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Ask HN: I don't want to be a founder anymore
565 points by throwaway10595 on May 25, 2017 | hide | past | favorite | 479 comments
Hi HN,

Using a throwaway account because there's a lot to lose from speaking about how I feel.

I founded a company several years ago. Fast forward to today and we're profitable, growing steadily, debt free and are about to be acquired (there are LOIs on the table). You may ask what the problem is? Well, the problem is that I'm supremely unhappy.

Each morning for the past couple months, my first thought has been "What could today be like if I didn't work here?". I drift off into exploring what it would be like to work at Wal Mart, or the construction site outside, or as a bagger at a grocery store. It seems so stress free. Then, my phone starts ringing for the day and I'm snapped back to reality. This morning, I locked myself in the bathroom with the shower running (don't want wife to know) and cried my eyes out. I haven't cried in many years. It felt great, but only for an hour.

So, from my (possibly skewed) point of view, I have 2 options:

- Quit, which effectively kills any acquisition and likely the company as well

- Suck it up and work on the same thing for 2-5 more years

I'd been mulling over a third option (hire someone to do my day-to-day), but don't know how to make it work. The product is just too complicated (tons of domain knowledge required) for someone to come in and take over. Additionally, the product just isn't that interesting (glorified CRUD app) and it's been hard to retain developers.

Please tell me I'm missing something! Maybe I'm just being ridiculous- it's getting hard to tell. Is it common for a Founder to go through this train of thought before an acquisition? Is there a trick to convince yourself you want to keep doing this? Maybe I'm suffering from some kind of depression and need drugs.

Any advice appreciated.

- A founder in pain

I don't know directly from any of this, because I am an unlettered redneck with air-cooled teeth and a net worth in the middle four figures. But if I had a serious prospect of ending up with genuine fuck-you money, and all I had to do to get it was keep doing what I was already doing and gut it out for a few more years, then that is precisely what I would do, to the best of my ability.

I get that you're suffering, and I am not without compassion. But the kinds of jobs you're fantasizing about are kinds of jobs I've had. They are not without stress, as you imagine them to be. They are physically wearing and not at all secure, but most of all, the kind of stress that comes with those jobs - more to the point, that comes with those jobs being the best prospect you have - is not a kind of stress that ends, save to give way to something worse.

Your current travail, conversely, certainly will end, and based on what admittedly little I know about how startups work, you have a very real prospect of a great big payoff at the end of it. It would, I think, be the regret of a lifetime to squander that enrichment of all your years in search of a more comfortable day after tomorrow.

You're right about those jobs being physically wearing and not secure. My brother works at Target and lost 100 pounds over the course of a year. He wasn't trying to lose weight, it just happened because he was on his feet all day running around and because of other physical demands of the job. He does not seem stress free and it is not a job he likes, nor does it pay well. I would definitely never want his job.

My experience is the opposite - paid workout without many responsibilities is nice job. It's monotone as hell and you have to forget any real ambition. Also bosses often suck ... But when you find position under good managment it IS stressfree job imo. It's more about tradeoffs - what you want from life vs. how hard are you willing to work for it.

Out of curiosity, how much is the stress in those jobs linked to the fear of losing the job, and how much to the job itself?

Neither, mostly. Or both. Let me see if I can usefully elucidate.

In the short term, the stress originates in the fact that the pay sucks; even if you work as hard as you can all the time and get all the hours you can handle, you still barely get by in the best of times - and one serious medical issue, for example, is more than enough to wipe you out financially for good.

In the long term, these jobs entail extensive physical labor, and it takes very little time to realize that there's eventually going to be a hard limit on your ability to continue to do such work - especially if you work as hard as you can all the time and get all the hours you can handle. Sooner or later, you're just going to be too old and too beat up to continue, and the longer you do this kind of work, the higher your risk of the kind of injury whose repair costs will wipe you out as I describe above.

And even if you beat all the odds and never get sick or get hurt, what happens when you can't work any more? Funding even a minimally feasible retirement runs to the mid- to high six figures at best, and doing this kind of work all your life, you're lucky to top out at fifty thousand a year - and that's if you can get such work at all, when illegal day labor is so much more cost-effective.

So you're pretty much screwed both ways, when this kind of work is the best your abilities enable you to find. You don't make enough money to provide a stable life for yourself and your family, and when you run up against the physical infirmities that come to us all but most quickly to those who use their bodies hardest, you cease being able to make even that much, and then what the hell do you do?

Thanks for the answer. In most of the EU your healthcare costs are mostly covered by the State and, if you become unable to work, you usually get some kind of disability pensions. But I understand that, without this kind of "insurance", there is a lot more stress even in jobs where you don't have big responsibilities.

In most of the EU, the US subsidizes your defense budget, too.

Do you really think that, if we spent more on our armies, you would spend less?

Anyway, I'm not saying that our system is better - for example, here it's more difficult to find a job, and wages are usually lower enough (also because of the taxes necessary to finance the welfare state). What I was really thinking about is how much having to worry about medical expenses and retirement money changes the stress level in certain kinds of jobs.

I think that if we spent less on our armies, we'd have more to spend on the sorts of social benefits Europeans regard as table stakes and pride themselves on having.

In the abstract sense, it'd also be curious to see what effect on those social benefits would result from a termination of the security guarantees which the US has extended to an ever broader fraction of Europe since 1949. I'm not so cruel a man as to actually wish such an outcome on anyone, but I certainly would like to see the people charged with the responsibility of governing my nation take an interest in the wellbeing of my nation, rather than investing so much expense and effort in defending an entire continent which can barely be moved even to a token expression of gratitude, much less any actual quid pro quo, in exchange for it.

As regards the remainder of your comment - yes, without social guarantees of medical care and a livable retirement, life is much more stressful than it would otherwise be, and this additional stress is inversely proportional to socioeconomic standing, with an exponential term in the function. Is this really such a novel thought as your comments here make it seem? I find it obvious beyond the point of triviality, but I suppose someone who's never actually lived with it might not previously have had cause to give it any consideration.

Yes, the fact that we can take for granted some things that you don't was exactly my point. Here, when you think about getting seriously sick, what most people think about is the loss of health - the loss of money comes very far behind.

Regarding military spending, I'm surely grateful of NATO - especially during the cold war - but I think you're severely underestimating European defense capabilities and, most importantly, needs.

Let's say that for an act of magic NATO went away tomorrow and a EU-only army or alliance had to be created to replace it, and let's say we didn't even increase military spending from the current level. Who would/could attack such EU alliance?

The only neighboring power that would have the resources to even think about it is Russia, but then again - with current spending and capabilities - Putin would have exactly zero chances of successfully invading the EU. Just look at the size of our combined armies and the difference in economic potential (in case of a prolonged war). This, even without even counting that France (here I'm making the UK magically disappear as an ally too) has enough nukes to make such an invasion an act of folly, and that several other EU countries could easily develop nuclear capabilities if required.

Of course you're free to disagree, but my very strong impression - as someone who also has some family in the US - is that this "we can't have good, affordable health care because of NATO" is just a very convenient way for your politicians to put the blame elsewhere. The US is so rich that it could easily give EU-level healthcare at EU costs to everybody, but then doctors, insurance companies, big pharma and everybody related would need to be less rich, and all other high-income people should pay higher - and not even so much higher at that - taxes, as it happens in the EU.

You could do that even without cutting military spending which, by the way, is mostly geared towards the ability to project US power overseas wherever and whenever it's needed, not to protect Europe from Russia. I don't have the numbers readily available, but I'm pretty sure that your 11 carrier strike group cost much, much more than all your troops stationed in Europe.

Well, hell. I've been arguing against NATO for years, for much the same reason as I've tended to argue against the scale of our military expenditures in general - namely, that it's an obsolete waste of money better spent elsewhere. You're right about the cost of our carrier groups - what's worse is that, in any war with a serious opponent, they're just going to be gone, because they have no meaningful defense against mass attack with supersonic cruise missiles. That's why I want to see them scrapped in favor of something cheaper and more defensible - that, and as a means of helping restrain the tendency toward ultimately counterproductive military adventure that's been so much a feature of US foreign policy, regardless of who happens to be in power at any given moment, for a century or more. And quite aside from the fact that I actually do believe these are worthwhile ends, this argument is much easier to make go, with people who aren't in any sense progressive, than the one where we look out for people because it's the virtuous and compassionate thing to do, and hang the tax rate increase and medical-sector profit cuts.

(Does this sound hypocritical of me? Perhaps it does. On the other hand, if I have to choose between some notion of my own personal ideological purity on the one hand, and on the other acting in ways which make more likely a state of affairs in which poor kids don't die of toothache and one mishap doesn't render entire families destitute...)

Unfortunately, because I've tended to avoid the news lately, I had not previously been aware that Trump's lately been arguing that NATO is obsolete and overpriced as well. This makes it an impropitious time to advance the same argument myself - even if the damned Johnny-come-lately happens to benefit at this moment from the broken-clock principle, it's hardly wise to associate oneself too closely with whatever he happens to be saying, whether by accident or otherwise. I'll have to keep a closer eye on that in future.

I see your point. Anyway, I don't think that NATO by itself adds a significant amount of expenses on top of the national, "non-NATO" military expense of the participants.

Regarding Trump, IIRC he already changed his mind about NATO being obsolete, the point now is "just" that the allies should spend more.

Please look up numbers before you claim such ludicrous things next time. http://data.worldbank.org/indicator/MS.MIL.XPND.GD.ZS

So you spend 3,3% of your GDP opposed to what, EU's 1,5% of GDP? And how much of it is for failed wars such as Iraqi one?

You might not look so misinformed next time if you find some sources for your claims...

I see 14.5% vs. 4.1%, US and EU respectively, in the 2015 figures listed there. US and EU GDP being roughly equal, this works out to an absolute factor of ~3.5x as well as a relative one, which strikes me as fairly significant.

To be sure, US military spending isn't purely motivated by our concern for our NATO commitments. But, considering that the US contribution constitutes by far the lion's share of resources available to the alliance in both absolute value and percentage of GDP, it seems to me that much more effort is required, than you exert here, to argue that the termination of such commitments, or even simply the reallocation of significant funds away from US military expenditure, would in no material way affect spending priorities among the EU nations.

Please notice that the 14.5% refers to the "central government" (ie, federal) budget. It doesn't account for the fact that much of your public expenditures are done at the state level - here in the EU, "centra government" means Germany, UK, etc.) nor the fact that, with lower taxes, your budget as a % of GDP is of course lower.

Look at the share of the GDP being spent. You probably have smaller (% of GDP) budget than we do.

That is GDP percentage. I'm not sure where else I should be looking.

Wow, USA is pretty terrible place to live. Here cashiers and such actually ARE stress-free jobs. Managing people is always bigger PITA than just smiling all day on the customers ...

Eloquently said and I 100% agree. I worked as a blue collar worker for many years and the number of times I've heard people claim that working construction or retail was 'stress free' have no concept of that which they speak. I could elaborate, but your comments make the point exactly.

    They are not without stress, as you imagine 
    them to be.
I guess they imagine they wouldn't care about doing a good job, losing it, or making money - which would probably alleviate a bunch of the stress!

(source: I've twice left my own companies- both companies continued to grow and prosper after I left).

Personally, I'd suck it up and get the sale done, working hard to make the price as front-loaded as possible. Depending on the buyers appetite for you to keep working there you could:

A) Suggest that you're excited to stay with the business, but if they feel there'd be too many chefs in the kitchen and that you should phase out, you'd like to know about that now... i.e. open the door for them to express how critical you are to the deal.

B) If they DO really want you, push hard for a front-loaded deal (i.e. initial payout versus earn out) and then give notice 6 months after the deal closes. You'll leave some (maybe lots) of $ on the table, but who cares. Selling a company isn't indentured servitude. Someone else owning the company might relieve some stress. If it doesn't, punt.

Broadly-- I'm a believer that happiness is generally internal. If you can't find a way to be happy with this job, I suspect you'll have a hard time with a different one. Starting ASAP, I'd make some changes to see if it makes a difference. Get therapy. Try anti-depressants. Shut off your phone at 6pm and don't open your computer. The sky won't fall. Exercise. Meditate. Try psychedelic mushrooms (only half kidding-- there are some studies that one dose positively impacts depression and anxiety). Eat better. Go into work late AM twice a week so you can take a long walk with your wife. Schedule vacations. Go into the woods a lot (exposure to green space helps depression too). I just read that doing tai chi helps with depression. Schedule weekly lunches with friends.

Please do not advise people who are clearly depressed to take mushrooms. Always remember that whats an elixir for may be poison for others. Yes, mushrooms do help anxieties BUT it is also known that if you are not in a good mental state, you can have bad trip and a bad trip... is not going to be relieving any anxiety, it will make it worse. That said, maybe Microdosing is okay.

I agree with all of your other points but I think it is important to point out that mushroooms will grab you by your genitals and take you for a spin. Not everyone can handle this. I am speaking anecdotally. These things have been mentioned way to often now. I get that its a new thing, and given that the stigma is no longer there - at least in our community - it is also important to know the 'cons' along with the 'pros'.

Anecdotally, bad trips do not cause bad feelings after a trip. The overall feeling of improved outlook can result even after a truly harrowing experience.

That said, I agree that downing a bunch of psychotropics is probably not going to solve OP's problems.

Okay, I was trying to not put my experience on this website. But here goes

I did some in the first year of uni with a floor mate. Two sober.

When I was on it. I got the feeling as if I was in a prison, and started feeling like I was being experimented on. I got super paranoid and I'm bought I can fall asleep. Tripped for hours in my bed and my eyes were open, though they felt as if they were closed. I was told every now and then I would sit up like the undertaker from WWE and ask how do I get of mushrooms. Lol

Then apparently I went down and upstairs like 10 time. Reaching bottom I, I'd want to come back up. They wanted to get me out of the room but it just made me feel like I was being taken out for an experiment.

