
Ask HN: I don't want to be a founder anymore - throwaway10595
Hi HN,<p>Using a throwaway account because there&#x27;s a lot to lose from speaking about how I feel.<p>I founded a company several years ago. Fast forward to today and we&#x27;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&#x27;m supremely unhappy.<p>Each morning for the past couple months, my first thought has been &quot;What could today be like if I didn&#x27;t work here?&quot;. 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&#x27;m snapped back to reality. This morning, I locked myself in the bathroom with the shower running (don&#x27;t want wife to know) and cried my eyes out. I haven&#x27;t cried in many years. It felt great, but only for an hour.<p>So, from my (possibly skewed) point of view, I have 2 options:<p>- Quit, which effectively kills any acquisition and likely the company as well<p>- Suck it up and work on the same thing for 2-5 more years<p>I&#x27;d been mulling over a third option (hire someone to do my day-to-day), but don&#x27;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&#x27;t that interesting (glorified CRUD app) and it&#x27;s been hard to retain developers.<p>Please tell me I&#x27;m missing something! Maybe I&#x27;m just being ridiculous- it&#x27;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&#x27;m suffering from some kind of depression and need drugs.<p>Any advice appreciated.<p>- A founder in pain
======
throwanem
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.

~~~
patorjk
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.

~~~
_Tev
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.

------
webwright
(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.

~~~
ziikutv
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'.

~~~
lstyls
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.

~~~
ziikutv
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.

------
ridgeguy
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!

~~~
hitekker
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,".

~~~
tigershark
It's a common metaphor. There is also a risk measure explicitly based on this
concept:
[https://en.m.wikipedia.org/wiki/Bus_factor](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.

~~~
hitekker
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.

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

------
chatmasta
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.

~~~
LeifCarrotson
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.

~~~
dnautics
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.

~~~
misium
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.

~~~
transitorykris
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.

------
mabbo
> 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.

~~~
gallerdude
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)

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

~~~
gallerdude
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).

~~~
voidz
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.

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

------
ori_b
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.

~~~
agotterer
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.

~~~
rlabrecque
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.

~~~
therealdrag0
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.

------
dfuhriman
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.

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

~~~
kilroy123
I really don't understand why it's not more common practice to have an
assistant.

------
bsvalley
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.

~~~
dsacco
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.

~~~
johndotsun
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....

~~~
disiplus
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.

~~~
johndotsun
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.

~~~
dsacco
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.

~~~
Domenic_S
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.

------
apohn
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.

------
scottbartell
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](https://en.wikipedia.org/wiki/False_dilemma)

~~~
scottbartell
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/](http://heathbrothers.com/books/decisive/)

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

~~~
AstralStorm
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.

------
coreyp_1
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.

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

~~~
linkregister
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."

------
reckoner2
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.

~~~
dsacco
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.

~~~
adventured
> 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).

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

------
jly
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.

------
Lordarminius
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 :)

------
ParameterOne
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.

------
arkades
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.

------
8f2ab37a-ed6c
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.

------
lastofus
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.

------
sarah180
"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.

------
masukomi
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.

------
nhod
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/](https://startuphappiness.com/)

------
o2l
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.

~~~
gadders
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.

~~~
o2l
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.

------
mindcrime
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?

~~~
throwaway10595
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.

~~~
BjoernKW
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.

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

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

[https://sivers.org/delegate](https://sivers.org/delegate)

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.

------
gdubs
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.

~~~
unoti
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.

------
endlessvoid94
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](https://www.youtube.com/watch?v=OqmdLcyES_Q)
as a jumpstart to getting your org ready for life without you

~~~
wetyareyjrut
> 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.

~~~
endlessvoid94
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.

------
agitator
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.

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

------
rbobby
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).

------
molyss
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

------
yanilkr
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.

------
threesixandnine
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.

~~~
creepydata
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.

~~~
vacri
> _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.

~~~
eeZah7Ux
Don't generalize - it really depends on the country.

