
Ask HN: Do you have the courage to abandon your high paying job? - tsetse
I&#x27;m in my early 40s and live in a rental condo with my family in a West Coast city. I have a high paying job in one of the FANG companies, making close to 500K&#x2F;year. At the same time, I have a decent amount of savings (600K 401k and 1.1M in cash in my bank account from a property sale).<p>The only problem is that I can&#x27;t really stand my job. I had prestigious positions in other major companies but I pretty much hated them all.<p>Yes, I should be thankful to have a gig at a major tech company. But just because I&#x27;m okay at what I do and was able to profit from my skills, it doesn&#x27;t mean that I like it...<p>I&#x27;m considering moving to a cheaper area of the country (also due to family reasons) to start my own company. I&#x27;m not ready to share what I&#x27;ll do, but just for the sake of my question, it will be something I love with a risk profile similar to creating a mobile game company - high chance of failure, average to low chance of making some money and low, but not zero, chance of making a lot of money. I&#x27;m decent at this particular activity, but not world class (yet)! This company will need at least 2-3 years before actually having a chance to make good money. Due to my savings, I can wait this much and then some.<p>The reason I&#x27;m writing this is because I&#x27;m panicking at the prospect of throwing away my high income, high stress, low happiness career for a risky enterprise that will likely not work out. I&#x27;m particularly concerned about having to come back to the job market if my company fails, likely working on an even worse job outside the major tech centers (the bright side is that if the company fails, given its small costs, I&#x27;ll still have ~500K in bank)<p>My question is: has anyone here, in a similar situation, done something like this? And if your company failed, have you been able to come back to the market in a good situation?
======
poof131
Avoid drastic moves. The older I get the more I realize most “drastic move”
stories are bs PR pieces. Think how you can move in the direction you want to
go in steps. Move to a cheaper location: see if you can move to a satellite
office or work remote. No, then look at other jobs you could interview at in
the area you want to move to. Translate your FANG experience into a career
jump. Then you will have experience and connections in the area, so if your
business flounders you have options to fall back on and aren’t starting cold.
Starting your business: find a job with better work life balance and lay the
foundation for the jump in your spare time. Focus on the some money path vs.
the a lot of money path. See if there are people in the area you move to who
can help. Take steps and avoid jumps. But it sounds like you should start
moving in this direction now so you don’t get so fed up at work that you make
the move in a reactionary fashion. Good luck and godspeed!

~~~
tachyonbeam
I agree that drastic moves are not always wise. OP said they had 1.1M in the
bank. If that money was invested in dividend stocks, they could have over 38K
of passive income a year. In the US, dividend income is only taxed at 15%,
too. They could opt to withdraw the 600K from the 401K, use that to buy a
condo in cash, and live off the dividend income. Retire now, basically, and
live a fairly comfortable life.

It's not princely living, but if I had that option, I would seriously consider
it. Having the freedom to do whatever you want with your own time, without the
pressure of a job, sounds amazing. I think if I were in that position, I would
end up doing something monetizable anyway, through hobby programming projects,
but it would be so great to have the freedom to do it at whatever pace I want,
and to get to pick what I work on.

If retiring on 1.1M cash + 600K 401K doesn't seem like enough, then sucking it
up and staying at the 500K/year job for 2-5 years more is also an option. Cut
down on champagne a bit, delay the yearly car upgrade, and you should easily
be able to put away 100K a year.

~~~
segmondy
If you retired with a family and have 38k and got $28.5k after tax. Do you
know how much health insurance costs for a family? Property tax on a property
that's $600k is not going to be cheap either. Add utilities, property
maintenance. You are going to be looking for another job fast or dipping into
your savings.

~~~
toomuchtodo
In the right states (ie, those who took ACA subsidies from the federal gov),
your premiums are based on your income. Low income = low health insurance
premiums.

Agreed that a 600k condo is a poor choice; move to a college town where you
can get a single family home for $150k-200k and the property taxes are only
~$2-3k/year. Avoid an HOA.

You can retire at any time if your investment income can support your
expenses. Think about those expenses carefully. It is entirely possible for a
family of four to live off of ~$30k/year if you receive ACA subsidies, your
house is paid off (no housing expense), and you have no outlier expenses.

------
lacker
In 2009 I left my well-paying job at Google to start a startup. I wasn't
terribly unhappy at Google - I just didn't want to spend my whole life there,
so it seemed like a good time to do something else. Over the next year and a
half or so, that startup fizzled.

Psychologically that point of failure felt pretty bad. But it seemed pretty
clear that I would be able to come back on the job market in a fine situation.
Employers seemed to consider a year working on a startup as either a neutral
or a positive item on my resume. And I had certainly learned a lot more about
many different things than I would have in a few more years at Google.

Anyway, I felt like I had more fun working at the startup, and since my
fizzled startup was actually able to pay me a bit I still had decent savings,
so I did another startup. Investors thought the experience at the previous
failed startup was a positive, and the experience from the first failed one
really seemed like it was helpful to me too.

For you, if you have a high paying job at a FANG company and had prestigious
positions in other companies then you are a pretty competent person. You are
going to be able to find a job that pays you well enough to live a good
lifestyle, even if you take some time on a failed venture, and even if you
move to a different part of the country. You don't need to be afraid of a
negative outcome.

You only have one life to live. Are you going to spend the rest of it in a
well-paying job that you hate? Knowing that it might have worked out better if
you had been willing to take a little risk?

TLDR Do it!

~~~
justonepost
Wrong advice. First live the life before doing it. Going to move somewhere?
Rent first. Going to live a life with a lower living standard? Start living on
a budget first. So when you are forced to do this, you and your family will be
able to accept and adapt properly.

~~~
tsetse
Good news on the living standard - I grew up in relative poverty, so that
won't be as much of a problem. I still don't spend a lot these days...

~~~
kamaal
>>I grew up in relative poverty

Not sure what you are trying to say here. Do you want to go back to those
days?

~~~
tsetse
I'm okay with that, yes.

------
derekp7
Before you do this (quit to start your own company), consider FIRE --
financial independence, retire early. With a 500K salary look at reducing your
expenses to bare minimum for the next 2 - 5 years, and see if you can build up
your investment portfolio to a couple million -- that would give you 80K a
year (using a safe withdrawal rate of 4%) to live off of. (Remember that
income from long-term investments is taxed at a lower rate, and no FICA is
taken out either). That is more than enough if you move to the middle of the
US. Of course, many people do FIRE at much lower, all depends on what you are
willing to accept.

------
Trundle
Have you looked in to FIRE (financial independence; retire early) at all? At
your income it doesn't seem like it would take all that long to get to a point
where retirement is a possibility. Then you'd be free to pursue your low cost
hobby business without fear of returning to the job market in a reduced
capacity.

It would come down to how important your lifestyle is to you and your spouse I
guess, but if you consider an expensive lifestyle highly important then
torpedoing your career doesn't sound like a smart move either.

There's also the option of a middle ground where you go to a smaller company
at a pay cut in exchange for whatever concession it is that's important to
you. Remote, tons of vacation days, etc. There are smaller companies that want
experienced bigco talent that know they can't compete on price.

~~~
mykull
I don't understand the idea that living off investments is "independence".
It's just a different kind of dependence. You're depending on other people to
do work while reaping the benefits. Sounds great, except when too many people
do it.

~~~
toomuchtodo
> Sounds great, except when too many people do it.

It's a self regulating system. The more money that flows into investments, the
lower returns will be pushed, causing more money to be required to support
yourself off of investments alone.

~~~
mykull
It isn't that simple at all. When the returns are pushed lower, the means of
extracting wealth from low class workers get more brutal. Suffering builds up
at the bottom because of decisions at the top, and decision makers don't care
because their experiences are entirely disconnected.