After a while, they tried to make me realize I was just tripping. We got downstairs and I yelled okay.. I get it.. I'm tripping balls.

I left out a lot of the details but, it was embarrassing that entire year since people knew I had a bad trip. I felt as if I might have said or done shit I did not remember too.

So, in summary, place, people, time, mental state and stability are all factors to be considered.

Btw on the comedown I was super introspective but could not differentiate it from a placebo.

The point of the original message of mine is to realize that there are no Soma pills (Brave New World reference). Nothing works for everyone. We just need to realize this and not suggest something potentially dangerous to someone who is clearly in a bad mental state at the moment.

OP you'll get through this. Diet, exercise, jogs, meditation will take you a long way. Also, tell your wife everything. She is your wife, you oughta be in it together. Also... if she doesn't get it then don't be upset; anger starts from an expectation.

I wish you the best of luck.

P.s I am going to delete this message after a couple of days since my story is too specific and I want to maintain some kind of annonymity.

Edit: so from my description it should be obvious that I am a socially awkward, introvert who is super self conscious. This is one reason it did not work for me. Think of psychedelics as breaking a mirror of the existence. It is really really ducking intense. I was better off doing it though. My point still stands. I am going to try microdosing when I can.

There are studies that show a sub-recreational dose is beneficial for depression and for chronic headaches. I haven't met a person yet that suffers from chronic headaches that is adverse to trying a low dosage.

That said, it's always best to do it with someone who has experience, remains sober, and can guide you in a positive manner. It can be easy to become caught in a negative place, although, maybe not at a small dosage, still ill-advised, in my opinion.

Definitely not bad advice. Especially if it's your first time trying to dose correctly. It could be easy to get it wrong and it would always be better to have a buddy; like these folks from Netherlands: https://www.youtube.com/watch?v=kz9yC6WkWA0

If you want to delete your comment lower down, you should do it soon. There is a fairly short deadline.

Anecdotally, bad trips do not cause bad feelings after a trip. The overall feeling of improved outlook can result even after a truly harrowing experience.

That said, I agree that downing a bunch of psychotropics is probably not going to some OP's problems.

> Try psychedelic mushrooms

Don't do this. Psilocybin has the tendency to "turn out what's inside you" and might make your feelings much worse. People do get bad trips and the consequence can be panic attacks and severe anxiety for months after the trip. It's incredibly dangerous advice to tell someone "take drugs, despite your psychological problems"

>It's incredibly dangerous advice to tell someone "take drugs, despite your psychological problems"

It's far more dangerous to tell people with psychological issues to avoid "drugs".

uh, how?

I think they mean legal, prescription drugs. Self-medicating or attempting to resolve mental health issues with psychedelic drugs can be very dangerous and make things much worse. I strongly advise individuals to not trust the advice of random strangers on the internet in this regard.

"Try psychedelic mushrooms (only half kidding-- there are some studies that one dose positively impacts depression and anxiety)"

As a founder, I generally agree. I have also done mushrooms a lot, I don't know if it is very wise but I enjoy it a lot. I also excercise daily and try to follow other tips you gave, though I'm not into meditation, medication or tai chi. I'm quite happy, but I can't really agree that the situation will fix itself with only these tips. Sometimes there are problems at work that need fixing, and the situation only gets better if you fix them. Often fixing these problems requires lots of dedicated work and leaving your comfort zone. But once they are fixed, you are a little bit happier.

For example:

- Too much responsibilities -> define new roles and delegate responsibilities

- Problematic employees -> try to work out the problem with 1-to-1 discussions, or as a last resort, fire them (or talk them to leave).

- Difficult to retain employees -> find out and research how to make employees more happy at their work. Try to research which perks are cheap and improve employee happiness. Give free candy.


If you'd like the stress relieving effect of mushrooms without the guilt of illegal drugs and all that comes with it, try surfing. Apparently, there was a study with PTSD soldiers - one group took, I think it was some kind of amphetamine, for a couple of days and the others went surfing for a couple of weeks with roughly the same positive effect on their PTSD.

If you want to know more, I read it in "Stealing Fire" by Steven Kotler and Jamie Wheal.

> I'm a believer that happiness is generally internal. If you can't find a way to be happy with this job, I suspect you'll have a hard time with a different one.


Your job is unlikely to be the root source of your depression. Meditation and introspective thinking will likely tell you what's wrong.

>> working hard to make the price as front-loaded as possible

This. You say the company is profitable, growing and debt-free. The sale should look more like a purchase and less like financing given the condition of the company. If you're that critical to the function of the company, then a priority should be to reduce that dependence.


It's a thing.

At the risk of sounding obvious: you've identified that your job is the source of the stress and unhappiness. That's certainly not an irrelevant factor, as my parent and sibling comments claim. Make the sale, maybe move to a cheaper apartment, use your newfoud buckets of money to work in your community garden for a month. See how you feel then.

First, talk this over with your wife. She deserves to know what's going on with you and you need her counsel and strength.

Second, recognize that an acquisition is a change of life - that can certainly make one feel anxious and depressed, no matter how much you may have looked forward to this milestone.

Third, nobody is indispensable. If you died in a car crash today, the company would find a way to continue.

In your place, I'd go through with the acquisition (and do my duty to my investors & employees). When the dust settles (3-6 months), I'd go to my Board of Directors and tell them I need to change roles at the company. That would include dropping all my day-to-day responsibilities and dropping back from full-time. Be explicit that you're on a transition out of the company, and you want it to be orderly (for the company's benefit) and time-limited (for your benefit). When the time expires, leave with thanks and go live your life. Good luck and congratulations!

Excellent advice, though I must say that

> If you died in a car crash today, the company would find a way to continue.

might not be the most comfortable way to describe a person's importance when they're feeling down. I would instead say "if you quit today suddenly with no warning,".

It's a common metaphor. There is also a risk measure explicitly based on this concept: https://en.m.wikipedia.org/wiki/Bus_factor But I guess that there are not that many buses there in US so a car crash may be more appropriate.

Oh, it is technically correct. The issue is that when comforting the depressed, violent or overly negative imagery may distract from the point being made.

The metaphor is perfectly unnoticeable in everyday contexts, but in his state, careless edges of arguments must feel awfully pointy.

I learned that the hard way when trying to support a friend down on his luck.

i wish you godspeed in your quest to control what other people say on the internet.

You're right - with a bit more thought, I would have given a less "terminal" example of sudden unavailability. Will keep that in mind, thanks.

>Third, nobody is indispensable. If you died in a car crash today, the company would find a way to continue.

If the company is large enough or has enough debt, sure. But if this is a 10 person bootstrapped shop and the founder is the only one that really knows everything, it would probably fold up if he/she disappeared with that knowledge.

Take a vacation, preferably to a beach. Use it to learn what processes at your company are dependent on you. Then when you get back, start documenting and delegating every process until you are no longer a critical dependency. Then take another, longer vacation. Sounds like you need one.

Beaches aren't for everyone. In burnout situations, I find going backpacking (mountains/hiking, canoeing in the Canadian wilderness) to be even more relaxing than a beach. None of these annoying humans that seem to be always present on beaches and at workplaces. And also none of the attention-sucking internet access.

Those are probably more effective venues for killing burnout not for the reasons you give, but because those activities usually incur some goal (covering certain mileage, getting to a destination) that restores the association of reward with effort... Versus being at the beach, which simply doesn't.

I love the beach, but it's passive, so I'm still turning over work in my mind as I'm there. Swimming, hiking, camping, etc. give me tasks and actively distract me.

Yes! I've also found that having to focus on something different relieves stress. My go to activities for this is either driving in the hills down the peninsula from SF or cooking dinner. If I'm not in the moment it's either dangerous or I ruin dinner.

Wow, this gave me the realization I needed about why I've been procrastinating on a project. Thanks.

It's a minor point, but there are plenty of beaches around the world that are pretty quiet people-wise.

Ha yeah plenty in Australia where you're so alone you're in actual danger from it.

I agree that humans and internet access are suboptimal. I'd just like to point out that there are beaches without humans or internet access.

Yeah, shitty ones.

And the best ones. Amazing, that.

>Beaches aren't for everyone.

Yeah, for me it's fishing or hunting...requiring a total disengagement from technology and (most) people.

Beaches are fun, but I wouldn't consider them a truly contemplative vacation unless it's some super expensive, exclusive, far away place...and like you said that's not for everyone.

Why does it have to be super expensive? The far away beaches are the cheapest ones.

If you don't account for a very expensive plane ticket sure.

Yeah that's what I meant.

How about backpacking TO a beach or hotspring? :)

The problem here is the founder thinks he / she is so indispensable that it would fail if he quit. So taking a week off for vacation is likely to just lead to more stress.

However, the longer vacation is good advice. When I was severely burned out at a previous job (start-up) I was eventually fired because I couldn't continue the 70 hours a week and have the same, high output as I originally did when I started (I was averaging 70 hours a week for almost two years in addition to a long commute time and this is after working with the same people at a job before that where I was working about the same 70 hours for almost 3 years where I was also expected to have high output).

When that happened I ended up having roughly 3 months off of work. Joined a new company and it was amazing. My burn-out, which plagued me for years and caused an anxiety attack so strong I thought I was going to die of a heart attack (very severe chest pain; tried explaining to my 2 year old what to do if "daddy passes out") to feel essentially dissolved.

Burn out isn't fixed within your typical vacation period at a job. Most of my friends who have been, or are still, burned out have never had it go away until after taking months of time off.

Even a short vacation would help with two big things.

First, physically resting and getting outdoors in the summer months can certainly just help you rebalance enough to make good decisions. You might realize that very short-term problems are weighing more heavily on you than you realize.

Second, it's a test of how indispensable you are at work, and forces other people to try to do things before asking you. You'll learn which things you need to make sure to train them to take over when you leave, and they'll remember the answers and approaches better if they have to figure them out themselves.

I guess it's possible that two weeks would cause irreparable damage... I have no idea what you should do in that case. I can't say I'd stick with it in that scenario, that's a horrible trap to get stuck in especially if you can't imagine it getting better.

If things are "that bad" at a particular work environment, I'm not sure any amount of time away will "fix" the root problems if you still have to go back there. You described taking time off (months) but you didn't go back. I have to think that the switching of jobs had something to do with your anxiety level going way down but I'd agree it would still have been "go go go" if you just switched employers overnight and started at a new place the next week.

Yeah, since the vast majority of companies in the United States don't give more than a few weeks off (which is far below what you really need, in my opinion, to undo burn-out), you pretty much have to quit. I guess I didn't really make that clear :)

Essentially what I was getting at was: a short vacation isn't going to do anything. If he can make it so he can take a very long vacation then that means he either transitioned enough so others can run it for him or he quit. Either way sounded like it would work out for him at least which is what I was aiming for with my comment.

Oh you're right - 100% agree. When you've got that level of burnout/anxiety, a week or two ain't gonna cut it.

In most cases, the anxiety and stress from a work environment didn't happen overnight, and it's not going to go away overnight.

I do think most people don't quite get that until they're in the thick of it. Seen it with more than a couple of friends, and in every case, the only option was to walk away and switch work situations. If it's causing you that much stress, there's almost never a great reason to go back vs getting something new.

Vacation/holiday is not something that I particularly enjoy (and thus by extension the OP may not): I like what I do and want to keep doing it a reasonable pace.

But taking a break from the stressor, and/or delegating some of the work and stress, yes.


This is the "E-Myth Revisited" route, which to summarize is about decoupling the business from yourself and enabling other people to take "critical" work off your plate (because it really isn't that critical).[0]

[0] https://www.amazon.com/E-Myth-Revisited-Small-Businesses-Abo...

+1 for vacations. I used to vacation only when I burned out. Now I plan in advance several months ahead. It helps me pace myself so I don't burn myself out before the vacation shows up. Personally I try to schedule two week vacations, leaving the work laptop behind when I go. Letting people know you'll be traveling, so they can plan around it, also helps decouple you from the work. If everything catches on fire when you are gone, they will realize it's necessary to reduce their reliance on you.

+1 for learning what processes your company depends on you for. The vacation is a bonus.

I agree. It's your company so you should be able to do whatever you want with your time, now that the company is able to support you. Why not take a sabbatical, work remotely from anywhere on the world etc.? Basically find whatever you really want to do without giving up the responsibility as a CEO (yet)

+1 on vacation, also maybe read a book like Deep Work, he has some interesting concepts that might be helpful involving exercise.

This is very solid advice

> Each morning for the past couple months, my first thought has been "What could today be like if I didn't work here?". I drift off into exploring what it would be like to work at Wal Mart, or the construction site outside, or as a bagger at a grocery store. It seems so stress free.

Here's the thing- it probably isn't stress free, just different kinds of stress. And you also need to ask yourself whether the feelings are caused by your job and stress, or if they're just coinciding with them.

As many others have said, look into talking to a therapist.

Also, talk to you wife about this! If she was crying the same way, you'd want to know, and you'd want her to trust you enough to tell you. If there's any person you need to be able to open up to, it's your spouse.

Can confirm - right now I personally work as a "Party Associate" at Party City - not very stress free. Customers can be very specific with what they want. Running a startup sounds like a dream - I'd much rather have your job, even if I still had to keep my $9.75/hour. (Anyone looking for a college sophomore eagle scout in the MN area for the summer?) (gallerdude@gmail.com)

You should have your contact info in your profile...

This is interesting. What part of running a startup sounds like a dream?

Being able to make choices, determine the best path of action, and (if you work hard enough) make something great.

Right now the best things I make are balloons (but I do have some fun side-projects).