------
gumby
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.

~~~
tudorw
+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.

------
lunaru
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.

------
brightball
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:

[http://www.brightball.com/articles/what-exactly-happened-
to-...](http://www.brightball.com/articles/what-exactly-happened-to-
brightball-for-hire)

------
throwaway122394
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.

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

------
jacquesm
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!

------
twobyfour
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.

------
mindfulgeek
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.

------
thiagooffm
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.

------
sharp_heat
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.

------
mst
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.

------
carlsborg
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.

------
sebastianconcpt
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.

------
daniel_levine
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.

------
owens99
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.

------
rbistolfi
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

------
nerdy
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.

------
leandot
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

------
soneca
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.

------
gadders
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."

[https://techcrunch.com/2011/03/31/what%E2%80%99s-the-most-
di...](https://techcrunch.com/2011/03/31/what%E2%80%99s-the-most-difficult-
ceo-skill-managing-your-own-psychology/)

------
mrwnmonm
> 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.

------
zeta0134
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!

------
Mikho
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](https://sivers.org/hellyeah)

------
burner_qwert
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.

------
inuhj
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.

------
ryandrake
> "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 :)

------
lazyjones
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...

------
damm
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.

------
smt88
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.

------
rcazangi
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.

------
daxfohl
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.

------
cathaeichert
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

------
jondubois
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.

------
koolba
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?

------
WarrenBaker
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!

------
philip1209
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...](https://blog.staffjoy.com/staffjoy-is-shutting-
down-39f7b5d66ef6)

------
deepGem
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 !

------
enknamel
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.

------
manigandham
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.

------
yeukhon
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.

------
pmarreck
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.

------
my_throw_away
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.

------
Jare
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.

------
Mz
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.

------
maxander
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?

------
timwaagh
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.

------
SFJulie
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.

------
themantalope
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!

------
omarish
> 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!

------
DamonHD
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:

[http://uk.reuters.com/article/uk-lloyds-
idUKTRE7A10Y62011110...](http://uk.reuters.com/article/uk-lloyds-
idUKTRE7A10Y620111102)

[http://www.telegraph.co.uk/finance/newsbysector/banksandfina...](http://www.telegraph.co.uk/finance/newsbysector/banksandfinance/8959785/Antonio-
Horta-Osorio-the-bank-chief-who-just-could-not-switch-off.html)

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...

------
_notme
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.

------
rubicon33
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.

------
fipar
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.

------
smoyer
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!

------
0x4f3759df
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.

------
ge96
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.

------
whistlerbrk
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.

------
Grustaf
Since your company seems quite mature, it's got to be possible for you to find
someone you can help run day to day. Even if you have to be there 80% in the
start it's a win, and you can slowly ramp it down to say 20%.

The aqcuirint company probably don't expect you to be super passionate after
their takeover, so they shouldn't object. Even if they do, the worst that
could happen is probably that they knock off a chunk of your earnout package,
you'll probably make much more than if you simply leave now.

If money is not the issue at all then you should definitely leave as soon as
you can. There is absolutely no point in being miserable if it doesn't pay off
big time. You already did something awesome, be proud of that and move on with
good conscience!

------
contingencies
Execute on the LOIs pronto and get paid external help, preferably from the
acquirers. If you say its urgent they should jump. It's in their interest.

Remember:

1\. Even if in the _very worst case_ the result is a slightly lower price,
that's way less important than your health.

2\. Life balance is a real thing, burnout is a real thing, _they cannot be
ignored indefinitely_.

3\. You work hard and they obviously value you and your team's achievements,
which means they also can relate to the situation.

4\. Don't feel shameful in admitting your limits, we all have them.

5\. Acquirers will work with you to hand over responsibilities in a way that
works for your situation. Remember from their perspective that, since every
acquisition is different, complexity of handover is actually _normal_ and
_expected_.

------
Baobei
Consider to take a break for 2 weeks, rather than resigning, replacing
yourself or talking to your wife. After 2 weeks you may feel less burnt out
and see things more clearly. You can get medication (and I for one can confirm
it does work) but ideally that's to get you out of the rut not a permanent
solution. It's possible that your lack of passion for this idea, combined with
how much time and dedication it takes is making you feel this way. Your
mind/body doesn't understand the inherent contradiction. I'm married to my
cofounder and it's hard to be honest when one is feeling weak, but hiding
stuff damages your intimacy and closeness. Protect that, it's worth more than
your company.

------
congerous
I've been there. A ton of good advice is on this thread. You need to try to
influence your internal state chemically if you want to stay on track.
Exercise, medication, meditation, eating and sleeping healthy are all helpful.
It's also good to reconnect with people that matter to you: family, friends,
etc. If you're closing the deal, and the money is significant, just think what
you could do for them, or for other people who need help. And find ways to
spend more time with them, because our lives are defined by our relationships.
You could say your self exists to the extent that your in conversation with
people who understand you. So go find with and be with them. It'll help you
refuel.

------
robg
The problem with stress is the physiology is fundamentally fight or flight. No
surprise you are seeing flight, esp after several years of fight. You're also
likely suffering from burnout (extensive, prolonged stress). The most
important consideration is taking rest and recovery seriously, not on
weekends, every day and throughout the day. Find moments to cherish, take
walks outside, exercise more, get good sleep, quit using alcohol and start
eating better. The brain is an organic computer, connected to every organ in
the body and yours is running low on juice. You can't make good decisions
right now, your brain is compromised by a health condition. Finding calm
should be your priority toward inner peace.

------
pwh
I can't say that I know your pain, but I can sort of feel your pain. Simply
because I've been there done that. Taking advice from HN, no matter how well
meaning, may or may not help, it may even frustrate you more. Best thing to do
is to step back. Find a way to clear your head. A long hike worked for me.
Even washing dishes. You may have your own thing that works for you. Do that.
Talk it out with someone you trust or who is willing to listen. You can talk
with your wife later when you have your bearing back. Heck if you are in bay
area and need a sounding board, you can ping me. Keep in mind though, the best
answer probably will eventually come only from yourself.

------
vcool07
Option 2 : Suck it up and work on improving the situation. Instead of throwing
in the towel and going on a quest for self discovery, find ways to avoid
stress. Take up yoga/gym classes or play some video games in between. Take
your wife shopping, have quick power naps just google and see what works for
you. You are not the first person to be in this situation, discuss with your
peers on how they handle it and try to see if you can incorporate some of
their good habits.

You're having a company which you started and which you say is profitable,
don't throw away all that due to some temporary situation. Instead of running
away, face it and see how you can improve on it !

------
nish1500
I was in the same position sometime back.

I was convinced that chasing startup money and fame was some objective form of
happiness. The chase never made me happy.

Luckily, I woke up before I made any hires. My startup is still profitable,
but it's more of a lifestyle business now. I work enough to make sure the
profits don't fall.

I use my time to travel the world, live out of a backpack, make friends, do
shit that scares me. Still struggling with the last part.

Last month I volunteered at a not-for-profit pay-as-you-go restaurant taking
orders and cleaning tables and it made me the happiest I have been in almost a
year.

I am also exploring my other passions - fitness, food, nutrition.

You know best what you need to do. I thought I'd share what I did.

------
dudul
May be a stupid question but: can you suck it up until the acquisition goes
through, take the money, leave, and try bagging stuff at a grocery store for a
few months?

Does the acquisition involves you signing a contract and being forced to stick
around for a few years?

~~~
throwaway10595
> Does the acquisition involves you signing a contract and being forced to
> stick around for a few years?

