would wake up in a radically improved home where broken things I’m constantly trying to extend the life of with stressful diy repairs would be replaced by creature comforts. That’s undeniably a change in my day to day quality of life. In many other ways, of course, my life would be the same. I wouldn’t quit my job, move, or upend any of my relationships. I think some people use more the first definition of “my day to day life is noticeably improved” and others use more the second definition of “everything in my life has changed.”

        4. Liz T*

          $300,000 is our rent for 10 years. In Brooklyn. With enough left over to get us completely debt free.

          Some of y’all are weird.

          1. EchoGirl*

            For me, that would almost certainly be enough to pay off our house. It wouldn’t be enough for us to never have to work, but it would mean being able to live a different kind of life on the income we currently have (i.e. no more putting off non-essential home improvement projects — some of which will likely pay for themselves in the long run — because we can’t afford to have the work done).

            1. EchoGirl*

              I should add that in regards to the letter, I’m not saying that the potential for this kind of money means OP should stay, especially since it seems like it really is just potential, not something that’s in any way certain. I’m just saying that I too am taken aback by people acting like it’s not something that could have a major impact on someone’s life. I guess maybe people have different definitions of “life-changing” or something, but yeah, this could change a lot about a person’s life.

      4. MsSolo (UK)*

        There was a letter here once from someone asking about red flags at a job interview who popped up some years later in an update section to add that the job in question had been Theranos, and they were very glad they hadn’t taken it up!

    2. Jessica Fletcher*

      Right. And it doesn’t sound like the manager fought to keep them. It sounds like he grumbled about it and maybe his boss offered this way to keep them. But they’re thinking about keeping primarily the EA/HR/payroll person. They aren’t trying to retain a great accountant, because they don’t give LW those responsibilities.

      I agree LW will be better off leaving. The new company will see them as an accountant first, not the EA who helps open PDFs.

    3. MissGirl*

      But this isn’t her only chance to leave. There maybe other opportunities—some worse and some better. She could wait and see what six months does. Whatever she chooses is a legitimate path.

      1. Daffy Duck*

        She isn’t going to get a big payoff in 6 months tho. She **might** get one in 3 years. That is a long time to work a job you don’t like. Also, a boss that can’t open a PDF or hire an office manager/HR person but expects to navigate the next big tech deal… it takes a lot more than a good idea and a kicking developer to bring a product to the national/multinational level.

        1. Falling Diphthong*

          Is the metric by which the 30-person startup is ahead of Dell and Amazon something those companies care about?

          That just sounds to me like what you say when your retention strategy is to promise great things down the road.

        2. Chauncy Gardener*

          Agree. MIGHT is the key term here. And it doesn’t sound like any of this is in writing i.e. options or equity grants. And the boss didn’t have any interest in keeping the OP until they quit. It’s all bad, in my view

        3. NaN*

          Be very, very wary of startup stock options! The company my friend works for just got acquired by a bigger company, and not only did she get laid off but her options are now worthless. The acquiring company doesn’t have to honor them.

          1. identifying remarks removed*

            Yes – there are so many variables – when you started, how many you have, what your strike price is and of course if they company does well. I had stock options in a company but joined late in the game so I had a small amount, vested over 3 years and my strike price was 10 times that off my boss who was one of the first employees. He made millions and I got 50K my first year and the 2nd and 3rd years they weren’t worth the paper they were written on.

    4. Janet Rosen*

      Totally this. Grab the job you actually have a solid offer on and don’t look back. Heck, with his attitude I wouldn’t have offered to continue part time. Not your problem.

    5. Seeking Second Childhood*

      If you really want to keep the door open, set up a contract where you work X hours a week to do their accounting only. Pre-determined hours, contractor rates high enough to pay your self-employment income taxes fixed hours, and a steep surcharge for working outside your predetermined hours.

      3. Storm in a teacup*

        I was coming here to say the same! If the actual accounting work is only 2-4 days per month and you have the bandwidth offer to do only this element as a contractor (with commensurate pay and share options)

    6. Saraquill*

      I knew someone who was contacted at random to write a TV script. They claimed they produced TV shows before, implying his work would certainly see the light of day. He sent in the script, they said they’d pay him when they got funding, then nothing.

    7. RebelwithMouseyHair*

      It’s not even as if OP works in a tiny niche: everyone needs accountants. As I see it, the new job could be a stepping stone to even greater things.

  2. Cait*

    I was in your boat a few years ago. I chose to stay and as soon as I did they pulled the rug out from under me and took almost everything they promised me off the table. I did manage to backtrack with the company that made me the offer and they accepted me (although eating crow never feels good), but of course this isn’t a guarantee for you.
    Take Alison’s advice and take the new job offer.

    1. HarvestKaleSlaw*

      I was about to give similar advice. LW, if you take the offer, please get it in writing, get a good attorney, and get that attorney’s eyes on the contract.

      A lot of startups pay in promises. If you are taking that risk, at least get paid in blood oaths.

      1. GammaGirl1908*

        “A lot of startups pay in promises” neatly sums up what I was thinking about this letter. They are throwing hypothetical money at her to solve the problem of having to hire somebody new.

        There’s a whole lot of IF here that may or may not ever come to fruition. LW should take the bird she has in her hand. The old office can hire someone to solve all of these problems; they just are irked about taking the time and effort to do so. Yes, it would be easier for them if she stayed, but that doesn’t have to be LW’s problem.

        At its core, this is a “should I accept a counteroffer?” question, and the answer to that generally is no. That doesn’t change just because this platform may blow up someday.

        1. RebelwithMouseyHair*

          Yeah I mean who doesn’t dream of being bigger than Amazon and who has enough ruthless business acumen to actually do it

      2. Your Local Password Resetter*

        Goodness yes. Get those promises black in white, in a really strong contract that doesn’t leave them loopholes or escape clauses to pull that money away again.
        It’s a life-changing amount of money, don’t take gambles and don’t just take anyone’s word for it.

    2. Clara*

      I agree! I’ve had bad experiences with startups. They know you’re hoping against hope you’ve picked the next Google, FB, etc and they use it against you. Meanwhile they will only really try to keep the superstar sales people or coders when push comes to shove.

      One thing that stood out to me was if your boss isn’t tech savvy enough to use PDFs or excel… how is going to be leading the next big thing in tech?

      1. Ya Girl*

        Ding ding ding! I also wondered about the boss who doesn’t know how to save a PDF creating The Next Big Tech Advancement.

        1. Metadata minion*

          Eh…yes and no. I know quite a few tech-y people (and I’m sure this is true of tons of fields, but more obvious here since there’s so much basic office stuff that now overlaps with technology/computers as a broad term) who are utterly brilliant in their very narrow area of tech, and kind of hopeless outside of it, even sometimes at things that most reasonably computer-literate people can do as part of daily life.

          I think startups also probably tend to attract the kind of people who “don’t need to learn that stuff”, because they’re the Genius and can make their underlings do all the boring bits.

          1. Anatanyia*

            OP here. Since I’m in finance my boss is the CFO. The CEO, CTO, developers and sales guys know their stuff in the tech world. I only vaguely understand exactly what our tech does because when they explain it to me it all goes over my head. They’re geniuses when it comes to what they do but my boss only has to know enough to get through a meeting with investors and make small talk while the tech guys set things up. He’s great at raising money and drawing up contracts for new revenue streams, general computer skills just aren’t his strong suit.

            1. Bay*

              That makes it really hard to tell if your company is actually the next big thing or if they’re full of themselves, if you don’t know the tech behind it. A lot of companies make big promises in the tech world and don’t actually have the means to follow through.

              1. Momma Bear*

                The “next big thing” is also dependent on other factors, like someone else not scooping you with a similar product. See: VHS and Betamax. Beta was better but VHS snagged the market.

            3. JSPA*

              Based on what you wrote, he’s excellent at convincing people who have no way of judging the facts, that things are amazing–while at the same time, he himself doesn’t have a grasp on what he’s selling.

              And you’re not equipped to judge, independently, the validity of the product.

              So….

              Sure, he could be sitting on a goldmine, and be gold. But he’s more likely sitting on his ass, and being an ass.

            4. Coder von Frankenstein*

              Based on this additional info: Get. Out.

              The tech world is crammed with people who talk huge, and sound convincing if you’re not familiar with the tech in question, and are totally going to be the Next Google–who are in fact full of hot air and going nowhere once the venture capital runs out. Anybody can file a patent. Often they are even granted.

              If you do not have the expertise to evaluate the technology for yourself, you should assume you are dealing with one of these folks and plan accordingly. The odds are overwhelmingly tilted that way.

              1. Nanani*

                “Anybody can file a patent. Often they are even granted.”

                As someone who works in patents, this made me laugh
                +1 internet to you

            5. Not So NewReader*

              OP, if they can’t explain it to you then how do they plan on selling it the Average Jane or John out there? Don’t skate by this, they may have the best gizmo in the world, but if I can’t figure out what it is, I am not buying it. There are lots of other people who think the same.

            6. Amanda*

              If even the “sales guys” can’t explain it in a way that an intelligent but non-tech person can follow it, run. They are really going to struggle fulfilling their promises.

            7. RebelwithMouseyHair*

              yeah OP if you’re not capable of understanding exactly what the tech does and why it’s better than Amazon, those “geniuses” could just be telling you the same impressive-sounding bullshit that they used on the non-tech bankers who’ve put up the money for the time being.

      2. Seeking Second Childhood*

        Well someone has to make the hardware. You don’t have to be good with Microsoft Office to be a genius with a circuit board.

      3. JSPA*

        Exactly! I mean, on one level, I get it–I know people who do supercomputing, and have no idea how to cut and paste except by using a command in a terminal window.

        But on a very different level, someone who outsources the sort of basic competency with “normal user” tasks? That’s not a great sign, as far as developing and selling those patents effectively.

        ten years ago, you’d say this was something a competent high school student could help with; now it’s a competent 12-year-old.

        also, if the LW isn’t vested in any stocks after 2 years…if the options only pan out after years of nonsense, if ever…this smacks of a, “jam tomorrow, but never jam today” scenario. There’s no need to burn a bridge. LW can absolutely say, “when the company has grown to where you need a full time accountant, I would dearly love to come back!” (Or even a job that’s only accounting plus payroll–that’s a normal merge.)

        But the thought that a company will rise or fall based on an accountant playing HR, office manager AND handholding the CEO for tasks that a child can do? That’s more than a little bizarre.

    3. Sara without an H*

      I seem to recall a comment on a post a few weeks back, recounting the sad tale of somebody who worked insane hours for a startup — only to be fired right before the company went public and they would have been entitled to stock options.

      OP may think their current employer would never, never do that, of course. But there’s no guarantee.

    4. Falling Diphthong*

      I recall an example of this where the boss was so fast to haul the almost-departing employee into the “Actually all that stuff we promised? Right back off the table as of now! Ha!” meeting so fast she hadn’t gotten back to the other company to turn down the better job offer. So she just continued on out the door, despite the brief hiccup for “Wait! You can have the moon! We totally promise!”

      1. KK*

        This is exactly what I thought. Whether or not the company hits it big won’t matter when they pull the rug out from under OP once they’re back in their clutches.

  3. Anon for This*

    Definitely if you stay, get the arrangements for the “life-changing money” in writing. My husband joined a company that was about to go up for sale and was told that he would be “taken care of” at the sale; he worked for an awful, soul-crushing boss and did a huge amount of legwork on the sale–late nights, long hours, all of it. At the end he was given one of the the smallest payouts in the company–others did get life-changing money, but he did not. We’re fine, and he’s working elsewhere now, but he definitely learned not to trust anyone to “take care of him” without getting the promised arrangement in writing …

    1. Aunt Vixen*

      Even if there’s no ill intent, getting it in writing may not help if there isn’t life-changing money to throw around. With the best will in the world, promises that you’ll get the biggest piece of the pie don’t help if it later turns out that there isn’t any pie.

      1. many bells down*

        Yeah my husband works at a company that has profit-sharing, and in 8 years we’ve only seen that money twice. The company definitely doesn’t make a profit every year. He’s well-compensated otherwise and he loves his job, but if we were banking on a huge cut of profits every year we’d be disappointed.

      2. what am I, a farmer?*

        Yeah, this is super important. They don’t have to be lying to you, or scamming, or anything else to just be wrong about how this will play out. It can seem like startups are binary — either you sell/IPO and stock option holders all get filthy rich, or they go bust. The truth is there are a LOT of options in between those, and most of them don’t end with you getting rich.

        Some possible scenarios:
        * You stay at the job, get the options, everything goes great, you IPO in a few years and make a lot of money (enough to deal with the logistical and tax consequences of options, which could be significant). Yay! Everything went according to plan.
        * You stay long enough to get the incentive options and have them vested (meaning they’re yours if you leave). Then another new, great opportunity comes along before a sale or IPO, and you have to decide whether to spend a lot of money out of pocket to exercise (essentially buy) your options. (This has happened a TON at my company. Everyone I know left their options behind when they left.)
        * You get options, but when the time comes to exercise, you can’t afford to (if they’re ISOs, which you buy — I would need to put up $5,000 to exercise mine, and there were times in my career when I did not have that) or you can’t afford the tax consequences (if they’re RSUs, which you don’t buy but owe more taxes on).
        * You get options, but the company doesn’t gain that much in value between the options being issued and a sale or IPO, so you make $3,000 or $30,000 instead of $300,000. (This is the situation I’m likely in. I’m in a job with options, but I joined the company when there was a bit of a bubble in my sector. If we ever sell or IPO, I’ll make some money, but it will certainly not be a life-changing amount — basically the equivalent of what I would have now if I’d gone to another company for a higher salary a couple of years ago.)
        * The company is sold for more than it’s worth now but less than they hoped it would be worth. See previous scenario.
        * The company is successful enough to keep ticking along, but not successful enough that a sale or IPO is a real possibility, and then is mismanaged into the ground.

    2. turquoisecow*

      Yeah and make sure you understand what you’ve got. My husband has a friend who built a company from the ground up with his partners – he did all the hands on tech work while they managed funding and bought yachts. When the company was sold he was expecting a big payoff and discovered that instead of ownership stock he had a minuscule amount. Was it an oversight or did they deliberately screw him? Probably the latter but in any case it’s a good case for making sure you understand the financial promises you’re made.

        1. Richard Hershberger*

          The people who had lawyers review the partnership agreement get the payouts. Engineers often think this an unnecessary formality, to their later regret.

          1. turquoisecow*

            Yeah this is basically what happened. He thought he’d leave the business stuff to his partners and trusted them to take care of him.

            My husband also was involved with a startup as they started up, and he got a decent payout when the company was sold – partly because his company was doing better financially, but also because his company actually did take care of him, and he was smart enough to worry about the financial stuff and look it over himself. The company owner is a good guy but Husband also made sure he understood what was going on and that he actually could get money when they sold.

      2. Barbara Eyiuche*

        Yes, you must get a lawyer to look over everything if you are offered stocks or a share of the company, even if you are one of the founding partners. Your own lawyer, not a lawyer hired by the company.