Sounds to me like you're in a good opportunity to start your own start up. I might be being a bit presumptuous here but it seems like you have undemanding job but one that pays the bills none the less, this is a perfect time to begin working on your own business as long as there aren't any contractual difficulties.

I have to say it does sound very Zen, balloon making. In life, I have found that the trick is not about how to keep the mind busy, but about how, how often, and when to get it at ease.

It's Zen until someone walks in asking for a 40 balloon set, while there are 4 people in line for the register still.

The part where investors fall over themselves to throw vast amounts of money at you?

Of course, being a dream, this doesn't happen to the vast majority of startups...

Not the OP, but the ability to control your own destiny? :)

Investors, stakeholders and clients control that destiny.

everyone's got a boss, in some measure, but not every "startup" has investors. and, if/when you're the owner, you have more choice in which clients to serve, vs the OP working retail.

Customers... and employees everything else takes care of itself, IMO. Not being able to make a small significant change demotivates you significantly.

Groom someone to take over your role. Be honest with your cofounders, tell them you're feeling burned out and you need to take a step back to keep your sanity.

> The product is just too complicated (tons of domain knowledge required) for someone to come in and take over.

I doubt that this is actually true. It may take them time to ramp up, but you're there to guide them and mentor them.

> Additionally, the product just isn't that interesting (glorified CRUD app) and it's been hard to retain developers.

The fact that you're deeply involved and don't feel that other developers can step in, and at the same time feel like it's a glorified CRUD app hints that you may not be giving other developers enough autonomy or context on the problem.

If they are just working on simple CRUD stuff and have no context, the job is going to suck. But simple CRUD with context could be much more interesting.

And if all else fails, pay more.

"The product is too complicated", "The product isn't interesting", "it's been hard to retain developers" and the founder is burned out. To my casual viewing, it seems very like the founder is exercising too much control over the product.

Especially if the founder hates their job, and there is a revolving door for the developers -- the problem is not likely to be that the implementation is too boring. The problem is more likely to be that the work environment is stifling -- or there is a lot of conflict on the team.

My experience has been that in this kind of situation, the founder is afraid that the workers will fail. To be honest, this is very likely. However, allowing controlled failure is how you build a strong team. Rather than chucking the whole thing in the bin, why not start planning fun things that the team can fail on? If it kills the whole company, at least you had fun. If it doesn't, then you have built pillars on which you can build a platform of trust.

And yes, open the purse strings for at least 1 senior dev who can shoulder the load of fixing inevitable broken things.

I'd like to add something to the simple CRUD app perspective. Make sure you hiring the right people for the job. An engineer with 15 years of senior experience might be bored working on crud apps and might be the wrong person for the job. But a junior engineer, someone fresh out of an engineering academy, or someone early in their career might be excited by the challenge. Everyone says they want to hire "the best". The trick is to hire the best for you and not worry about if they would be the best somewhere else.

I'm in the middle of the road between those, but I love a good CRUD app. If it helps other people be more productive and remove stress from their day it's amazing.

I cut my teeth at my first job on a CRUD app; it was great. Since then things have been less CRUDy, but it can be nice to get a simple CRUD task as a break from more complex tasks.

Conversely, an engineer with 15-20 year's experience may have - and want - a life outside work. And be very happy to trade-off an exciting project for one that allows them to work without using all their mental energy. Because right now there's enough other challenges in life.

For that matter, what isn't a glorified CRUD app? Facebook? CRUD. Amazon? CRUD. Instagram? CRUD. eBay? CRUD.

FWIW it sounds like the founder is more of a techie that is disappointed the tech is so simplistic, and assumes everyone else will feel the same way. Hardly anyone will. A business is a business, a job is a job. Find someone who is more on the business end, customer relationships, product definition, whatever, and is excited to be working on something that's "tech" at all.

Or groom someone to take over some fraction of the role. Someone who can take over some of the load, not necessarily all of it.

The problem you are experiencing is a result of the lack of systems and processes in your business.

You need to make an important hire- you are missing a systematic. See, creatives like you are awesome at solving problems but hate to have structure and order because it doesn't allow you 100% freedom. But, as a result, you just have 100% creativity/problem solving- which is draining. The worst thing is, you can't even create the order you need to manage these things.

Systematics create structure and order in dynamic environments.

I wrote a book about this and other problems with innovation and how to solve them. It will be published later this year, but happy to provide an advanced copy to help work through seeing the problems you are facing.

The systematics in your business are meant to free you from the ongoing crap that you are experiencing.

I have experienced this first hand. Felt really insecure about my lack of passion for creating internal systems and processes, and instead hired a great person who is amazing at it and it's freed my co-founder and I up to do what we really love and excel at. I now know I don't need to be great at that other stuff, I have unique value to add on my own.

I'm late to the party but OP if you are still checking dfuhriman's post is the right answer. You're making a classic mistake. If your company has revenue to support employees you need to start working yourself out of the tasks that you can offload.

You start by documenting everything you do. Don't start by trying to get your documentation perfect- think of an MVP for it and improve over time. If it's boring, use a voice-to-text app (I hear Naturally Speaking is excellent now) and dictate it.

Get someone in there to do the job. Pay them well. Work on strategy and make your exit. Good luck!

This, exactly. I recently hired an assistant and the way that my mind was freed up was insane.

I really don't understand why it's not more common practice to have an assistant.

I would be interested in reading this as well...I've faced (and face) many of the same issues myself.

Read the E-myth Revisited.

This is also good advice and a good book.

What I add to this aspect of innovation is a differentiation between standardizable work and original work. OP's approach to creating systems are different for each.

The other thing I define is the roles in innovation; creatives, systematics, and bureaucrats. The problem I see with OP is that creatives usually cannot implement the systemization that is required for the "franchise prototypes", let alone manage the system.

Do you have somewhere we can sign up to be notified when the book comes out?

Reminds me of the e myth

Replied in another comment, but posting here to reply to your comment too.

This is also good advice and a good book.

What I add to this aspect of innovation is a differentiation between standardizable work and original work. OP's approach to creating systems are different for each.

The other thing I define is the roles in innovation; creatives, systematics, and bureaucrats. The problem I see with OP is that creatives usually cannot implement the systemization that is required for the "franchise prototypes", let alone manage the system.

There is a huge misunderstanding from people in tech regarding blue collar jobs. You guys are way too naive about what it entails to work at a grocery store or on a construction site.

I've done it a few times during summer while studying CS to pay for my bills. They do shifts from 4am-12pm, or 12pm-8pm, or even night shift... They treat you like a bad kid, you get humiliated 24h/7 by who ever is higher in the "hierarchy". On top of that your body takes a hit since most of these jobs are very physical. You get back home sore, exhausted, sometimes it turns into real health issues like tendonitis, chronic lower back pain, etc. Trust me after 2 months working at a factory you'd hate your life. You'd hate yourself. Some people get stuck in this nasty world for decades...

You-I-we, the tech people, love to think there's a better world out there by lowering the level to its bare minimum. It's actually the opposite effect but you have to experience it to understand what I'm talking about. So go back to work and keep cashing out, or, go fishing on an island.

I have two issues with this comment. First of all, the OP just described very serious signs of burnout and stress, but the top comment (this one as of this writing) isn't helpful - you are using the OP's raw discussion of their current emotional state to condemn a faceless portion of society for their privilege to not have to work blue collar jobs. You nitpicked the fact that the OP admitted wishful ideation about jobs and inadvertently invalidated that perspective. That's really not productive.

Less importantly, I agree construction sites are likely not a good candidate for the grass is greener perspective, but you're seriously overstating the difficulty of grocery store work. It's not abject misery the way you describe it. When I was younger I too worked in jobs like retail, restaurant and grocery stores. No, it wasn't as fun and liberating an environment as tech, but it was absolutely a more simple environment to work in. There was far less responsibility, and the stakes are lower when the job is basically just a throwaway one and not impactful for your career. The worst that happens in that context is you fail to sell as many TVs as your manager wanted, or you bring out the wrong food to a table, or you misscan an item as a cashier.

My point here is that I believe the OP is having ideation about jobs that seem less complex, not necessarily less difficult. This goes hand in hand with burnout - those jobs are not as fulfilling, but the OP would not have nearly as much responsibility, and the responsibility of running a successful startup on the verge of acquisition that he doesn't enjoy is clearly causing him a lot of anxiety. What the OP needs is an empathic perspective, not a lecture about how the grass isn't always greener.

While retail work was a very simple work environment as you state, I found it to be an experience in misery. it may be simple but dealing day to day with the coworkers and managers in those environment was pure hell. If my only option in life was to work retail, factory, or construction I would kill myself today before going back to that type of work.

Have you ever had an assistant manager in her mid 30s shout at you the generic company values off of the company propaganda posters in a closed door meeting because you weren't quite living the company line? I have....

i dont get it. i worked in factory during summer. while it gets boring, you dont have stress, and after you have finished your work you go home and dont think about your work.

i probably could not work it long time, but if you are stressing in that line of work its you not the job.

Obviously it's a subjective experience. If you are able to work in those types of jobs without hating that every second you spend there is a second doing menial low pay tasks; that it is a second of your life that's been wasted on meaningless shit work that you'll never get back then good for you. A substantial amount of people aren't like you.

Honestly, I hate to say this but your perspective here sounds more like outright arrogance than anything inherent to the job. You speak about these jobs as if they're utterly beneath you and inflicting misery on your time. I'll reiterate: I have done most of the jobs you mention, and while I certainly didn't feel personally fulfilled by them or buy into the company mission, I didn't spend my time in abject misery - I made the most of it and found that my coworkers could actually be fun, even if they weren't bound for tech or a similarly intellectually exciting field.

I personally don't believe there's anything inherent to any job that makes it meaningful or not meaningful; you admit that your opinion is subjective but then provide a backhanded compliment about the parent being able to enjoy "meaningless shit work"...it doesn't sound like you've conceded that it's subjective there. With a few poignant exceptions, you can choose whether or not to derive meaning and enjoyment from a job, even if you recognize that it's not what you ultimately want to do.

I spent about a decade in retail-ish jobs (started young). They are substantially easier to deal with when you know you have something else waiting for you. The difference between a lifer and a just-passing-through youngster is hard to overstate.

> They treat you like a bad kid, you get humiliated 24h/7 by who ever is higher in the "hierarchy".

That is not unheard of even in programming gigs. I've seen it around me, coming from bad management. I've been exposed to it but I've been good enough (at least compared my workplace) and managed gathering enough respect from both my coworkers and my superiors that I've been shielded from it. But it happens, they feel you're new, they feel they have an ounce of authority above you and they go crazy with every mistake(and mistakes happen).

You're describing a poor work environment which can occur in tech, especially in startup. There's also thousands upon thousands of blue collar work that don't have a poor work environment.

I felt much better after a day of unloading trucks in a wearhouse than I do now coming home from a day of sitting in an office chair programming. Sitting all day is terrible for your body and it's exausting to boot. One of the biggest shocks of my entire life was the first day I got home from my first programming gig and being more tired than coming home from the job I was working a week before (food service) (1)

(1) https://opinionator.blogs.nytimes.com/2010/02/23/stand-up-wh...

And yet you still choose to be a programmer rather than a cargo handler? It's not just the physical toll as to why unskilled labour jobs suck.

I only choose to be a programmer because of the pay. I don't intend to program forever, only until I can afford not to.

Isn't it a general human tendency, to assume that whatever other people do must be trivial while my own job is really challenging and can only be done by sophisticated people like myself.

It is, but people also admire other jobs and assume they are incapable of doing them.

Regardless, the OP wasn't wishing to own a construction company or manage a grocery store. He was wishing to do individual contributor work in a field that uses his body more. It is not arrogant to want that. OP may find after some months that they are ready to go back to tech, and it seems that would be a good outcome since the burnout would have abated.

Factories don't have to be nasty. I have one, with 6 automated machines and 10 people. We have fun, try to make the automated machines build everything. It can be demanding at times, but so are startups.

Programming welding robots, laser cutters , CNC milling machines and making whatever you can dream up is pretty fun. I was in Las Vegas last week walking through the fancy hotels and casinos admiring all the laser cut steel they use in architecture now. It was fun to tell my wife that I could make the giant metal cards at the ARIA poker room, exactly the same on the new machines I just got. She was quite impressed. We are planning our backyard remodel using all the machines at work. Should be quite spectacular when complete.

Man, I loved working construction. Admittedly, I was young and strong, and my body could handle the workload. That stuff will flat out use you up over decades of strain.

But working outside, with my hands, making something tangible I could see at the end of the day? Fuck yeah man. It was deeply satisfying.

Unfortunately, I had the aptitude and training to do more demanding, less fun, arguably more important work, so no more ladders and hammers for me.

The last company I worked for acquired 2-3 companies per year, And it became obvious that in some cases the people who part of the acquisition were burned out and wanted to be free of their responsibilities. But they didn't have the financial wherewithal to just quit and move on.

A lot of them shifted into roles with different but less critical responsibilities. One person basically just turned into an evangelist, meeting customers and painting visions. It wasn't easy for them to keep going, but it's easier to keep going in that type of position because they weren't responsible for keeping the lights on.

I realize this isn't an answer, but maybe this is a way to keep going if you decide to stay with whomever acquires your company.

>The product is just too complicated (tons of domain knowledge required) for someone to come in and take over.

This is a very heavy burden. I was here once as an individual contributor and I ended up in the same state you are in now. It was absolutely awful. Even if somebody can't take over 100%, can they take over 25%?

Also, as others have said, find somebody to talk to. Assuming you have a decent marriage, cry in front of your wife so she knows what's going on. It's hard to move when you feel the whole world is resting on your shoulders.

Are you familiar with the concept of the False dilemma[0]? It seems as if you've limited yourself to an "either/or" situation when in fact there are countless other possible solutions to this problem.