Yes they range from 3 to 5 years, with much of the compensation coming from
future earnings.

~~~
jaclaz
Don't take it the wrong way, but there are some unresolved problems that most
probably caused your current feelings, you should make a list of them and try
and solve them.

It is not possible - no offence intended - that you managed to lock yourself
in a position such as the one you described, where your
product/company/service/whatever can't live one week without you in the
office.

And by the same token it is not possible that someone - knowingly - is going
to give you money for something that can only work if you are not only at the
steering wheel, but also doing the most relevant work all the time (it would
be far too risky).

Now that is more clear that the offer is actually largely linked to future
earnings (and obviously your future work) it sounds a lot like they are buying
you and your competences (and not your company/whatever).

Maybe you should really talk first with someone that can help you with your
(momentary) crisis (that would be psychological support, if you can stay away
from prescribed drugs would be advisable) then - as soon as you have regained
some objectiveness and a peaceful state of mind - take some time to talk with
your immediate associates (be them co-founders, executives or employees) and
try to make a plan to solve those problems (which seemingly essentially
revolve around either missing resources in the company or missing attitude to
delegate some of your work).

------
ravimalik20
Hi.

Have you considered the possibility that what you are facing is probably
because of depression? I know, you would say that the work is the cause of
depression.

Either way, you should seek medical help for it. I have seen people waste away
because of depression, my grandmother for one.

It would be much better once your depression is under control and you'd be
able to make a better decision. There is one thing thatI learned growing up,
"Never make a decision when your head isn't straight". You'd be able to make a
better decision once you are free of the burden of depression. Trust me, and
see a doctor for depression. There's nothing bad about it.

------
focii_e
Been there. One of the biggest mistakes I made was thinking people are
indispensable, I was indispensable. I thought after I walked out of the door,
the company would fall apart. Nope. A successful organization often has
multiple roots for productivity and success. So here is the advice if you
like, take a month long break. Have the cashflow taken care of, and ensure
customers are treated well in your absence. Rest can be fixed if it falls
apart. A month break and you will not only want to go back but will probably
redefine where the organization should be in a few years. A month long breaks,
that is all it takes.

------
TallGuyShort
If the third option of hiring someone to do your day to day really was
impossible, this would never end. I would strongly recommend getting someone
to come on board and start trying to take off some of the load / get up to
speed. It might take a long time but either you're going to quit and ruin it
anyway, it's going to kill you and that'll ruin it anyway, or that has to
happen eventually. Start now. I get why it's hard: attracting someone who's
committed, getting the incentives right for them to not feel the same way in 2
years, etc. But it's really worth focusing on attacking those specific issues
as soon as you feel up to it. Even if the person just takes over some QA work
/ automation / simpler features and fixes, etc. Doesn't necessarily require an
unreasonable amount of domain knowledge but if it frees up a couple of hours a
day for you, you could take a hike in the mornings and stop feeling like
crying about what you're not experiencing every day (or whatever it is you'd
love to do instead of work).

More immediately - it sounds like you need a vacation. I've been there with
the whole fantasizing-about-walmart-construction-sites-and-grocery-stores but
it's a dead-end in the long-run. Every job will wear on you and come with it's
own set of hardship. Mentally less stressful? Possibly. But think of the very
different set of people you'll interact with - possibly a huge culture shock.
Think of what a bad day at work might look like at a construction site. In the
rain and cold, a little physically injured, maybe having to deal with a client
that's trying to screw your crew over on the contract? Probably making less
money? And dealing with all the comes with? It's not much of a greener pasture
once you get into it. I would bet what you're really in need of is a break and
a change of scenery for a little while. If you can make that happen (and again
- you need to or this is all destined for failure at some point), try that and
see how you feel when you come back.

By all means keep talking to people who have been there to get input -
probably a lot of us on HN. Don't take all of it as gospel, but you're
definitely not the only person to go through this, and you won't be the only
person to figure out a way through it.

------
netaustin
Vacation aside, I have a tactical suggestion that could help quickly if you
can afford it: Hire an assistant. You get two things from this pretty quickly:
instant help with your petty day to day tasks to allow you to save your energy
for the truly grinding chores that only you can do, plus a teammate who will
be by your side as you fight through the next couple years.

I have a relatively stressful founder job and have recently been able to do
this. Just having someone who's in my inbox, seeing the same demands I see,
makes it much easier to get through each day.

------
bowthy
It could be the routine and long hours that's driving you to this dispair. I
had many jobs before being a dev, including supermarket and bar jobs. They
mostly sucked because I had close to zero control of my environment.

Being a dev is the best by far. I have a lot of control. Not without stress
though. Best antidotes to stress for me are cycling to work, swimming in cold
lakes, weight lifting, hours of device free time with wife and children.

As a founder aren't you in a priviledged position of being able to change
whatever you want? If not, what's the point?

------
thepaulstella
FWIW, as someone who's worked those jobs (hard labor and customer service) for
roughly 7 years prior to becoming a full-time programmer, I can assure that
those jobs aren't stress free. Quite the opposite, actually. I try my hardest
to never take my opportunities for granted and I can't imagine pining for the
days of being treated like a low-level grunt of a company. I now have
unyielding respect for those working those jobs by not idealizing their
"simple" profession.

------
akeating
I wonder whether you know how to nurture leaders under you and how to delegate
effectively? Many founders are relatively inexperienced and I understand this
might not be the case for you. But if it sounds like something that resonates,
consider reaching out to a mentor who can help with this. With an exit on the
horizon, there's an end-game. It's likely the acquirer would anticipate you
would leave anyway. You might start a dialog about building the skills of a
replacement, you know, if you get hit by a bus, wink wink.

------
graphememes
I'll take it over for you, I'm tired of being in a position where you make
suggestions and it's only realized two to three years later thats the path
that should be taken anyway.

------
KirinDave
I deliberately took a few steps back in my career after this last exit as
well.

I've learned that being in charge is ... Sort of awful. I'd make many of the
same decisions again, but I have regrets.

------
point78
Outsource the work to me, pm me and go do whatever you want for 3 years

------
hartator
> I'd been mulling over a third option (hire someone to do my day-to-day)

Don't do this. It's the easiest way to be exited on not your conditions. From
personal experiences. Just quit now on your conditions and name someone else
as CEO. It always easier than it seems to gain domain knowledge. On a personal
level, reading stoicism philosophers helped a lot too. If it's actually about
your state of mind and not the job itself, that can trigger a switch to liking
sucking it up if you decide to continue.

------
ingenuous2
If you read this, I want to say, "it's OK". seriously.

I have depression episodes, had one while my company sold.

Today isn't tomorrow, tomorrow isn't yesterday. Accept how you feel and make
the best decisions, holistically, that you can.

If that means letting your partners negotiate because you're unable to? In
spite of you building much of the value? Then giving you a dime on your dollar
of equity?

That's fine. Seriously. I went through that literal situation, and it was the
most important thing I've ever experienced.

------
heimatau
For what it's worth, my advice would be to get the sale done with conditions
that you DON'T have to work for 2-5 years.

If you have enough money to take a Sabbatical, then do it, 3 months or 6
months. I know many (mostly in academic field) that tend to 'find themselves'
when they do these every 10 years or so.

You sound like you're suffering from burnout. When is the last time you took
an extended rest? I'd strongly advise that. Best of luck to you and I hope
this reaches you! :)

------
postwait
Find a group of fellow founders that you can talk with. Even if it is just one
or two. As a founder, I can relate to the stress and suffering. Sharing can
make all the difference.

------
wcummings
If youre financially secure, and can line up a new job, which I'm imagining
you are and you can...

Sure, fuck it, quit. Line up a new job at a big enterprise shop with lots of
process and 9-5ers, tell them you'll start in 6 months. Spend that time
exercising, enjoying your hobbies, and doing things with your
wife/family/friends.

This board is filled with people who fetishize entrepreneurship, the responses
are going to slant that way, take them with a grain if salt.

Hope everything works out for you.

------
nradam123
It happens to a majority of founders. I have panic attacks, i sometimes cry
and I get sleep paralysis all the time. And unlike you, i am yet to even build
a profitable business.

------
JabavuAdams
I am amazed by the number of responses that aren't "find a mental health
professional to talk to".

Talk to your wife, then talk to your doctor. Don't wind up dead or making a
rash decision that would seem silly when you're in a healthier frame of mind.

I have had the experience of wanting to kill myself on a Friday, and then
thinking "boy that was stupid" by Monday.

Please seek help, before it gets worse. There is no shame in this.

------
retreatguru
As a fellow founder my advice is to take a break - go on a retreat - yoga,
meditation, ayahuasca, nature, etc.. Sounds like you are highly stressed. A
break will give you some perspective. I bet those around you will understand
and support a week or 10 day break.

Happiness mainly comes from appreciating what we have. When you are stressed
and too close to the action it's easy to lose sight of all our blessings.

I'm happy to connect on a call and listen if you feel it would be helpful.

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

Why do you assume you have to work on it for 2-5 more years?

It's pretty common for founders to quit within a year or two of an
acquisition.

------
kcdev
I'm not in your shoes, but I'd happily trade places. I assume you're calling
most of the shots, so if you take a step back and reflect, where is this
stress coming from? Who is putting pressure on you? I'm guessing it's you
doing it to yourself because you hold yourself to a high standard and have a
strong work ethic. Excellent qualities.

So take a few days off, refocus, slow down, and just do what you can do. No
pressure.

------
osmala
Tim Ferris: Four Hour Workweek . Eliminate, Automate, Delegate...

It can give you ideas on how to delegate more.

Secondly figure out how to retain developers. If it causes you stress and
hiring is real expense then you should invest in fixing it. Make developer
work environment as good as possible and maybe pay slightly above market
pay.Your job is to fix the environment to reduce turn over to compensate the
boring product with other factors they value.

~~~
xemdetia
Another thing here- you are having exit interviews right? You aren't just
letting people walk out the door in a huff? If people are genuinely unhappy
and are leaving because of it there's an obvious signal here that you can get
some feedback about. Does the pay suck? Is the work unrewarding for them as
individuals? Are you not letting them share good ideas and not just shooting
them down?

------
stevenalowe
If the product is complicated, requiring tons of domain knowledge, but the
implementation is an uninteresting, glorified CRUD app, then part of the
grinding suck for you and the developers might be the mismatch between the
product domain model and the software's implementation model. As an advocate
of domain-driven design, this situation would make me sad, too. Happy to
discuss if you're so inclined.

------
siliconc0w
Take a vacation (even a short one) and maybe look into talking to a therapist.
They can help you figure out where the clarity of your thought process may be
caving a bit to the stress/anxiety of your job. I.e Working a wallmart isn't a
stress free life. (Which isn't to say you shouldn't leave your job, it's just
good to make that decision from a place of clarity rather than emotion).

------
AmIFirstToThink
May be you don't need superstar developers.

Someone appreciative of a paycheck that barely gets assigned tasks done is
fine. Hire non-comp-science interns and build their careers. see them buy
their first car, first rental place, go there with a wine and eat their
burgers. It's good seeing people happy, providing them a career and paycheck.
Their smiles, their families smiles will make it all worth it.

------
losteverything
I hope you get better.