      3. Tessandthelion*

        I’ve spent my career in tech and can tell you tell you there are a lot of other factors that come into play when determining if you’ll see a payday. For example, your investors get paid first in any sale, the more rounds of financing the more people in line before you get paid. I’ve seen investors get paid and employees get nothing. Consider this a lottery ticket, a huge gamble, don’t stay for this because it really may never happen, despite people’s best intentions.

    3. Daniel*

      I was going to come in and say this, but it sounds like the “life-changing money” is really only going to come if a) the tech this company is working on truly does take off in a few years, b) OP’s current company really is positioned to take advantage of that, c) OP’s company successfully takes advantage of that, and d) OP’s company keeps their end of the bargain to give OP the stock option.

      That is a lot of moving parts.

      Looking back at the one “start-up tech company” I ever worked for, I realized in retrospect that for me, a) wasn’t there, and b) almost certainly wasn’t there, so c) was irrelevant. In OP’s case I would also be skeptical of d) because why didn’t they bother giving OP a stock option before? Not to mention that the performance of a stock option is never ever guaranteed.

      Incidentally I would describe this company that I worked for as more of an ad agency than a tech start-up. I was miserable, and was planning on resigning after a year until I got fired first.

      I hope OP just takes the new job and doesn’t look back.

      1. LilyP*

        Also (e) OP choosing to exercise their options and/or sell their shares at the optimal timing!

    4. Archaeopteryx*

      Get it in writing BEFORE you give a yes to staying, absolutely. Get it signed. Include changed job duties, not just the money.

    5. Momma Bear*

      Stocks are a gamble. There’s a possibility that it could pay out. Or there’s also the possibility that it won’t. I would take the bird in hand. Yes, we talk about the guy who didn’t invest in Apple but there’s also a lot of “lost everything” stories, too. Instead of pinning your career on this maybe, take some of that salary increase and invest it where it is more likely to grow, like in an IRA, for your future. The stock price depends on a lot of external factors. Any of them going wrong means the stock isn’t worth much. What if life changes and you can’t wait out the 2-5? Do you just lose out? Five years is a long time to hold tight for a maybe.

      ALSO there are things that matter as much as money – your career growth, your work/life balance, your satisfaction with work. What is your time worth to you?

  4. serenity*

    It’s not clear to me from reading this if the OP is working two jobs now – the new one, and the “part-time” version of the old job that they hated. Is that what others are understanding too?

    1. Eldritch Office Worker*

      I can’t tell if the new job has started yet but I think that’s the ultimate arrangement

      1. serenity*

        That’s what I figured, which sounds like that adds another layer of complexity to the situation. OP probably cannot sustainably continue to work two jobs in this fashion.

        1. Eldritch Office Worker*

          I read it as transition help. 4-5 hours a week until someone else is trained up isn’t a ton, I’ve offered that to jobs before.

          1. A Simple Narwhal*

            Plus they offered it at half his salary! Doing 4-5 hours of work but essentially getting paid for 20 hours is a pretty good deal.

            1. Sparrow*

              Right, even if it was work I didn’t particularly like, I would sign on for 4-5 hours a week at half my full time salary, at least for awhile. But if the boss got too annoying, or started to push for more time, or it looked like no replacement would ever materialize, I would reassess.

    2. Anatanyia*

      OP here. I accepted the new job offer and start on the 13th. My last full time day at my current company is the 3rd so I have a week between the two to relax and destress but also to test the part time arrangement and make sure it works the way it’s supposed to. However I’ve only committed to part time until the end of the month since they haven’t found my replacement yet.

        2. Empress Matilda*

          Yes, and don’t let that end date be dependent on them hiring your replacement! Because otherwise there’s no urgency for them, and the replacement is going to be “just another few weeks” and another few weeks and another few weeks until you burn out from working two jobs. Set a firm end date for the end of the month – that’s more than generous of you – and stick to it, no matter what happens on their end or what promises they make.

          Also, congrats on the new job! I hope it goes really well for you.

          1. Sara without an H*

            +1000. It sounds as though what they really want is an office manager/payroll manager/executive assistant. They can hire a temp for all that if it takes them more than a month to locate a permanent replacement.

            Good luck, OP!

      3. Nanani*

        Good! Hold fast to that end of the month deadline. Do not let them guilt you or sweettalk you into working yourself ragged for even less money from them. Even if its really hard to find a decent replacement, that’s not your problem.

        Congrats on the new job!

        1. Chauncy Gardener*

          THIS! Them finding your replacement is not your problem.
          Congrats and best of luck in your new job!!

      4. Librarian of SHIELD*

        That’s excellent! You were wise to give them an end date for that part time work. I hope your new job goes brilliantly!

      6. aiya*

        thank you for clearing that up! from the post, i assumed that you had taken on the new FT job, but you were pondering if you should extend the old job (which is now PT) going forward. once i started reading the comments, I became a bit confused.

        Anyway, I always think it’s wise to put an end date to the PT transition period. As for whether you should keep going forward with this PT arrangement, I have a feeling that you’ll have a better sense of what it’s like to juggle both your new FT job and this old PT job at the end of your month, and then you can decide from there? If you still don’t feel like you have a good sense of what that’s like by the end of the month, you can always extend your transition period by, let’s say, three months and then decide from there.

        My personal gut feeling says that it’s a risky gamble to stay on for a job with benefits that might never materialize, and that the month-long PT transition period will confirm that feeling. Of course it’s always nice to make some side money, but from my perspective, it’s not worth the soul-crushing hours and the mental damage that may come with it.

      8. Professional Human*

        Congratulations! Even aside from the extra money I hope the new job brings you a lot of fulfillment!

      9. Jackalope*

        I’m so glad to hear that you’re leaving. From the first couple of sentences in your letter I thought, “Don’t stay! Go, go, go!” I’m happy that you came to the same conclusion.

      10. Tina Belcher's Less Cool Sister*

        Yay! Congratulations, I think this is absolutely the right move for you. It’s exciting to get caught up in the idea of a windfall, but the reality is that money (if it ever even materializes) is not enough to outweigh the happiness and career advancement you’ll find elsewhere.

      11. Pyjamas*

        Make sure that the time you put into the part-time is not greater than what you agreed to. Work 4-5 hours a week and then STOP. I have a feeling this boss will ask you to do the work you previously did full time, and you might be guilted into putting in more than 5 hours. This boss doesn’t seem like he’s good at letting go

      12. Not So NewReader*

        I think this is very wise, OP.

        You were working in hell for $X per year.
        If you get a raise to 300K you are STILL working in hell. Nothing has changed– except how many times a year you go to the doctor because the job is eating your insides.

        I think you will still hit all of your goals, but not as fast. And you WILL have your health intact to enjoy the successes you do have.

  5. Sparkles McFadden*

    You should go to the job that will make you happier. Staying in a soul-draining work situation to (maybe) collect a payout down the road is not worth it. You have the opportunity to do something you enjoy in a new workplace and be paid to do that the thing you trained for and the thing you want to do. Weigh that against “Maybe you’ll get a big payout in a few years while you work in a place you don’t want to be doing things you don’t want to do.”

    I think you should go to the new job. Doing something you enjoy while getting paid for doing it something not everyone gets to do. Go do it!

  6. Eldritch Office Worker*

    OP, I also grew up poor and I know that’s a lot to shake – but I’d go to the new job. (I also went to school later in life to get my business degree and am now working for a solidly middle class salary so I think I really feel you on this)

    Being in a job that makes you miserable is a real drag on your mental health and overall happiness. That’s harder to put a number on – and I know you like numbers. But it’s a practical concern just like college and rent.

    There’s also no guarantee that money will come. If it doesn’t you’ll have paid the opportunity cost of not working the job you want, not taking the raise (and the numbers Alison points out), and continuing to do work you call soul draining. If we’re managing risk, especially risk wound up in the tech sector of the stock market, I wouldn’t take the gamble.

    If you get hit by a bus in six months, it’ll be best to have spent those six months doing something you’re excited about. Not to say long term planning isn’t good, but in this case it’s such a volatile option I don’t think it’s worth it.

    1. Not Tom, Just Petty*

      The “went to school later in life” part I’d like to address. OP, you were a non traditional student. This meant working, going to school, having fewer relationships with your peers than tradition students. It’s hard. But you succeeded.
      And you found a job in your field.
      But they changed the job on you. Now you have a chance to get back on track professionally, not just economically. Take it.
      You’ve had at least two serious job offers (and a counter offer) in less than a decade since earning a degree… you are doing great.

      1. Eldritch Office Worker*

        Yes! And because OP doesn’t have the same timeline as their peers, I think finding work in their desired field is all that much more important. Jessica Fletcher says it below too, but to get accounting jobs, you want a track record of doing accounting – which you have less of if you started later than your peers.

        OP your career will be much more satisfying if you stay focused on building your resume around what you WANT to be doing. The money will follow – you’ll have sustainable long term gains as you move forward as an accountant. Always take the long term payout over the lump sum (particularly the imaginary lump sum)

        1. Cj*

          As a CPA, I agree with this in full. The longer you don’t have a “real” accounting job, the harder it will be to get a job that focuses solely on that. You are likely to continue to have to take jobs that include a lot of admin work if you don’t jump on this new job now.

          1. No Longer Looking*

            I agree as well. Remember your Time Value of Money, and factor in the raises you’ll get over the next five years even if you just stay at the new company. Higher base salary usually leads to higher raises, which was never fair but is understandable.

        2. Chauncy Gardener*

          As a CPA and finance exec I totally agree with. Follow your accounting bliss, OP! Compensation will follow!

      2. Anatanyia*

        OP here. I didn’t really consider the non traditional student aspect of college since I was the first person in my family to go to college. I worked full time, did full time classes and have three kids who were much younger back then. I realize I’ve been very lucky since graduating in that I’ve been working in finance ever since (sometimes accounting, sometimes payroll) but I definitely have a smaller history in the industry than some of the people I’ve worked with/for in the past.

        1. Girl Seriously*

          That’s incredible. Full time work, school, and THREE young kids?? All the ‘luck’ you’ve experienced is just the universe paying you dividends for your hard work!

          1. allathian*

            Yeah, absolutely. I feel like I’m going into burnout just reading about what the OP did. I could never live with that kind of schedule. I guess for some people, a change is as good as a rest, even if it means pulling triple shifts with work, college, and childcare and chores.

    2. Jessica Fletcher*

      Good point. The longer OP stays in a job not getting experience in their field, the harder it might be to move to another company in an accounting job in the future. The current boss isn’t going to be a reference for accounting work, if they’re barely doing any accounting. That’s another cost to staying.

  7. Gelie Fish*

    I would lean towards going, but either is acceptable. This is which is better not right and wrong. And whichever you choose don’t second guess in the future. It was the best decision made with the info you have right now.

  8. ENFP in Texas*

    “A bird in the hand is worth two in the bush.”

    The solid offer you have at the new company, with a 401(k), better insurance, and more pay is the bird you have in your hand.

    The possibility of maybe getting a big payday (but no guarantees) if you continue doing a job you hate is the two birds in the bush.

    Is it worth losing what you KNOW you have (stability at a job doing what you want) to take a risk reaching for something that may fly away, leaving you with nothing but a job that you know you hate?

  9. Love WFH*

    My partner and I have worked in high tech for a long time — a lot of startups. Some ended with the company shutting down, some with a few bucks. Just one resulted in a significant — but not life-changing —amount of money. Ironically enough, the 2 year stint at huge company included stock options that paid out more than all the startups but one.

    Then again, big payouts _do_ happen occasionally. Are you going to hate yourself if you miss one?

    Don’t downplay the value of doing a job that you actually enjoy, and which builds your career experience. And sock as much as you can into your 401(k)!

  10. Massive Dynamic*

    Go to the new job!! Old Job is not for you – you’re doing fine there but it’s not the work you want to be doing. Time to move on. Your old boss and old company will figure things out on their end. I wouldn’t even commit to the 4-5 hours/week; I’d say I’m going to be too busy at my new job.

    1. Anatanyia*

      OP here. The part time commitment I made is already something I wish I hadn’t done. I haven’t been able to get excited about my new job as much as I should since I’m not fully leaving my old job yet. Essentially I will just be helping make sure the bare minimum is covered until they have my replacement hired. That payments go out on time, payroll is done, etc. And I gave myself a buffer week in between to address any issues that might come up with my old boss continuing to expect me to be available 24/7.

      1. aiya*

        “The part time commitment I made is already something I wish I hadn’t done” and “my old boss continuing to expect me to be available 24/7” really jumped out at me. You’ve already stated that you want to start with a clean slate at the new job and not have to worry about old job 24/7 (even though it’s technically now PT). OP, unless you REALLY need to money (money that might not even materialize!), I’d completely cut ties with the old job.

        If you genuinely want to look for a side-gig to supplement your income, I’d put that time and effort into other PT/contract/freelance opportunities that aren’t as time-intensive or soul-crushing.

      2. HumbleOnion*

        You can push back on the 24/7 expectation and tell the old boss that you’re only available at certain times. What’s he going to do – fire you?

        2. Storm in a teacup*

          +1000!
          You are doing them a favour so make sure it is on your terms and if it isn’t working after a week you can walk away

        3. Chauncy Gardener*

          YES! Like 7-8pm only.
          Or never. I think never is really good. And they’ve gone back on their word to you, OP.
          Just sayin’

      3. Perfectly Cromulent Name*

        You can still change you mind about the part time commitment. It’s okay to change your mind. They don’t own you!

      4. Wolfie*

        Hi, OP. I’m just wondering, how long have you been thinking about this decision? My situation is similar-ish. I’ve been in my job 2.5 years, to be an instructional designer, but mostly I’m just editing and running the LMS, but my boss and grandboss have recently told me to do NO instructional design because there is no time. They want quantity over quality.

        My issue is, this job pays at least $15,000 more than other similar jobs in my area, so it’s the money that is keeping me. But I am pretty miserable every day and feel like my boss doesn’t care about me at all.

        I’m so glad you wrote in! I’m still reading the comments.

        1. Anatanyia*

          OP here. I’ve been with my old company for almost two years and I started thinking about looking for something else after about a year. I had essentially no training when I started so it took me awhile to get my feet under me and then the pandemic happened. We went fully remote but the instability of the economy contributed to me staying.

          Once it got to about a year in, I started casually looking at job postings on LinkedIn and talking to recruiters if they reached out to me. I had a few interviews over a few months but nothing really panned out. For me, seriously looking for something new was complicated by my old company giving me a significant bonus in the middle of pandemic when I hadn’t even been there a year yet and then a promotion/raise at the beginning of this year. However when I took this job it’s because I moved out of my home state (where there’s nothing) to a really good job market so I knew I could find something else pretty easily. I had 4 other job offers when I moved down here. I just started looking more seriously a couple of weeks ago and found my new job within a week of putting in resumes and reaching out to recruiters.