------
WheelsAtLarge
Don't... Most jobs suck. There's no way around it. Most jobs have aspects that
you just don't want to do. That's why you get paid rather than you pay. You
need to figure out how to make your current job fit your needs, financial and
psychological.

One thing you can do is to decide how much it takes for you to retire in a
more affordable part of the country and work until you reach it at the fastest
rate.

Starting a successful business is harder than what you imagine and you'll be
surprised how quickly it sucks up your money. Don't put your self in a
situation where you have to find whatever job comes along because you are
desperate for money.

~~~
watwut
"Have aspects you dont like" and "can't really stand my job" are two
fundamentally different statements. It is not the same.

Majority if tech jobs are not "high stress" either. They are "somewhat stress"
at max.

~~~
kazinator
Also, nowhere near 500K.

------
fusiongyro
I live in a small town in New Mexico. My ~1200 sq. ft. house cost $95k. My
wife and I lived comfortably here, the two of us, on essentially $70k/year for
the first four years of our marriage. Since then, the money has gone up, we
have two kids and raising two kids here has been fairly inexpensive too.

Across most of the country, you could take an 80% pay cut and still be
considered rich by 90% of the people around you.

Life is different out here but I think you have enough money, and you know it,
and it isn't making you happy or you wouldn't be contemplating your move. So
fuck it, what have you got to lose? You'll probably find that the abundance of
time and massive reduction in stress is adequate compensation.

------
chrisherd
Just founded my startup - left a high paying job, have two kids, own my house,
a lot of liabilities etc.

Figured if I didn't take the risk now I'd always regret it. Things are tight,
but each morning I awaken invigorated by the opportunity to create something
that matter. Never underestimate the vitality gained by working on something
you love.

Realise the liklihood that I don't succeed is high, but when faced with the
certainty of lifelong regret if I didn't it simplified things. Time is the
only thing I can't get back, honestly, I'm just upset I didn't do it sooner.
Managed to convince the CEO/Founder of an existing unicorn to invest, but
probably won't be able to draw a salary for 6-12 months, and that is scary.

Would love to discus more, drop me a line if interested: chris@nexves.com

~~~
CyanLite2
This!

------
bsvalley
I’ve been in this exact same situation. My best advise would be to start your
business aside while maintaining your current job. Do not quit until you have
some sort of version #1 of your product or whatever that is. You need data
before making your desicion. I planned everything in my head but my steps were
way too vague. I will build this kind of products or I’m even gonna try that
business that has nothing to do with tech since I have these extra skills.
That’s BS. In reality the only smooth transision from a guaranteed paycheck to
your own net profite is huge. I lost too much time “trying out things” rather
that executing tasks that were already planned ahead of time for a specific
business. A business I knew from a fact that would generate an income right
away based on feedback or prior experiences. In other words, time was the only
missing variable in achieving those steps. In which case it would make total
sense to quit your fulltime job to complete your tasks. Again, I didn’t have
the data prior to leaving my job so I was running off of guesses and hope.

Back to reality after running out of savings and after freaking out, I took a
huge slap in the face interviewing for 30 companies... trying to get the same
job I hated before, having to go through all the painful and stressful
interviews while seing my bank account getting closer to $0. At the end of the
day I took a huge pay cut, I’m no longer working for a top tech company and I
feel like I took 5 steps backwards in my 9-5 career. There are hundreds of
young candidates out there who have the same skills, same background etc. And
they all want your job. I don’t have any savings and I’m back at a crapy job
at an average tech company. That sucks, but at least I still know I will ot
retire from a 9-5 job in 20 years from now. I will try over and over until I’m
able to generate a sufficent income from my own business. I had to go through
this experience in order for me to learn something. Today I know exactly what
to do next. Just need to recover from that free fall.

~~~
throwaway93192
At many companies, including all FANG-like companies, you can't start a
business on the side. Your employer may claim ownership and you can be fired
for breaking your employment contract.

~~~
drenvuk
In California, that's not the case. As long as it's not a competitor or in a
similar space the company should have no claim to your business or ideas
generated while not using the companies resources.

~~~
siberianbear
I asked a California business attorney this question. She said that you really
don't have that much protection. If your idea/company is valuable enough, your
huge tech company employer will just sue you into oblivion. The legal costs
alone will bury you. The specific California statute that protects what you do
with your own time and resources doesn't protect you very much.

~~~
drenvuk
It's some protection, and there are niches that none of those tech companies
have touched yet. I don't see why people don't see them. If it's a thought
that should normally occur in your work day because it could related to your
job description or company's products that you could reasonably have an impact
on then you're not protected. If it's completely out of left field relative to
the previous items then there's no way they could lay claim to it. How could
they? Tech is much broader that a lot of people generally think about. Let's
say you're doing front end work and your company is some social network but at
night you have a brilliant idea for automating biological sample isolation
using some robotic system you conjured up during a cup of hot cocoa on the
weekend? How is the company going to even attempt to sue you for it when you
used none of their resources, the idea was worked on during non-standard
hours, and it has nothing to do with them?

If by tech you mean "along the same lines of what I'm doing at work" then
you're gonna have a rough time. I do hope that your mind has the ability to
wander a bit further from the train of thought you have you typically have
while doing what you're paid for.

This goes for the other two replies above as well. If you have an original
idea then you're safe. The hard part is having an original idea or even an
idea that is several steps removed from a previous idea but still useful.

------
haser_au
Take a year of unpaid sabbatical leave. If the company you work for actually
wants to keep you around, they'll give you this opportunity to take a career
break to really have a go at something different.

It works for you and for the company. You get to go out there and see what
it's like for startups, the challenges, etc. And then apply those lessons
internally.

I know lots of people in their 40's and 50's who have done this, with exactly
the same golden handcuffs you're talking about. Some of them came back, and
rewarded the company's trust with a revitialised vigour. Others decided to
leave and pursue their chosen option.

Example: A guy I know was a senior Account Manager at a major telco in
Australia. He decided to start a scuba diving business in Thailand. He took 6
months to 'test the waters' (sorry, that was a terrible pun) and decided that
was his dream.

Life is short. Live it to the full.

~~~
maxwin
Most company can’t leave a position open for 1 year. If they can , then they
probably don’t need this person anymore.

~~~
badpun
I'd say that, especially in a large corporation, if you're a company veteran,
with X years of knowledge of the internals, systems, business cases, managers
etc., then you're really worth a lot more than a random guy from the street,
even he matches your CV in terms of generic experience. A smart company would
be more than happy to take you back after your sabbatical.

In other words, in large organizations, organizational complexity can be the
main challenge, while tech challenges are really secondary. I see that in a
large bank every day.

------
GoldenMonkey
I have done this many times. Failing each time. The last failure left me with
a job at 1/2 of my previous salary. And that after burning thru savings.

What I have discovered. No matter how well your product meets the needs of
your market. It is sales that will make your company. And sales can be a lot
harder than it seems. Even in a b to b business where companies stand to make
$, using your product.

What I am working on now... my free by age 50 plan (i am 42). Create enough
streams of income to not need a job. If you don’t want to work. Become anti-
fragile... no debt, not reliant on a single source of income(job). So, I am
not quitting the crappy job anytime soon. Reduce expenses, save more, create
income streams in your spare time. The Mr money mustache blog has this figured
out. You can do anything you want, after you have secured your future forever.

------
tsetse010
I was at a FANG peer, making > 900k/yr. I have savings similar to yours, a
little bit more perhaps, but also expenses (mortgage, private school x2 kids,
2x car payments). I'm not bragging, just providing context.

I quit my job a month ago to go join a much smaller company and took a 70% pay
cut. I'll still make enough to pay the bills, and I have some equity so that
if it works out I'll probably break even in 5-6 years. But it probably won't,
and if it doesn't I won't be crushed. I am making this decision for a reason
(personal development, interest, wanting to learn something new, etc), and if
it's a disaster I'll be able to find another job relatively easily I hope.
Luckily, I'm not changing cities.

Anyway, you asked if someone had done something similar, so wanted to jump in
and mention it.