Here are some possible alternatives:

- find a leadership coach and/or mentor

- delegate the parts of your job that you like the least

- find a way to reduce stress in your life (exercise, hobby, etc)

- try professional therapy

- share how you feel with your friends and/or family (maybe even leadership team)

- take a vacation

- work less

- define and respect clear work/life boundaries for yourself

- read about/learn how to manage stress more effectively

- create a project plan for yourself (what do _you_ want to accomplish for _yourself_ in the next 3,6,12 months)

I could go on and on.

Another thing I think that you should ask yourself is: would you really be happier working at WalMart? Is it really this specific job and role that's causing your unhappiness? Is there really nothing you can change to make you job more enjoyable? Is it possible that you're creating your own unhappiness?

From personal experience I highly recommend finding a great leadership coach. I had a leadership coach who really helped me tackle some potentially similar challenges I was having.

If you want to talk more feel free to ping me. Good luck!

[0] https://en.wikipedia.org/wiki/False_dilemma

As you make your decision, you might want to consider applying the WARP decision framework from Decisive by Chip & Dan Heath[0]:

1. Widen your options

2. Reality-test your assumptions

3. Attain distance before deciding

4. Prepare to be wrong

The heath brothers offer a useful workbook[1] that goes into details for each of these steps. It might be worthwhile to go through it as you decide.

[0] http://heathbrothers.com/books/decisive/

[1] http://heathbrothers.com/ot/wp-content/uploads/2013/03/HBDWB...

The problem with reality testing is that reality tends to exclude options permanently while testing.

Unless by reality testing you mean testing tour perception and prediction against perception and prediction of reality that is.

+++++ for - take a vacation Nothing else will give you better clarity.

I don't think it's so much of a false dilemma as it was the OP's inability to find other options. They're posting here to find those options, which you've given a bunch of.

The trick for the OP now is to not just dismiss them all out of hand. I hear so many people throw advice away on the flimsiest of excuses, when just a little massaging can make them work.

This is a great list but feels unsorted. I'd go with:

1. Take a vacation.

2. Converse with someone you love and trust

The rest will likely follow. Again great list!

I feel that one of the most common pieces of advice to stressed people is to take a vacation. I am not sure how well that works. In my experience, stress is created not by the amount of work that I do but by the work that I feel that I don't get done.

Unless I would be able to comfortably disconnect completely on such a vacation, it would do little good or possibly make things worse.

Great advice, thanks, to add to this, don't worry about the state of your existing product, it's what it is, if you are acquired it is more likely for your presence, reputation and talent than for actual lines of code. [edit] spend some time forest bathing if you can!

You're right: 1 person can't replace you. Can 3? Can 5? You must reorganize, if merely to save your sanity. Hire 1 person and start training them, then hire the next.

For 1 week, write down everything that you do for your company, and then group the like tasks in order to figure out how many/what type of person(people) to hire/train. Start looking for that person, while writing down everything that you do the 2nd week. Rinse and repeat as you go through the month/quarter, and you should develop a better idea of what it will take to replace you.

The LOI writers know that you are doing the job of multiple people, and that you are indispensable, and that's why they want to require you to stay. Make yourself replaceable, and then there would be no need for you to stay. Work from a beach if you want, but take action now to permanently lessen your stress.

Feel free to reach out if you want to talk (or just vent) privately. You can find me through info in my HN profile.

They already said "it's been hard to retain developers." One retention method is paying a fuckload of money.

Another method is to provide a path for career progression. It sounds like the solution for "I'm overloaded" is "give more responsibility to bored employees."

...which presumably you now have because you're being acquired.

Another note is that if you're irreplaceable and your (potential) customers or your investors know this, your company is less valuable. If they don't know about the problem, it's still less valuable but you may be able to pretend it's more stable than it is.

Having a non-unity bus factor is not only good for your sanity (you can take breaks, or quit) but also good financially. And even if you continue working, increased documentation and sharing domain knowledge can only make the day-to-day go more smoothly.

+1 Hire Product Managers and groom them a bit to become Product Owners. I'd suggest doing it before the acquisition.

+1 for this. I think the idea of hiring a small team to replace yourself is the way to go OP.

There are professionals out there whose job it is to help out people in situations like yours. Before you make any life changing decisions I would talk to one.

CEO's, Hedgefund Managers, Sport Stars, they all talk to psychologists. Give it a try.

I strongly second this suggestion. Unfortunately there is a stigma to speaking with mental health professionals, but I'm a strong proponent of doing so even when there is nothing necessarily "wrong" in your life.

Speaking as someone who just recently experienced burnout for the first time in his career (along with losing several friends in the past year), and is now taking it easy for a while, you owe it to yourself to speak to someone about what you're feeling.

You've gotten to the point where you're hiding in the bathroom with the water running so your wife doesn't know you're crying. There is no shame in admitting weakness, and you have a lot to be proud of in your position. Let people in who can help.

While you're at it, take a vacation (even if only for a few days) and clear your head. If you don't want to talk to a professional, go somewhere with your wife and talk about what you're feeling.

>If you don't want to talk to a professional, go somewhere with your wife and talk about what you're feeling.

In my experience, a friend and a spouse or a parent cannot replace a psychologist. I think the reason for that is because psychologists listen differently. In whatever you are telling them, you are hiding a call for help in a sense. A friend or a wife might not spot that call for help. Additionally, a psychologist can answer better than a spouse or a friend does, I think.

Maybe that was just my experience, but I felt I had a much better talk with a psychologist than with a friend. Probably, because the barrier is much lower. Like you don't have to worry about them judging you or whatever.

I agree. But if someone is resistant to professional help, then opening up to friends and family is better than nothing if they're supportive.

The simplest analogy usually works here.

You take your car in for regular maintenance even if nothing is wrong. Is your car that much more important than your mental health?

I strongly agree, and add that if you don't get along with your therapist, shop around. Like most professions, practitioners range from awful to amazing.

> Unfortunately there is a stigma to speaking with mental health professionals

That's pretty easy to solve: you don't have to tell anyone except perhaps a spouse (who should understand once the context is fully explained).

In my experience the stigma is not people struggling with judgement from others, but people struggling with judgement from themselves.

Not necessarily true. People might see you going to the office of the mental health professional, or leaving it. If the practice has no other purpose, it can be easy to infer you are getting some kind of mental health help.

If it is a touchy topic for you as an individual and/or if you live in a small town or otherwise have a situation where someone might see you, make the inference and make it into an issue, this can be a not insignificant logistical detail to deal with. Just because for you personally all would be fine by simply not mentioning it doesn't mean this is true for everyone.

Yes. I see psychologists as professional manipulators-for-hire. If you're having a hard time manipulating yourself into doing what you need to do, a psychologist is trained in the arts of influence and, theoretically, knows what to say to assist you in actually doing what you know you want to do. We tell them our goals, they move us into a headspace where those goals are easier to attain.

Do be wary, though. This is a very trusted position. If you sense something is not right, or that the psychologist is moving you sideways or backward instead of forward, don't go back. Find another professional manipulator willing to manipulate you honestly.

Another vote for speaking to a therapist - Also please don't give up if the first person you talk to doesn't gel. It took me three tries to find the right therapist, and it is SO worth it.

Talk to the specialist - it's kind of obvious.

Wish I was more determined and following my own advice.

This is minor depression, related to your work. I would emphasize that your thoughts are not irrational or misplaced, no matter how much money is on the table or how the situation might look to an outsider. The fact that you are currently hiding it is also not abnormal. Your mind is unconsciously focusing energy on analysis of your problems and how you might solve them, and you may be on the edge of signaling for help, implied by the crying.

You’re tightly ensnared in an overly restrictive set of obligations. Perhaps it’s classic burnout from just plain working too much in a demanding role, or perhaps you have new ideas about how to make a living that would require new employment which is restricted by your LOI terms. Perhaps it's something else altogether or a combination of things. In any case, the symptoms are a direct response to these socially-imposed constraints hindering your pursuit of something more appealing, that in your view are beyond conventional means of renegotiation.

It would help immensely to talk with someone - therapist, your wife, etc - and help work through why you are feeling this way and what changes can be made to alleviate the mismatch. There are many good pieces of advice already in the comments here. Just remember that things cannot continue the way they are now without some kind of situational change (not drugs) or your symptoms will only get worse and more debilitating. Good luck.

I have a few thoughts.

First of all it sounds a lot to me like you are suffering from burnout. You need to see someone about this (not necessarily a health professional, perhaps a mentor or confidant, someone accessible, whose opinions you respect)

You have come a long way and achieved something that is not trivial. You are entitled to cash out. I am however wary of the terms you hint at. I would NEVER do a deal where a significant portion of my compensation is dependent on future income from the business I am selling. NEVER. Once the acquirer takes over, decisions are out of your hands and it is his/her prerogative to grow the business or run it down. Why should you tie yourself to such an uncertain future ? My reading of your situation is that you should try to get a deal where you stay on only long enough to transfer your knowledge to your replacement. 1 year is sufficient for that; 4 years essentially makes you a bonded servant. Have you retained the services of a professional to help with the acquisition? If 'No', do so asap.

I mention these points because although your intention is not to stir up a debate about terms of purchase, I think they stand out as potentially significant stressors.

Every field looks green when you are in burn-out-land but resist the temptation to think that dish-washing, bar tending or whatever menial task you presently romanticize, represents a step up from your present condition. I agree with @bsvalley. His answer is on point.

I would talk to the missus. That's what she's there for - moral support; but its difficult to give support to a person who hasn't asked for it.

Finally. I will say congratulations! You are on the last lap of a very difficult race. Not many people get to this point. Don't falter here. The reward for all your effort and sacrifice will be financial freedom, time for leisure and a sense of accomplishment - and maybe opportunity (on much better terms) to become a bartender after all :)

After astronauts came back from space a lot of them became alcoholics or developed other problems. NASA found that the reason for this is because most of them had only one goal in life, one target, to travel in to space. (what tops that!) With out any other goals they became lost, confused, and depressed. I say stay and take the buyout, and while you are bored in your boring day job chair, start thinking of awesome new goals, big and small, great new things to change your life, make a huge list of them that will keep you going till you are well over a hundred years old.

I don't do internet diagnoses, but before you make any career- or life-altering decisions:

You need to meet with a psychiatrist (MD) and be screened for depression.

Being Depressed doesn't feel the way you think it does, and you're throwing up several flags.

Please consider that your emotions right now might not be what you think they are, and that for mild depression (which one often sees in people in stressful life situations), very mild medications can be greatly efficacious.

Please, please take this advice seriously.

- an anonymous health care professional, who's been where you are.

Seems like a complex issue, but at least as far as your mental health goes: reach out to your doc, get connected with a therapist.

I've been in a very similar situation as a first time founder for over half a decade, and getting professional help to deal with anxiety, burnout and depression was super helpful. I was spending days staring at the screen phasing out, couldn't get out of bed, crying, deriving no pleasure from anything, and all that jazz. This lasted over a year before it got bad enough I had to reach out for help. I was going to either quit and/or accidentally take the company down with me.

No pills involved to fix it in my case, just a lot of techniques and practices prescribed by the therapist that help you keep your sanity over the long term. You can get over it within a couple of months if you are diligent about staying on top of the process.

I suspect that almost every high performer who pushes hard in their career will eventually get to this point, it's normal, you need to learn how to deal with the level of anxiety that these positions can induce. Just like most super successful people have coaches, I think most super successful people have therapists keeping them afloat.

I think part of the problem is that being a founder of a profitable tech company is painted as the promise land, filled with riches and being the master of your own destiny.

The reality is that it's a job like any other, but with way more stress, hours, responsibility, and people's livelihood depending on you not fucking up.

A big part of the problem is that it is rather difficult to talk about burnout, depression, etc with others as people think you are living the dream. Not to mention, it's expected you keep up appearances as the person steering the ship.

The only way to survive this and keep going is to find people you open up to, to talk things out and work through the shit. It kind of sounds like you are keeping this from your wife, at least in part, which is a big red flag. If you don't feel comfortable sharing everything with your partner in life, who can you talk to for support?

Don't keep on trying to fix this on your own.

"Sucking it up" isn't actually an option. You're describing a mental health crisis. Unless other people might literally die (e.g., you're a soldier, police officer, etc) then your job is not worth sacrificing your own life.

Consider another perspective: if you get to the breaking point, which you're near, you're going to leave—either because you quit or because you wind up in a hospital. You think you're important—but you are not helping the company if your only options are to quit or die of overwork. Both of those situations end up with 0% of your energy going to the business.

Many people mentioned therapy, which I think is a good idea for everybody. My recommendation is to draw a boundary. Say "here's how much energy I feel comfortable putting in." Then really reflect on how to use that energy in the way that will help the company the most. That might mean hiring or training people. It might mean continuing to do what you do now, but letting more things fall to others—or just letting some things not happen.

You are more valuable to your company if you are healthy and present than if you are unhealthy and quit. When you start to feel "my only option is to quit because I'm too important" you're just indulging in a fantasy of running away.

Once upon a time i was pretty similarly stressed about my situation. I had a good job, and worked with good people, but was just completely burnt out. Based on my personal experience i believe that you will end up destroying yourself, the people you love, and possibly harming your company, with this all consuming depression.

Get out.

For me i spent a month riding my motorcycle across the country. Came back, worked for a little while met a fantastic woman, then quit and spent four months riding our motorcycles from Boston to the bottom of South America. Came back, and started working again. Of course, 6 years later i'm daydreaming about doing it all over again. ;)

When i was young I was the child of an artist. We were pretty effing poor. But, we had food. We had a roof over our heads, and every day my mother worked doing something she loved. We were happy. Money isn't everything.

Now, you've got the compounding aspect of the acquisition and not wanting to screw over your friends/coworkers just because you're depressed as all get-out. You are absolutely wrong that you can't offload your work to someone else (as you noted in the comments). You probably can't hand it over today, but you can start training someone else, and if you're like most people who think that then you're probably overestimating your capabilities and underestimating those of the people around you.