I work at that hated huge retailer and you would have to learn to smile before
we hired you. Depressed people show through and lower our Friendly scores.

Personnel at my store are very leary of hiring just anybody and having a mondo
career -> Walmart has to be explained.

I do work with 2nd career elders. Several just work to be among live people.
It really is enjoyable.

All the best but hold off on walmart.com/careers

------
23david
I can relate... I'm not sure it helps, but what you're going through is not
uncommon for startup founders.

I know someone who just came out of a job where he was hired to take over most
of the day-to-day for a founder in a similar situation. It might be useful to
discuss the situation and see what recommendations he has. Feel free to
connect via Linkedin and I can put you in touch.

------
newera2016
I am in a similar situation other than the fact that I don't have acquisition
offer and startup is not making much money even not able to pay my own
expense. I have lots of customers though and working on it for more than 3
years. Feeling depressed every day and try to ask the question "what to do?".
However, I have people who are managing that well.

~~~
wolco
Raise prices immediately x3 if possible. You will lose some customers but make
more with less work.

------
powera
What you need to do is go to the company acquiring you, and make sure that the
deal allows for you to leave a year and a day after the acquisition closes
with "minimal" penalties. You'll get less money, but you should get at least
half, and everyone else will end up OK.

Also, take 2 weeks off after the deal closes and the money for the acquisition
is in escrow.

------
NicoJuicy
Go to your wife and talk to her. Plan a vacation and depending profitability,
check to shift some responsabilities to someone else.

Why is it hard to retain developers? It would definately be easier to retain
developers to ease your burden. ( that's a problem where $$$ can easily be
thrown at, if it's possible off course)

PS. For some (busy) people, doing sport actually helps a lot

------
tarikozket
If your wife doesn't know about this, I can easily tell that you are doing
something wrong. Believe me, your wife is the only one who can help you on
this and give you the power needed. A little support she would show would make
you feel like a baby. People are not around just to celebrate successes,
especially the partners.

------
dmitripopov
You need a break. It's an obvious burnout and you won't get out of it unless
you stop and go for vacation.

------
jansho
Lots of good advice already:

\- Let it all out to a psychologist (definitely this)

\- Take a holiday somewhere sunny and not too crowded (definitely this)

\- And most definitely this, your new job: how you can delegate your work _as
much as possible,_ AND how best to upskill your new "minions"

Hang in there, OP :)

Edit to add: don't forget to talk to your wife about your _real_ state!

------
jbannick
Quit immediately. No transition. Sleep. When you're rested, decide what you
want to do with the rest of your life

------
meerita
Hi, I hope you find out the light at the end of the tunnel. Regarding your
situation, I would think about this as a project, a project to go out. It has
to be planned and executed. That helped me out many years ago. You don't need
to quit now but bear in mind crying doesn't take to the shore.

------
radley
Sounds like you may want to take a sabbatical, which usually lasts 1-12 months
and can be flexible. I suggest making it part of your acquisition
arrangements.

Many professionals need a timeout to reset. Often they return to their current
/ new role refreshed, but sometimes they decide it's time to move on.

------
x0ner
Talk to your co-founder if you have one. If not, your wife is she's
understanding. Having sold a company, it's one of the hardest processes to go
through. It's not clear if your pain is from multiple years or the sale
though. That clarification would help in the advice you get

------
dkarapetyan
Quit. Given what you've described 2-5 more years of this is not going to be
good for your mental health.

------
arsenico
Speaking from a completely different perspective, where we had a wonderful
company, and would have never sold unless could not raise money anymore -
_sell_ , take money, then indeed hire someone to do your day-to-day, take a
sabbatical and come up with a new idea and a new company.

------
robmcvey
Are you in a position to discuss with your co-founders? If there's money in
the company maybe they could buy you out based on the EBITDA of the existing
offers, getting you out of the company sooner and not scuppering any deals on
the table (which might take years to complete).

------
JepZ
1\. Get help (e.g. by a professional)

2\. Find ways to cope with the stress (identify the real sources)

3\. Decide if you want to continue the work for your company

In that order. Otherwise, you might regret your decision at a later time. Keep
in mind that your recovery might take some time. The pain does not vanish
within a day.

------
exclusiv
Agree with disclosing to your wife; that will help. Apart from that I'd say
suck it up and plan on working at the acquiring company for only 1 year with
the next step being something you're excited about. That will make the
transition a little easier.

------
jaxomlotus
Hey founder in pain - I've been in a very similar situation as you and
ultimately decided to stay to fulfill my duty to investors and employees.

And in the end, post-acquisition, I _was_ happier. If you want to chat, shoot
me an email to muchnick/a/gmail

------
Animats
If you're about to be acquired, what's the problem? Does the buyer want a
contractual commitment that you stay with the company? If not, this is where
you can cash out and retire. Stay 3-6 months after the acquisition and phase
yourself out.

------
ljf
For option 3 check out: [https://medium.com/the-modern-team/lazy-
leadership-8ba19e34f...](https://medium.com/the-modern-team/lazy-
leadership-8ba19e34f959#.afzawx2jq)

------
babyrainbow
>It seems so stress free.

Try it.

Or talk to someone who works at walmart, or a bagger at a grocery store. See
if they would like to be in your shoes. Might help put things in perspective,
and it seems to be that just a change in perspective is all you need..

------
donpark
I recommend, exploring other options. For example, work on same thing for 2-5
more years but from a remote location of your choosing, like Thailand, or full
Nomad life-style.

If result improves your productivity, it may be a WIN-WIN solution.

------
dorianm
Why post it on Hacker News? What kind of advices were you expecting? Why not
ask your wife? Why not ask your coworkers? Why not ask your friends? Why not
ask your family? etc.

They know you and your situation much better than any of us.

------
BrailleHunting
Delegate - Hire some competent people to take over sales, product and
engineering management.

Depression - Examine heirarchy of needs: Sufficient exercise, sleep,
nutrition, social interaction and maybe medication if CBT doesnt work. Feeling
not depressed is like a release from constant internal judgement, cloud of
doom, negativity spectacles. For some people, it's only temporary, situational
and existential to change one's agenda; for others, there is a genetic
component which causes permanent, unrelenting major depression which is
unlikely to be addressed without finding a suitable medication.

Transistion to a social venture - Setup a school or hospital in Botswana or
Somaliland, or join the Peace Corps. There is plent of work that needs doing.
Teach, mentor and/or build something that builds people ready for tomorrow.

------
creepydata
1) Seek professional help

2) take a vacation/staycation

3) Learn to delegate. Hire people if you need to.

4) Set boundaries between work and life, keep them.

5) Practice some sort of meditation. Meditation is a broad category.

6) Build and/or rebuild your interpersonal relationships outside of work.

------
baxtr
This may be of help:

[https://bothsidesofthetable.com/how-do-you-motivate-
yourself...](https://bothsidesofthetable.com/how-do-you-motivate-yourself-and-
stay-focused-70dcf5987ec0)

------
rodrigosetti
Try to find a motivation to get thru this - think about the good that you can
make it to your employees as you lead them through the acquisition. This might
help you to gain some more time to think about your options

------
ecksor
[https://gettingreal.io/why-do-i-fantasize-about-quitting-
my-...](https://gettingreal.io/why-do-i-fantasize-about-quitting-my-
startup-3fc425004a21)

------
simonebrunozzi
Dear founder, I want to give you my $0.02 of advice:

1) Seek out a mentor, either someone you know well, or someone who can be
introduced by a good friend of yours. The mentor should be someone with
experience with founders, and hard situations like these. Another person, with
a fresh, different perspective, can help you look at the situation and really
see what's wrong, what can be fixed, etc. As good as Hacker News can be, you
can't share too many details which prevents most of us from being effective at
helping you out.

2) I don't think a vacation is going to change anything. I've been in a
situation like yours before, and a vacation would simply be pure suffering -
you would be thinking about your issue all the time, and wouldn't enjoy the
vacation.

3) You are a founder, which means you convinced other people to invest in you
(with money, or with their career), so you somehow OWE them something. If you
are very close to an acquisition, you should consider staying until the
acquisition goes through. You can leave afterwards (and lose most of the
economic benefits), but at least you wouldn't be damaging these other people.
This is the behavior I would expect from you if I were one of your investors,
or one of your early employees.

4) You never know what's going to happen after an acquisition. Perhaps you'll
be able to spend more time with your friends, or on hobbies, and less on the
job - which might bring some happiness to your life.

5) You might be depressed, or in a weird mental state, which might or might
not depend on your job situation. Sometimes it could be wise to see some
medical advice, although I am NOT a big fan of drugs/medication/etc, as most
of the time they fail to fix the problem at the source.

6) Usually, sharing an issue makes it easier to face it. Besides the mentor
(see #1), you might want to share your state with 1-2 very close friends,
assuming you have any. That might help too.

7) Sometimes I use this "mental trick", which helps a lot in tough situations:
I try ti imagine myself 10 years from now. I spend several minutes trying to
get the details right. And then, usually I realize that I am giving too much
importance to the imminent problem I'm facing, and that "everything is going
to be all right" at the end. I don't know if it can work for you, but it does
for me. And it worked, wonderfully, at least three times, in situations that -
I think - were a bit worse than yours. Well, you never know, suffering is
subjective, and relative to circumstances.

I hope this helps.