~~~
ganeshkrishnan
I think you responded to the post rather than a comment. Not sure what is the
parent of this comment

------
DubiousPusher
If your job is making you miserable, how are you even worried about some
hypothetical future job?

You have a 1.1 million dollar safety net and you're worried about having to
take a random job. I think this is a classic case of having too much money for
to long. You need to make a change but you need to be 100% that change is
likely to increase the happiness of the people in your family. You have the
finances to live your life 1000 different ways. Think for a moment if these
two really are the only options.

Make a change soon or you never will. And if that change is needful for family
reasons it's even more important it comes soon.

~~~
JBlue42
The other advice is rather sensible but I'll go ahead and support this point.

I'm at a $22/hr help desk job on the phone for 90% of the day and every
morning pray that I don't end up getting killed by a moron on the freeway
going to a job I vehemently dislike. I'm only there to buffer my savings while
studying and working towards something else but even if it goes to shit I know
I have other options (this being in my early 30s and having been unemployed
prior).

Having money in the bank and real estate gives you MANY MORE options in terms
of a worse case scenario. OP honestly might just need a break (I like the
sabbatical idea) and/or long periods of time to think about themselves and
what they want vs reacting. Don't let anxiety get the best of you, especially
in terms of making drastic moves. Off the cuff, it might even be a good idea
to check in with a therapist. Even being relatively cash-conscious, I found
seeing a therapist on a sliding scale for a couple months while unemployed to
be extremely helpful.

~~~
DubiousPusher
I think if you want to view your life as an economic asset then the advice on
offer in most of this thread is pretty good. If you want to view your life as
anything more than that it's completely insane. Think about this. The only
really good thing about making lots of money is it gives you freedom. And what
people in this thread are saying is this person makes too much money to be
free to change their life because of "opportunity cost". Then what's the point
of getting rich at all!?

I love economics. It's totally fascinating to me, the way money can be seen to
behave like physics in many ways. But it's not physics and seeing everything
in terms of Econ 101 island economies breaks down eventually.

Think about it this way. The advice in this thread would say that you could
quit your job whenever because of the low opportunity cost of $22/hour. But
whose life is going to get more messed up by quitting their job today? Yours
or this person with 1.1 in the bank? And if you need any time at all to answer
that question you need to burn your PhD in Econ right now, move to a small
apartment in a working class neighborhood and live in the real world for a
couple years.

~~~
JBlue42
I'm not sure we're disagreeing here. Maybe I read some of the thread wrong -
most of them seem to be saying "you have money - you have options. take a
break, do something else, etc". Then there are the FIRE people kinda saying
'suck it up and get true independence' and the like.

Maybe I was tired and my comment didn't come across as intended. I was
intending to say "I'm much poorer than you and still, due to my personal
circumstances - white, American, passport, etc, have options so OP, in
seemingly far far better circumstances has far, far more options"

~~~
DubiousPusher
Gotchya.

------
ryandrake
OK, time to blow some karma. This is one of those “only on HN” posts.
Seriously? “I have $500k income and $2M savings but I’m still not happy!”

Here’s some blunt feedback: get some perspective.

You can do pretty much whatever you want with that kind of coin. If you milked
that job for a decade or so, you could retire in opulent luxury almost
anywhere in the world. Hell, you could retire now and live modestly in a low
cost area. Most people in the world couldn’t imagine having that kind of
opportunity. I’d trade places with you in a heartbeat and so would 99% of the
people reading this.

Stick with that $500k job that makes your feelings sad, and wipe away your
tears with $100 bills. Sheesh!

~~~
rebaco
I thought that when I first started - if I just could go make X/year, I'd
retire really fast and it'd all be great!

it tends not to work out that way for most people, I think. Life gets
complicated. Sometimes we are the ones doing the complicating, some of it is
just that life gets more complex (promotions, kids, wife, stuff).

Being able to wipe away your tears with $100 bills comes at its cost too. Once
you have a bunch, you really start to wonder whether it's worth what you paid
to get them.

Viktor Frankl observed in a small book that the only thing we truly control is
our attitude to our situation, and that small book became a true classic.
Unfortunately, he had to live in a concentration camp for a few years to reach
that enlightenment. Zen teaches us that we need to let go of the struggle.
Again, few are enlightened. Christ called on us to follow Him and worry not
for the future because the cares of today are enough, and He was right, but
few of us can manage that either.

Perspective is everything, I always used to say. Perspective (and thus what
you ask) is, however, very difficult.

------
soneca
I am 38 yo now and I made 3 career decisions in my life that significantly
reduced my income. I never regretted them, quite the contrary.

I was never as wealthy as you, but proportionally, it is a similar situation.
My reserve wouldn't allow me to live for 3 years with no income, but I had the
benefit (in my last move) of my wife being able (and willing) to pay the bills
on a stable job she likes.

My decision process for those radical moves is: will I be able to endure the
realistic worst case scenario?

In your case, I imagine this scenario would be something like this: failing
miserably at your idea, not only financially, but not even enjoying working on
it as you predict you will. During this period your family would be living in
a significantly lower standard of living. A lot less luxury that 500k/year can
afford. After 4 years and having consumed 1/3 or 1/2 of your reserves, you
have to go back to the job market. You will find a job that will pay you
250k/year and you will hate _less_ than your current one (this is the
realistic part, I really doubt the skills that took you to a 500k job will not
get you choices, even after a 4 year gap, if you are willing to earn half
that).

Do you think you would be ok facing this worst case scenario? If you think it
might lead you to desperation, depression and hurt your family relationships,
don't do it. If you think it is not the end of the world and all your family
is on the same page, do it.

~~~
AnimalMuppet
Yeah. Your enjoyment of your work matters. It really does. It affects your
mental health. You don't just leave it all at the office when you walk out at
night.

But your family also matters. Whether your spouse is comfortable with your
move matters. If you're happier at work, but she hates living in the new
state, or is stressed about the new financial situation, you don't get to
leave _that_ at the office, either.

------
piotrkaminski
I doubt you'll find a consensus on this question. My opinion, for what it's
worth, is that this also follows the dictum of "asking if you should fire
someone means you've already made your decision", and prevaricating only
prolongs the pain.

I made a similar decision with much less of a financial cushion (and without
moving away from the west coast) and it worked out OK. I'm happy now and don't
regret giving up the millions. YMMV, of course. One tip: make it your goal to
get to ramen profitability ASAP, not in 2-3 years -- it has a wonderful way of
focusing your work.

Good luck whatever you choose, and keep in mind that either decision will
remain reversible for at least a few years. If you go out on your own, I don't
think having "I tried to run my own startup, failed, and learned a lot" will
be a negative when seeking another tech job, and you can always move back.

------
j32fun
I left a high paying job as well (400k+/year) and have a similar financial
profile as you about 2 years ago. I pursue my own projects, at my own pace. No
regrets.

In terms of finances, let's just say the year leading up to executing my plan,
my family (wife and kids) trimmed down a lot on expenses. No more crazy
vacations. We ate in a lot more. Psychologically, every one needs to be on the
same page. It goes without saying, but a spouse that is supportive helps a
lot.

Good luck.

~~~
ApolloRising
a rare spouse that would do that

------
andymoe
I spent two years on a self funded hardware startup. It failed and I spent all
but 10k of my money (including retirement) by the time I paid off debt that
would have trashed my credit for years. (Thanks partner) It was hard and
painful and I’m not sure I’d do it again. Certainly not that way. There is
something to be said for capital preservation.

On the other hand.. my absolute worst case was losing all my money and getting
another six figure job... which I did.

(36, two young kids)

~~~
AstralStorm
Second worst case would be doing that then... not getting a job. This is
always a possibility, the old adage of markets staying irrational longer than
you can stay solvent is very true.