I think you need to get out. Even if you decide to stay, you absolutely need to start offloading your stuff.

Also. talk to your wife more about this, and maybe talk to a psychiatrist. Many of us have aversions to them but they have tools they can offer you to help you work through the more difficult moments until you can get yourself out of this situation in a way that works for you.

I would recommend investing in a CEO or Executive Coach. It is lonely at the top even with mentors and spouses. Hiring my CEO Coach years ago was among the best decisions I have ever made on any level. It paid for itself immediately – certainly from a financial perspective, but also (and more importantly) from an emotional and mental health perspective. This, in turn, allowed me to see things through new eyes and push through barriers I otherwise was stuck behind. I became a better leader, a better husband, and a better person as a result, and I transformed my life and my company in the process. Not sure if it's kosher or not to push someone's services here but I don't really care; this particular coach changed my life for the better, and I know he could change yours too. Dale Larson at Startup Happiness: https://startuphappiness.com/

I have not been a founder of any company so I can't comment on that part. But I can strongly related to this part - "what it would be like to work at Wal Mart, or the construction site outside, or as a bagger at a grocery store"

I am a passionate web developer but a few months ago, I had these exact same thoughts mainly about switching to a low stress job. Later I realised that I needed a break badly and the monotonousness of work ( building some kind of CRUD all day ) for me personally was making my life severely discomforting. So I left the job against everyone's advice and for the next few months I had terrible arguments with my family about this decision. But I was at peace the moment after I left the job and I think it was the right decision, even though my family wants me to regret it.

It's not that you hate what you do, but you definitely need a break and not just like a vacation, but actual handing over of responsibilities to someone else. After a few months, I felt like being back into the business and the optimism for work was back.

So this is probably against what everyone else is advising here but if you don't like it, leave it. Your wife should understand this too, if this is so important to you that it makes you cry. And definitely take up a stress free job for a change. It should help.

As far as leaving the company goes, you might find someone in ranks just below you who could be able enough to take over most aspects of your position.

Let me know, if you think this is a completely wrong advice.

I have these thoughts too, and then realise basically all jobs suck at some level. If they didn't suck, people wouldn't need paying to do them.

May be most do if you look at them from one person's perspective. The point here is to try something else for a change until you figure out whether you want to go back to doing something you liked earlier or moving on.

I mean, it's hard to truly know what somebody else is experiencing and to give advice in a situation like that. But if you're that close to an acquisition and if the acquistion stands to make a material difference in your life going forward (like, does it get you to "fu money"), then I'd lean towards "suck it up and stay long enough to cash out". OTOH, if the acquisition gets you, say, enough money for a new car, but not enough to retire, (just to use made up parameters), then maybe it makes sense to just walk away. But even then, I wonder if you'll feel a lot of regret over spending so much time building something, and then walking away right before a big milestone.

Maybe a nice, long vacation would be a good step before making any drastic decisions. Could you arrange to take 3-4 weeks off and go somewhere quiet and relax for a bit before deciding?

I'd say it's not fu money. We're talking total deal size of < 40mm split 3 ways (much of that isn't up front, but earned out over time).

I do think I'd regret not following through, you're right. The question is whether that regret is worse than multiple years of hating work. I guess I'm probably the only one who can answer that.

I just took a week off and went out of town. Although everyone did manage to leave me alone while I was gone, people tried to do my job because they didn't want to keep customers waiting. That resulted in a lot of problems when I got back (they had no idea how to do my job).

I'm still paying for it now. Maybe I do just have to force another > 1 week break and deal with the consequences later.

Thank you for taking the time to share your thoughts. It is helpful.

That's $13 million each. If that doesn't count as FU money I don't know what does. Even what you'll get upfront might already be in the FU money bracket. Calculating that threshold actually is quite easy (as per Mr. Money Mustache): If you have more than 12 times your annual expenses in assets you never have to work again.

12 times annual expenses in assets is almost certainly too little. The usual number is 25 times (assuming a 4% safe withdrawal rate).

It's more like 25 to 33x annual expenses.

> That resulted in a lot of problems when I got back (they had no idea how to do my job).

There's your problem right there. You need to start training someone to do your job so that you can go away without having things fall apart. You need to do this regardless of whether or not you want to walk away because you could get hit by a bus tomorrow. Your main goal as a founder should always be to insure that the company can get along without any one particular person, including you. If you don't know how to make that happen, hire someone who does.

P.S. I've been a principal in half a dozen startups, so I've seen it all. If you want to talk you will find a link to my contact info in my profile.

Money stops to matter when the stress gets too high and you still have to close and all that takes plus stay years on the earn out. I think the thing you have to realize is that you are the company. The past is past, so can you train (and hire) people to do the things that you are currently essential for? If you can't, do you know for a fact that the acquirer will let you hire and train those people? If not, you need to find a way to cash out less in exchange for a maximum of 6 months of training people how to do what you do now. It could be that 6 months isn't enough time. If the company has no value without, then the company has no value, only you do. (exaggerating a little for effect)

$10 million is definitely FU money.

Ya, $10m is comfortably above fu money even in silicon valley or NYC.


The size of the house you own and get to say fu from will vary, but the sentiment is the same as long as you own it.

That's FU money. Even 25% of that would be FU money.

Invested with reasonable money managers, you'll never again have to trade your life for a paycheck.

Finally, train your replacement(s).

I went through a smaller acquisition which had milestone based earn-outs. Are your earn-outs time-based or milestone-based?

Mine were milestone based and I negotiated for 25% to be time-based. The company underwent a big re-org and the new leadership had their own projects which were prioritized so the milestones were never realized.

Just some food for thought while you're nearing LOI stage.

If you're being acquired, then somebody wants to see your work live on. But you seem to be a fairly large bus factor. If someone is spending 40mm to acquire you and your team and your product, is it possible that one of the priorities becomes hiring someone or a small team that can bring some more domain knowledge in? You're obviously critical to this operation, but no one wants a team where one person being out for a week means customers are sitting around waiting for you to get back.

If you can find a way to live on a salary of $300k per year, then ~$10M is definitely FU money. You can invest that money and safely withdraw 3% for the rest of your life.

Maybe try a staycation next time. Hang out in the office, let people do your job, watch over their shoulders and instruct them, but leave your own PC turned off for the duration. (And definitely don't do 8+ hour days).

In fact, maybe make that into a company policy where you do that one week per quarter such that the company doesn't fold if you get hit by a bus. Employees may actually like the idea.

Regarding hiring somebody for the day-to-day, maybe you'll find this story from another founder useful:


I suggest that you have two kinds of problem: a daily happiness deficit and a long-term happiness debt. Your day-to-day life has been grinding you down for a while.

You'll have to make two kinds of changes. One is to pay down the giant debt. E.g., once you get acquired, take a serious vacation. But the other, the more important one, is to make sure that most days are at least modestly positive for you.

I'd also suggest you find a therapist. You may have to try a few before you find one that's a good match. They can help you figure out whether it's depression or just a reasonable reaction to a bad situation. Either way, they can also help you figure out ways of coping

Think of it like hiring a lawyer: Sure, you could figure all the contracts out yourself, but the lawyer has more training and much more experience. It's the same deal with therapy. A good therapist will be able to see patterns you are missing because they have seen it many times before.

Feel free to email me (contact info in my profile). I'm glad to correspond or talk on the phone if you'd like to discuss this further.

Have you ever meditated before? Sometimes in these situations our minds just swirl non-stop and we spend all of our time aganozing over everything that might happened, or has happened.

Meditation can help quiet your mind, and for a lot of people it can lead to being able to appreciate what's happening right now, in this moment.

Nike founder Phil Knight said, "if all you see are problems, you're not thinking straight."

You're probably not getting enough sleep. Perhaps consider taking a day or two to really just rest. No matter how important everything seems, you can almost always take a day or two. In fact, it sounds like you pretty much can't afford not to take a day or two and rest. Really sleep.

I'm a believer in the idea that when we're rested, when our thoughts our quiet, we're able to see the right way forward. When things feel hopeless we're often just burnt, and need to rest.

Phil Jackson, the champion NBA coach wrote a lot about his mediation practice. He had plenty of times in his life were he felt the way you're describing. He said knowing how to breath and quiet his mind saved him from many sleepless nights.

Good luck and remember everything feels better after a solid 8 hours of sleep.

Excellent advice. Get sleep. Exercise. Eat well. See a psychiatrist; its very possible a single visit and prescription could make a radical difference in your life. Meditation/mindfulness, read the book "10 percent happier" which is available on Audible.

How big is the company?

You're right to identify this as a hard problem. I've been in your exact shoes before. 100+ person company, the weight is heavy.

The good news is that it's totally possible to get out without wrecking the company's outlook. But it does take a minor amount of time investment. Perhaps it's possible to view it as a new challenge: how to quickly hire or find someone within your org who is capable of taking over your day-to-day responsibilities? Who do people ask for decisions / advice when you're out sick?

Frame it as a promotion for them. Give them a (small) comp bump and a new set of responsibilities that include most (or all) of your existing responsibilities.

Coach them for a quarter, give them enough rope to hang themselves with, give them radically candid feedback, and then you can step away. (Or even go do something else interesting at the company!)

I can go into a lot more detail if you'd like -- please email me. The username in my profile (not my HN handle) at gmail.

Good luck, positive vibes!

P.S. Watch this: https://www.youtube.com/watch?v=OqmdLcyES_Q as a jumpstart to getting your org ready for life without you

> Give them a (small) comp bump

If you did this to me I'd give you the finger and find another job.

You want me to take over running the company - you'd better be ready to give me a large increase in compensation.

Stating my assumption here: If you're already demonstrating the ability to do my day-to-day, I'd suggest you should already have a nearly congruent compensation (otherwise I'm doing something wrong).

Otherwise, yes, obviously compensation is a crucial component of this plan.

Dude, talk to your wife about it. I feel like I wouldn't get through 50% of the stress in life without having someone who cares about me more than I do to bounce ideas and thoughts off of.

just opening up to your wife and taking some time off could help reset your mindset

You could be suffering from major depression, aka clinical depression (maybe not... but some of what you said rings that warning bell for me). The crying in the shower is probably the biggest bell ringer for me.

I've known a couple of tech types (one dev, one a pm) that both found out that they were clinically depressed. They've both bounced back from it and are their old selves again.

Major depression is a serious medical issue and can happen to anyone... there's nothing to be ashamed of (and anyone who thinks otherwise is ignorant). Treatment is usually talk therapy and antidepressants (and usually some time away from work... expecting a sick person to be at work while they're undergoing treatment is plain wrong).

Googling "major depression" will show you lots of resources... but talking to your doctor about this is your first step (this can be tough... but you can do it). Don't put that off. Especially don't put that off due to worry about step 2 though N.

So... your 2 options are really 3: See a doctor!

Best of luck (and feel free to reach out and I'll offer what advice/help I can).

If you don't already have professional help (therapy), seek some.

I've experience the hour long crying showers first hand, and I don't wish it to anyone. Don't minimize how you feel, and don't blame/shame yourself. Therapy can be scary and still cary a stigma, but it's basically allowed me to be myself.

I am no founder myself, so I don't pretend to know what you're going through, but I know the symptoms. Let me know if you want to discuss this further

I can relate to the pain. The mind seems to never stop and it seems to be in a perpetual state of anxiety.

I dealt with burnout several times. The only thing that helped me deal with it was turn off electronic devices after certain time of the day and before certain time of the day. No tv, no phone, no laptop, not even your favorite meditation app. Do anything which does not involve electronics or information heavy.

Much other advice about how to deal with such issues over long term are easier said than done. Some of my favorite ideas are

Build sustainability into your engineering, product and sales process. It's like running a marathon. If you run too fast in the beginning, you get tired so easily.

Be less outcome dependent and more discipline driven. If you plan to make incremental progress, you will eventually have something stable and it gets easy to continue. If you need a constant rush of positive outcomes to get you to do something, it does not build resilience to last longer.

Go work on a contruction site for a few days. You'll be running back to your old 'miserable life', believe you me.

What is it with this romantic view of supposedly stress free jobs of filling shelves with food or digging a hole for a garden tree ( the easiest thing in construction ).

I feel your pain since I get similar feelings as you sometimes but then I remember 20 something me doing roofing and breaking ice on a path with a big ass hammer for tourists to enjoy a walk around the lake. It sucks.

I can only offer you one solution that I would personally do if I were at your place right now... Sell asap and move on.

I'll offer a counterpoint, as long as your management is effective there's plenty to love about those sorts of jobs. They are actually not bad at all other than the pay. No stress, no thinking, lots of moving around, no worry about the "bigger picture" as a founder must do. I've cleaned hotel rooms, stocked shelves at a discount store, worked the register at a grocery store, and unloaded trucks in a wearhouse. The only shitty "unskilled" job I had was due to mismanagement.

Call me lazy but I would never want the responsibility of being a founder. Seems like much too much to worry about.

> No stress

I've had my share of these jobs as well, and they pay terribly. Living hand-to-mouth is a stress in itself. And I had zero dependents. Being a founder is exceptionally stressful, but don't overcompensate and pretend that life as a minimum wager is carefree.

The proof in the pudding is this: people don't move into these jobs if they have something else going on. Hospitality is a classic example - full of young people, but unless they become managers or chefs, they're out the door as soon as they can do something else. There are very few middle-aged people working on their feet in hospitality.

Don't generalize - it really depends on the country.

What you are saying is nonsensical and objectively false. I challenge you to actually talk to these people and ask them their feelings on their job. Like any job some are happy, some hate their job, some are working until they can do something else, some are in school, some are ok where they are, some are semi-retired, some are living hand to mouth (unfortunately), some work because they want to, not because they have to, some are ambivalent​, some are lost, some are bored spouses, some are trying to find themselves, some are employed just until they start a family. Just like any other job.