~~~
rcazangi
+1

------
rpedela
I think the advice in this thread is generally good. The only thing I would
add is to at least ask for half cash upfront and half stock vested. That way
even if you end up quitting, you still get rich.

------
reilly3000
I was there. Didn't take the deal. Ended up filing chapter 7. That really
sucked. Life moves on, it really does. Try to know what your heart is really
trying to say before you say no or yes.

------
ottoid
I think you are preparing for the next stage. You want to sell the thing and
move on and just be a consultant on hand for the changeover. That way, you
have a path forward to do something else?

------
ggggtez
Sure, you forgot to talk to your wife. Come on man, you've entered a
partnership. Adding hiding secrets from you partner isn't going to make your
life any less stressful.

------
beejiu
If you feel like you are suffering from depression, see a doctor. They can
give advice specific to your situation, which might involve therapy or drugs.
The treatments do work.

------
fred_is_fred
Working at Walmart is as far from stress free as you can be. Ever had to
wonder if you would have enough money to feed your kids that night? Holy first
world problems.

------
seige
Building businesses is hard and emotionally draining.

There is always a person to do a job. It's just the matter of what you are
willing to give up for your own peace of mind.

------
aaronblohowiak
Burnout. You need a few week's vacation. Maybe a month.

------
rukuu001
Burnout in action.

When was the last time​ you took a holiday? Like, a solid two weeks away from
everything?

If you decide to go through with the acquisition, I'd schedule in some time
off.

------
iaw
Is there an option between 1 & 2? Push the acquisition through but with an
exit timeline for yourself.

How much does the business depend on your day-to-day interaction?

------
venture_lol
Friendliest advice: promote someone NOW! or hire someone -- NOW!

It's just a load you are telling yourself your product is too complicated for
anyone else to take over.

------
ivanjaros
a) take a break, month or two if you need to and appoint someone that will
handle your d2d business in the meantime.

b) exercise more. I cannot stress this one out more!!!

c) wait until the company is sold and move to a new project. Negotiate that
you will be only an advisor(maybe only for the following year) and find
someone else as ceo.

d) do not quit without selling out. All that time you have invested in this
company will go to waste. So suck it up for now.

------
romanovcode
Why do you need to work there 2-5 more years if you're about to get acquired?

Why can't you cash in as soon as you are acquired and go pack bags in walmart?

------
paulajohnson
I'm not a doctor, but it sounds to me like you may be suffering from clinical
depression. You should talk to your doctor about this urgently.

------
flaviusas
So it's a glorified CRUD app and domain knowledge is required.

Why is that domain knowledge not built into the app?

------
dyeje
I mean, if you are about the be acquired then just take the pay day and start
working on an exit strategy. Seems pretty straight forward.

------
gargarplex
I can't believe nobody's recommended "The E-Myth Revisited" yet.

Take a month vacation and transfer the domain knowledge to paper.

------
pbreit
I don't understand what the problem is. If you have LOIs on the table, SELL
THE COMPANY!!! You can leave the day the deal closes.

------
doppioslash
What you're feeling is sanity giving you a reality check.

The possibility of starting to hate your own startup isn't much considered,
but as you found out definitely exist. You might be heading towards a nice
nervous breakdown. Definitely consider seriously making your load lighter,
either by delegating your job, or quitting altogether.

You're not going to get those years of life back.

------
donohoe
1\. Talk to your wife. She is there for you too.

2\. Talk to a therapist or counselor. They can be amazing and helpful in ways
you don't realize.

------
andreapaiola
Maybe you can start to read
[http://notalwaysright.com](http://notalwaysright.com) :D

------
Zaskoda
We know it's you, Zuckerberg. Hang in there.

------
zecg
Working at Wal Mart or in construction is stress free? Try it for a few years
and for full effect, try living on those wages.