------
jasonkester
The ultimate first world problem, but still a real one.

Around the time my first kid was born, I took a look at the profits from my
little handful of SaaS products and decided that, even though we were happily
living off it, it wasn't really "put a kid through college" money. So I picked
up a remote contract.

But, SaaS being Saas, business picked up. After a few years, the product
business was bringing in more than any full-time job I'd ever had before. But
I had negotiated my "Bay Area Rate" for this contract, and was therefore
_also_ bringing in a significant fraction of what the OP describes each year.

House paid off, savings saved, no money troubles on the horizon, but it
_still_ took a long time and a lot of effort to convince myself to drop that
contract. When the getting is good, it's really hard to deliberately stop the
getting.

But I did. Took the kids out of school for half a year and hopped a flight to
Southeast Asia to show them how mommy and daddy used to travel with backpacks
and sleep in tin huts on the beach. Then slowly settled back in to working on
the business stuff, when the weather didn't favor being outside, implementing
all those things I'd had to put off for 5 years and shaping them up to be the
solid revenue stream they'll need to be going forward.

But yeah, it's tough to do. Well worth it though.

To the OP, though, I'd recommend getting your spending sorted out. The math
above doesn't work out for me, and it sounds like you've ramped your lifestyle
up to consume most of that half million a year. Don't pull the plug until you
have that comfortably down to around $50k all in. Otherwise you'll burn
through your $1M savings in, well, 2 years. That would be no fun. And
completely unnecessary.

~~~
tsetse
My rise to riches was relatively recent. I was making 100K/year 10 years ago
and 200K/year 5 years ago when I moved to the West Coast.

------
kvz
Translation gradually if you can! See if you can work a day less, maybe via
contracting at your current firm, or for different ones. Make sure that you
have at least 1 real workday to crank out a MVP (and if you can, add evenings
and/or weekends sometimes). As soon as you have real customer/investor
interest, you can dial down your contracting as you dial up your business.
This is not without risk but it’s way less risky than a Big Bang approach, and
this worked well for me personally (founded Transloadit exactly like this
which I’ve been doing 5 years fulltime now, with 4 years of gradually ramping
up engagement while contracting for my old employer and a few others). I do
realize all situations are different and I was rather lucky/privileged to be
able to pull it off like this. But given your position & savings you are in a
better spot than I was. But maybe also more to lose, so I won’t pretend it
will be easier for you!

~~~
kvz
/Translation/Transition/

sorry for the typos I was on mobile, a dutch keyboard, and in a hurry :)

------
drawkbox
Use Jeff Bezos 'Regret Minimization Framework' to decide [1].

Basically, when you are 80, will you regret having tried and possibly failed
or regret having not tried at all?

Granted you aren't going to be Amazon probabilistically but it will definitely
make your life more interesting and put you in control of it and fully
responsible for it.

Personally I'd rather try and succeed or fail on my own than just be a cog in
the machine and possibly be on a ship that sinks out of my control or merely
latching onto success. I'd rather be the captain whether she sinks or sails
smoothly, hopefully the latter.

I went fully independent six years ago, originally just planning on a year,
and there have been times of awesome and times of rough waters, but she is
still sailing and it has been an adventure I know I won't regret having
embarked on. Three of my six years are the highest revenues/income I have had
annually in my career but one was the lowest ever, prepare for more volatility
if you do.

If you do, my recommendation is make good habits early, cut your costs, be
disciplined, aim for revenues as early as possible, work hard but work smart,
be sure to take time off, and especially enjoy your successes and learn from
your failures. Ship on the regular, and if you aren't, kick it in gear to go
all in.

[1]
[https://www.youtube.com/watch?v=jwG_qR6XmDQ](https://www.youtube.com/watch?v=jwG_qR6XmDQ)

------
fapjacks
I am considering it right now for exactly the same reason. I'm almost your
age, but I don't have a family. I don't have anywhere near your savings but
I've done this once before with almost nothing, and I didn't have any problem
coming back to the job market after my multi-year "hiatus" when I ran my own
company. I even took a multi-month "sabbatical" before returning to the job
market to travel and party and be a slob and pursue my own interests (with
basically no money), so there's a big hole in my work history. But nobody
seemed to care except for a couple of companies which I wouldn't have enjoyed
working at anyway. But I'll tell you the one thing: yolo.

------
rebaco
I'm in a somewhat similar situation, but I'm 50 and the equivalent of a cobol
programmer - useful in my niche (financial services), and a lot of general
experience in the field, incredibly useful to a few firms but I don't know the
latest hottest tech stacks so not generally employable. Also not an
entrepeneur, so a startup is out (don't have any good ideas anyway).

If I go, it'll have to be along the FIRE line, and I haven't figured out what
the alternative revenue stream is. Probably consulting back to the industry
part-time, as long as I don't take a couple years off and stop being
"somebody".

I get the panic. It's hard to walk away from the job and the money and the
status. It doesn't matter if you objectively don't need it - you get used to
it. It's a massive security blanket - not just the money, but the perks, the
being coddled by the company. And while hard work plays a part in getting
there, you know that some of it's just pure luck. Are you going to just throw
it away before you're sure you're done forever?

I've been at this level for 10 years now and all of the above just sinks into
the bones. It's harder as you get older - age discrimination and all that, and
you have fewer years in which to recover if you really do screw it up.

Have you thought about the health insurance angle? That's the biggest bind-up
of all for me. You can't get decent health insurance without a full-time job.

I don't know how much help I am, because no I haven't screwed up the courage
yet, and I don't have a good plan. But I understand the boat you're in.

~~~
scarface74
It's not about age discrimination. I'm only 6 years younger than you and while
I'm not going to be working at the next cool hipster startup, I've been
aggressive about learning the latest technology and moving around jobs to keep
my skills current. It's never taken me more than two or three weeks from the
time I started looking until I got an offer - and that's with me being
relatively picky.

I would have no "security" being at the mercy of one company knowing that if
they let me go, it would be hard to find another job. I felt a lot less secure
between the time I was 28-34 when I had let my skills atrophy than I do now in
my mid 40s and I look at job requirements in my market when I know I meet the
qualifications.

As far as title, who cares? I left a job as a "senior architect" because I
knew the road map wasn't going to allow me to stay current and took a job as a
"senior developer" (making more money) at a company that would let me level up
in my technical skills.

You can get decent insurance without a full time job - the ACA is still a
thing. It costs a lot, but if you have savings or can generate enough income
from your business - it's just another expense.

------
hfdgiutdryg
$500k per year?! You would be insane to walk away from that. Keep it up for a
decade, save as much as you can, and retire in your 50s.

~~~
smilesnd
$500k a year Cali translate to $100k a year where I live. Cost of living in
Cali is crazy expensive.

~~~
dmoy
Cost of living in Cali is crazy expensive, though your example is a bit
exaggerated. $250k if it's medium-ish midwest town maybe.

~~~
smilesnd
There is a website that calculates this kind of stuff.