Believe it or not some people don't actually believe the work is beneath them.

What you are saying is like "living without a wage is stressful, being a homemaker doesn't pay a wage, thus nobody is a homemaker if they have the ability to get a job." Of course that is totally untrue. People aren't exactly like you. Being a homemaker would be a nightmare for me - I hire a housekeeper and I absolutely hate kids. However, I can appreciate many people find enjoyment in that, just not me.

I was talking about work stress - I assume a founder of a successful startup probably has enough money in reserve to be able to take a pay cut, even if temporarily.

I know a few people in hospitality who genuinely enjoy it and have the ability to do other jobs - they just would rather not. I have a friend with an engineering degree, ended up hating engineering and tried several "good" jobs. Hated them all, always ended up back in food service. She finally made peace with the fact she really really likes doing food service and that's what she decided to do permanently. Another friend got a business degree, hated being in the business field, though it was too cut throat, didn't like what the felt she had to do to get ahead. Decided to dedicate her life to non-profits for a fraction of the salary she could get anywhere else but feels it's worth it. I know a guy in his 50s who washes dishes 5 days a week. He gave up his cushy office job to do that. He said office work was getting him down and he has enough money to take the pay cut. My aunt cleans offices for a living, enjoys doing so, doesn't want to do anything else. Shes an immagrant and her husband owns a very successful business. She has absolutely no monetary need to work yet she still cleans offices at night. My mom's best friend works at Kohl's, no need to, just wants to, gave up a (State) government position to do so.

I truly enjoyed most "low skilled" work I did. I also enjoy being a programmer, for the most part. There's a lot I miss about the old days though. The pay isn't one of them, of course. I really miss moving around heavy objects, oddly enough, as unusual as that may sound. Just doing so for the hell of it (gym excersing) is incredibly unappealing to me - I enjoy seeing the fruits of my labor. I don't want to sit there lifting meaningless weight, I want to be moving objects from one location to the other and have some sort of satisfaction afterwards that I met a business objective and earned my salary.

Right now I'm programmer until I can afford not to be. Programming for me is only a means to an end, to be financially independent/semi retired. I sound like someone unhappy but I actually enjoy programming, just not as much as physical labor.

Yeah construction is great. Me: "boss can I take a break?" Boss: "You got a break when you got this job, nubmnutz."

I've been there. I was unhappy, I left, I felt better. Later I started other businesses.

In my case the threshold is ~200 people; after that I don't really recognize everyone. In once case I was having fun but my wife was miserable.

In all these cases I was glad I left.

Now: if an acquisition truly is imminent, and you can hang on a bit longer, go for it. The buyer will be able to find someone to run the business, perhaps internal, perhaps not. It likely won't happen overnight (unless they have someone in mind already) but some pressure will come off you immediately.

If the acquisition isn't truly imminent you can indeed start looking for someone to run the business. Believe me there are people with domain experience and executional experience you can find. Use an executive headhunter. Have your board members help.

Sounds like burnout. Take it seriously, but it doesn't mean all is lost! Those LOIs are light at the end of the tunnel.

Oh, and consider therapy. You may or may not need drugs, but they probably aren't the first line of therapy. The talk therapy is good, and as a CEO you probably have nobody else to talk to about certain things -- especially if you think you can't talk to your spouse about stuff. Talk therapy is not a sign of weakness -- in fact you sound like the kind of person who has their act together (probably you don't feel like it, but your note says you understand something's not right), and so you probably will benefit a lot from it. Many people in the valley, especially top execs, are in therapy and it helps them a lot.

+1 for talking therapy, all drugs have a risk profile, however low, I've never encountered anyone who has come to harm through talking therapy (prove me wrong, but it's rare right!), and trying that first still leaves the drug option if things seem to reach a crisis point.

Being a founder is tough and the grind several years in can feel like a heavy burden. However, it sounds like with the LOI, you might be looking at an opportunity that comes with a welcome change of pace.

Directly answering your original question, I would take a serious look at option #2 ("Suck it up and work on the same thing for 2-5 more years").

In my personal experience, I sold my previous company to a much larger company some years back and it was a great change. Even though it was "working on the same thing" for 3 more years, there were new people to meet and new challenges to tackle. After all, humans are a social species and just having a different set of people to interact with can be a much needed change.

You might be thinking you'll be working on the same problems, but really it will be nothing alike. Your work might get better or it might get worse, but I guarantee that you and your company post-acquisition will be experiencing something very different. And I'm not just talking about the money part. That might be very helpful to get you out of this unhappy burnout.

If you need someone to chat with over email about what might be upcoming if you decide to take the deal, feel free to hit me up. Contact info in profile.

I'm a little late on this one but I'd echo what many others here have said, find a way to push through to the sale and then talk with the board to first, distribute your workload and/or define an exit strategy.

You're essentially sitting on a lottery ticket and when it hits, you'll have a heck of a lot more free time.

Just looking at this from another perspective, I tried running a contract programming business for a few years that sucked up my life and eventually put me in the hospital at age 30. That business never consistently made money. Contract programming is very much a peaks-and-valleys experience and once you experience that for long enough you end up working like that. You kill yourself on the peaks in hopes to not experience the valleys. When it was over I was so happy to have a 40 hour a week job...it's a vacation by comparison.

Consistency is the key. If you've got something that is generating a steady income, enough that it's profitable enough to be acquired...then it's on you to scale yourself down.

It's also within your ability to do so. I see that you've cited domain specific knowledge. All knowledge can be learned and taught. You might not be able to hire somebody off the street like that, but you can most likely hire a few people and delegate. If the work isn't interesting, then you need to find a way to enhance the experience for people working there. Make the hours creative or the opportunity unique. See if you can find ways to let people experiment or add their own flavor to it. If it's wood-chopping dull, then maybe those creative efforts are better focused on automating the day to day?

Wrote about my experience here if it helps:


As a founder I can definitely relate.

Everyday driving to/from the office my chest is so tight it feels hard to breath. I constantly think about my old friends that have real weekends, have time for hobbies, and get to leave their work at work.

The main reason I keep going is that I actually enjoy the work. When I take a break I get excited about going back and continuing to build the company.

Having worked landscaping/construction before starting a company, I can say I often think fondly of the simplicity of those jobs. Though when I was there I all I could think about was starting my own company.

You really need to find a way to be happy regardless of what you're doing. That may be by just cutting back on how much you are working, delegating more, and finding meaning outside of work.

Hehe, someone in landscaping saying the grass is greener on the other side.

Well, you're about to be acquired. Tough it out, insist on being paid in cash and live long and happily ever after. Simple!

The idea that you are essential to allow the company to be acquired is most likely nonsense, I've yet to meet someone that could not be replaced with some goodwill and hard work to transfer responsibilities. Better that than to have someone that does not really want to work!

Why don't you want your wife to know?

Your personal support network is exactly what you need to be able to lean on to get through stressful times.

In my experience, if I am wondering if I am depressed it is because I am, it just happened slowly over time, like a frog boiling in water. I didn't realize it happened until the water was bubling all around me and I was doing things like crying in the bathroom, alone and scared. Please get professional support. Things are much better than they seem. You are on the brink of many founders dreams, but you are stuck in a nightmare. It will go away and you will find joy again. You've already taken your first step in finding it. Good luck. This too shall pass.

You are overvaluating the wallmart job and thinking it "seems" stress free. The truth is that if you want to do anything at a very competitive level, even packaging goods at the counter, it WILL be stressful.

You could also stop stressing: don't answer the calls, let your business slide and go bankrupt.

Running a business is no easy feat. As you've got that far, you probably know that. You are likely tired because of it, which is normal, everybody gets tired and there's nothing wrong with you or your business.

I think what you need is to perhaps promote someone or get a friend to help you. I don't see how a domain can be so insanely complex and out of reality for everyone. You probably just need someone and that someone to spend enough time with you.

My point with stress is that I don't necessarily own a business anymore and never had as much success as you doing that, I'm not about to cash in some big money which would allow me to follow other passions I have. After some failed startups, I work for a big business and the only thing that changed was the job "security". Instead of having to look for a new job every year or so, now I don't anymore, but it's stressful: I want to do my best.

The same happens when I try to play the guitar, I get also tired, stressed out. Then I give it a pause. As with a business or work, you can't pause, but you can always ask for help.

This is what happens when you do a startup that you're not truly passionate about. Thank you for this, for making me realize the very real risk of being trapped a few years in.

If you can find a psych/counselor that works for you, that's almost certainly a good idea - but when I hit a point of stress/burnout where I probably should have done that, I was also at the point where I was completely unable to actually make the call to set it up.

After six months of waffling back and forth stressing myself out even worse over the fact that I wasn't doing the obvious thing about it, I concluded that if I was going to manage to do it I'd've done it by now, looked for other options, and suddenly realised that Tianeptine is (a) entirely unscheduled and hence not actively illegal to posess in both the UK and US (b) easily mail orderable from Hong Kong.

Also Tianeptine is acute so if it works for you, you'll be able to tell by a few days in (three in my case). I've been deeply fond of it and far more productive since.

Note to anybody about to reply telling me that's a terrible idea for any of the obvious reasons it could be a terrible idea: Yes, I know, but I was incapable of doing any of the things I should have done to fix it and I had a company and team I was letting down and this worked for me. I am now slowly getting back to a point where I don't feel like I'm letting everybody down, and that's more important to me than pretty much anything else.

Book into a high end beach resort for a week and work from one of those terrace lounges overlooking the water with wifi. Strictly limit the scope of things you will work on. This worked really well to soothe that decision fatigue/burnout feeling for me at least.

A crisis of meaning. Need to understand better the sources of unhappiness. Is just being tired or bored? is being close to burnout? is because you are alone too much on job tasks? All those areas are "workable". I wouldn't hesitate to have a session with a psyche professional to help to dig on those things in an manageable way. Maybe the best outcome is to be acquired, maybe you are close to reach something important and this is your inner resistance.

Ping me. I know some folks who would probably consider buying the product without forcing you to keep working on it. It's more common than you might think.

There's a lot of great advice here on what to do. The one thing I want to add is see a doctor for your depression. It sounds like everything in your business is going well and you should be proud of yourself, yet personally you feel at the lowest point. Burn out is real and happens to most entrepreneurs who go the distance. When you get depressed, your mind focuses on negative memories and situations and you get trapped in a train of negative thought. Even though, almost every negative memory can be thought of in a positive way. There was one time where I felt like you do, and after working on my depression I was able to recognize the negative thoughts in my mind and start to look at them in a different way. Once this happened I felt like a completely new person and was able to look at the same data in a different way that made me feel empowered and hopeful. Depression will destroy you if you don't get it treated. Happiness is a conscious decision and you can recover from your burn out if you shift your perspective.

Hi founder,

I think you are idealizing other jobs because you are suffering in your current position. I am from a development country where many would give it all in exchange of being in your shoes. I don't mean that your problem is not real or important. What I want to say is that you may be missing a lot of positive value because your perspective is narrowed by how you feel. Talk with your wife, you will feel way better, I am sure she will understand and support you. Find professional help, like a therapist. Compensate your day at work with activities that you enjoy, this can do wonders!. Hire someone, maybe not for replacing you because that is too hard, but for helping you with your tasks and having more time for doing things you enjoy. I am sure you will be able to build the strength you need for going through the acquisition an collecting the goodies of the hard work you have done over the years.

I wish you all the best

I'd encourage you to be transparent with your wife.

Tell her your situation. Ask what she thinks. Discuss options. Execute upon your mutual decision. Do it when you two have time to dig into the details.

Don't rush it but if you're unhappy that's no way to live. I'm leaving my company this summer, my business partner has known for some time. My wife knew first.

Look, I really don't know your situation but you might want to ask yourself why you felt it necessary to hide it from your wife. Can you not be honest with her? Are you trying to protect her? And if so, does it really protect her from anything or just give her a warped perception of the circumstances? Her opinion of this makes way more of a difference than anyone on HN.

Love your wife and be open and honest with her. She's far more important than any business.

My sincere 2 cents: 1) talk to your wife 2) get the best deal out of your pending acquisition - highest cash component upfront 3) find and train someone to take your place 4) at that point check if you are still so unhappy - leave or stay 5) do what makes you happy

Holly shit a lot of weird things being said about the role of the wife. I agree with most of downvotes and wholeheartly agree with sharing with your wife.

Just commenting in a new thread to give a suggestion: have you considered promoting someone to your executive position? A founder stepping down to a "more suited" executive might not hurt the acquisition.

And I would give another thought about hiring someone for the role.

I think "sucking up" is the worst option and leaving without a plan the second worst.

Anyway, I wish you good luck. I am not a founder, but fortunately you can find advice from the right people.

Never been a CEO or a founder, but I always thought this was a good read:

"Given this stress, CEOs often make the one of the following two mistakes:

1. They take things too personally

2. They do not take things personally enough

In the first scenario, the CEO takes every issue incredibly seriously and personally and urgently moves to fix it. Given the volume of the issues, this motion usually results in one of two scenarios. If the CEO is outwardly focused, she ends up terrorizing the team to the point where nobody wants to work at the company any more. If the CEO is inwardly focused, she ends up feeling so sick from all of the problems that she can barely make it to work in the morning.

In the second scenario, in order to dampen the pain of the rolling disaster that is the company, the CEO takes a Pollyannaish attitude: it’s not so bad. In this view, none of the problems are actually that bad and they needn’t be dealt with urgently. By rationalizing away the issues, the CEO feels better about herself. The problem is that she doesn’t actually fix any of the problems and the employees eventually become quite frustrated that the Chief Executive keeps ignoring the most basic problems and conflicts. Ultimately, the company turns to crap."