------
sharp_heat
Just curious, why did you start this company in the first place, if it's an
uninteresting "glorified CRUD app"?

~~~
mindhash
Most successful (revenue making) products are simplistic.

Also it could be his perception because he has done it over and over. Someone
new or outsider may not have same view. If you ask Larry Page to re-work on
search engine, he may not enjoy it so much as he has done his time.

------
wilsynet
Why wouldn't you wait until acquisition closes and _then_ decide to quit or
not.

Quitting before the acquisition is ... harmful?

------
kgc
Why not just complete your sale? Then you can do whatever you want without
letting down those that depend on you.

------
rebelidealist
A business should work for you. Find a team of smart people. Gradually train
them to replace you.

------
palerdot
Maybe you are under depression. Give yourself some slack and take one day at a
time.

------
jjm
I'd like to know details on why you can't be automated. My info in profile.

------
keerthiko
There's a lot of hyperfocusing on the comment that you don't want your wife to
know. From everyone on HN, you're the best judge of whether she should know or
not, so I have no choice but to trust your judgment on that.

Something I find missing from your narrative is what exactly is making you
unhappy -- the title of Founder? The pressure of the job and the impending
sale? The mundane-ness of the technical details of the job? The fate of being
handcuffed to this job (that you don't care for) after the sale? Are you
financially constrained and feel tethered to the company to stay afloat? You
mention the stress, but it doesn't sound like that's the kicker by itself.
There's no magic bullet to fix all your worries in one go. So write down in
order which parts of the whole situation you hate. You'd be surprised how many
of those can be solved independently of the others. Maybe you can hire a
personal assistant to sort through all your communications and scheduling and
logistics, and can filter out the domain-knowledge-needed parts to you.
Perhaps you can invest in transitioning various boring technical portions of
your product to be outsource-able, so your in-house developers have only the
more fun stuff to worry about. Consider the best and worst case outcomes for
each of these options. Check the risk. Some of them will be worth it, some
not. If you can improve your situation even a little bit, it's a step forward.

I can relate to some of what you say. Luckily my cofounders are wonderful and
take responsibility for lot of the shitty parts of the job of running a
company, so I have a fun time mostly gallivanting in technical and product
design spaces without stressing out much, and we're profitable and
bootstrapped. All in all, my job doesn't really stress me out much, I work
with great people, I love our product, I have lots of freedom and make enough
money to use it to work out of a different country every other month. It
sounds pretty great, but I have shared your fantasy of working as a grocery
bagger or as a Starbucks barista or something. For me it's because I am in
America on a work visa that won't allow me to be employed outside of my field
of expertise and study, ie, engineering. So I fantasize about what I can't
have, think how cool it would be to have the freedom to be an uber driver or a
waiter or just simply be unemployed before I look for a new opportunity, even
for just a month, without the threat of violating my visa agreement and risk
deportation. A little reality check reminds me that I have these fantasies
from a position of privilege -- all those people who's jobs I envy do not have
the right, or freedom, or training to start and run a company building
something they care about in the first place, and I happily return to my day
job.

------
edo
Quit. Life's too short to spend it doing something you don't love.

------
dustingetz
Hey there, are you exercising every morning? That is how I be happy.

------
alfon
Just came here to say:

Don't do drugs for this, that's as far as I can say.

------
tehwebguy
Would happily share my similar experience privately if you like.

------
amelius
So what is your analysis of how you got into this situation?

------
staticelf
Weird to read since you're essentially living my dream.

------
napperjabber
Don't Make the decision until after you take a break.

------
gigatexal
Get bought out and go on a much deserved vacation?

------
synthecypher
Take a holiday dude, get someone to cover for you.

------
unabst
To be honest, I think all founders are in some degree of pain. I mean, I say
that hoping it will make you feel a little better, but it certainly won't
solve any of your problems. For me, knowing I can quit whenever I want helps.
I mean, I would literally quit and move on if things got too bad. There are
plenty of opportunities. But as it turns out, either my pain tolerance is
pretty high, or it's never gotten bad enough -- probably out of sheer luck.

To me, your situation is straight forward. This is what you're missing. Well,
two things.

#1. You are burning out. Pretty standard, frankly. And anything could cause
it. For some it's the mid-life crisis. For some it could even be diet. My
mother took pills that caused night terrors. They stopped when she changed
medication. The typical entrepreneurial cause would be "lost your passion".
That thing that got you motivated before you went to work is no longer there.
Your entrepreneurial mojo is gone. But of course, that makes for a good
narrative, but in reality it could be anything. Even just plain fatigue.

#2. I'm not sure how conscious entrepreneurs and founders are of this, but if
you're a fan of first principles, you should be a fan of this one.

An entrepreneur is someone that creates jobs. Though we can define it many
ways, ultimately the core competence of an entrepreneur is in their ability to
grow a company beyond just themselves, and... move on.

So a successful entrepreneur is either serial - moves on from startup to
startup, or is monolithic - they build one business but with multiple
departments under one umbrella (a la Amazon or Microsoft or Apple, but head
count still keeps growing).

So #2 is your third option. This is what you need to do.

> don't know how to make it work

Figure this out, just like you did everything else.

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

Simplify and document until you're out of paper, then train someone.

> isn't that interesting

Doesn't matter. Money is interesting. If they're being paid for work they
agreed to do, it's just a matter of finding a professional worker.

The thing about your third option is, at least to me, it's the obvious final
step. If you're looking to get acquired successfully, then you are looking to
be replaced, no? And the hurdles for your third option are exactly what would
turn off anyone looking to take over. So for your own sake, and for the
incoming new boss, you need to continue on with your third option.

Anyway, hope that helps!

------
akarshsatija
No job, no work, no role is stressfree my friend.

------
hprotagonist
hang in until you're acquired -- if there are LOIs out it can't be _that_ much
longer.

Then cash out and walk.

------
bobbybobbybob
Go do some CBT, then reevaluate.

------
niftylettuce
take a vacation. get outside of comfort. environment change helps vastly.

train + delegate + automate

------
johndotsun
Before attending college I worked at walmart for several months, and I also
spent a few months working construction. You do not want to work in either of
those environments.

You're a person with intelligence, agency, and presumably the strong drive to
succeed at various goals that motivated you to start your company in the first
place. Your skill set and ability to learn new skills is such that you are
useful for more tasks than stacking shelves, pushing carts, or hauling and
shaping re-bar.

By and large the people I met at walmart were, to say it bluntly, not very
smart and were consequently aggravating to interact with because of this.
There are people in this life who struggle to reach full competency at
stocking shelves, dusting, pushing carts, or other menial retail oriented
tasks despite an earnest effort from them. A work environment like walmart is
structured to run a billion dollar business using these people, and to do this
their workers are subjected to a system that at times seem arbitrary and
overly restrictive but ultimately necessary given their labor pool. So not
only will you be inside of that system, but you will be required to find ways
to work with coworkers who have managed to reach levels of incompetence that
you wouldn't otherwise think was possible had you not seen it with your own
eyes. This is not to say that there are no intelligent people working in the
various walmart stores, and I did meet some during my tenure. However those
people were few and far between, and were usually there due to unfortunate
life circumstances beyond their control.

General labor construction work involves working with the same people, but
without the strict and arbitrary system. This is replaced with coworkers that
show up drunk and high starting as early as 7 AM and while this isn't a
problem in some work environments, in a work environment involving power tools
and heavy equipment this can be life threatening not just for them but for you
as well. If you choose to train in a specialty such as electrical or other,
you'll be fairly well separated from these people but then considering the
amount of effort you have to go to in order to get these jobs you might as
well just use the skillset you have in programming. You'll get payed more and
you won't be working in environments with toxic dust, ambient noise levels
capable of causing permanent hearing loss, and repetitive physical movement
that slowly destroys your mobility so that in your old age you're completely
sedentary (my electrician grandfather can no longer lift his arms above level
despite several attempted corrective surgeries)

I don't know what the solution to your problem is but I do know that working
in a grocery store or basic construction is not the correct course of action
if you desire to reduce the amount of stress in your life.

------
JakeAl
Sounds to me like the problem is managing stress due to a lack of healthy
growth. You are lacking leadership fundamentals guiding you in your life and
career. Leadership is about awareness, knowledge, experience and skills in
growing roles and responsibilities. That's a trite summary, but in short we
are individual contributors, team managers, managers of teams, managers of
managers, or organization leaders. We grow throughout these stages and healthy
growth means not too fast and not too slow, but at a rate where we develop the
experience and master the skills necessary to level up. Often we take on roles
before we have the skills to do so, and when this keeps happening the damage
piles up and eventually comes back to haunt you. That sounds like where you
are now.

In your post when you say you want to do something menial it says that you
want to go back to the level of individual contributor. It means in moving
past that role you didn't master something to prepare you for the next level
and/or what you are doing at your current level is not commensurate with your
skills and experience. That means what you are required to do in your role on
a daily basis is beneath you or beyond you. Something is not consistent
between your level/roles and responsibilities and your experience or else you
wouldn't have a problem.

Healthy growth keeps you engaged and moving forward at a rate consistent not
with your wants but with your needs. You may not like doing something but that
doesn't mean you have developed enough to move past doing it. You may like
doing something but that doesn't mean someone at your level should be doing
it.

When you get stressed by something. It means you haven't mastered managing
stress associated with tackling problems at that level. It may also mean that
the organization is requiring you do things a person at your level should not
be doing. Either way you shouldn't be getting stressed, you should be taking
the appropriate action for someone at your level -- developing what you are
lacking to manage stress (awareness, knowledge, experience and skills) or
doing what needs to be done so someone at the appropriate level deals with
things you shouldn't be.

In short leadership of the company is mess. Most companies are because few
understand the most basic principles I've vaguely described here. If you're
getting stressed you need to understand why. Look at the levels I've described
and start asking yourself in each role/level what stresses you out. That's
where you failed to grow as you moved up, and where you need develop your
experience and skills before you can move forward.

Stress management and awareness are two of the most difficult things to master
because of how entwined they are. Don't listen to anyone telling you to do
drugs to manage stress or emotions. Instead, start by getting physical
exercise. Go for a long walk alone regularly. It does wonders. It gives you
time to reflect and think and plan. Getting the blood flowing physically
allows the body to do what it does to manage stress chemically. If you need to
do more, then level up your physical exercise to something more strenuous and
active, but most people don't find walking to be a burden and can motivate
themselves to go for a walk. It will address the most basic physical needs and
buy you the time to reflect and address what mentally causes you stress.

------
Majorburn
You can't be diagnosed over the internet so I'm not diagnosing you with
depression. And it does sound like you have that. Things you used to enjoy not
doing it for you anymore? Trying to handle it yourself and not talking about
how you feel? Definitely, I recommend you talk to a counsellor / therapist /
psychologist. I mean, you're already reaching out to the tech disapora for
help ( Ask HN ), so take what may be a more effective and qualified step and
talk to person whose profession is helping people.

Now I want to enjoy a vicarious "I told you so" ( since I didn't tell you
anything ! ). I have however heard the advice said many times that before you
startup a startup consider if you really care about it so much that you shall
want to be doing it in 10 years. Didn't you think about that? Haha.
Schadenfreude.

Or maybe it's just a case of "You need to love what you do, because shit gets
really really hard, and any rational person would give up." Maybe shit is just
really really hard and you don't love it. So, nothing wrong with you. Just
your situation is sub optimal.

I don't know how this works, but if you can get your stock options ( if
they've vested ), just take them, and to do the acquisition or not depending
on whether that will net you more money.

Dude -- screw the duty to investors and employees -- take care of yourself.
You probably never know how much time you have in this body, so do what you
wanna do. Pull the trigger, since time is your most valuable asset. Why sink
another 3 to 6 months ? ( Sunk Cost Fallacy ) -- just get out and be with your
family. What if you try to white knuckle this, choose to be a slave to your
investors and employees ( slaves ), "do the right thing", and your
relationship with your wife frays, and you can't fix it...and you're in worse
shape 6 months down the line?

Take care of your mental health. Fixing the company, finding a replacement,
serving your investors and employees doesn't sound to me like it is going to
improve your mental health. So do something that will.

And remember, depression is really just anger ( barring "chemical imbalance"
believers -- sorry where does that imbalance come from? either you've always
been nature / nurture fucked up, or you made choices that didn't work
emotionally for you, and "chemically imbalanced yourself" ), turned inward on
yourself, that you haven't found a constructive outlet to express. So work out
what you are angry about ( maybe about this company, or something about this
situation ) and work out a constructive way to fix the problem. You are a
problem solver, right?

Working at Wal Mart, doesn't seem to me like it is a constructive solution.
But yeah, talk to a professional. And are you dealing with some loss of a
close family member or friend? That's definitely capable of contributing to
how you are now. And it certainly pays to talk to a professional to help you
through that.

------
graeme
The good news is: you built a functioning system!

Within thay structure, there is likely much room to make it much more
tolerable, even freeing.

I say good news, because many people manage to have both a restrictive
structure _and_ a failimg business.

So you'rs already halfway there, and frankly, you've done the hard half.

What you need do is figure out how mucn _actually_ depends on you. Likely far
less than you think.

Then, once you've done that, figure out how to have the other responsibilities
taken care of otherwise.

For a couple of days, track everything you do and how long it takes you. If
that doesn't capture the variety, do it for a week.

Then look it all over, and classify it. It is:

* something only you could do * something someone else could do (well enough, even if you'd be better) * actually unnecessary. (You'd be surprised how much stuff doesn't matter)

Then, you focus on:

1\. Eliminating the unncessary 2\. Identifying who could do the stuff in the
second category, and create processes for them to follow. 3\. Then you're just
left with the essential. If you do ateps 1 and 2 well, you can then switch to
replacing your higher level functions.

Pretend you're the acquiring company, and your (the founder) have quit
abruptly. How does the acquiring company run things? They are surely under no
illusion that you are an irreplaceable part of the business.

You might need a vacation, or a break, as others suggest. (You will
eventually, for sure). But I find that when I get overwhelmed, addressing some
of the stuff above is the biggest stress reliver.

I do find a week of comparative isolation helps for this task though.
(Actually, removing yourself from the office periodically can be a good way to
digure out what _has_ to be done. Feix Denniss wrote this is how stuff ended
up delegated from him)

Strongly recommended reading:

 _The Four Hour Workweek_ The e myth revisited This:
[https://sivers.org/delegate](https://sivers.org/delegate) And this, as a
caution: [https://sivers.org/abdicate](https://sivers.org/abdicate)

Re the four hour workweek: selectively read this one. You're obviously not
about to found an automated business from scratch. You're instead trying to
make an existing operation less dependent on you.

So read for that purpose. It is an incredibly productive book if read the
right way.

I run a business without employees, so take all this with a small grain of
salt. I've been there with the overwhelm, but you have responsibilities I
don't.

But I believe the above method will apply to your situation. You can turn your
business from a drain to one with far more autonomy. It will be good
preparation for phasing yoursef out with the acquistion.

Trust me, if you can make it to the other side, it's worth it. To decide every
day what you want to do is an incredible freedom.

You do _not_ get that as a walmart clerk. But if you've built a successful
business and just need to optimize it, you are surprisingly close to a very
free life.

Edit: Just reread and spotted the bit about domain knowledge. I'm in a bit of
a similar situation in that the work I do is highly specific. For growth, I
basically can't hire _anyone_ to do part of what I do.

But, for all the admin work, I can, so I outsourced most of it.

For developer retention, I'd reach out to other software business owners in
your city, and ask them how _they_ do it. But that's likely a later stage
thing. There are probably easier to deletate components you can take care of
first.

------
karmajunkie
This sounds like a fairly classic case of burnout, which you've probably
gathered from reading the other comments here. There's good news and bad news
in that.

On the good news: there are some short-term fixes you can pursue that will
probably help a lot.

* Antidepressants, while I don't think they're a long-term solution for anybody with exogenous depression (i.e. you're not someone with a chemical imbalance in your personal biology) can be really, really useful for helping you climb out of a rut. I was dealing with a really bad streak of depression awhile back and didn't even realize it because the character of it was so different from what I was used to in my 20s. After a few months and some targeted counseling, I found I was operating with much more clarity.

* Better sleep—you didn't mention it, but I can guess that you're burning the candle at both ends and have been for some time. My particular antidepressant helped immensely with that as well.

* Counseling. This is one a lot of us have trouble with when it comes to taking that step. But do it, seriously. And you might be surprised to find out your wife probably already has a good idea about it—mine saw it way before I did. She didn't know exactly what the problem was, but she knew we weren't just fighting about whose turn it was to do the dishes.

* Perspective. This is really hard to get when you're in the midst of a depressive cycle or dealing with burnout. You are highly unlikely to be the only one who can do your job. It may take some training to get someone else to learn this stuff, and there may be some hiccups along the way, but unless your business is incredibly brittle you'll be ok. Look around at your industry and try to identify people who could do slices of your job, and then maybe have some conversations and see what it would take to get them to join you. If the programming is really just dead-simple CRUD for the most part, consider outsourcing it to someone or a team who will work on it hourly or weekly.

The bad news:

* Yes, as a founder you're likely part of the acquisition. This doesn't mean you don't have some room to negotiate with the acquiring company for a month or two of vacation after it closes. Take some time and go to the beach and recharge. You may not want to come back at the end but you'll at least feel rested enough to do the job.

* If you're really burnt out, this can take some time to climb out of. Be patient with yourself and put structures in your life to help you get out of it. I started taking a karate class in a style I spent almost a decade in 20 years ago—its really helped a lot to be physical, and since I'm not the kind of person who is terribly motivated to go to a gym, its probably my only real option realistically to get myself to work out. Whatever your thing is, you gotta build in breaks somewhere.

When you get through this, put a reminder on your calendar far in the future,
far enough you'll forget you did it, and if you can predict stressful periods,
during or just before one of those. Give your future self some words of
encouragement. Mine popped up on May 1 and was a much-needed reminder of a few
things going into my busy season.

You'll be ok man, just try not to do anything drastic when you're feeling this
way. When "here" looks bad, sometimes "anywhere but here" seems like it'd be
better, but all that baggage you just bring with you.