[https://www.bestplaces.net/cost-of-living/charlotte-
nc/palo-...](https://www.bestplaces.net/cost-of-living/charlotte-nc/palo-alto-
ca/100000)

*Edited: Should also say I fully understand that if your duckduckgo skills are hardcore mode you can find a website to support anything you say.

~~~
dmoy
Sure if you cherry pick like literally the most expensive 25sq mile
neighborhood, and are dead set on buying real estate and not renting.

But even then, the calculation on bestplaces.net appears to be a bit farcical:

Assuming you spend $8k/month on renting a large modern 2500+ sqft house, and
are in the tax bracket which knocks your after-tax income to $300k from $500k,
you still have ~$200k after tax and housing. The rest of your expenses are not
going to be so much more expensive (~4x) that they don't vastly exceed $100k -
tax (~25k) - housing (24k for similar) in NC.

$250k in NC vs $500k in bay area though sure, that's in the right realm.

------
milliondollar
I just quit a $1M a year job at 45 years old, moved out of the city into the
country, am working to bootstrap something from scratch, and am the happiest
I've ever been. (That said, I'm one week into my "retirement", so time will
tell.)

I did the math and realized that I had "enough"; anything more would just be
working to enlarge my kids inheritance. So there was nothing really stopping
me except peer pressure. Given that cultural pressure, it was one of the
hardest things I've ever done, and all my peers were simultaneously jealous
and incredulous.

On the risk, I think you are really over-weighting the downside scenarios. I
realized that given my track record and resume, in the worse case scenario I
could always "get a job" if things didn't work out. You will never starve.

And if you are bootstrapping something with low capital costs, you will be
able to monitor and see in advance if it's working or not. The decision is not
binary. You get to adjust as you go!

~~~
shanghaiaway
Can I ask what kind of job pays $1M per year?

~~~
simantel
[https://news.ycombinator.com/item?id=13421078](https://news.ycombinator.com/item?id=13421078)

------
thrwy473727
I quit my high paying big tech job in 2014 to start a YC company that failed
miserably after about 6 months. I spent another couple of years funemployed.
Money was tight but I really enjoyed spending week after week reading, playing
videogames, and working on side projects. I’ve had a real job for a year now.
Interviewing was hard —- trendy tech stacks shifted significantly in the time
I was away.

If its possible, get a ramen-profitable version of your idea launched while
you still have your job.

Post an email address if you would like more specifics.

------
drenvuk
There have been others saying don't quit your day job and to do it on the
side. I agree. It may be more stressful and you might lose a bit of sleep but
it is far preferable to racing against the emptying of your bank account. I've
done it twice and each time I've failed. However each time I've gotten a tech
job in about a month and a half's time after trying to get back to 9-5. But
the stress and occasional bouts of depression are not worth it especially
considering when you keep your day job you'll have more money to pump into
your ideas. The golden handcuffs you're trying to escape from are actually
what will enable you to be successful in that escape.

I _heavily_ urge you to stay in your job and make sure that your company is
profitable and has a very good chance at sustainable growth before you quit
your day job.

Good luck either way.

------
waytogo
The problem you face is pretty simple, your opportunity costs are just too
high:

The probability that you create a company as a first-time founder that
generates $500k/yr or $42k/month is...

\- in 12 months ultra low

\- in 24 months super low

\- in 36 months low

And being a founder lacking success over a period of many months or years
might be much worse than what you experience now. You would learn a lot
though. But I doubt that your mental health would be better.

------
justonepost
If you are panicking do not do it. It’s really that simple. Work with a
therapist to understand first why you are incapable of being comfortable with
your life choices. Let me just say when I made the choice to accept a lower
living standard I had first spent several months living that life first, so
when it was forced on me there was no difficulty adapting.

------
tyingq
My experience..the older you get, the more willing you are to give up income
for freedom.

Happy to trade my nice house and cars to get a lower monthly cost basis. That
then allows me to take a lower stress, lower hours, but lower salary job.

I guess it's as simple as ageing makes your non-work time seem more valuable.

 _" Very few sit on their deathbed wishing they spent more time at work"_

------
1290cc
Maybe you could articulate what you dislike so much about your current job?

It sounds like you're seeking an outlet for creativity and the current job is
not giving you that. I personally don't see $500k/yr as an important factor as
for the majority of people there is no real difference after $150k/yr. The
burgers taste the same, great schools are available, same nice holiday
destinations. Anywhere outside of the US is cheap and your standard of living
would be high. Unless you have a weakness for luxury watches, high maintenance
women and overpriced champagne. I admit I do enjoy the odd bottle of
bollinger.

You're also thinking about starting a business completely the wrong way, you
never use your own money. This is what investors are for and you need to spend
time finding the right investors. The world of ICO's has made small
investments easier than ever before. For games you can use a kickstarter to
get it going. You could also move to a smaller company with a role that takes
up less of your personal time and start the company on the side or even become
a consultant giving you even more free time to move between paying projects
and personal ones. I would also see if you can network and contribute to an
existing game company to get a better feel for the business.

I'm earning more than you and work from home and have complete autonomy. I
live in the bay area and go kite surfing every afternoon in the summer and
work from a rented cabin in tahoe during the winter with my wife and little
corgi. I do not associate with the tech crowd outside of work or hob nob with
VC's in Palo Alto or the rat race of the peninsula. Keeps life fairly simple
and straight forward. I imagine this is something that would be attractive to
you.

------
csomar
I'm an advocate of change. However, you are not a free man. No one forced this
situation on you but that is another story.

Here is what I'll do to regain my freedom.

\- Figure out the cheapest/best (aka best quality/price) location in your
country. There is certainly a place with low taxes, low cost of living, good
schools and cheap housing.

\- Figure out the dollar amount to survive on that location without you
working a single hour. (ie: $50k)

\- Figure out how much you can make, passively, on investments in the stock
market or otherwise. (ie: 15% of your capital)

\- Figure out how much capital you need. Put 1/1.5 years costs ahead.

Have the capital? Move and never look back. Life is short, don't waste it
chasing expensive doors and meter squares. If you are spending your hours
doing a job you don't like to overspend on a hot real estate market; then you
can do better.

You have a family. You got the social part figured out already.

------
marcrosoft
Quit tomorrow. You’re smart enough and capable to make a salary most people
could only dream about. You’ll be fine. Most people retire on two years worth
of your salary.

~~~
fapjacks
Well, most Americans anyway appear to retire on about one-fifth of two years'
worth of his pre-tax salary. [0]