          I’ve been grumbling about not liking my job for awhile but my grown kids think I’m an idiot for leaving due to the money and hours flexibility and WFH aspect. They don’t see the downsides. My fiancé fully supports me doing whatever will make me happy. I can’t wait to start the new job and get back to doing what I love!

          1. Sara without an H*

            Alison has published several responses forbidding people to take job advice from their parents (because it’s usually way out of date). In your case, I’d recommend not taking job advice from your children, even if they’re grown and gainfully employed. They don’t have your perspective.

            1. Momma Bear*

              Agreed. I had a job with a lot of flex and WFH and a terrible manager. I left for a job where I’d have little WFH but the pay and benefits are better and no bad manager. Some things are priceless.

            2. aiya*

              yeah, I agree with that fully. Your adult children are influenced by their own perspectives and may not have all of the information that you have when it comes to this particular decision process. I don’t know how old your kids are, but generally speaking, there’s also a huge “hustle culture” that is very pervasive among younger folks. I’m part of that younger generation, so I’m surrounded by folks who often have side gigs outside of their main job and are hungry to build their wealth as quickly as possible. There’s nothing wrong with this if it works for you, but as I’m getting older, I’m recognizing that I’m losing the stamina needed to maintain the side hustles + my FT job. It’s not sustainable for most people in the long run.

          2. Wolfie*

            Thanks for your response. Initially I thought I was miserable all last year due to Covid. I’m sure that was some of it. But I hated working from home, and now they’ve closed the office.
            It really is soul-crushing to be in a job you hate every day, even one that’s easy and flexible.
            I’m going to start applying elsewhere!

      5. e271828*

        They can hire an outside company that does this for them. They just don’t want to, because it’s easier for them to use you. They won’t hire a replacement until they are uncomfortable enough.

        All of which is to say: turn them off.

      6. Caroline Bowman*

        I have a very dear friend who got caught in a broadly similar situation. The thing is, you have absolutely no requirement to continue this arrangement. I know you don’t want to burn bridges or be unfair, but you count too. Your new job is going to require all your mental energy and you deserve just a few days where you get to relax completely and do the life admin stuff that might be tricky to negotiate in the midst of brand-new-job-ness.

        I would strongly suggest telling your old boss that your timelines have changed and that you will be completing with a hard end date of X and there will be no buffer week. Indeed, if it’s longer than 2 weeks from now, this is your hard-date 2 weeks notice.

  11. SJ*

    OP, when you are running this comparison, remember too that in 3-5 years you may have gotten another promotion at New Job, or maybe parlayed your experience at New Job into an even better position down the line.

    Also, “life changing” money often changes lives for the worse – lottery winners, etc are full of horror stories. Better to work at increasing your income steadily and reliably over time, in my opinion.

    Good luck with whatever you decide!

    1. SJ*

      Oh, one other idea — you could try thinking of it this way: if you had never worked at old job before (had been at new job this entire time), and today old job came along and made you this offer (but you had to leave new job to take it) — would you?

    2. Guacamole Bob*

      Your first paragraph is a really good point. OP, what do you want to be doing career-wise in 5-10 years? It sounds like New Job would let you use your professional training, build your resume in your field, and therefore help you build a career over the long run so that in 5-10 years you’ll be in higher-level positions (potentially ones paying more!).

      Staying in Old Job sounds like it would mean stagnation, and that in 3ish year you’d be starting a job search for the kind of position that New Job is now. So you’re potentially setting back your entire career trajectory, unless you can be sure that your current boss will re-shape your current job in a way that will build your resume. And that doesn’t sound super likely.

      I can’t tell you which path to choose, but definitely consider the long-term big picture, both in terms of happiness and income.

      I wouldn’t worry that much about $300k being life-changing in a bad way if you’re generally good with money and if you trust that you’re going to be putting it toward major life goals like retirement and a house down payment. It would buy you a lot of security and peace of mind, but it’s not exactly private jets and multiple homes kind of cash.

    3. T. Boone Pickens*

      I’ll push back on the life changing money part. OP described that if everything broke right, they would make about $300k which they mentioned would help with buying a house, helping with college funds, all really reasonable stuff. $300k isn’t exactly getting you into solid gold rocket car territory.

      1. WellRed*

        Yeah, I was surprised by that number. Tbh, it would be life changing for me but I have a pitiful low bar.

        1. Guacamole Bob*

          I was also surprised. It’s easy to see how it would be life-changing to someone who’s never had much in savings. But it doesn’t strike me as “be miserable for years on the chance of getting a payout” kind of money for someone who describes themselves as currently middle class.

          But OP, have you really run the math on what it would do for you? After taxes? You mention that you’re living reasonably comfortably right now, so just how much faster would it get you to your goals than banking the $12k salary increase from the new job and enjoying the retirement benefits?

          1. New Here*

            These are questions that came to mind for me as well. Let’s say federal/state/local taxes take about half the money. So then you’ve got $150K, equivalent to at most 2-3 years of full time work. What’s the value of the additional 401K and medical benefits for the new job? And what about the in-field expertise gained in new job that make OP more competitive for their next job? Those seem much more valuable. Now if the payout is actually closer $1M+ that would change the risk assessment, but doesn’t seem worth it at $300K.

            1. No Longer Looking*

              Point of order: Taxes would only take 15% of a stock-based incentive if managed correctly – look up Long Term Capital Gains Tax.

        2. Caroline Bowman*

          I think so much hangs on what one defines as life-changing. Obviously every person has unique personal circumstances, but 3 years on ”maybe” for an amount like 300k *if everything works out perfectly* feels on the low side.

          So glad to see the OP took the new job and is happy with that decision.

      2. Metadata minion*

        Yeah, this amount of money seems like the good sort of life-changing. Especially for someone who grew up poor, this could open all sorts of life choices, and is very different from “I have been handed more money than one person could ever use and also enormous public scrutiny”.

        To be clear, I’m not necessarily saying that this amount of money is worth a job you hate, especially when there are other options to make a perfectly comfortable income.

      3. alienor*

        I thought the same thing. That amount of money would be very helpful and I’d use it for similar purposes, but I’m middle-class now and I’d still be middle-class afterwards. But, I also grew up poor, and that trains you to really value windfalls, because if you’re a poor kid it’s the only time your family can afford things that aren’t food and rent. If your parents get a good tax refund, that’s when they buy you new shoes, replace the leaky tire on the car instead of pumping it up every morning to get to work, fix the busted heating, etc. So I can see why the promise of a potential $300K would be extremely hard for OP to pass on.

    4. LilyP*

      ++ on calculating out your likely salary growth over the next 3-5 years and beyond if you leave this company and target high salary jobs elsewhere. Startups offer stuff like stock options *because* they can’t compete with more established companies on straight salary and benefits. I think it’s very possible the accumulated difference — calculated out over the rest of your working years! — from increasing your base salary now (and maybe investing some of the extra) would be more than what you’d get from this startup. I think the idea of a lump sum is just more enticing because it’s something you can fantasize about :)

      1. Tau*

        I think it’s very possible the accumulated difference — calculated out over the rest of your working years! — from increasing your base salary now (and maybe investing some of the extra) would be more than what you’d get from this startup.

        I wanted to make this point. In OP’s shoes, I would be very concerned about having difficulty getting back into my field after such a long stint with almost no accounting work. And although $300k is a lot of money, it’s not “retire early” sort of money. The monetary difference between investing in your career now and taking your next steps on your ladder vs staying in your dead-end job for longer not getting any useful experience might, over your entire working life, be big enough that even if the $300k gamble pays off it could still leave you at a deficit.

        1. Guacamole Bob*

          Or even if it doesn’t quite even out, the cumulative difference over the next 10+ years may be small enough that the uncertainty of the gamble and the misery of the current job are much more clearly not worth it.

  12. Uncle Bob*

    Another variable – As the company grows there will probably be more accounting work that needs to be done. You should ask about this specifically because there will also be more HR, and other work you don’t like. You may be able to grow out of the stuff you don’t like. The alternative is that the company does not continue to grow in which case your options are also probably not worth anything.

  13. knxvil*

    I start a new job next Tuesday that on paper is about a $7k raise from my current job in just salary, but when you add up the “total compensation” package, which my soon-to-be-former employer makes a point of mailing to us at the start of every year in hard copy, it’s a net loss for me. What *isn’t* a loss is that I’m leaving a stagnant position that alternates between boring me and frustrating me on a daily basis for one that’s a promotion and full of learning opportunities on top of putting my existing skills to use. I won’t be surrounded by constantly miserable people, and that alone has me breathing easier as the days at my current job wind down. So many people write into AAM feeling guilt over leaving their jobs and wondering what to do about the carrots being dangled on a stick to get them to stay–whether genuine or manipulative on part of their employer–and after the last 2 insane years, you know what? We’re too old for this sh*t. Take the job you want and tell the other place to have a blessed day, you’re done.

    3. Purely Allegorical*

      This is to-a-tee how I felt when I was in the same position just a month ago. Took the new job at a slight net loss, but I already feel so much healthier and in a better head space. It feels weird to be excited about my job again.

  14. Gipsy Danger*

    Your situation is very similar to a friend of mine: he was working for a medium-sized tech company, had stock options that were worth, at their height, about $4 million. Then Apple released the iPhone, the market changed overnight, and his options were worth essentially nothing.

    You are not guaranteed anything but a $10,000 raise from your currently company; if that was all you got from them, would you stay?

  15. Governmint Condition*

    Being in government employment, and never having such an offer, maybe somebody can explain this to me. If you are offered shares of stock at a company you work at, and therefore have inside knowledge about, wouldn’t that be considered insider trading?

      1. Ruh Roh Raggie*

        Um, no. It’s still illegal if you sell your stock because of insider knowledge. Now, are they going to pursue you as a rank and file employee? Seems unlikely. Do you actually have enough inside info as a rank and file employee to matter? Seems unlikely.

        1. Eldritch Office Worker*

          It’s legal buy and sell stock for the company you’re employed by and any subsidaries. This is written into trading laws.

        2. T. Boone Pickens*

          The SEC absolutely goes after rank and file folks all the time for insider trading. There is a story on the SEC’s website about them going after some residents from Missouri after they got a tip about Vail Resorts. They ended up making about $15k on the tip. Guess what? It’s gonna cost them a lot more than $15k.

          1. Ruh Roh Raggy*

            Thanks, didn’t know that!

            I was picturing the situation where a rank and file person happens to sell for an innocuous reason just before some big news item breaks.

            My current company has tight trading windows and has to approve any sales, which must be scheduled in advance. For everyone.

            1. Littorally*

              If a rank and file person just so happens to sell right before a big news item breaks, there would definitely be an investigation, but hopefully that person would be able to demonstrate 1) they didn’t have access to know about the news item (ie — if you’re a customer service rep, you don’t probably know much in concrete detail about the company’s strategic planning) and 2) they did have a significant cost come up, such as medical bills or their kid starting college. Between those two it’d be unlikely for it to go to prosecution.

    2. turquoisecow*

      My understanding is that employees can only purchase or sell company stock at specified times, and there’s a bunch of regulations and rules about how much they’re allowed to sell.

      1. Damn it, Hardison!*

        All employees are prohibited from insider trading, but not all employees have restrictions around buying/selling times. At my previous company, I could buy or sell whenever I wanted and in whatever quantity I chose. In my current company, I am subject to blackout times, and I have to go through an approval process to sell my shares. This is because I’m in a department with access to sensitive materials that potentially have an impact on stock price.

      2. Enginuity*

        Yes, this is how it works for an already publicly-traded company. Usually these trading windows are right after quarterly earnings reports so that it’s unlikely most employees would be sitting on significant info that isn’t out to the public. Also, a lot of times shares are on a vesting schedule, so you have to wait a period of time before they are fully yours to do what you want with them.

        But in LW’s case, I’m guessing the company hasn’t gone public yet, so she’s probably dealing with something more like a private stake that would be a payout if they get acquired or convert to shares of stock when they go public.

    3. Ruh Roh Raggie*

      Stocks and options are common for professional positions at publicly held companies; even more so at startups.

      Some companies address your concern through mandatory training courses; mine requires employees to get permission to trade their stock, and we can only do so within certain windows. Some companies take their chances.

      Insider trading laws can be a bit confusing, but ultimately the question is, If I only knew what everyone else knows about the company, would I be selling right now? So if you’re selling because you want to buy a car, fine. If you’re selling because you’re overly invested in one company, fine. If you’re selling because you read their quarterly filings and don’t like what you see, fine. But if you hear about something in a confidential meeting and start having doubts, so you want to sell now? No. And you can’t just tell someone else about it to give them a leg up, either.

      Sounds complicated and fuzzy? It is.

      1. Governmint Condition*

        So, as a follow-up question, would accepting stock as part of an offer also be illegal, if you did so because your insider knowledge is that the stock is likely to shoot up in value? Or, theoretically, choosing not to sell when you otherwise would have, based on that same knowledge? (Obviously, it would be harder to prove somebody used insider knowledge to chose not to sell their stock, or to accept it as part of a promotion offer.)

        1. Ruh Roh Raggy*

          I should definitely point out that I’m not an expert! I’ve just worked at a few publicly traded companies. This is all off the top of my head, etc etc, and I am not an expert on insider trading.

          There is a distinction between options and stocks. In the case of options, insider trading laws don’t apply. The structure is “On X date (or when the company IPOs or gets bought) I will be given the choice of whether to buy stock at the price of $Y.” There are usually time bounds around it, and you lose them if you leave the company. Insider trading laws might apply at the time you can exercise the options; not sure.

          I’ve never heard of any concern around choosing to accept stocks. For one thing, there’s generally a vesting schedule – it’s not so much “Here’s a bunch of stock” as “Here’s 30 shares, theoretically, but they vest on a three year schedule, so one year from now you’ll actually own 10, and then 10 more for the next two years. It happens automatically and is scheduled a year out. If you leave before the vesting period, you get nothing.

          It can also get more complicated – privately held companies can give you “options” or even “stocks” that are evaluated by an external party every year … but I don’t think insider trading laws apply there.

        2. hbc*

          If shares are part of a normal package, I don’t think there’s any way to suss out whether you’ve got some major inside track that lets you know if those shares are about to be toilet paper or blank checks. Presumably, you would turn down the job (rather than just the shares) if you knew it was all going to fall apart. And realistically, any inside information you have from your work there or the interview tour is mostly made of optimism and company koolaid with a tiny sliver of possibility that it actually comes through.

          I mean, is it possible that you know about a super secret funding round so that your shares acquired in September will be worth 10000x as much in October, and you suspiciously negotiated hard to take your whole salary in options? I suppose. But if you’re close enough to have that kind of significant information (vs “my engineering group hit the milestones for our deliverable and this looks way cool so I’m sure there’s a market for this”), you’ll be watched pretty closely, and taking the same 2.5% share that was offered to others won’t raise any eyebrows.