> I drift off into exploring what it would be like to work at Wal Mart, or the construction site outside, or as a bagger at a grocery store. It seems so stress free.

I feel this too, when it comes to programming, there are small number of positions that would makes me happy, but if i would have to deal with CRUD apps, i would prefer a job like you have mentioned.

Now i want a job that i don't care about, that leave my mind in peace, so i would dive in theoretical computer science with a free mind.

Throwaway, this sounds like a classic case of burnout, and I don't know how to say this in a way that isn't going to sound rough, so here it is: You're doing your company a disservice by staying in your current state.

If you're unhappy with your work, you won't be passionate about leading a company. Especially through an acquisition, your colleagues are looking at you, a founder, as a leader, and drawing on you for strength. If you can find it within yourself to be that leader, then that's great! In that case, you probably shouldn't also be the lead developer, and given your extensive domain specific knowledge, it sounds like you might be doing too much all at once. I can't know; I'm not in your shoes, so this is all an outsider looking in.

It sounds like for the moment, what you really need is to pull back and relax, take some time for yourself, and recover. Your body only has so much willpower to go around, and if you get in the habit of exhausting that regularly, you'll burn out every time. Figure out if reducing your role at the company will let you continue, and do that if you want. Or, if you need to craft an exit plan, do that as well, and find someone just as passionate as you to fill your shoes. But take care of yourself first!

What you describe is usually result of being reactive, not proactive in life. When you don't proactively control your life and rather react to other people's agendas, need to always face problems when they already happened, and extinguish fires, you end up exhausted physically, mentally, and emotionally. Instead plan well ahead and make the world around you stick to your schedule and life rhythm. Being more proactive let you enjoy life much more while predicting fires and troubles well before they happen and, hence, being able to solve them on your own terms.

Definitely it's only one of the reasons and maybe not even the biggest one. This is symptom of bigger disbalance in life that requires more free "me time" time for you, more calming and wondering to decide what's important for you in life, what you want from life.

As an actionable solution I'd recommend 1/ to start meditating. It helps a lot to calm down and enjoy life. Also, 2/ start lead you life by saying more NOs to what's not on your own agenda.

I like a lot Derek Sivers on saying NO: If you’re not saying “HELL YEAH!” about something, say “no”. https://sivers.org/hellyeah

Had something similar, but alone ...

Weekdays: appear strong, I'm responsible for 30 people, nobody can see that I'm vulnerable.

Weekends: massive bingie, parties, alcohol, coke, hookers...

Last year in april after a 4 day weekend I almost died, had to call the ambulance on myself. My legs and arms started to feel numb, couldn't move them, was scary. Called the ambulance, they said that go to the street wait for them, and under no circumstances close my eyes. It was really hard to keep them open, but when I heard the sirens just snaped. Had this thought closing my eyes that I may never open them again. Turns out that I didn't drink enough water, and my blood got so dense that my heart couldn't circulate it. Wake up in the ambulance car still in my street feeling pretty well, bribed them so they say they haven't found me, because I had a big contract signing in 5 hours.

Then I reached out for help, on therapy since. Before that I was thinking about it for long, but how should I choose, etc. Doesn't matter, just went with the first one I found sympathetic online.

The second one is sport, get your self time to move 2-3 times a week, does wonders.

I wish I could say I haven't touched any substances since, but currently I feel much better.

So get therapy and start to move, that worked for me.

If it's any consolation I feel the same way. Company is doing 1.6MM/mo in revenue but I haven't been excited about it in over a year. I've put good people in place but I'm tired of getting up everyday and facing the exact same problems we faced 4 years ago. I'm at least 2 years out from acquisition so I'm spending my time trying to develop some satisfying hobbies. I restarted therapy a month ago and that's helping.

> "The product is just too complicated (tons of domain knowledge required) for someone to come in and take over."

This statement is almost certainly not true. Anything can be learned by someone sufficiently motivated. You, yourself, were not born with the knowledge needed to run your company, were you?

> "Additionally, the product just isn't that interesting (glorified CRUD app) and it's been hard to retain developers."

People's motivations are different. Some people want to work on some super-interesting cutting edge product. Fine, you can't offer that, so forget them. Some people will do any job so long as they're rewarded with enough money. If you're about to get acquired, you may find you suddenly have the ability to hire these people. There are also tons of underemployed tech folks out there suffering away as "engineer number 7 from the left" who would love that rare chance to lead a project, move into product management, and/or finally have some ownership stake in what they're working on. They're probably super easy to find too. Just wait in the parking lot of any major tech employer at around 6:30-7:00PM and look for the people walking out the door with sad, exhausted faces :)

I was in a similar situation a few years ago - not as badly burned out and wanting to quit, but having a strong desire to do something else after 17 years(!) on the same project, with me as sole founder and still major developer/"architect". We were also in acquisition talks back then and minor health issues (that turned out to be rather major ones later) didn't help.

What happened next:

* the acquisition - I discussed the possibility of leaving and insisted that the new owners obtain much more than just a slim majority, so I didn't have to worry as much about the future of the company if I left (it would have been annoying to have a major stake and no control, particularly as an opinionated ex-founder). It wasn't easy and my plans certainly didn't affect the price positively, but we found a good solution.

* I left rather quickly (a few months after closing the deal) and nominated a most suitable candidate for CEO who had been in the company for ~12 years. He's not a developer, but he's doing great and the company is thriving. They hardly ever need to ask me things about old code now. In hindsight, everyone is happy that a larger stake changed hands.

So, that's my recommendation based on personal experience. Stick around till the acquisition and make sure you can leave without causing major problems. Good luck! Remember that as a founder, you might misjudge/overrate how much the company actually depends on you.

PS. as for "other plans", life makes its own - I have been mostly dealing with my health issues lately, so it's safe to say I was better off beforehand. C'est la vie...

I don't really see a problem here; your mind is drifting wandering. Pretty clear that you are restless but it's likely mostly in you.

1. Meditation and taking time out of the day to enjoy your life

2. Take time out of your day to enjoy what you have

3. Remember to take time out of your day to enjoy life for what it is. Not what it can be.

4. Take time out of your day to appreciate your peers and your loved ones. Take them out to dinner or just show how much you appreciate them.

5. Lastly if you really want to quit; you need to setup an exit plan. It's clear you have a few excuses; hell don't we all. Can't find someone to replace you? well if the domain knowledge is high; it's likely needing to be documented and distilled down. Maybe it's too much for 1 person maybe 2 or 3 people could replace you.

Lastly stop assuming life has to be a certain way; it's hard enough with all these assumptions and expectations lumped on us. By beating yourself up you are just doing yourself a disservice.

Don't forget to tell yourself how amazing you are; I mean you are a founder at a company that is not in debt. You could be acquired; you don't have to be a founder forever it sounds like.

Time to take time and celebrate.

I have a friend who buys boring SaaS and doesn't require any existing employees to stay on. Send me an email via my HN profile if you want me to put you in touch.

First congrats on taking the first step and sharing your pain.

As others have said, this is not uncommon and you're not alone. It has everything to do with your mental health and well being. I've been through something very similar and it basically revolves around burnout, stress, depression, anxiety and some times panic attacks (e.g. crying uncontrollably). While you don't treat those and their root causes, you won't be solving the problem.

Treating means reaching out to experts (psychologist/psychiatrist) and sharing your burden and feelings with others. It's fundamental that you share it with your wife and once you feel more comfortable, with friends. You will notice how that will make you feel lighter and better.

Remember, people care about you and you're not alone. If your current situation is destroying your health, it's not worth it whatever $$$ is involved. Thus, take care of your health first and foremost. In parallel, learn (via therapy, meditation, physical activities, hobbies, etc.) how to deal with tough situations like this - life is full of them. That will not only prepare you for future difficulties but also bring joy and excitement back to your day-to-day work.

Take a trip to the doctor, get some antidepressants or anti-anxiety medication prescribed. They'll level you out so you can focus rationally on getting stuff done without the anxiety. I never had much luck with therapy, but meds worked phenomenally. (And I was very very reluctant to start, fearing long-term effects, but after a few months I was able to come off of them with no problems).

This project sounds like not a big life goal for you, so once you're stable, plan a nice end game. Plan for it to happen sooner rather than later. Think about other life goals you have, and how you can pursue them afterwards. Try to make time for these things. Anti-anxiety meds will help you do this. You regain a lot of time that unconsciously allocated to fretting.

Let good enough be good enough. Try to get the company into a reasonable position but don't feel like it has to be perfect. Downsize a bit if need be. Learn to say No. People's lives are not dependent on your ability to do stuff for them. Focus on those things that create the most value with the least time/stress.

Once you get to this point, you may even decide you like the company enough to stick with it.

It is always the things we do not have that we crave the most, don't let yourself be fouled by the romantic "when finally this and that will have happened, when finally I work at McDonald's" ideas.

As a psychologist it sounds to me like you're in a serious crisis, a mixture of burn out, depression and lack of meaning. There is no "trick" to magically just "snap out of it". You might find counseling, coaching or therapy useful (especially logotherapy which focuses on finding meaning in life). Please do not just see a GP to get some drugs, antidepressants treat a symptom (namely brain chemistry) but it doesn't solve the underlying Probleme. Just "sucking it up" will not work, please do not mistake mental problems as "oh it's ONLY mental, it's not like I'm REALLY ill" - psychological problems are DEADLY!! Depression on deadly!

From my point of view it would be best not to give up all that you worked for for so long but to find someone you can train in your job and who can help you out. It might look like only you can do this job because it's so complex but it will not all collapse when you find someone to help you out for now, who you can train to learn how you manage stuff. They will learn and they will be able to manage it even though that might seem unrealistic to you at the moment. You NEED to take care of yourself before doing anything else at the moment. Don't go "but I have to be strong now and push through this" ... You will only become more miserable...Many people find it helpful to talk to a counselor to get a clearer picture about what they need now and how they can overcome their current struggle. Feel free to message me on Catharina.eichert@gmx.net if you have any questions, I'm happy to help out if anything I said resonated with you. Kind regards, Catharina

I'm so jealous, I feel offended reading this post. I would shovel pig shit for 2 years straight if it meant that I would be able to retire at the end.

Take the money and run (figuratively).

Do the acquisition. Presumably there will be some mandatory retention period. Once their check clears, mentally check out and see what happens. Take a vacay, start coming in around 11am, don't answer emails off hours...

One of two things will happen, either the rest of the company will pick up the slack or the whole place will fall apart. Either way your money will be in the bank so who cares right?

If at all possible, I'd hire someone and gradually teach them the real pain points for you. Don't forget, something you hate may be something that someone else finds to be the coolest challenge! By giving them some things they might like as well as a few of the worst things in your work life, they could thrive and it cuts you some slack. Yes, it may be difficult domain material but people can learn and you may be surprised at how fast and how much of it someone who has a real interest in it can absorb.

One of the reasons you feel completely trapped is that, effectively you are. You need to get one or two people who can start giving you a break. Then you will get perspective and can make reasonable career decisions. When you're trapped, it gets worse and worse and you may just toss all that work to now and walk.

Hire someone, or delegate bits to others (or do both) to get some space from the things that are driving this ideation. You will be much happier and it will buy time to determine what you need to do for you to thrive.

My heart goes out to you!

I agree with others that you should take some time off, talk to a professional, and try to fix things if possible. That being said . . .

I was in a similar position: last remaining founder having to pick between an acquihire where I'd be locked in to a job I didn't want, or pivot. I had cash in the bank, so I felt obligated to not stop. I talked to my investors, and they said "it's ok to shut down."

The thing to keep in mind is that early-stage investors don't care about 1x or 2x returns - they hope that one or two out of dozens of investments make enough money to return the portfolio.

For me: I chose to shut down [1] and travel for a bit. We open-sourced the code, which made clients happy. I kept my phone in "do not disturb" mode for a solid month after shutting down - it took awhile to decompress. (The shutdown process is still ongoing after 4 months, unfortunately). Feel free to email me if you want to chat.

[1] https://blog.staffjoy.com/staffjoy-is-shutting-down-39f7b5d6...

I feel your pain. I honestly think you should talk to your wife or your close friends about this. You'll be surprised how people help out when they know you are in distress.

Also, taking on a different activity that involves leadership might greatly help in boosting your morale. What you have done with your company is quite commendable that you should be proud of. If I were you, I would focus all my energies on the company's future post acquisition. To think of ways of growing the company beyond what it is today and see the acquisition as a possible out in that direction, not the end goal in itself might be helpful. You might also want to try to accomplish something in a field that you have no clue about but is not super hard on your brain. For instance, you could learn ballroom or Tango. You could also join a basic mountaineering course. You'll be out in the nature and accomplishing an endurance task. All your energies will be focused away from your day to day mind numbing activities and towards accomplishing a very different goal.

Good luck !

I see many founders manage themselves out of their position. You hire a VP or Director to replace yourself in the day to day and then you transition out to the point where you can just go do whatever you want inside the company. Want to go back to being an individual contributor? Go for it! Want to just do skunkworks projects? Go for it!

There are many routes to happiness while maintaining your company.

Why do you think you only have 2 options?

Suck it up, get the sale done (especially when you're so close to improving the lives of your other founders) then take a vacation and recharge.

If you need to quit at that point then do so, but at least you're not taking the rest of the team with you. Would you feel ok if they did the same to you? You signed up for a team sport, hold the line and finish the job.

Hi I agree with a lot of the positive comments here. Take the money ASAP and go on a nice vacation. Do what you afterward. If I were ever a founder and sold off a company with a big check, I would go back to shool, get my master degree, and become an adjunct teaching. I enjoy that more than coding all day. So bite it, talk to your wife, see a therapist (I am depressed myself) and begin to offload your work to someone else. Remember many founders would leave after aqusitions probably felt the same as you ("they come in and want to take over a product I built")

It sounded like you are attached to your work and if so I understand because you were a co-founder. I am also very attached to my work but I am beginning to build up resistance. I just keep reminding myself if at some point I stop finding my job fun and enjoyful, then I need to find an exit, just like I would go home if I haven't slept for teo days.