[0] [http://www.transamericacenter.org/docs/default-
source/resour...](http://www.transamericacenter.org/docs/default-
source/resources/center-research/16th-
annual/tcrs2015_sr_retirement_throughout_the_ages.pdf)

~~~
tsetse
Unfortunately (or fortunately depending on the perspective), I'm still
relatively young and will likely have to pay years of living costs. The
average retiree is much older - which is an advantage in this case.

------
ebcode
The title question is about courage, and I think that's what you're after. So
I would say, yes, I do have the courage to abandon my high-paying job.

Your description of what you'd like to do sounds like an adventure, and if
you're looking for someone here to tell you, "Yes, I started my own business
--- it was awesome, and now I'm a ba-zillionaire!", well, I can't do that; but
I can tell you that I too am chasing my dream like a fucking madman, and you
should absolutely go for that thing you love with all your heart.

... the more conservative side of me thinks you'd do well to put in a good
show/do some good work for your current employer, before setting off for the
high seas. If not enough for the golden handcuffs, at least enough to part on
friendly terms.

good luck to you!

------
Bombthecat
I would call it : prepare for retirement.

Reduce cost. ( Change house / Appartement)

Reduce working hours ( don't need to be drastic)

Get a hobby! ( Make sure it is one with social interactions)

Look for a position you like. With even less working hours. For example 40.

Prepare for retirement with a nice hobby. New friends and stress free
environment.

------
muzani
Bit of advice if starting a startup: make sure it's something you are willing
to cry over. A lot of smart people out there start startups, only to bounce
over one thing to the next for several years, never achieving something
because they don't care enough.

Startups get harder the more you age. If it is something you really want, that
you would regret not doing when you're old, make the leap.

If it is something you're doing because you think it's a better way to make
money, then don't. In your situation, you have other options, like buying a
team. I know a great guy running a startup while he's working, about as well
paid as yourself. He could afford to pay a lot of young, ambitious people.

------
jasoncrawford
You can absolutely return to the job market and get a good job again after
failing at a startup. This happens all the time. You are still just as
qualified after failing as before – probably more so – and employers know
this. I say this both as someone who has done this myself (and seen
friends/colleagues do it), and as a hiring manager who is more than happy to
talk to candidates like this.

Relocating outside the Bay Area will make it harder to find that job. But
there are lots of remote opportunities today, and in the worst case you might
be able to relo back here.

Life is short. If you are excited about this prospect, and you can afford to
spend the money if it doesn't work out, then go for it.

------
thomasghjkl
What the hell ?

Yes do it ! You re gonna move in a less expensive place, just stop working,
you can live at least 1year without working if you cut your expenses, it will
give you all the time to figure out what to do with your life. And if you
finish nowhere after 1year, just get an other of your boring stressfull, high
paying job !

If you are too scared and don't want to "loose" 70-100k by not working, just
find a part-time job, work like 2days per week as a freelance, it will be
enought to sustain yourself with a low cost life style, and give you 3 more
days of total freedom to work on your personnal project...

Damn, stop being scared. You can get a job again, if it doen't workout.

------
lasgsf
Somewhat similar...I was at a FANG and not as high salary as you about
$250K/year but had about $2.5M in net savings (mix of 401k, retirement and
cash). Just wasn't happy being in a large company as came in via an
acquisition. Once the golden handcuffs expired left for a small start-up with
only about 40 people. The start-up did not go anywhere but overall I am happy
with the decision and would never go back to FANG. I think if you worked at
FANG the pedigree is easy to get another job anywhere for the most part. Now
would it give you a $500K salary? prob not.

------
siculars
Clearly you're very good at what you do. Speak to the folks at your company
and help them help you make the situation better. Stay at your job. Especially
if you have people depending on you like a spouse, kids or parents. Hold out
longer and build a bigger cushion. Remove the risk from your plan by building
a passive income stream now through investments in the market and/or real
estate. Life is a long time if you're lucky. You don't want to get to the
latter parts and not be able to afford the things you want or need.

~~~
badpun
> Clearly you're very good at what you do. Speak to the folks at your company
> and help them help you make the situation better.

I'm in a very similar position (less money, but in a much cheaper country, so
I still make about 40x minimum wage). I think in my case partially the reason
why the company is paying me so much is precisely because the overall
conditions there are so shitty, not because I'm some genius. So, as soon as
they improve the conditions, they can start paying less.

~~~
jackgolding
I think this is the case for most Enterprise

------
throwaway93192
The typical HN answer is "yes, and start a new company", but I think there's a
lot to be said for "yes, and work remotely for the company you're at." It's
probably not too difficult to swing, you'll get to enjoy life instead of
panicking at your struggling new venture in a new town, and you'll be able to
take advantage of all the experience you've gathered at current company.

Honestly, I don't know if I'm giving you advice or myself.

------
jackgolding
Just wondering has anyone found life coaching useful in circumstances like
this? I live in one of the most expensive cities in the world have been quite
career driven but I'm worried about hitting the ceiling where taking on more
responsibility isn't worth the extra coin.

FIRE seems attractive and is very possible but based on the two three month
periods where I haven't worked so far in my career - I'm worried about how
depressed/lonely I would get?

Any ideas?

------
mod
I wouldn't trade one job for another (in the same field), if that's how it's
going to feel to you.

I would quit my job in a second to pursue a dream or retire. I have different
financial expectations & desires than most.

I actually just pulled the plug on quitting my "high paying" job. The pay is
quite nice considering my cost of living (I'm a remote worker), but nowhere
near what you're making.

It would be easy for me to continue at the job feeling burned out, hating my
day-to-day, but having no financial concerns. But I'm not proud of myself. I
want to do something radically different, and I don't want to work for anyone
else anymore.

So, I put in my notice and I'm taking the "scary" route instead. I'm excited
about it, rather than concerned, and I don't have a million bucks guarding my
flank, either.

If I were in your financial position, I would retire immediately and pursue
whatever I desired without jeopardizing my already-achieved wealth. For me
that would be hobbies, not income--but many hobbies also generate income. You
could achieve a nice middle-class passive income forever, and that would suit
me much better than wasting one more second in a job I hate.

Best of luck!

------
surds
I am not in a position to give any advice to OP, as I am not experienced
enough, don't have that kind of financial options but not in a position where
I can't stand my job.

That being said, I look forward to be independent some day and try to spend my
free time building something on the side. The problem is that it is not not as
easy as some people make it seem. Depending on how the day at work was, I
might be completely exhausted mentally and not in a position to do anything in
the evening.

This part-time approach might not work for the OP as the job already seems to
be stressful. Given that he has a cushion, is probably quite competent AND
hates the current job - in his position - I would quit and do something that
drives me.

Make a time bound plan with milestones that keep you on track and evaluate
after a year or two. If it does not work out, you can always come back to the
industry with your current experience and whatever new you learn starting up.

Would you get the same package or better? Maybe. Maybe not. But you can look
ahead knowing that you tried. Then you get back to the job till it gets tiring
again, or you get the bug of going out and doing something else again. :)

------
hispanic
Yeah, it can feel stupid to let go of a "golden ticket". But, like others, I
suggest looking into going the FIRE (financially independent, retired early)
route. Once FIRE'd, you'll be in a better place to start your company. That
$1.1M of unsheltered assets, invested properly, can yield you more than $40K
of passive, nearly tax-free income. But, you'll need to get your expenses down
to live off of that and start investing that cash hoard. Take the next year to
work on that. Over the course of that proceeding year, you'll earn another
$500K. The $300K-400K of this that you'll take-home can be put toward long-
term housing (whether that be renting or owning). If you keep your income low
enough, a huge portion of your health care premiums will be subsidized.

I just this year started my own FIRE "experiment". Feel free to email me or
read here - [https://blog.michaelscepaniak.com/starting-stopping-
working](https://blog.michaelscepaniak.com/starting-stopping-working)

------
nl
I am 40+, had a high paying job (not that much but good money).

I quit and took a small investment from an accelerator program (not enough to
pay myself, but enough to pay some costs and travel). Who knows if it will
work out, but I'm liking it...

Some arguments on the positive side:

At this point in your life, you don't need the job for the critical elements
of life (food, shelter, health). Your trade off is in opportunity costs, and
only you can balance the financial vs non-financial trade-offs.

You have the background to give yourself instant credibility as a startup.
People will take meetings with you, and that's a big deal.

People will want to work with you because of your background.

You've outlined the negative arguments nicely.

I'd put forward another option: get some investment. That reduces your risk
because you can pay yourself, and possibly move towards profitability more
quickly. I'd suggest listening to the Sasstr podcast with Kolton Andrus from
Gremlin[1].

He was in a similar position to you (working at Amazon, wanting to save enough
money to bootstrap), but he had an argument with a VC at a conference about
that approach, and the VC made some points he couldn't refute.

As for coming back to the market if it fails... are you serious? You are
engineering management at FANG, and you ran a startup that didn't work out?
Email me in three years time and I'll hire you or find someone who will
(seriously - my email is in my contact. I'm in Australia, but you don't mind
moving somewhere nice, right?).

[1] [https://www.saastr.com/saastr-podcast-169-kolton-andrus-
foun...](https://www.saastr.com/saastr-podcast-169-kolton-andrus-founder-ceo-
gremlin-secret-ensure-high-conversion-trials/)

------
wei_jok
I think positions at FANG-type companies are relatively risk-free (compared to
other industries, such as finance), and also relatively stress free (if you
allow it to be stress free by consciously ignoring the stressful).

Is it something you can start as a stealth project after work, while you
collect the 500K/year coupons?

------
thrownaway954
i would talk to your family (significant other/kids) first before you make any
moves, not a bunch of people on a tech forum. remember that whatever you do
will affect your family first. so if you fail, you better come to the
realization that you could lose your family if things go south.

i'm not trying to tell you what to do or scare you... follow your dreams if
that's what you want to do, it's your life. just look at the WHOLE picture
first, both achievements and consequences that your decisions will bring. a
wise man told me, "you can do anything in life if you are willing to accept
the consequences".

remember that your family are the ones that will have to go on this journey
with you, for good or for bad, the people on this forum aren't going to be
there if things go south no matter what they might want you to believe.

------
charlesdm
So, not in my early 40s and I haven't quit a high paying tech job, but I have
done well creating apps. Years ago I decided not to go work at a large FANG
company because I knew I would be miserable.

Having the freedom to do your own thing is amazing. You will love it. But you
need to switch from an employee mentality to an owner mentality.

Assume you're not going to make $500k a year in the first few years (if ever).
The main advantage you get is that you build up assets; say you create an app
that nets 200 or 300k in income a year and run that for a few years. You can
eventually sell that for a 2 to 5x multiple depending on the space it is in.
Those gains are then generally taxed as capital gains, meaning you pay (lower)
tax on them. Self employed people can take more deductions and pay less
overall tax -- look at after tax income.

Another thing to consider is, if your current compensation for a large part
comes from stock based compensation, that these stocks will not keep going up
forever. If you've been at Facebook for years and received stock at $20, it's
not going to go another 10x in the next 2 to 3 years. Meaning you won't
actually make 500k/yr (should that be the case)

You will also need to learn how to invest. I don't think there are many
entrepreneurs out there who don't invest their money. You're leaving a ton of
money on the table and honestly, there is no excuse to have $1.1m sitting in
cash in a bank account. But at current valuations perhaps wait until the stock
market has a proper correction.

Also, mobile games are hard. I know how to make money from apps, but games are
insanely competitive. Have you considered looking into other things?

Quality of life is worth more than anything, in my view. My father died at 55.
Even though I've done well for someone in his late 20s, living and enjoying
life / family is more important than money. Taking a moderate risk (on a
'lifestyle' business) might be enough -- there's no rule saying you need to
shoot for the moon.

------
yranadive
Your risk tolerance should be a function of your confidence in turning your
company in to something of future value. It seems like you haven't done your
research on your probability of success yet. I'd advise talking to investors
about your idea to get a sense of that. Try approaching them to get seed
funding. If you can't raise, quit, and try raising again.

If you can't raise within a year, go back to work. You need to talk to
investors to get a feel of how people will value your company if you take the
plunge. If you feel your probability of breakeven is at least 50%, I'd say go
for it. Keep in mind, every person that joins your company after you will do
an implicit probability calculation, so think about what makes you unique and
hence more likely to succeed.

------
wizardofmysore
> My question is: has anyone here, in a similar situation, done something like
> this? And if your company failed, have you been able to come back to the
> market in a good situation?

Not first hand but I know two folks who were in senior positions in a high
paying job (one product head and one VP of marketing) who quit their high
paying jobs to start their own companies. One of them failed and the person is
now the CEO of another well funded company. The other one is doing fine and
got an investment from a good investor.

My personal opinion is that if you are able to get a gig that pays 500k at one
of the FANG companies you should have no problem getting a job back if your
company fails.

------
sigi45
I don't get why you would invest your money into it?

You have more than enough money to retire for life. Get a nice house, add
solar power, get your water out of the ground, make your living expense low
but with quality.

THAN start putting the most valuable thing into your idea/startup: Your Time.
When you have something good enough, to show, find investors. IF your idea is
good enough and it is relevant enough, you get help from others. If not, yeah
forget it.

I have tons of ideas and do non of them. I have accepted that when i even had
an idea, which spun enough in my head that i would talk about it to others,
others always didn't like it as much i did.