        3. Sharon*

          There has to be “trading” for insider trading to occur. You aren’t disadvantaging other investors if you accept stock or stock options directly from the issuing company as part of your compensation. However, in order to sell publicly traded shares on an exchange, you’d have to wait until all relevant information was publicly disclosed (e.g. in a regulatory filing or earnings call) so you were no longer in possession of insider info (or I think there is an exception for systematic withdrawals over time).

        4. Littorally*

          Not really. When you’re talking about insider trading, you’re generally talking about specific material knowledge that will have an immediate impact on the stock. Something like what the OP describes — “I think we have a great product that might revolutionize the industry” — doesn’t really qualify.

          Insider trading is generally stuff like “we’re about to announce quarterly earnings and we got completely crushed this quarter” or “we’re about to close a major acquisition deal” or similar.

    4. software eng*

      When people talk about ‘shares’ in tech startups, thay usually mean ‘options (the contractual right) to purchase shares in a private company at some point in the future for a price we will put in writing now’. The profit you could make on that is considered part of your compensation, but there are also tax implications you need to deal with and the risk that you may not be able to sell the shares for what you paid (as ever).

      As turquoisecow noted, once the company is listed publicly on a stock exchange (i.e. no longer private), there are also strict rules & windows about when you can & can’t sell any shares that you have purchased.

      1. Falling Diphthong*

        I knew someone working for a company that had to rewrite things so the employees who had stock options to buy at that “low price” would not be on the hook, since the stock was trading at 1/10th that.

    5. Snow Globe*

      It’s not considered insider trading because the stock isn’t being purchased on a stock exchange. It’s not even clear if this company is publicly traded. But when publicly traded companies offer stock to their employees, they pay it out from stock that have in a treasury. Stock that is owned by the company for that purpose is disclosed in public filings.

    6. CAA*

      Once the company goes public, or is acquired by a public company (which is way more likely), there are very strict windows during which insiders and their immediate family members can trade in the company stock. Usually the window closes up to a few weeks before a quarterly report and reopens up to a few weeks after. I’ve worked at places where we only had about 2 weeks per quarter to make trades and at other places where windows were only closed for a couple of weeks each quarter. The timing can be a huge pain if you’re trying to resign and want to exercise in-the-money options before you do.

      Most ordinary employees who don’t have much insider info can just trade during the regular window by contacting the broker who handles their stock option accounts. Senior execs who have a lot of forward-looking insider info and would never otherwise be allowed to make trades can set up approved plans in advance and those are public. If everyone knows that on the last Monday of every quarter the CEO will sell 1M shares at whatever the market price is on that date, it’s not an illegal attempt to manipulate the market or take advantage of non-public info.

    7. Littorally*

      Nope.

      Many people own shares of the company they work at, and simply sitting and holding those shares is completely aboveboard. Selling those shares, which is subject to certain limitations on volume & notice, is generally fine.

      Insider trading occurs when someone with non-public information about the company takes action (buying or selling) that can be shown to be linked to that non-public information.

      IE — you hold shares of your employer, ABC Corp. You have access to the company’s books and know that they’re about to have their earnings call and announce a heavy loss for the last quarter, which will drive the price down. You sell your shares before the announcement is made. This is insider trading.
      Conversely — you hold shares of your employer, ABC Corp. You need to raise some cash because your car just got totaled and needs replacing. Within the next month or two, no major price fluctuations occur that you could plausibly have known about beforehand. This is not insider trading.

  16. The New Wanderer*

    There’s also the risk that your company gets bought out – happens a lot with startups with valuable IP. That could be good or it could mean your job is gone.

    FWIW my husband had worked primarily in startups and only two have done well enough to have been a good bet (many more folded after mass layoffs, deferred salaries, and so on). The first “success story” only paid out a fraction of what his stock options should have been worth because of how the CEO set it up – in fact he left that company because the CEO seemed shady and turns out he was. The second success story worked out decently for my husband, but that was a situation where he hedged his bet on leaving (due to perceived mismanagement) by exercising some but not all his options. All the options would have been a life-changing amount of money, but there was a far greater chance that the leadership would run the company into the ground before they succeeded. So, you never know.

    All told, you’re probably better off with the current solidly better job offer that’s what you want to do, and not the lucrative-sounding but very risky counter offer that only offers you more of the same reasons you wanted out in the first place.

    1. lb*

      This is EXACTLY where my mind went. If they’re not yet public, and promising her stock options – theres’s a good chance they could get acquired and those options end up not being honored & worth nothing. That happened at my last job; company got acquired, and all the employee stock purchases were voided as part of the sale and at least one person got completely hosed as a result.

      1. General von Klinkerhoffen*

        “Yeah, we promised you stock in Llamas LLC. Sign here.”

        One week later, you own 100 shares in Llamas LLC, and the big boss sells Llamas Holding Inc to Mammals PLC for $2000 a share. It was Llamas Holding Inc that held all the patents, trade marks and design registrations. Your 100 shares are worth 43c each. Enjoy your takeout pizza.

      2. PT*

        YUP. I worked at a startup (as a temp, but I got the job through a friend so I was along for the ride.)

        Anyway, they had 4 employees in April and the tech was Ready for the Big Time. By July they had 30 employees. Wow they were going places! It was so great! FAN-TASTIC. Big big big. New new new. CEO’s Amex on the table for everything: snacks, drinks, lunches, Ubers, tickets to anything, you name it, the money was flow-ing. KA-CHING. More new employees! Conferences! Travel! Fun fun fun!

        By December they’d been bought out. Well, specifically, the product had been bought out. Which meant that the tech plus the 10 person engineering team were now part of a different company and everyone else- marketing, customer relations, design- got a severance check for Christmas.

      3. Sola Lingua Bona Lingua Mortua Est*

        That’s where mine went as well. If you have a lead on Amazon and Dell… either or both would be happy to buy you out once you become a threat.

        I’d take the offer on the table and not stay with your startup, but I’m considered pretty risk averse by those who know me well.

      4. Gumby*

        Whoa. That was a terrible buyout! Had that happened for the one startup that I held shares in when it was acquired I would have been livid. And, frankly, my stock options were not expensive at all so it would be the principle of the thing and not the financial loss.

        The deal that was eventually struck for us priced the employee-purchased stock at a reasonable value. So anyone who joined in the heady days pre-dot com bust was probably disappointed that they never got their $500/share just like Amazoogle! But we all got *something* and I actually felt pretty good about it since I had low expectations to start. I figured I might break even or possibly double it (early employee = very cheap options).

        OP – do not count on the stock options being worth a huge, life-changing amount! I wouldn’t stay at a job I hated on the off chance that in a few years we might go public. Or, realistically, get acquired by all of the “big guys” who are currently behind the game technically. It is just too unpredictable – which is why the exercise price is generally on the low side.

        Also, I am a little concerned that you have to stay at this job to get any options/shares at all. That makes it sound like they don’t have a regular options setup. Because IME most start ups grant you a set number of options on your start date which vest over time, mostly over 4 years, which would mean that you could exercise half of them right now before you go on to your new job. If they are just now offering them as a retention strategy – are they actually going to do that? Do they even have the right paperwork and stuff set up to do it? I mean, I can’t imagine a tech startup wouldn’t, but then I also can’t imagine that you wouldn’t already have vested options available to you.

  17. Jennifer Juniper*

    Don’t do it. I can almost guarantee the org is lying and will certainly never keep up their end of the bargain. You’re not 18. Get out get out get out.

  19. Zach*

    Don’t stay. I got yanked around like this at a startup once before and felt really stupid afterward. They will promise “next year” over and over again. Just go to a place that actually pays you well instead of making you beg. (Not to mention that accepting a counteroffer is usually a risk on its own that you might not have a job in 6 months)

    1. Zach*

      Oh I also missed the part about options- there’s a 99% chance that they will be worth absolutely nothing and are as good as Monopoly money no matter how promising the company may appear to be.

    2. e271828*

      Got yanked around and saw so many people yanked around. Startup mythology from the 1970s or earlier is still being used to sucker employees out of time they should be well paid for. It’s an exploitative culture. They all cry poor mouth and offer crappy benefits and lowball salaries.

  20. donkeys*

    If I were you I would go. There are so, so, so many gambles with startups! Your boss is highly confident in himself and his product, which of course he is because he’s the boss, but in reality things are much less certain than he’s pitching to you. SO many things have to fall into place in order for this hypothetical payout to occur and zero of them are within your control. For every startup that does succeed and get its early employees that payout, there are dozens which disappear into the ether, leaving everyone with nothing. I know it’s really difficult to turn down money, but make sure you are prioritizing your happiness as well. You’ll be getting an extra $12k anyway at the new job. A potential further $8k after that is not really very much in the grand scheme of things, especially when it comes with a job you don’t enjoy! Is a job that’s “soul draining” and “dread” every day worth an extra few hundred bucks a month for a few more years, just in case someday you MIGHT get a payout?

    Also, think about it this way: you’re a relatively early employee at a startup working closely with a boss who is increasingly reliant on you to fulfill his goals and day to day accomplishments while he’s completely ignoring your strengths, interests, and talents. His offer to get you to stay is only because he doesn’t want to train a new person to do all the random crap he’s been throwing at you; it has nothing to do with you personally or what specific skills you bring to the table. A boss like this who can’t or won’t properly recognize capabilities within his staff and figure out how to leverage them is less likely to be able to shepherd his company all the way to ‘success.’ I would be really wary that this guy can make the company succeed, regardless of how groundbreaking the tech supposedly is. If one company can do it, others can, and if the first one isn’t managed properly it’ll fail.

    1. Nicotena*

      Good point, the factors are beyond the control even of people doing the core work of the start up, but at least they can tell themselves if they do the best doggone software designing in the world they’ll see the payoff. You’re the accountant. You’re depending on other people not to mishandle the logistics here; the best accounting in the world won’t save them if they screw up their parts. I wouldn’t gamble my happiness on that.

    2. Falling Diphthong*

      Zero of them are within your control.
      This is an important point–whether the gamble succeeds or fails is almost wholly out of your control.

      The second paragraph reminds me of the recent letter about managing someone who doesn’t need the money, and ways to make that work–this is not what your boss is doing now. (Interesting work, strong mentoring, development of career goals.)

    3. Anatanyia*

      OP here. Your second paragraph is essentially why I decided to leave in the first place. My boss has known for awhile now that I wasn’t happy with all of the “extras” that came with the accounting role and has mentioned multiple times that we’re going to hire more people eventually. But I used to tell my fiancé all the time that even if we had more people I doubt he’d be handing off the random stuff he asks me to do because now he’s comfortable having me do it.

      My grown kids think I’m an idiot for leaving because it’s not a difficult job, it’s very flexible on hours, and I get paid well but I can’t seem to get them to understand that if you’re not happy at work everyday it drags down everything else in your life too.

      1. Sara without an H*

        My grown kids think I’m an idiot for leaving because it’s not a difficult job, it’s very flexible on hours, and I get paid well but I can’t seem to get them to understand that if you’re not happy at work everyday it drags down everything else in your life too.

        I suspect they’ll figure that out eventually.

      2. The Man, Becky Lynch*

        With your skillset and background, you’ll find a lot of not-difficult, very flexible hours, paid well opportunities out there. This is not a “once in a lifetime” setup for those with your background.

        I say this as someone who is in your position, only I thrive with the different tasks. Your boss will find someone to fill the spot once he stops complaining about you leaving ;)

        Your kids are painfully unaware of what they’re saying. But that’s very typical of people who are removed from the actual situation and job!

  21. Brett*

    You are in your mid to late 30s with no substantial retirement savings and still renting at a high cost (as well as several major expenses on the horizon). Right now, you are no solidly middle class. And, having been there, you are not in a good position to gamble on startups.

    Go with the stable job with higher salary now _and_ a retirement account option. You need that stability to become middle class, not the gamble of a startup where you need more cushion for failure. Remember that the stable job will likely come with raises too. Maybe not $10k now and $10k at the end of the year, but you almost certainly get raises.

    1. FG*

      This is exactly what I came to say. In your 30s with zero retirement? Go hug that higher salary & better benefits pkg and start socking away that retirement money. You may be an ace accountant but you need a quick wake up call about money management. $300K sounds like a lot right now (and that’s gross, not net, right?), but in your position, counting on that is a huuuuuge gamble. And honestly, he’s probably lowballing you. Tech with that much potential should be worth a whole lot more than that if you’re supposed to be a recipient of the rain of money. You may end up worse than you are right now if you stay & things don’t pan out.

      Get thee to a FEE BASED financial planner & take a hard look at how to have the life you want without selling your soul and taking a risk on a tech start up.

      1. Plant*

        Oof, I missed that $300k when I read this. That’s a lot of money and life changing in some contexts, but also not a lot of money in the context of saving for retirement for people in comparable careers.

    2. Jaydee*

      You’re an accountant. Crunch the numbers. Sit down and figure out what you and your fiancé need to do with your money to start saving more for retirement, saving for your kids’ college, paying for your wedding, and paying off debt or saving for a down payment on a house.

      Regardless of what choice you make, put any pay increase toward those goals. Trust me, it’s way too easy to just increase your standard of living and not put those pay increases toward your actual goals. And it’s especially easy to do that if you’re banking on “life-altering” money that may or may not actually come.

      Honestly, if you can take the new job and temporarily stay on at old job for 4-5 hours/week at half your current salary, that seems like a good deal (depending on what your current salary is). Put the extra $12,000 from new job plus the half salary from current job to work for you. Maximize your 401k contributions. Open 529 accounts for each of your kids and set up a recurring contribution every pay period. Put the rest toward whichever of your other goals you want to prioritize (wedding expenses, saving for a house, etc.).

  22. Nicotena*

    I enjoy risk taking but I always take risks calculated to boost my happiness in the short term (without blowing up everything else, I mean). I’ve seen too many loved ones struck down in the prime of life, never realizing it was their last day. Take risks on behalf of happiness, not future vague money that may or may not materialize.

    1. Falling Diphthong*

      Having spent the last couple of years getting my health absolutely battered, this really resonates.

      Decent health insurance, lower stress, and the time and emotional reserves to do stuff you love is really worthwhile, LW.

  23. e271828*

    Having ridden in this rodeo, I advise you to leave and go to the company that offers you a 401(k), more money without it being a panic offer, and cheaper better health insurance.

    Your present employer, though a startup, could have offered you all of these things all along and has not. Retirement plans are available even to very small companies. Health insurance is more difficult, but good plans are available. The other company values you more up-front and your chances for better money there going forward seem better too.

    In startups these days, people at your level do not get the life-changing amount of money which is invariably dangled before them. It goes to the VCs and higher-ups. Unless there are hard numbers in legally binding documents on the table before you, you should not count on anything from this company.

    Also, don’t stay on. There will absolutely be mission creep and time creep and if they can’t hire an accountant (and, it sounds like, someone else) to handle the work you’ve been doing, that’s not your problem.

    1. Rusty Shackelford*

      In startups these days, people at your level do not get the life-changing amount of money which is invariably dangled before them. It goes to the VCs and higher-ups.