~~~
contingencies
_Stay away from antidepressants._ At least research heavily before considering
this path - they have really bad side affects including addiction.

~~~
karmajunkie
Or, you know, go to an accredited medical professional instead of taking
medical advice from randos on HN. Incidentally, a side effect of depression is
also addiction.

------
YuriNiyazov
Drink some St. John's Wort.

------
cat199
pretty much been said here but..

1) Step sloowly.. It's easy to lose perspective here and make decisions you
might regret later..

Case in point - worked at a company that was acquired for lots of $$$ - while
the founder did well, his 'explanation to the company for selling' email
basically sounded like someone whining about not being able to handle stress
when essentially he was running the place 24x7 and could have easily
structured himself at arms length.. and it was not a small shop at that point
either with several 100s of employees.. I'm sure with proper perspective he
could have done much much better (like, orders of magnitude, potential
internet mogul, etc) in the aquisition.. Those who are buying are not your
friends, and are looking for anything to maximise their side of the deal..
taking advantage of your stress level and 'need' for escape will be one of
them, and this only serves to let the team down in the bigger sense.

2) _This_ is your challenge now. The company is up, it's running, it's doing
well. The challenge now is adapting. Apparently you're having some difficulty
with that. Others have mentioned vacation and refactoring your role and
therapy or finding better life stress skills. I think that is your plan.

If I were you:

a) mini vacation: a couple days (e.g. long weekend) as unplugged as possible,
possibly with trusted advisors or so, to think of any/all things that could be
restructured to relieve immediate short term stresses in the course of 1-2
weeks, as well as personal planning for 'c' If advisors present, present it as
'getting ready for the next stage' (if you do still end up leaving, this will
only help the transition anyway). include in this some kind of expectation for
a longer trip coming up, and how to manage during this time (others have
mentioned this as a way for process inventory.. exactly)

b) implement the mini vacation plans during work in next 1-2 weeks.

c) do some quick hits in life structure while mini vacation plans are getting
done: implement stress relief activites, reach out to a few ppl who can assist
with venting/discussing in a constructive way. this would be the time for
wife/friends/therapy/spiritual/healthy stress relieving hobby

d) Go on the longer trip. bring wife. rebond, get perspective, think of more
in-depth ways to restructure your role going forward over the longer haul
(e.g. 6mo-1y). Don't do this all day - make it a significant but not all
encompassing part of your day. structure is key. also to see you are taking
control of the situation - time managment here,getting perspective there,
being 'in charge' yet not in the weeds, etc.

e) come back, implement longer term strategy. add further break at end of
this, and revisit results. make another similar plan, resolve only to decide
on the effect of the 1st 6mo plan after another period. (e.g. let your changes
sink in).

not sure of your age/life experience but there could be other things afoot
here.. e.g. you are dreading 'what's next' since life has been leading up to
this moment and don't know what to do after, so better to 'take control' by
quitting and then you don't have to deal.. the mind can play significant
tricks.. so yes, hence #1 - redefining your role as accepting this challenge,
and stepping carefully.

------
flamedoge
sell and get out. fast.

------
futun
Been there. It's a hard choice.

I took some risk off the table and did the deal.

Was it the right choice? I'm still not sure. I was certainly less stressed
about money afterwards. But I was also left feeling like I probably short
circuited many more meaningful (and profitable) levels of success. How much
would we have been worth? I'll never know.

But... looking back on it... If I had it to do over again, I probably would
have made the same call.

I know exactly where you're at.

Here's the question: What else do you have going on that gives you hope,
enthusiasm and energy?

If the answer is "nothing". Don't do the deal.

If you have a list of other things in your life, or things you want to try. Do
it.

------
bitL
Don't talk to your wife about it, you'll show her a weakness, she will start
subconsciously resent you, become colder and distant and your stress will
double. She has you as her rock, she doesn't want a weak man to rely on.

Start instead some sport, take care of your body (try sauna + cold baths
together), eat brain-boosting supplements, kick out sugar/flour-based food for
a month, switch your phone off for 4 hours during work day and tell everyone
about your reachability, start learning something on a side which makes you
happy. You have a happiness deficit; do something you always wanted to do
though don't overdo it, and allow yourself to be a bit happy for no reason ;-)