~~~
badpun
> THAN start putting the most valuable thing into your idea/startup: Your
> Time. When you have something good enough, to show, find investors. IF your
> idea is good enough and it is relevant enough, you get help from others. If
> not, yeah forget it.

He may need work done that's beyond his skillset. For example, he mentioned
mobile gaming, where the brunt of the work is in the assets (art, audio).

~~~
sigi45
His idea has to be good enough to risk a shit tone of money, live savings and
the future/well being of his family.

For a demo or something special enough, it wouldn't hurt him at all to invest
10-50k in assets but everything else would be down right crazy.

I don't think it would make sense at all to hope for a second minecraft or
whatever and risk a million bucks for it.

------
scarface74
I don't see how it takes "courage" or how it's a risk. If you're a software
developer with in demand skills and have one of the FANG companies on your
resume, it shouldn't take long to get a job if your startup fails. I don't
have but one company that anyone has ever heard of on my resume, and I
historically I can get a job in less than two or three weeks.

If you have $1 million in cash you have plenty of runway to find a job.

If you try, and your company fails, at least you tried. Studies show that
people have a lot more regret about things they didn't try to do than things
they tried and failed.

Life is short, go for it.

~~~
bsvalley
It depends how long the OP has been working at that FANG company. At 40 the
only difference is that you’ve built solid roots inside of a company and that
your high salary is there to keep you around for a long time. You’re
definitely smart but how many young and fresh people are smarter that you out
there? How many people want your job? You’re like an octopus holding on to a
lot stuff so as soon as you leave your power goes down by a lot. They will
replace you and you might be forgotten. If you apply at a different company
later on you won’t have the same arguments to justify such a salary/position.
I think if you’re very good (which I’m sure is the case for the OP) you’ll
have to work your way back up. Meaning it is not that easy to get back to
where you were before you quit.

~~~
scarface74
I didn't think about the context of his question - if his skill set is more
managerial than technical and not as easily transferrable, it might be
riskier.

I was only looking through the lens of someone who had transferable skills.
I've found that once you get away from being hands on, it takes a lot longer
to get a job even if you are willing to be "just a software developer".

But he may not need the same salary if he has already funded his kids college
like he said he has, saved for retirement and is willing to live in a cheaper
area.

------
arenaninja
That's a lot of cheddar OP. As many people have already said, many of us think
you're in an enviable position. I'm curious what makes this highly stressful
for you though. I think "low happiness" is pretty common overall, as in I make
a fraction of what you make, and it's a job pays the bills and it's all OK so
I've come to terms with the job and doesn't really provide happiness, but one
year into it it's not stressful to me in any way

Any reason why you can't start on your side gig during off hours, like many
others do?

------
mikikian
Since a game typically doesn't have a first mover advantage nor suffer from a
"time is of the essence" problem, and given your opportunity cost of income,
you should consider outsourcing the development of your game to a cheaper
labor market. With your technical know how, you can supervise your team to
your liking, launch the game, and see how it goes. While you still might be
unhappy at work, this will preserve more of your savings than quitting, and
give you a more viable option to quit in the future.

~~~
pyoung
Not sure why you are getting downvoted, as this is the best solution that I
have seen so far. Even in the Bay Area, 500k salary is an outlier, and the op
can easily afford to hire a part time local developer or full time in a lower
cost of living area.

Another similar option would be to look for a co-founder, and 'self-finance'
the company initially. I am sure there are some folks out there who would
happily take a lower % of equity in exchange for a small salary. And the added
advantage is you essentially have unlimited runway.

------
smilesnd
From my experience companies love a failure since it means you got your one
idea for a business out of the way. As long as you fail gracefully then it is
a selling point for companies because you became more diversify in dealing
with business related matters. It also shows you have a passion for what you
are doing. Who wouldn't hire someone that could make this kind of statement "I
had the experience and knowledge to start x company, but bad luck and timing
played against me, and I ran out of run way"?