      Yes, that’s what I was thinking. There is a limited amount of life-changing money available at this company. It will go to the people whose lawyers made sure they get it.

    2. Batgirl*

      I love “panic offer”. The whole time reading this I thought “If this is what she’s worth, why wasn’t this always the deal?” Also, as it came after some salty and unhappy comments from the boss, he clearly feels his hand has been forced. Fun!

    3. EventPlannerGal*

      “Panic offer” is so apt. Right now the boss is clearly thinking “oh god, if OP leaves we’ll have to hire a new person or maybe two and they won’t know all the stuff that OP does and we’ll have to do interviews ughhh” etc etc, and is throwing some cash at the problem. But he doesn’t actually value her work that highly or they wouldn’t be in this situation, and at some point it will sink in for him that he’s spent $20,000 on retaining a person whose job he seems to believe is to make PDFs for him. That won’t be a nice working environment and he will undoubtedly try to either claw back the money or stick OP with even more random duties since after all, now they’re paying her more. No thanks.

  24. Nanani*

    Take the new job, don’t work extra hours at your old job.
    If you’ve already agreed, set a HARD LIMIT in writing and do not go back.
    Finding your replacement is not your problem and don’t let the startup make it your problem.

    Working two jobs will be exhausting and probably make you look bad to your new job by draining your focus and energy.

    Old job are not dear friends or family members. They are a job. They will deal with your absence. Go to your new job guilt-free.

    1. Batgirl*

      I think when you’re been really honest to God poor there is no such thing as enough money, or enough safety net. People forget to include their quota of time and health in their wealth countup, though. If you do get a rainy day, yes you’ll need money, but you’ll also need energy and enough time to deal.

    2. ten four*

      Normally I would 100% agree with you, but if they are offering half her salary for 4-5 hours a week that’s a pretty good deal, particularly for someone who is prioritizing getting her retirement going. Use all of that money for retirement: first top out tax-advantaged retirement funds and then low-fee index funds through Vanguard or something similar.

      I have to agree with everyone else that the Big Payout is not a super likely outcome, and not one worth sacrificing your day-t0-day happiness for. I suspect if you crunch the numbers you’ll see that you’d net out pretty close to 300k in three years by taking the bigger salary/benefits now and riding that 5 hours for half salary as long as you can.

      I’ve also been in and around startups since 2007. The one I was involved in fizzled out and laid me off. My husband has been actively screwed once, gotten the fizzle once, and got one payout – it wound up being about 60k. Our joint rule is to focus in first on the salary and the day-to-day: if this is all we get are we still satisfied? If not, we don’t do it.

  25. Laure*

    300 000 is not enough to take such a risk. 3 millions, maybe. But if you make more money in another job, you will get your 300 000 “bonus” after a few years… Just thanks to your biggest salary. And the money will be guaranteed, and go with a job you love.
    I am an artist, and a few times I unexpectedly earned a big sum of money. My friends who have a regular job were all, oh how wonderful! You’re getting rich! But if we look at the numbers throughout let’s say, ten or fifteen years, they will always, always earn more with a regular income than I do with my unexpected windfalls.

    In short, take the bigger, certain, guaranteed salary, and in 20 years you will have earned much more than the 300 000 you are willing to endanger your peace of mind for.

    1. Nicotena*

      True, OP is in a lucrative field and could possibly make this kind of money as CFO of an established company, without the risk. Your future is bright, OP! You don’t actually need to make a gamble like this.

    2. Tina Belcher's Less Cool Sister*

      $300,000 isn’t enough to buy a house in a high cost of living city; in many, it isn’t even enough to buy a condo. Even if the company does everything right AND honors their agreement AND OP is able to exercise their options for, let’s say, half a million dollars, that isn’t enough to buy a house AND save for retirement AND pay for a wedding AND pay for multiple college tuitions (not to mention the wedding and college will likely be over with by the time this windfall rolls around).

      OP, I hate to say it, but $300,000 is not going to change your life in the way that you imagine. It would greatly help, no doubt about that, but you’d still have a mortgage, need to save for retirement, and/or have student loans. You might as well focus on building your career and your happiness, because this money, if it ever materializes, is not enough to outweigh the costs to your long term livelihood and quality of life.

      1. Teapot Repair Technician*

        Over the years, my net worth has increased from less than $0 to more than $300k and my life is about the same as it’s always been.

        The good news is I accumulated my modest wealth by working for well established companies doing jobs that I (mostly) enjoy. No big gambles or soul-crushing needed.

      3. Elenna*

        Yeah, I live in a high COL area and I was thinking, has OP actually looked at the numbers on what stuff costs, or are they just thinking “wow, 300,000, such a big number”? Because yeah, 300k would be helpful – it would probably cover a 20% down payment on a small house, plus maybe some extra to put towards college (like, a couple tens of thousands for each kid, depending on the price of the house). But you would still have to pay the mortgage and take out student loans.

        1. Tina Belcher's Less Cool Sister*

          If OP is close to 40, they would probably be best served by putting that entire $300,000 into retirement savings. Maybe half into savings, $50k for college, $100k for a healthy down payment on a house. But that still leaves them with (reasonable) debt and a need to continue saving for retirement. They’d be fully in the middle to upper middle class at that point, but not “won the lottery” level of wealthy.

  26. prufrock*

    Don’t do it. Don’t take the counteroffer.

    Speaking as someone who has worked for two different “promising” startups in the past 7 years. Company 1 (where I exercised my stock options as I left) has been getting bigger and bigger valuations with no new products but plenty of rumours about going public. Company 2 just got bought and made our stock options worth absolutely nothing. (And that’s not even getting into the raises/benefits shenanigans the acquiring company pulled.) Startups are gambles. Stock options are lottery tickets. Future “if” raises are just promises.

    Go for the new job.

  27. Sleeping Late Every Day*

    If you’re worth so much to your current company that they’re promising you the moon and stars, why didn’t they offer you any of that before you had an offer from somewhere else? They sound like chronic goalpost movers and I wouldn’t trust those promises.

    1. Generic Name*

      Exactly. Look at it this way, they can’t even match your current job offer! Their counteroffer is $2k LESS than what you will be making at the new job. Sure, there’s the ~promise~ of an additional $10k next year, but if you were so valuable to them, they’d be paying you more already.

  28. Not Tom, Just Petty*

    He hired a bunch of people to do jobs in their fields, including you. Somehow, you, out of all those people, became chief bottle washer/jack of all trades. Guess what’s going to happen when the company does take off?
    Not sure because you can’t see the future?
    OK, look at the past.
    Any work that requires a specialty, but can be done part time, went to you. Any job that everyone else claimed was out of their scope, went to you.
    Of course the boss is losing his mind at the thought of you leaving. Please stay part time…why? To do the part of the job you hate, the part that made you look for another job?
    Even if he put $1o0,000 k in your hand to work part time for him, the job is doing work that you do not want to do.
    He had his chance. He showed you where you fit in the company.
    Thank him for his time and get on with your career.
    He can hire HR/comptroller/office manager for what he’s paying AND what he’s offering you to stay. He doesn’t want to. Oh well.
    Good luck moving forward. Please do.

  29. card shark*

    Startups are essentially very high stakes Vegas gambling. Yes, some of them get well funded and and even smaller percentage of those do succeed — but they’re literally called unicorns because it’s really a long shot.

    The next funding round your company is hoping to get will be a few million dollars, which sounds like a lot. But remember that venture capitalists are throwing their money around on a card table. The $15 million or whatever that your company gets is only one bet of dozens the VCs are throwing down at the same time and it doesn’t necessarily mean that “your” $15m is special — it’s just one of the many bets they’re making and they know not all of them will be successful. Don’t bank on those VC bets coming out in your favor.

  30. Silicon Valley Girl*

    I have $$$$ on paper in shares that never materialized from two different startups (at least I really enjoyed working at one of those companies; the other was awful). The math Allison did at the end of her advice is more realistic than a *possible* windfall in several years.

  31. McS*

    Is it stock, or options? If it’s stock, how much do you pay in taxes on them now, and what is the likelihood they are worth exactly $0 in 2-5 years? If they’re options, what is the vesting schedule? Next do the math on that $300,000 number. Over 5 years, with a 50% chance of happening, that is $30,000 a year. Discounted at 4%, now it’s $24,000 this year (I might have done this wrong, but you can do it right). You said you wouldn’t stay for any amount of money, and I would guess that includes a $24k raise. Personally, I work at a startup and have options. I frequently refer to them as “monopoly money.” I talk about them this way when considering a job offer and when advising network connections who are considering an offer. I know you have access to the numbers and know your company better than I do, but if it was worth what you are hoping it will be, you’d be IPO’ing, and you could sell the stock today, not wait 2-5 years (if it’s stock, not options). A lot of things can happen in that time that will mean your stock is worth nothing at all.

    I love the idea of negotiating for a change in responsibilities though. Presumably your boss is doing more accounting work. How much of the admin stuff is he willing to personally take off your plate and assign you some of his tasks in order to keep you?

      1. McS*

        My main doubt on that point was them saying they could get a payout in 2-5 years. In my experience, options vest over 4-5 years, so they would not even be granted more than half the options at 2 years.

    2. LilyP*

      ++ you need to be clear on whether you’re getting actual shares or options, and if it is options you should do some reading on vesting schedules, how to exercise options, and especially especially on the tax implications. If you exercise options then then around and sell them for a profit right away you will need to pay taxes on the profit — how much would that eat into your total net gain?

    3. Anatanyia*

      OP here. They’re not really stock but that was the easiest way to phrase it when I wrote in. They are security token offerings that are tied to net profit of the company. If I had stock or options and the company is sold then I’d be screwed as everyone has mentioned. With tokens they aren’t handled the same way as stock and even in a sale they would still be worth the same. The company is currently preparing for a SPAC (which is like an IPO) at some point in the next 12 months probably but if I was going to stay I’d keep my tokens for a couple of years to make the payout worth it. And collect dividends on them in the meantime.

      But I’m not staying so all of that is a moot point now.

  32. nekosan*

    During the dot com boom, I had several friends offer me jobs at promising startups; most were at 60-80+ hours per week. I thought about it, but I just wasn’t willing to sacrifice all my free time for a maybe. Some of these places imploded after several months of “Sorry, we can’t pay you this week, maybe next week” (while I was thinking “I’d say ‘sorry, I can’t work this week, maybe next week'”). One did make it big, and I had a good 20 friends who were suddenly millionaires. I wondered if I made the right choice, but overall I mostly didn’t regret keeping my sanity or my free time. And, as it turned out – most were millionaires only on paper – they couldn’t sell their stock options until a certain time period had passed. And it all collapsed before it did, so suddenly they all had houses they could no longer afford. (insert scream emoji here)

    Do what’s best for you, but realize that staying is a huge gamble.

  33. Mona-Lisa Saperstein*

    All I could think of when I was reading this letter were the people who stayed at Theranos because it was definitely going to shake up the market, change everyone’s lives, etc. I’m sure your company has a stronger foundation than Theranos (it’s hard not to), but still…nothing is a guarantee, no matter how strong the company seems.

  34. Falling Diphthong*

    I really agree with Alison about the gamble. I know one person who got the big stock payout and could have retired at 40. I know a lot more who hoped they were in on the ground floor of such a thing and… a decade or two later, nope, they weren’t. Guess which one makes a better story?

    Personally, paying into a stock index fund paid off more than any hoped for future IPOs.

    I was struck that the “more money now” stay argument was still less money than the new job, even before I estimate $5000 for the better benefits. That the next raise to move you above the new offer rests on new funding outside your control. That the whole company goes down if this funding doesn’t come through, while the new job is in a more stable industry.

    I would take the steady job in a more stable industry unless you are young and fully embracing the gambling aspect of this soul-draining start-up job–that it probably won’t pay off, but if it does that would be great. To embrace the gamble, it really helps if you love other parts of the job–you really enjoy the new work, or it’s teaching you new skills that move you toward a future desired career shift.

  35. WorkNowPaintLater*

    Speaking from (very bitter) experience – they will promise the sun, moon, and all the stars until the company is ‘taken over’ by new management, the department gets laid off due to ‘redundancies’ and ALL the promises and stock options become worthless.

    If the new job is truly what you wanted, wish the old one a nice day and go be happy…

  36. not a doctor*

    Just chiming in as someone else who was promised the moon by an “impressive” startup that tanked (18 months after I started working there!). Very, very glad I never agreed to trade any money for stock options, as I know some of my colleagues did. Save yourself, OP!

  37. Bamcakes*

    OP, one thing I would try is mapping out four possibilities for Where You Could Be In 2024:

    – stay at tech company, job boring, you turn 45 (or whatever!), company goes public and you get $300k bonus

    – stay at tech company, job boring, you turn 45 (or whatever!), company doesn’t goes public and you don’t get $300k bonus

    – leave for new job, job interesting, old company goes public and you see your old boss and colleagues get $300k (ish) bonuses

    – leave for new job, job interesting, old company doesn’t goes public and nobody gets $300k bonus

    Spend some quality time visualising each outcome and thinking about where you would be emotionally, financially, knowledge, skills, future career options, family life etc. Really try and get your head into how that would feel.

    The two I would spend most time on are “leave company, see everyone else get the money”, and “stay at company, money never materialises”. It’s really easy to get into the mindset of “benefit A but not B” or “benefit B but not A”, but actually you need to think about “what if neither A nor B” too. What if you stayed AND the company’s plans got massively derailed by pandemic / midterms / climate catastrophe / a critical person getting hit by a bus and the stock options never happen? What would you walk away with and how would that feel?

    I personally think if you could live with “leave, see everyone else get the money, but enjoy my job and have a ton of other options because of the skills I’ve developed”, that’s probably the way to go. But really dig in to how YOU’D feel!

    2. JessicaTate*

      I think this is really smart and gets at the crux of the emotional side that OP is wrestling with that is making this hard. Considering the two “lose-lose” scenarios seems really valuable.

      It reminds me of my mom always pitching in her weekly $2 to the office lottery pool in “self-defense” — because she could imagine the one week she doesn’t play is the week they hit it big, and she’s the only one left. It never happened, of course, but she was willing to trade $104/year as insurance against that feeling. OP, you’re talking about trading job satisfaction, an equivalent-to-better salary, and definitely better benefits for the long-term.

  38. RJ*

    They’ll promise you the moon and stars….and then you wind up with mud. That was the experience of two members of my network who took gambles with startups in 2017-2018, leaving behind traditional accounting roles. Both are still feeling the effects. Both would do things very differently if they could turn back time.

    Go with the stable job, OP.

  39. JBI*

    Counterpoint to many of the comments:
    I recently lost out on 2+million dollars by *not* moving to a startup

      1. JBI*

        Sales engineer.
        That said, I have a colleague who has a similar accounting type role who got a buttload of equity by virtue of being the 8th US employee in an office that subsequently grew to 800 people.