Find and do the thing(s) you enjoy doing now. You wil be happier.

couple thoughts. note: 45 and have seen much drama in my life:

1) At some point you SHOULD try one of those other jobs. Bartending, etc. See how the other side lives. Exercise your freedom and don't feel constrained to do this sort of work (even though the ship currently depends on you right now to keep acting in this role in order not to sink).

2) You should really have a better relationship with your wife. Open up to her in ALL ways, and she might surprise you.

3) I don't understand how the product could not be that interesting AND YET it is just too complicated. People generally find complexity interesting. What am I missing, here?

4) Perhaps you're burnt-out? When's the last time you took a 2 week vacation? You NEED to figure out how to make it possible to disappear for a while. Because your sanity depends on it.

That all said... here is a bro-hug. People obviously find your work valuable. Take solace in that for the time being, at least.

A) Make time to de-stress. Force yourself if necessary.

B) Exercise is a good way to de-stress.

C) Start planning how to implement your third option. You need to do this anyway so that you are not a single point of failure. This is good risk mitigation practise. However I don't know enough about pitching/diplomacy/PR to tell you the best way to spin this to acquirers. D) You many need to delegate to multiple other staff, not just one.

E) Once you are de-stressed, you will be better able to judge whether you are able to suck it up as necessary.

F) Personally, I think that if it's only 2 more years, it may be worth sticking out, provided you first implement points A-E above. There is a big difference between 2 years and 5 years. You could give yourself a hard deadline to be out within 2 years, and take steps to make sure that you are not a single point of failure by that time.

Let me add my voice to those already suggesting a therapist. There are a number of options you can take for each of the many things that are piling up in your head and heart, but I believe the only one that is non-negotiable is this one. Let me describe one possible way this may work for you:

- It will feel weird to open up to a stranger, and in the very beginning it may ADD to your stress; you will find reasons to cancel the session. Don't.

- It will level up quickly and after a few sessions, you will likely start to see improvements. The sessions may still feel a burden, but by now you know you do not cancel or skip them.

- Don't expect your entire outlook and days to be wholesome better, you may still have crisis like you described - the important thing is that you will also have more moments of energy and positive thinking. Use those highs to prepare your mind and agenda for the lows.

Other thoughts that may help:

- Making yourself less necessary may not be tactically wise right before the acquisition, but rest assured, afterwards it WILL be. Under stress time may pass too slowly, but it does pass, and you will get there.

- One or two trusted and loving family members may offer excellent emotional support, without the day-to-day baggage that may have made you feel you needed to hide from your wife. They will love you no matter your mistakes and weaknesses.

- A good friend you can talk to that has no ties to anything else that worries you - no direct link to your work or family. They can offer an objective point of view and help you plan, strategize and clarify the situations you face. And their mere presence will remind you that you are not alone, that you are worthy by who you are and how you are.

- I can't tell you how to involve your wife in your current plight. Ideally she could be one or more of the above, but life is not perfect. If you don't feel you can fully do it, do what you can and figure it out (possibly with marriage counsel) after you are feeling better and with less weight on your shoulders.

- Find some activity, even if it is infrequent or short, that is yours and yours only, and absolutely enjoyable for you. A TV show, a hobby, gym, swimming, a game, writing. Keep your support group 100% in the loop so they can help you keep it at a healthy level (they ensure that you do it, but they don't let you escape into it and neglect your "real" life).

All the best.

Several comments here say, essentially, "talk to someone to help you deal with your feelings." All well fine and good, but I will suggest you try to find a sounding board. Feelings come from somewhere. While there can be value in venting to get that part out of the way, if all you do is vent and get emotional support but you don't do any problem solving, it is sort of like drinking or taking drugs to deal with your problems. It is just sort of this feel good experience that bleeds off the big feelings and that's about it. And then you still have to face all this crap anyway.

But a good sounding board can help you hammer out why things aren't working and what might be done about them. They won't make your decisions for you nor tell you what to do. A good sounding board listens a lot and comments a little and makes thought provoking comments. They do a bit of reframing. They give you some perspective.

It can be a huge sanity saver to have a good sounding board to run things past. This is much, much, much more valuable than a psychologist or crying on the shoulder of a friend or loved one. Sometimes friends or loved ones can play the role of sounding board, but that isn't guaranteed.

I don't know how you can find a good sounding board. But I think this would do more for you than talking just to vent about the stress. I agree that you need very much to talk with someone, but not just to blow off steam. You need to be able to go "AAAARGH!!!! The Whatsit is NOT fucking working AGAIN for the third fucking time this fucking week" and have someone say "So, with that much downtime, would it make sense to buy a second Whatsit? Would having two of them eliminate one of the major sources of stress in your life?" or even "So, explain to me what a Whatsit does. Why is this such an enormous source of stress for you?" and then in the course of explaining its role in the business, you have some epiphany about how things work and why you keep tripping over X, Y and Z issues.

This thread has become piled high with self-help advice already, and none of us know whether our advice will help any with your own situation, but here's another take; make the best of one advantage you have, which is an endpoint.

Pick a date and say to yourself (and probably also your wife), "on that day, I'm out of this shit job." Maybe with the uncertainty of selling you can't pick an actual day now, but do so as soon as you can, or say "at most X days after the sale." You know you probably aren't going to just quit outright, since the stakes are too high, but if each day is part of a process towards eventual quitting, that'll give it a bit more meaning.

But also, for goodness' sake, take a vacation. The office is going to have to get used to your not being around eventually, why not practice now?

two - five years isn't much if you're going to be rich. unhappiness is part of life. and when you get rich enough, just quit. because you will be able to.

if you're not going to be rich in any case then the answer is simple: you should quit. let it die. i know there is emotional investment, but there is no reason to continue to be unhappy. get another job you like better. assuming you need to get another job:

construction is not stress free. its not normal work, its labour. its risky. people develop physical problems. but yes i understand the appeal. diy'ing is fun. construction could be fun as well if you have the talent for it.

retail pays enough for kids, not adults with a house. so although it could be chill that is not really an option.

finally i recommend having some people around you to distract you from your worries. roommates. a loving wife. whatever you can get.

I have made a hook in my coder life as a mover.

PRO: It was indeed a breeze and stress free. CON: without social help or illegal secondary activities you don't earn enough to sustain your life (pay rents, food, clothing and that's all).

But, it has been the moment of my life I was the happiest to work everyday.

Maybe that's how you could make a vacation. It helps you forget everything about the business brain washing that is strong in the IT, it clears your head of the noise, and you might come back more efficient, and retaining more employees by sharing their day to day concern of working to make a living and not living to work.

My take is simple, life is too short to not try to live some of your fantasies, some may actually prove to be fruitful.

Simply remember that there is no success in trying if you don't accept you also may fail and be disappointed.

I was lucky, may you be lucky.

OP, sounds like youre experiencing some real burnout. It's OK, it happens to a lot of people. Couple things to think about.

1) Are there ways you can keep going but change something to help? Going to see a therapist? Taking a short break? Talking about what's going on with your family? When you're stressed it's hard to remember all the support structures out there.

2) You need to ask yourself what is it worth to stay where you are (from a financial point of view). Is it worth a big payout in a few months to a year? Getting acquired is a good way to earn a big pile of FU money quick - and that will buy you all the time to relax and recoup that you need.

Do what you need to do to get better, and dont trash what youve worked hard to build! You can do it! Hope to see you post your success story a few months/years from now!

> The product is just too complicated (tons of domain knowledge required) for someone to come in and take over.

Are you sure about this, beyond a reasonable doubt? Reading your post, this sounded to me like the kind of story I sometimes tell myself to boost my self-esteem when I feel like I'm in a bind.

If you are in fact irreplaceable, that means you're unique and one-of-a-kind. Feels good, doesn't it? Everything is hard, but at least you're valuable and unique.

At the same time, if you're actually replicable, that means you might not be as unique as you think you are in this situation, but fortunately by admitting that, you're on the way to solving the problem.

It sounds like you're in a generally good situation, and maybe there's someone smart and ambitious out there who would be willing to step up and help you make yourself redundant?

Good luck!

I was in a start-up (as an expensive hire) some years ago where each day was horrible, and I thought I was suffering terrible 'flu. The day the board flew in to fire me* and I stepped out into the sunshine the 'flu lifted instantly. Stress not 'flu in other words, which is I suspect is where you are. The crying was probably good, and supports my suggestion!

And when you're that deep in stress it's even more difficult than usual to see a way out, to be rational, to separate the short-term from the long-term.

I wasn't even a founder, and I have been founder of a handful of start-ups now, all with their bad moments.

Can you ease off a bit, get someone else to help out, and get through acquisition? That is, a less binary view than you suggest. I don't think the buyer is likely to want either a dead company or a walking-dead company with a burnt-out founder.

Even the big boys get overwhelmed and stressed out from time to time and have to take a break:



And all these years later he's steered Lloyds back into profit and the UK government just disposed of its final shares, also at a nominal profit.

There is light at the end of the tunnel. It is probably not an oncoming train.

But you need to give yourself a chance to get some perspective.

*I did point out as a contractor that all they had to do was pay me up to the end of the day and say goodbye and I'd be happy. And I got to leave at noon. Bonus half day. The company did less well, but that's another story...

I feel your pain, I'm not a founder, but I also work in tech as a developer and sometimes wonder what it would be like to be a bartender or waiter. I have a friend who works as a waiter and always seems to be on vacation in some exotic part of the world. Makes me wonder how he can afford to do that and I can't?

I realised I needed to do 2 things: 1/ Figure out what you REALLY want to do. 2/ Figure out how your work life can support it. Is your work life not supporting it? Figure out what you need to change to make it get there.

For me, that meant switching jobs to something that allows remote work and unlimited vacation and organising my work day so that I can just put in 8-5 and leave work at the door.

Also, try taking an open-ended vacation. Don't make any plans, just get the time off and do what feels right.

I'm really quite curious - At such a pivotal stage in the entrepreneurship life, one where you're having more success than most, you're still unhappy?

If I were in your situation, feeling the way you feel at this moment, it would be an indicator that something is VERY wrong with my life. But if that were the case, it would have been wrong for a long time, and I would have just been ignoring it.

I can't help but wonder if that's what's going on here with you. At the Nth hour, on the precipice of outstanding success, you're peaking in unhappiness. The correlation is likely not a coincidence. It's an unhappiness in you that has been there for a long time, and the more you continue to ignore it, the more it will rob you of your life.

Find peace, my friend. It may mean enormous life changes.

I'm sorry you're going through a bad time. Some things I can say:

- I think your wife needs to know. I have never taken a big decision like a job change without consulting my wife. We're in this together, and if I wanted to not have to share this decisions with someone else, I would have stayed single. Please don't take this as an attack, I am not judging you. I'm pretty sure you don't want her to know so you don't stress her, but you too are in this together, and there's no need for you to go through this problem alone.

- I think you may have a partial view of those jobs you mention. It's quite likely that a bagger at a grocery store does not suffer the stress you have at his or her job, but the pay is also much less, and the stress may come at other parts of life (for example, if that job forces him or her to live in a bad, dangerous neighborhood). Construction? working outside must be very hard in the middle of the winter or the summer, for example. I think it's good that you consider other options if being a founder is burning you out, but you don't need to go to the other extreme.

- You and your family are the ones to decide if quitting is a good option. Don't worry about the company in that case. You are entitled to pursue your own happiness, and people who work for startups (I know, I have) are or should be aware that failure is one of the options, usually the most likely one. So please don't feel like you need to put up with something that makes you supremely unhappy so that the company stays afloat.

So my summary is: Find what is best for you and your family, don't worry about the company if you really feel that unhappy, and if you do quit, if finances allow, take a short break and then don't go for the first thing that comes your way. You are smart enough to have started a company and getting it close to an acquisition. That's something I was never able to do, so I say 1) hats off to you, and 2) you won't have trouble finding a good job once you're ready to do that.

Good luck.

I've been in jobs that I've hated and have a fail-safe trick - hire people to do the parts of the job that you hate. There was obviously something that enamored by when you decided to found the start-up. Are you still in love with that technology/solution? Are you sure you don't just hate the increasing management and paperwork duties?

As a founder, you're always going to have to deal with strategic situations (like the sale of the company) but you'd be surprised how much of the day-to-day work you can pawn off on a recent MBA graduate. I'm also wondering if you've come to hate the job because of the work involved with finding a buyer and working towards the sale. It's grueling! But it's also over when the sale is complete.

Good luck!

You feel like you have no good options. There are always more options. Take a book-vacation. Get a bunch of biographies and go somewhere by yourself for a weekend and read other people's stories and you will get some perspective that might lead you to discover your options.

Isn't that funny the grass is greener thing... washing plates might seem stress free, but you're the dog of the kitchen... have to deal with people's shit. Everybody throws the word "sorry" around.

I'm just speaking my experience as a guy on the shit-end of the stick haha by my own doing. If you're at this level/credibility why do some shit job. I realize you said stress free but being a drone/laborer sucks I'd like to lobotomize myself to escape from reality sometimes.

Going on someone's thought of "died in a car crash... continue..." maybe once you're acquired someone can take over your role after you train them/and be a consultant. I wouldn't know I only dream to be where you are at this point in my life cycle.

Can you negotiate as part of the acquisition a sabbatical, frame it as you've been at it for so long that stepping away for a minute would help clear your mind and focus you on the road ahead with new better ideas.

Take like 6 weeks, hard travel and exercise, eat well, relax. Don't use email.

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