~~~
jwdunne
That's the most ridiculous thing that I've ever heard about marriage.

In a solid, loving, marriage, your wife will resent you for not being open and
honest. She's meant to be your best friend. She wants to be there for you as
much as you are for her.

My Mrs has cried before now because I've not let her in on my hard times, my
pain. She was devastated​ to know what I was going through alone. She assumed
I'd closed up because I didn't care, I didn't love her anymore.

Yeah take the latter advice but if you want a happy life don't take the
former. This will not lead to a happy marriage, which is, if good, the biggest
source of happiness you can get.

~~~
yuhong
That being said, I do dislike this having to be posted anonymously.

------
asia067
So does that mean you're hiring developers?

Hit me up - email is on profile.

~~~
bbcbasic
If anything he'd be hiring a manager or c level.

~~~
asia067
Apparently 3-4 people think it is in bad taste to volunteer my services. I
won't retract it. It was in good taste to offer help to an individual that is
struggling.

------
ultim8k
Welcome on earth. I don't want to be a developer anymore. I don't want to do
business with anyone. But I have to. I'm not giving up. Sometimes you have to
be tough man. Just stop moaning and work on how to survive. There is none else
who knows better than you how. Also don't try! Do it or do not.

------
thasdfjadfooa
Jason lemkin has a great post on this that might be helpful:
[https://www.saastr.com/is-burnout-especially-
intensepervasiv...](https://www.saastr.com/is-burnout-especially-
intensepervasive-in-failed-entrepreneurs/)

and [https://www.saastr.com/the-holidays-part-1-im-tired-of-
runni...](https://www.saastr.com/the-holidays-part-1-im-tired-of-running-my-
successful-start-up-after-x-years-what-should-i-do/)

Essentially it is about hiring managers to share the burden with you. It
doesn't have to be expensive either cause you can find hungry guys with lots
of brains that are fast learners and hard workers to take over the worst parts
of your role relatively quickly.

I would recommend trying to remove yourself from the critical path and release
control as different people make different mistakes.

Acquisitions sure look attractive at this point but they are outside your zone
of control so they could wind up being major disappointments too.