        On the other hand I turned down roles where I’m bloody glad I did

  40. My Brain Is Exploding*

    No one’s mentioned this: you already accepted the offer from the new company. Do you want to burn bridges with them? I am not a risk-taker, and would go with the new job; 401(k), better health care benefits, work I love? Yes, please.

  41. redflagday701*

    Yup, yup. And I love Alison’s math in that last paragraph. It’s easy to be dazzled by “$10,000 + maybe $10,000 more,” but then you break it down and, oh crud, you’re signing up to keep doing the work you hate for not even $20 more a day. And that’s if the extra $10,000 comes through, which is not a bet I would take.

    And OP, I would agree with the comment directly below from Cait about her former employer reneging on such a deal. The sideways comments from your boss are already a bad sign; dollars to doughnuts he will continue to resent you if you stick around, because in his mind, you’re causing problems by “forcing” him to offer you an extra $20,000. I probably wouldn’t even stick around part time, but if you do, agree on an end date beforehand (measured in weeks from now, not months), to be adhered to whether they’ve hired a replacement or not, and make sure the arrangement won’t have him demanding your attention while you’re at the new job. This start-up will either be fine or it won’t, but if your departure leads it to crash, then it had preexisting problems. Your job is not supposed to be indispensable (like a founder’s or other exec’s might be). If they have this extra $10K lying around, let them bump up the salary they’re advertising for your replacement and make clear that the job doesn’t just involve accounting. It doesn’t sound like a hell job; someone else will be happy to do it.

  42. Heidi*

    This old company doesn’t sound like it’s set up for explosive success if they are making their accountant do admin and HR. Their willingness to pay OP to keep doing this instead of hiring an office manager and HR person shows a level of inertia that doesn’t exactly signal readiness to grow. I guess a lot of companies start out with a few people doing a lot of different jobs, but that is hard to maintain once it gets to a certain size.

    1. General von Klinkerhoffen*

      Yeah, they’re not even taking those totally critical roles seriously enough to outsource them to an expert agency.

      I’m a patent paralegal so I’ve seen a lot of incredible-sounding tech never quite break into the market. Respectfully, an accountant is no better placed to judge tech potential than I am. Everyone I’ve met along the way who did well out of startups got in and out at the right time.

    2. KWu*

      I agree with this. I was a bit struck by the “my boss is not very tech savvy and needs a lot of basic help with things like creating PDFs or excel tables” at a 30 person tech startup. That doesn’t seem like a large enough tech company for that much value add from an employee to not learn how to make an Excel table?

  43. periwinkle*

    I’m side eyeing the LW’s boss, too. He added that tinge of guilt tripping – “woe is me, you are making my life harder by leaving” – before making the offer of added money and some vague promise of better things to come.

    Startups are volatile. You do have the advantage of a portable career not tied to any particular industry or location, putting you in a better position than others making this decision. Nevertheless, I agree with those who say to get everything in writing (with a lawyer review on how enforceable it is) or get out.

  44. Librarian of SHIELD*

    LW, I know how tempting it is to think of your boss’s offer as a thing that will definitely happen. But right now you really don’t know for sure if those promises are going to pan out. I think the key word in the title for this letter is “could,” and I would hate for you to pass up a chance at a job you would really enjoy that would pay well and provide you with good benefits in favor of something that might never happen.

    1. pcake*

      Librarian of SHIELD, I know this is off topic, but I’ve always meant to tell you that I love your user name :)

  45. Eve Polastri*

    “Do what you love and the money will follow”. I don’t know who to attribute that quote to but it seems to fit the LWs situation. Life is now, not in 3-5 years. Spending any time in a soul sucking job is mentally exhausting.

  46. CatPerson*

    I think that the $10K now, $10K later this year is a big red flag. If he really wanted you to the tune of $20k more, he’d give it all to you now. After all, it’s September already! My guess is that the second $10K would not materialize.

  47. AnonInCanada*

    You know what they say: “A bird in hand is worth two in the bush.” You know this company’s track record, OP. I personally would stay away and say goodbye to old boss. If you think you’ hated admin, HR and office manager tasks now, imagine getting even more of it! Because that’s exactly what you’re going to get.

  48. Spot the Tiger*

    The time for your present employer to offer you the additional $10,000 and stock options was when you took on FOUR roles (HR,payroll, office manager and executive assistant) in addition to the accounting role for which you were hired. The additional $10,000 should have come when you showed how well you were handling all of them. Take the new job and put an end to the drain on your soul!

  49. Bilateralrope*

    Here’s a news article from a few years ago about a company that was giving its staff shares instead of paying them a market rate. Then they decided to try and take those shares back. Take note of how they decided which employees “didn’t deserve” to keep the shares.

    https://www.cnet.com/home/smart-home/zynga-to-employees-give-back-our-stock-or-youll-be-fired/

    So go with the company that is offering you the better deal today. The one that is offering you a better health insurance deal in the middle of a pandemic.

  50. Engineer Woman*

    Chiming in here to take the new job. There is considerable risk that the startup will not be as great as you think in 2-5 years and it’s not worth it in my opinion to have your soul drained (a known outcome) for this duration of time for the possibility of hitting it big.

    I once worked at a startup. I really liked the work and team but an old colleague recommended me for a position at their large stable company. I made the change and although the startup is still chugging away, there’s been little progress to that “hitting it big” scenario despite several years gone by.

  51. learnedthehardway*

    If your current company is so keen to keep you that they’re throwing money at you to stay, I would suggest that you tell them that you’ll take the money and stay ONLY if they also hire an office manager to do the work you don’t enjoy – ie the HR administration / payroll, etc. At 30 people, the company is probably too small to hire real specialist functions like HR, etc., but they should have an Office Manager role that does the kinds of functions you are being tasked with, in addition to the finance/accounting work you enjoy.

    I would make that the measure of whether it is worth staying, honestly – if the company won’t invest in that office manager position, then they don’t anticipate growing fast enough to make good on the promises they made you. Also, from your career perspective, you won’t grow fast enough into a pure finance/accounting role to maintain your specialization and growth in your functional area, if you have to spend 50% of your time on administration stuff. You’d be pigeonholing yourself and would be limiting your career potential.

    Also, look at the company’s trajectory and growth – are they really, truly on a growth curve that looks sustainable? If yes, then get all their promises in writing (ie. in a written contract). (And ask for equity in the organization while you’re at it).

    If you get all that, then yes, it would makes sense to stay. If not, then I would agree with others that it is time for you to look at other opportunities.

  52. Monday Monday*

    This is a very hard decision.
    I played the money = happiness game and lost. It is a game you never win. I spent almost every night after work crying because the new company that offered greener pastures ($$$) pulled a bait and switch on me the day I started. I was hired as a software programmer and immediately delegated to help desk and answering emails for the company.
    I started my job search after my first day.

  53. Batgirl*

    My trust in the current boss would be gone as soon as he started making sideways comments about me looking out for myself. Not to mention the job wasn’t what it was initially thought to be. People who feel entitled to any and all help rarely reward it correctly, and most often attempt to reward you in promises.

  54. Anon today*

    I’ve had options as part of my comp plan for most of my career. The general rule of thought is to treat it like a lottery ticket. If it pays off, great. It can change your life. But you don’t make it the center of your financial strategy. I wouldn’t even consider them in my decision to decide to stay at a job.

  55. Curtis Jackson*

    I know this is a tough decision. I’ve been there.
    The problem is that it’s more complicated than it appears on the surface. One of the little-known ways non-executive employees get screwed is as follows: A big company decides to buy your startup. But they want a much higher ownership stake than is readily available. So they pay off the execs of the startup to restructure the stock as part of the sale so the buying company gets tons of newly-issued preferred stock*, and in the process the common stock – the stock for which you have stock options – is diluted to the point that it is all but worthless.
    The execs of the startup get their big payday, the buying company gets the tech, and the non-exec employees of the startup get a fraction of what they expected to get in the event the startup was sold.
    *It doesn’t have to be preferred stock per se. There are any number of ways to structure the deal so the common stock is severely devalued.

    1. photon*

      OP, please research this. Companies need to pay out investor preferred stock before they get to employee common stock. There are companies where investors make millions while early employees make maybe $10k. And that’s even assuming the company makes it big anyway – most startups won’t.

      You’re buying a lottery ticket. That’s all.

  56. Lora*

    OP, even when you ARE an expert in the startup’s particular technology, it’s often impossible to tell whether this tech is really all that and a bag of chips or none of that and wholly lacking in chips. Because they might be ahead of where Amazon etc are NOW, but you don’t know what Amazon and all those heavy hitters have cooking in the R&D pipeline. Maybe they already tried the thing the startup is working on, realized there were serious problems and dropped it. Maybe they have their own version in the works.

    I have worked for startups that were on the cutting! edge! of what they were doing at the time – now I look back on it and all the other things for the same problems that people have tried in the meantime, I have NO idea how we ever thought we would solve these issues with a few new grads and two senior engineers with about 20 years of experience between us! These are huge, intractable issues that nobody has been able to really resolve, what were we thinking?? I have worked for companies that had zero technology worth a crap, who were run by very Theranos-y type people, with data that did not meet commercialization standards at ALL, and they lucked into their IPO by just knowing the right people at the right time and Stevie from Marketing happened to say the magic words to exactly the right financial people, and for companies that had real solid data they couldn’t move forward with because as soon as they announced some level of success they got whacked with a bunch of patent violation lawsuits.

    I have never had stocks pay out even when they were from a big company – the big company got eaten by an even bigger company, who announced that even RSUs would be paid out at Takeover Company’s face value, not Purchased Company’s face value. A life-changing amount of money was rapidly converted into about $2000, overnight.

    Stick with the new job.

  57. I edit everything*

    Your calculations might be different, but $300,000 is pretty cheap for a soul. Value yourself higher than that. What good is the money–if it even comes–if you’ve no soul left to guide and enhance your use of it?

    Consider also how a soul-draining job might affect your relationships and well-being. What if you become so miserable in your job that your relationship with your partner comes apart? You might be able to throw a fabulous wedding, but will anyone but you be there for it?

    Finally, think about your long term career. If you want to do accounting and advance your career IN ACCOUNTING, then the new job will be the best path forward. You will become a better, more senior, more knowledgable accountant, earning larger and larger salaries, as you add years of experience. If you stay as an admin, I’d bet your salary trajectory will be much more gradual, and you might find yourself stuck and never able to get back to full-time accounting. Lifetime, an accounting-focused career could more than make up for the supposed windfall, financially.

    Take the new job. Tell your current boss that if he gets to the point where they need a full-time accountant, not an admin who can also do a bit of accounting, to give you call. Until then, do what you love.

    1. LilyP*

      Yeah for me to consider staying in a boring/miserable job for 3-5 years for a MAYBE payoff, the maybe payoff would have to be upwards of several mil….

  58. 867-5309*

    I’ve worked for a few start-ups and only once stayed once it became “soul crushing.” The stock options usually vest over a period of time – sometimes years – AND you have to potentially pay the value of them if you leave, since you can only exercise within certain windows. Read the fine print of your stock agreement so that if you decide to leave later, you aren’t screwed. It ended up not being worth it for me because I did not have the money to pay for the value of my stock options, which was necessary to take them with me when I left afterall.

    The personal money that I invested in that latter one still has not paid out, though I took those options with me and will probably cash out at their next funding round, if it happens.

    But conversely, a friend of mine worked for a start-up that was purchased for billions and she made a stack.

    It is a crapshoot. Read the fine print. Remember your day-to-day mental health and steady savings is what will hold you into retirement.

  59. cactus lady*

    OP, my brother was in a similar position to this at a startup – that sounds like a very similar situation to this one – for several years before it finally folded. It was a LOT of uncertainty (the last 18 months or so was “will we be able to stay open next week) and he was very fortunate that one of their investors offered him a job when it did go under. They had a really great and needed product, but it just didn’t pan out. It happens a lot more often than things like Amazon and Dell happen.

  60. willow for now*

    Also wonder why your boss waited until you had one foot out the door before he magically found that extra money he offered you. This seems so reactionary. Why could he not offer it before?

    And a job with better benefits? If you are in the US, your health insurance is through your employer, so even with a life changing amount of money down the road, one bad hospital visit could eat up most of that money if your health insurance plan is not robust.

  61. Parenthesis Dude*

    Fundamentally, it’s hard for us to answer your question.

    Your company may own 20% of the patents in the field, but are they useful ones? As an accountant, do you really know if your company is doing better than Amazon and Dell or are you taking your co-workers words for it? You mentioned that this company is doing another funding round. What type is it? Are you guys still in the seeding round or have you done many funding rounds? How much is your company valued at? Why do you think your stock options would be worth $300k given you’re one of the lowest ranking employees at the company?

    If you’re right about everything you said, then you probably should consider staying. If your company does indeed have a valuation in the $2-5 billion range, then it probably does have an excellent chance of going public in the near future. And it’s not like there’s one company that hires accountants. But you should do the research to make sure that you’re correct.

  62. LKW*

    Go. The reality of software is that the best software isn’t necessarily the software picked up by the big guys. They can go with “good enough” if they feel like it. There are no guarantees.

  63. No One Expected the Hit Men Walking Around*

    Oh Alison, this is why I love your column so. In addition to fantastic and compassionate advice, you always manage to throw in a giggle. But ARE YOU SURE there aren’t more hit men walking around?? Hmmmm? HMMMM? Asking for a friend. :-)

    2. Heidi*

      This is a good point. How would we count the number of hit men/women? It’s not like they’ll put it on their tax returns or join a professional association like the bar.

  64. Sylvia*

    There is a lot your boss could do to make the position more attractive, even if he can’t afford to pay you more. A better job title, flex time, working remote, taking over the duties you hate himself, having one of the other employees function as his personal tech support, are all things that could be done to keep you. The fact that he’s not offering those things makes me think that you’d be better off accepting the other offer.

  65. Anon Mouse*

    Your boss is the wrong finance person for such a startup and you are going to keep getting hit by his deficits unless something is done, and this is definitely a gendered dynamic where you are a woman cleaning up after a man. It is absolutely unreasonable that your boss works in a tech company and cannot do basic things related to finance or just generally being in a technical office like Excel, and he needs to see that as a priority to fix. You are not a secretary and right now you are acting like one. It would be plausible for him to be in a big tech company and do his core function well and have these deficits, but in a startup, not being able to do these basic things hurts everyone on your team. If you really want to continue at your current job I would speak up about the distribution of tasks and ask if he is willing to take a training in some specific things like Excel so he can cover part of the work; another alternative might be for him to hire an actual admin and maybe split that person with someone else in the company.

    Also, I have previously worked at a pre IPO startup with some interesting finance problems and they are now hiring an accountant – and while every finance department with only 2 people is going to require you to do some non-accounting work their finance lead is good at everything you mention and you can divide it up in ways that appeal to both of you. And you would definitely get options and equity so the same money is on the table, while probably having a better day-to-day work environment. I am happy to send the JD and connect LW to my ex colleague through Allison if you do want to pursue it (unfortunately, I don’t have the bandwidth to connect every commenter, please don’t ask), just comment and let me know.