------
thisisit
The real question you have to ask is - What do you want to do in your life?
There is no shame in saying - I want a well paid job which helps me sleep at
night. There is nothing wrong with it. The whole idea of going out and
building your own is romantic but it is not for everyone.

But, if your aim in life has been to build something of your own, then Go for
it.

Talk to people closest to you - friends, families and colleagues. They are the
best people to help you arrive at a decision.

Lastly, if you get stressed easily over thinking stuff then maybe take up
meditation.

------
ApolloRising
Are you an engineer and coding on a daily basis? If so then taking some time
off and doing your startup should not hurt you too badly. Why would you move
at all instead of just keep renting and working on your project and cut your
expenses other than rent a bit to keep in your networks.

Maybe negotiate to change your role to something you would be happier doing?

500k/yr is a crap ton of money to let go. It depends on how miserable you are
but I would have to be seriously seriously miserable to drop that gig.

------
chrismcb
> high stress, low happiness career... Personally I feel like you've already
> answered the question.

While I haven't tried something like that, I'll tell you that doing something
you enjoy is almost worth the risk. Granted you have a family to consider. But
if you fail, so what? Yeah, maybe you won't be able to go back to the same
high paying job you have now, but you aren't happy with it. This isn't a
decision you can make alone, but happiness is worth a LOT.

------
mdn0420
I'm at a similar crossroads right now albeit with different numbers. I
actually work for a mobile gaming company, making a solid salary and get to
work fully remote. The job is no longer fulfilling and I feel like I need to
try going on my own at least once. Perhaps forming a support group for
individuals making this transition would be helpful :P

Have you thought about looking for a cofounder to share some of this risk with
you? However, I hear that's not an easy task either.

------
simonebrunozzi
I climbed my corporate career ladder up to VP/CTO at a large publicly traded
company. The total comp was... Wow. I didn't stay there too long, though. I
wanted to launch a startup, and I had enough saved that I could do it without
worrying too much about the first few years without a salary at all.

I am doing that now. Happiest I've been in years. This is not to suggest this
is the only way. I am only reporting one case, the only one I know very well.

------
herbst
I did. My company is slowly growing and I am getting more and more independent
again. The big difference is I am really independent this time as I can do
with my time what I want. Also my mental and also physical health is better,
better than it ever was before since I started working.

You even have reserves, I think it's more likely that you would hate not
having done it than when you would fail.

IMO freedom is always worth some risks.

------
baalzaamon
This would be a great question for
[https://www.indiehackers.com/](https://www.indiehackers.com/) . Really
supportive community for people who want to bootstrap something on their own.
Most people there will tell you to ease into it. Can you spend a few weeks or
months doing both to see if you even like it, and then gradually transition?

------
martin_bech
Always optimise for happiness.

------
notjtrig
Started a mushroom growing business myself, self funded, ran out of money in 6
months. It was hard to get back to work, but I don't regret it. If I would
have conserved capital better it would have had a chance.

There are two groups of people when it comes to business those who are sure to
fail and those likely to succeed. I was no doubt in the former category at the
time.

~~~
rockandrollis
I left my full time job about 3 years ago and havent looked back since. Glad
you have some money put aside. Hold onto enough to get your family through if
times get tough, but do ehat you love. Life is way too short to waste on
anything. And money means very little compared to anything else in life.

------
TheSpiceIsLife
Is it possible to leave the safety of the high paying job and _not_ do
something risky?

Move somewhere the cost of living is lower then do something that earns a
regular income but doesn’t suck.

I think when we read HN a lot we are susceptible to think the only two choices
are working for FANG or risking everything on a startup.

------
rntksi
This article was posted a few weeks ago on HN, you might want to read:
[http://oliverzheng.com/2018/how-to-quit-a-top-tier-tech-
job/](http://oliverzheng.com/2018/how-to-quit-a-top-tier-tech-job/)

------
lazyjones
Unless there's unique opportunity right now to start your own company, keep
your current job until you have enough savings to sustain most of your current
living standard. I'm surprised you haven't saved more at your age with this
kind of salary.

~~~
tsetse
I haven't always had this salary... 4 years ago I was at 200K/year.

~~~
zerr
Did you get to 500K by switching the jobs/companies? I wonder how you
negotiated such number, or maybe they offered it right away?

------
lord_ring_11
I was in same situation and i ended up starting something in my own. Not
profitable but i am enjoying the experience. Think hard if you will regret not
taking a chance with yourself or will you regret leaving cushy job more when
you are on deathbed.

------
somtum
Sounds like you're in a high management role with potentially a lot of power.
Why don't you control you're environment to make it more suitable for you?
Delegate tasks you don't like. Make other people attend meetings for you.

------
cm2012
I would try consulting first since it has no start-up costs. It's a lot more
fun and you might even earn more. Source: made 100k in a corp job 1 year ago,
left that company, now make 360k ish as a freelancer.

------
pragmatic
Just off the top of my head, shouldn't your net worth be higher?

Might need to check your savings rate. The 1.1 from the property sale is great
but that sounds more like a lottery win.

~~~
pragmatic
When I left a stable job with good pay and excellent benefits for self
employment, I underestimated the costs of buying benefits on par with my old
job.

Also keep in mind your family may be used to a certain standard of living and
paring that back can be a challenge. We were frugal work a high savings rate.
I underestimated the mental stress in down months when more money was going
out then coming in.

With that much coming in, you could start it on the side, easily pay someone
or a few people to do some of the work.

But it really depends on you, your mental state, etc.

~~~
pragmatic
I ended up getting a different Corp job. Wasn't worth the stress. However, I
may try something else.

If nothing else, I leaned about the things I don't like to do and why.

------
auganov
Don't forget you can raise a round and take a salary. Probably in the 100k
range but still. And if you fail, a VC backed startup looks a bit better on
the resume too.

------
pragmatic
Maybe you should prototype it.

[https://designingyour.life/the-book/](https://designingyour.life/the-book/)

------
mygo
What are you afraid of more? A failed venture or taking your regret to the
grave? There's no right answer.

------
zfdrdg
Go read some mrmoneymoustache. He's a bit wierd but has some good ideas about
this type of thing.

------
kwame101
I would take the risk and go the other path. Why work at a place you don't
enjoy

------
raunometsa
Please, do not live a "high stress" and "low happiness" life.

------
NetStrikeForce
Geez. What does one have to do to earn 500k/year? Asking for a friend...

------
zerr
If you're an engineer, it seems like you work at Netflix, right?

------
gigatexal
No. Took me 5 years to do so.

------
lafar6502
You either have an unique talent or were very lucky so far. You don’t mention
any special abilities so it might just be luck. So don’t start with destroying
it, you might not be so lucky again.

------
q-base
I did it. Quit my high paying job(not anywhere as high as your though) got a
good compensation package and spent 4-5 years starting a company together with
my dad. The company still haven't succeeded but haven't shut down either.

Now I work as a freelance consultant and am starting with two new ideas. BUT
this time I will do it differently.

I will most certainly keep working my "regular" job until I have traction with
one of the other ideas. I have a high paying job, could of course cut all
expenses(this is not fun a few years in btw!) and live of very little. But the
other option with a high paying job is to invest all of the excess pay into
whatever endeavor you are planning. You most likely have enough excess pay to
hire one or two other people to work on your idea while still working your day
job.

This even gives a little more meaning to your daytime job as it then finances
your future startup.

------
xstartup
Already did and I don't regret it in hindsight.

------
thatfrenchguy
Move to Western Europe, enjoy the 7 weeks of vacation ?

~~~
pavlov
There are no engineering jobs in Europe that would pay anything close to the
poster's current $500k/year salary. He'd be looking at a 80-90% pay cut.