  66. Mrs. Basil E. Frankweiler*

    This…was me. You should not gamble on the payday. Your health and happiness is worth more. And the long-term consequences of suffering through this kind of work environment should not be underestimated.

    (FWIW: my company went under. And we were in a similar position as what you describe.)

  67. Just @ me next time*

    My mother got a job with a medical cannibas grower when it was still a start-up. She and her coworkers were given company shares as soon as the company hit the market. The company was still leading edge at that point, and the price of the shares skyrocketed, to the point they would be more than life-altering for my mother. But then all the other companies doing the same thing caught up, and suddenly the shares plummeted. All before my mother was fully vested.
    It’s still a good news story for my mother, because she likes the work and the salary is way above what she was making leading the 5 a.m. shelf-stocking shift at a massive bookstore. But when the golden goose of stock prices finally got around to laying, its eggs were just regular eggs.
    Imagine what your boss was actually offering was a handful of lottery tickets every week. Would you stick around for that?

  68. Littorally*

    Don’t take it. Getting offered shares in a startup has a miniscule change of making you awesomely wealthy and a very large chance of leaving you holding an empty bag. And even if this is one of the miraculous few that takes off — a steady job doing what you want to do and a 401k that will take care of you in retirement are much better than continued stress for a payout that is good but not mindblowing. A 401k with a generous match will net you more than $300k in the long run and you’ll be happier and healthier to boot.

  69. caffeinated_lab_rat*

    I’ve worked at several start-up biotech companies. It was hard leaving the first one for this exact reason; what if they hit it big and I lost out on money? It’s been a few years and I am much happier at my new job. I would feel a little bitter if my terrible old boss got a huge payout and I didn’t, but my happiness is ultimately more important.
    Additionally, I haven’t gone through the process of exercising stock options, but I hear from people who have that it’s a pain and you always make less than you expected. Ex: a company goes public at $14 a share, but its employees are restricted from selling for 6-12 months, at which point the hype has died down and you’re sitting at $6 a share. Or you’ve only had options vesting for 18 months when the company is bought and your company decides to only give you that much instead of the full options set aside in your 4 year vesting schedule. So many things out of a person’s control goes into that $$$ calculation.

  70. Asenath*

    Too much of a gamble for me – especially when the “life-changing money” isn’t really money, not yet, and might never be. Neither, for that matter, does the second $10,000 appear to be guaranteed. Add in the fact that you don’t like most of the work, your employer is trying to guilt you into taking this offer, and has already persuaded you to continue working with them part-time – and there doesn’t seem to be an end date in view for this either, when you probably should be putting your energy into starting off on the right foot with the new job, which will enable you to save for retirement. But I tend to go for stability over gambles.

  71. Pay No Attention To The Man Behind The Curtain*

    If the boss has that much money to throw at you, why wouldn’t he invest in outsourcing HR or hiring a person to do the non-accounting tasks you loathe?…think about why he’s SO interested in keeping you right where you are and keeping his leverage over you by convincing you not to take a better offer elsewhere. It’s not YOUR advantage.

  72. Meep*

    I am currently job searching while working for a small software company (less than 10 people). Our senior engineer with 16 years of experience working with the owner left recently for greener pastures. They decided it might be a good idea to make their three remaining engineers sign non-competes by *finally* giving us stock options. Options that were promised to me three years ago (I have been there for four years) and will not vest for four years. Did I mention they also gave me less stock than my coworkers who had been there for less than two years and another who has been here for two months? They are also planning to sell in 3-5 years.

    The stock is worth the paper it is on (which is a pdf btw) and unless they get their act together soon it will be even worthless.

    I promise you that equity and pay raises come at a price to you and are not worth it. Take the job that saw what you were worth before you left.

  73. Metadata minion*

    Ok, as a librarian this had me going “wait…how much *do* hit men make? How would you research that? I don’t think that profession is exactly going to be in the NBLS’s databases….” :-b

      2. Sara without an H*

        Doesn’t sound all that great, considering the risks. And if more people took it up, undoubtedly prices would go down.

      3. Heidi*

        I’m not sure someone would be able to live on this salary, especially considering that you wouldn’t be able to work frequently without greatly increasing the likelihood of getting caught.

        1. redflagday701*

          I think most of the working hit men out there also take care of other business for their regular clients. They also probably don’t have to pay taxes, which, as any self-employed person will tell you, that’s huge.

        2. Goldenrod*

          “especially considering that you wouldn’t be able to work frequently without greatly increasing the likelihood of getting caught.”

          Not if you were real good at it?

  74. mediamaven*

    I think the million dollar question is how confident are you that the company will sell? I left a tech job that gave me a whole slew of shares but I was miserable. People couldn’t believe I would leave it on the table. But I had no confidence in the viability of the company, and I was right. It went out of business. Meanwhile I started my own company and promise my second in command a payout if we sell. There is a decent likelihood we will. Not guaranteed at all but we are pursuing it now. And she can get a big payout and she deserves every penny.

  75. Fashionably Late*

    Tell him to let you know when there’s a full-time accounting job with no HR and you’d be happy to throw your hat in the ring.

  76. Goody*

    Miserable. Soul-draining. Bulk of my time spent on other tasks. All of these are compelling reasons to GTFO.

    Boss is dangling money and a future *chance* – not a guarantee of shares – at shares to try and entice you to stay. But you’re not leaving because of the money. You’re leaving because you’re miserable, because the job is soul-draining, because the bulk of your time is spent on other tasks and the job is not what you signed up for. Money doesn’t fix those issues.

  77. FD*

    I’ve stayed too long at a company that didn’t offer health insurance or 401k and underpaid me because I could see how big it could become, and I was given all these promises about being made a partner in the firm, how much I was valued, etc.

    And then they backed out of making me a partner and stood by while I warned them I was increasingly underwater on the work. And shrugged as I warned them that I wasn’t able to keep up with key deliverables.

    I stayed because I was loyal, and because I was afraid to change jobs, and because I could see the potential. But sometimes, seeing the potential in a job is like seeing the potential in a partner. Sometimes it doesn’t matter what they could be. It matters what they are.

  78. Mayflower*

    There is a shortage of accountants! Take the higher paying job, save up, start your own firm, and make way more than $300k!

  79. Salad Daisy*

    I took a job at a company for less pay that I was worth, because they gave me all these options that were going to be worth so much more in the near future. Then the company merged with another company, they called the options, and I was lucky that mine were not underwater. I made……wait for it…..$247. Many of my coworkers were underwater and made nothing.

    Your employer is not your friend. Your employer is not your family. You owe them an honest day’s work for an honest day’s pay and that is all. Take the new job.

  80. The Gollux, Not a Mere Device*

    So, my spouse worked for five or six start-ups that failed before the one that was bought out by Microsoft. The failures included one that was looking good technically, but out of cash. They had a promising meeting with investors, for Sept. 13, 2001. In lower Manhattan. It didn’t happen, the company folded, and it took him a couple of years to find something else.

    The success meant a move to Seattle, two years of soul-crushing work (soul-crushing because of the company culture, in the days of “stack ranking”). He gave notice in two years and a few days (because of stock options and relocation bonus) and spent the next year or so recovering. The money was life-changing in the sense that it meant retiring early, but not fabulous wealth.

    OP, not only does your old job want to give you work you hate, consider whether “life-changing” might wind up including horrible burn-out.

  81. Call Me Dr. Dork*

    I have worked at two startups. The first one did actually document in writing what fraction of the company they were offering me (and all the other employees). I did the calculation with a *very* optimistic valuation, and my shares ended up at all of $4000. Given how my co-workers were buzzing about stock! options! for a week, I’m guessing they didn’t do the calculations.

    The second one, about a decade later, never put anything in writing. It was all fluff, and when I dared ask about the promised stock options/piece of the pie/share in the company that I was told about before I got hired, I got blank looks. I got the same looks when I asked about a performance review or a raise.

    I am now working at a moderately large public company. Not everything is perfect, but I do have regular performance reviews and raises, and the (smallish, but more than $4000/year!) stock options vest in 9 months and can be sold a year after that. And everything is in writing, so there’s no bait and switch.

  82. overcaffeinated plant lady*

    Sort of on topic…when I started my current job making 60k, previously making 40k, seeing the VERY small jump in my actual paycheck was depressing to say the least. Alison’s quick math at the end is a good point.

    1. Eldritch Office Worker*

      Same, I just went from 40k to 60k and I was…underwhelmed. Gotta love that tax bracket jump.

  83. Regular Human Accountant*

    I could have written this post myself seven years ago–I was hired by a small software development company to be the accountant with the promise that eventually I’d be CFO, and ended up spending very little time on accounting and a lot of time ordering lunch, opening mail and going to Costco for coffee creamer. I was extremely unhappy and quit after a year, despite the high salary and the potential of a big payout when we hit the big-time.

    That company never hit the big-time; about a year after I left it fell apart completely. They had a truly amazing product but the owner had no idea how to sell it, and kept adding things on that no one wanted. He was a genius when it came to math and programming but a terrible, terrible business owner and sales guy.

    Here’s my advice, from having been in your chair: before you make a move, think about what the culture is like at your company. Do you truly see a future for it, or is it a fantastic product that no one is buying? Think realistically about what’s going on there–what’s the turnover rate, what kind of people are they hiring, how many sales are they making compared to how many sales calls they’re making? You have all the financial info; how healthy is it, really? Is it sustainable long-term if things continued the way they are right now? Are they hiring good people for reasonable salaries, or are they hiring friends who don’t really know what they’re doing for huge amounts of money?

    In my case, during the year I worked there we went from 12 employees to 22–but the owner fired 19 people during that same time frame. He would promise potential clients we were going to be the next Google (spoiler: we were not) and offer them features they had no use for. (One was the ability for employees to store all their personal medical records in our cloud-based software . . . do YOU want to store your personal medical records on your company’s software? Of course not, because you’re not deranged.) While I saw great potential in the product itself, I saw the revenues we were bringing in and how we were 90% supported by investor money, not revenue, and sales call after sales call ended in nothing. The few clients we had were unhappy; they wanted useful reports, not scatter graphs or a company wiki.

    I KNOW how tempting it is to stay, and for you it might very well be a risk worth taking. But make sure you’re seeing things for what they really are, and don’t be swayed by the sales pitches. Good luck!

  84. TootsNYC*

    Since then, he’s been making sideways comments about me leaving and how difficult everything will be on him with me gone.

    This is why I would leave.

  85. ampersand*

    Chiming in to say: take the new job, and leave the old one behind. I just don’t think you’re likely to see a large cash return if you stay at the old job. It’s soul sucking—everyone deserves better than that, of course, and you have the opportunity to leave. Take it!

  86. Rachel*

    If you stay (and I wouldn’t, but that is me and I am jaded with start ups), ask for and Admin for you or your boss as part of the package. We could be twins (also graduated with BS in Accounting at 32, worked 3 start ups with options that were eventually worth $0.00 when they all closed, now working as Assistant to Controller but still having to do the HR and Admin stuff).
    PT hours will suck the life blood out of you (I also did that for 1 company) and will not allow you to make the clean break. GOOD LUCK!!!

  88. Hare under the moon with a silver spoon*

    All solid advice above OP – just to stress the bright future you have, accountancy is a really solid, potentially lucrative career! Also you can live anywhere and work in any industry. And you enjoy the work it involves. These are all priceless things let alone all other benefits others have mentioned.

    Seen you are starting your new role soon – good luck and don’t doubt your decision.

  89. pcake*

    Anatanyia, I once agreed to stay part-time with my old company until they found someone new – which they never did. It turned out that as long as I was there, they didn’t bother to look very hard because they had me. After I left completely, they had to hire two people to replace me. I had a complete breakdown and PTSD (my doctor called it sever burnout syndrome) that I’ve never recovered from fully, although I am much better.

    Btw, if you work 30 years with a good 401K, you could end up with life-changing money with the new job. I hope to hear you’ve left the old job. Your happiness and health – and your family’s – are worth far more than the raise they offered you and the big payout that very possibly will never happen.

  90. teapot programmer*

    As someone working in tech, the description ‘ahead of the big guys like Amazon and Dell in terms of development and deployment’ makes me really suspicious — Dell & Amazon don’t have much in common technically, so it doesn’t make sense for your company to use that as a description or a comparison — what about those two companies do they think they’re benchmarking against? And likewise for ‘development and deployment’ — for a tech company, this is just basic every day stuff.

    The physical retail equivalent of this description would be ‘ahead of the big guys like Walmart and General Motors in terms of opening the store each day and making sure someone is at the till’… it just feels a bit off?

  91. Ampersand*

    Having worked in accounting at exsclusively “small” companies (>250 employees), you will never outgrow the duties you say you hate. Even if the company grows to the point you need one, and you make it to CFO, you will oversee HR and payroll and the management of the office and very little of your time will be spent doing accounting. Make your decision with your eyes wide open.

  92. Sara without an H*

    “…we’re not hurting for money although we don’t have anything substantial saved for retirement yet.

    I can’t overemphasize the importance of a good benefits package, including a 401(k)/403(b). I’ve worked in higher ed all my life and started putting money in my 403(b) account as soon as I qualified. What was life-changing for me was sitting in a Zoom meeting with my advisor and being told that I had enough money to retire whenever I pleased.

    Based on the updates, OP has already made her decision. (A good one, imho.) If anyone else is weighing the choice of chimerical stock options against salary, health insurance, and retirement — go with salary and benefits. In the long run, they’re more likely to pay off.

  93. A Random Thought*

    A few years ago at a previous job, someone who I worked with and thought would be there forever took a buyout (there were internal changes where people were taking buyouts or being laid off due to restructuring). When I next spoke to them they said part of the reason they left was that they asked for more money due to how much work they were doing, but the request was always turned down by management until they finally decided to leave. Then and only then did the company finally decide to try and pay them more. My former colleague’s mentality was that this meant the company had the means to pay them what they deserved, but were more than happy to string them along until it was no longer an option. I get that kind of vibe from your boss and your previous job. Do you really want to stay with a boss who is making “snide comments” about your choice to leave? You already said the work is soul-draining, in my opinion the only amount of money that could change that is a giant payout that would enable me to leave the job and retire immediately.

  94. anone*

    Ok but one of these days I want to see an AAM letter from a hitman. Preferably about a mundane annoyance.

    1. NopityNope*

      My co-worker scream-sneezes just as I’m about to pull the trigger, which makes me miss my targets. Plus, they always cram the office fridge with noxious poisons, and there’s no room for my sandwiches.

      1. ampersand*

        Hench is so so good! It’s what got me back into reading after a year plus of not being able to read because nothing held my attention. I recommend it frequently…whether I’ve been asked for a recommendation or not. :)

  95. Joy-Z*

    Don’t stay. If you stay, you are just going to be looking at LinkedIn job listings every day for the next two years. Change is usually the right choice, because you wouldn’t be looking to make a change if you were content.

  96. usually anon*

    I was director of R&D at a dot com that was on the cusp of greatness, complete with stock options and all manner of perks. Turns out their business plan involved being bought by Microsoft, which didn’t happen.
    All but the company founders were let go. Bye bye big money payout.

  97. JustSomeone*

    I haven’t read all the comments yet, but I’ve read enough to see that mine is an unpopular opinion.

    I would stay.

    Sure, the life-changing money isn’t guaranteed. But nothing in life is ever guaranteed.

    I would base my decision around the potential for regret. If you leave now and the big, life-changing payout happens in a couple of years, that’s a crushing regret. But in the column where you stay, the regrets are a lot more manageable and mitigate-able (why isn’t that a word?)

    You have a job that you don’t love. Some of the work excites you, but most doesn’t. First of all, that’s most jobs. Your employer is willing to overpay you for work that doesn’t challenge you—the salary bump immediately brings you to almost equal to your other offer, and on the whole, full time accountants make much more than people who spend 35 hours a week on basic, assistant-level tasks. Your job is also in an in-demand field. This isn’t your one-and-only chance to change companies. If the additional $10,000 doesn’t come through, you can move on at that point. If you decide the money isn’t worth it, you can move on at that time. If you stay and start to feel regret, it’s easy to undo. But not so in the other direction.

    2. Paris Geller*

      I think I would agree more with your perspective if it wasn’t for the fact that OP has very little in retirement savings & the new job offers a much better health plan. I do get where you’re coming from, but from what you’re saying, OP gets 10K now and then gets another 10K after funding (if it comes through) and comes out slightly ahead and can move on at that point if it doesn’t seem the life changing amount will materialize. However, that means OP is losing out on a better health plan for at least–what, 6 months? a year? — and a year of retirement savings at an age where they really need to start building those savings so they haven’t been able to yet. Plus, if they get the other job, OP has a lot of room for growth (maybe not at their new job, but they have the chance to levy that into more in the future and their career has a high earning cap).

      I do understand your point and it is compelling, so I get it. I don’t think really any of the perspectives that have been shared, for or against OP staying, are wrong. Like you said, nothing is guaranteed. I am just not a risk-taking person and I think OP would be better to start building savings with the guaranteed income rather than hoping for a modest windfall.

  98. TG*

    I’d still leave unless specific items are done 109% – your boss immediately changes your job – in writing – to the duties you’d like to be doing and in writing guarantees both $10k increases by a certain date without new funding.
    Also options can be tricky so I’d be sure you could exercise them whenever you choose and that you’d be 100% vested immediately.

    Otherwise without that exact control over your job happiness and finances, I’d leave.

  99. FrenchCusser*

    The one thing I learned from growing up poor is that I NEED very little to get by on. The rest is gravy.

    I wouldn’t give up my happiness for gravy.

  100. NopityNope*

    Just sharing my experience. Everyone has to make their own decisions, and Alison raises important things to consider.

    Back in the early 2000s, I took a job at a startup and was given stock options when they went public, in lieu of a raise. They had a unique product, and about 75% of the market. The founders were convinced that the shares, offered at around $6, would be valued at $25 within a year or so. The founders very generously gave themselves literally millions of $$ in stocks, which they promptly cashed in and bought huge houses and toys, while the peons got a few thousand. Not life-changing, but a nice amount if they did perform. 16 years later, the stock is currently hovering at $7. So just because the founder says it’ll go through the roof, and even if you think it’s a good product, the market may not agree.

    (Unfortunately, the job was soul-sucking, and I ended up quitting when they wouldn’t give me even a single day off after 6 months of 100% travel. That was just the final straw; the camel was struggling under many, many previous straws.)

  101. Pyjamas*

    Aside from anything else, I’d hesitate to go on working for someone who can’t take no for an answer, let alone one who makes future promises based on future profits. Leave. Now. Make a clean break

    1. Forty Years in the Hole*

      Even the finest Lalique Crystal ball can develop a crack…and sideline your future plans. It’s risky business.

  102. Karate Saw*

    I don’t know how to say this in a way that doesn’t make me sound like a clueless dick, but my first thought when I heard “$300,000” was, “oh, that’s…not that much.”
    Not that it wouldn’t be a wonderful amount to have, but it’s exactly 5 years at 60K, and you say it could be 5 years before it comes through (if it does.)
    I feel like you could be happier for those five years. 300K is a lot, but the potential for 300K it’s not enough to hate your job 39 hours a week, in my opinion. I wouldn’t do it.

    2. Raida*

      I think this is one of the best ways to look at it :]

      $300k in one hit would be great but $10k + $10k + $10k… in regular savings from a new, higher salary would get there all the same. And with better health coverage it’s a huge potential financial hit just not to be worried about.

    3. June*

      It isn’t that much. Not to wait years on. That amount can be earned other ways. A stable 401k for one.

  103. St Dymphna Admirer*

    That’s a tough situation LW, but it might be helpful to consider the stock options etc as lottery tickets. You say yourself that you’re in no position to assess whether or not the startup is in good shape, and essentially only know the marketing points your boss is making. Even VCs who have billions of dollars and do nothing but invest in startups regularly put money into products that ultimately fail. If people in that position with that knowledge base can’t pick the winners from the losers, then you (or me!) can’t either.

    I grew up extremely poor too, so I totally get where you’re coming from. But honestly, while $300k will change your life, it won’t really change it as much as you think. It’s not like, “retire and spend the rest of your life sipping drinks on the beach” money. It’s not even “my kids will be set for life” money. Don’t get me wrong, it is a big amount! But to return to the earlier analogy, you’d be doing the job you hate and not even getting lotto tickets, but scratch offs. I’d also wager that number is the top end of really rosy and probably not realistic estimates.

  104. JustKnope*

    You are losing valuable accounting skills and experience in this role! Just a few hours a month doing a certain kind of work isn’t enough to keep your skills sharp. You have something like – 20+ years of working left ahead of you? With that in mind, the experience you’re losing right now will hurt you worse in the long run. Plus, that 401(k) the new company is offering is REAL. That investment will pay off way more than the ~maybe happening~ stock payout.

  105. the cat's ass*

    Bail now, and go to the other job, knowing you’ve made the right decision. As the partner of someone who is a veteran of many ‘awesome’ start-ups, it’s all vaporware until it isn’t and none of us can eat pies in the sky. And BTW, do NOT ‘help out a bit’ after you leave.

  106. Macaroni Penguin*

    What if you stick with the soul draining job for a few years, and there’s no life changing compensation?
    It’s a possible future that’s worth considering. There are no guarantees that you’d absolutely get the big payout.
    If your comfortable accepting a lot of risk, maybe aiming for the Big Payday makes sense.
    My risk tolerance is low, and I wouldn’t want to stay in a job I disliked intensely. I’d pick the new job with an appealing salary and benefits.

  107. Raida*

    Instead of comparing the crappy job you have to the nicer one you want – can you get rid of any of these tasks?
    Specifically the ‘executive assistant’ ones. Anything that is not reporting or analysing HR information, accounting data could be done for a fairly low salary.

    The boss is leaning on you too much, and it’s not your responsibility to decide that you’ve just got to pitch in and do it – tell him this is not your job and he needs another staff member to do it. Just the assistant parts! He needs to learn the technology and not send tiny time-sucking requests to the head of Accounting ffs

  108. Deezil*

    “The second thing is, it’s okay to turn down money because you don’t like the price it comes at.”

    WOW. If that didn’t speak to me in a way I needed it to.

    A month ago, a friend reached out to tell me about a position working with her doing something I had never done, and at a 15k raise to what I was making, which I had just got an increase of 8k a month prior at my (very late) yearly review. Aced the resume/cover letter/interview (thanks Alison!) and landed it with no issue. Told the owner of my current company, and he countered back with a 20k raise over what I was making, a net 5k increase, and if I would be patient, I would get everything I wanted my position to be. I turned it down, even at the raise overtop the new job, and Alison’s sentence says it perfectly. I turned down the money because of the price it comes at. It comes at working 9-10 hours a day while on salary, diluting my hourly pay, being on call pretty much all the time, and we’re so taxed I can’t take a vacation day without getting called and having to work an hour or two anyway. The new job is straight 8, HOURLY so they have to pay me if they run me over, and the hours are better for my home life and sanity. I usually work 7:30-4, but today I worked 7:30-5:30, and wasn’t really done and had to call coworkers to hand off a few things on my drive home. The new job is 8-4:30, and I asked my friend how many after hours calls and emails she gets, and got a reply that “it’s not a thing here”. We all work the same hours, and we all get to go home and have a life. I start Tuesday and I can’t contain my excitement.

    1. Cher Horowitz*

      Not sure if you will be back to this comment section but CONGRATULATIONS and good for you for putting yourself first!

  109. Charli*

    If you decide to stay, get the amount of equity in writing before accepting.

    Also, startups are notoriously fickle. Getting a round of financing is not guaranteed. If you have an idea of what the company’s financial position is given your role, factor that into the equation as well.

  110. Yessica Haircut*

    By giving up the new opportunity, you are trading real, tangible stability for fairy gold.

    And don’t be dazzled by the company line about being better than Google/Dell or holding All. The. Patents. There are a lot of two-bit patent troll shell companies that can boast they hold more then 20% of patents in their particular niche, but they have zero capacity to succeed in that niche in a real way. A patent is not much more than an idea someone has written down, and ideas without strategy and a realistic business plan are virtually worthless.

  111. Ellie*

    I would leave if I was you.

    I wouldn’t factor that 300K into the equation at all. I’ve seen far too many startups that make promises like this and then fail to deliver. I worked for one of them, the company went under and the stock ended up worthless. You’d be better off taking a month of your salary and putting it on number 12 at the roulette wheel. Would you consider doing that OP? Because its the same thing.

    So what it comes down to is, 10K more now and the promise of 10K later on down the road, for a job you don’t like with no promotion prospects, or 12K now, and better insurance, for a more enjoyable job with room to move. I don’t see how you could pass it up. Staying is risky, the startup could go under, and you’re reliant on their references. A new job on the other hand will help to flesh out your resume, and provide you with better networking opportunities as well. You won’t become a better accountant unless you spend most of your time doing accounting.
    If you enjoyed your existing job then that would be different, but you don’t, and this is a real opportunity for you.

  112. June*

    Three million is a life changing amount. $300,000, not so much. I could live with passing over a possible $300k sometime in the random future for a job I really liked that paid more with better benefits.

    The check may or may not be in the mail. A possibility does not always equal a probability.

  113. Boof*

    OP – sounds like you’ve already decided to go and I agree. Someone who only scrambles to offer a little more to keep you when you’re headed out the door and ignores your dissatisfaction before that (or promises to deal with it “soon”… then months go by and no changes are made) won’t change at all.
    Whether the $300,000 is enough to gamble on; let’s say there’s a 1/10 chance at that 300K in 3 years (I’m just basing this on the fact hat about 90% of startups will fail in the long run). Odds are you will lose out if you pass up more than 10K/year of salary/benefits/”psychic income” (stress/wellbeing) for that opportunity (logic: [$10,000/year x 3 years] * 1/10 chance of success = $300,000 – risk any more than the 10K a year and odds are you will lose out, don’t gamble more than 10K/ a year and odds are break even vs in your favor if significantly less)
    Yes that math is a little fuzzy and only you can fill in some of the variables but if you apply it to repeated “gamble” opportunities in theory you should at least break even

  114. Miss Keith*

    2-5 years is a looooooooooooong time to stay in a job that makes you miserable.

    And at some point the company is presumably going to realize they can replace you with an admin assistant for a lot less than your accounting salary.

  115. Pink Geek*

    Go and get your better life today.

    I work in tech, the chances of seeing the life-changing amount are the same as winning the lottery.

  116. Badasslady*

    I also have concerns regarding where the “life-changing” money comes from. For the start-up stage OP is describing, it would be really hard to actually evaluate how much of a payday OP will actually get even if everything goes smoothly. Shares are going to get diluted with each funding round, and it seems like the estimates of the payday is based of the company’s evaluation of its own future worth. Even if the company becomes a success and OP will get what she was promised, it would not surprise me at all if the payday ends up being a lot less than what OP is expecting, and might not be life changing at all.

  117. Carlie*

    If you really believe company 1 will rise that much in value, use your raise from the new place to outright buy a few shares of stock. Then you’ll have the great new job and the gamble of the life-changing money without the downside. Or, change your part-time consulting fee from money to stocks so you don’t even see the initial outlay.

  118. anonymous73*

    No amount of money is worth a job that you hate IMO. Yes you need money to survive, but if you have the opportunity to leave for a job that you would find more fulfilling, go for it. Don’t let your current boss guilt you into staying because he would be overloaded. The only person that’s going to look out for you is you. People often make promises when they’re desperate, and often times those promises never come to fruition.

  119. Eddie*

    My dad has had two recent payouts from companies he used to work for.

    One was $700,000; a sum that allowed him to help me with a down payment for a house and still have plenty left over for retirement, home improvement projects, etc. Life-changing money.

    The other was for $2.10.

    IMO, it’s not worth the risk, especially if you’ve got a good offer now.

  120. Despachito*

    I see only promises, which may or may not materialize, and a job you hate in your Old Job, against better CERTAIN pay/better benefits/work you actually want to do, in your New Job.

    Given that you said ” I’ve come to dread hearing my computer or phone go off with messages from my boss because it’s always for some task that I dislike ”

    “I was fully set on leaving immediately and no amount of money would change that because I’m miserable”,

    this would clearly tip my scales towards leaving.

  121. Chickaletta*

    Best career advice I ever heard, which I’ve commented here before:

    Don’t search for your dream job, search for a job that lets you follow your dreams.

    In other words, instead of focusing on whether you love the job (because hey, at the end of the day a job is a job and it’s always going to come with not-so-fun parts), instead, look for a job that allows you to live the life you want.

  122. File Herder*

    Run, do not walk, to the nearest exit.

    One of my friends got a job at exactly the right time to be able to retire on their Google stock. The reason they were free to get a job at Google was because the previous job at a tech start-up had below market pay but had been promising to give stock that would be worth a fortune when they went public. Then it was no pay and only stock, but “if your friends invest they too will hit the big time and in the meantime we’ll be able to pay your salary”. At this point the rest of the friend circle were “this house is full of evil bees”. Friend had drunk the Kool-Aid, and knew it needed only a few more days before the venture capital deal was signed off. Needless to say, the start-up did not get bought out and did not interest venture capitalists, and friend did not get a giant stock payout, or even the last week of pay owed.

    The only money you have from them is what they are giving you right now. That money is your current salary and benefits with possibly the first $10k they’ve offered (assuming they even bother paying it once they’re certain you’ve turned down the other job), and the rest is fairy gold. Given what you’ve said about the company, it would not surprise me in the slightest if they say they can’t afford the second $10k bump by the time it comes due – and be telling the truth.

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