Ask HN: Do you have the courage to abandon your high paying job? | Hacker News Reader

Ask HN: Do you have the courage to abandon your high paying job?

147 pointstsetse166 comments

I'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/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).

The only problem is that I can't really stand my job. I had prestigious positions in other major companies but I pretty much hated them all.

Yes, I should be thankful to have a gig at a major tech company. But just because I'm okay at what I do and was able to profit from my skills, it doesn't mean that I like it...

I'm considering moving to a cheaper area of the country (also due to family reasons) to start my own company. I'm not ready to share what I'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'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.

The reason I'm writing this is because I'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'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'll still have ~500K in bank)

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?

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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!

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.

> 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.

Yep, I agree. This is my first thought as well. I don't think it necessarily needs dividend stocks either, general stocks should do the trick. My back-of-the-envelope is:

  * expected return on investment from US stocks at current valuation [+]: ~6%
  * expected inflation rate: ~2%
  * expected real return: ~4%
  * assumed tax rate: 15%
  * annual investment return: (1100000 * 0.04) * (1 - 0.15) = USD $37.4k / year after tax

Assuming you don't have a large family with many dependants or unusually high expenses (medical care, etc) it certainly sounds doable, but perhaps with a dramatic decrease in annual spend for non-essentials (overseas holidays, living in an expensive part of the country, etc).

[+] Compared to historical prices, US stocks are currently very highly priced, hence expected real returns (~4%) are lower than historical average real returns (~7%). See e.g. http://www.philosophicaleconomics.com/2018/01/future-u-s-equ...

The 4% rule is a good one as it's (as you mention) much more likely. Also, if your withdrawal rate is 4%, the likelihood of you seeing that income until you die is much, much higher.

As stated elsewhere, getting yourself down to spending 37k a year is going to be the hardest part, no matter where you live.

The problem I see, time and time again as a bystander to the financial industry is that people simple aren't saving enough, or what they have saved is overspent at a rate that's unsustainable. If one needs to live off of 24k/80k/200k a year in retirement; then their investments should reflect that.

15% is for long-term capital gains. Dividend income is taxed at a much higher rate.

> 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.

Definitely. Decide how much a modest retirement is, and then hit that goal. If non-city dwelling is something you like, you can live far away from the city very cheaply.

On top of that, I'd try to find ways to cheapen your life now. 500k/y is a lot, and while everything's relative, you could lower your standard of living and put away a ton of money in just a year or two, getting your goals faster.

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.

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.

withdraw the 600K from the 401K, use that to buy a condo in cash

OP wants to move to a lower COL area. Around here $600k, even if you take the tax + penalty hit for an early withdrawal, buys plenty of house. We're talking 5,000 sq ft on 3-5 acres about 15 minutes outside town if rural living floats your boat.

I'd do it in a heartbeat!

Excellent advice. Esp thinking ab how u can minimize risk as much as possible!

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!

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.

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...

Oh, I get you now. I grew up super poor and the thought of falling back into it keeps me up at night to this day.

That's what's making this decision hard.

>>I grew up in relative poverty

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

I'm okay with that, yes.

I agree with the buying/renting thing (I don't see a reason to buy except as investment anyway)

However it is very easy to simply start from a lower standard and increase as you feel you need to than to start at the top and decrease to a lower standard gradually.

Overly cautious approach. The guy has a very nice cushion as it is. He doesn't need to live off a budget before switching to a startup. And obv he would rent something in a new place before straight up buying a place in a town he's not familiar with.

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.

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.

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.

Isn't anything bad by definition when "too many" people do it?

This is also morally suspect. You're putting extra load (taxes if anything) on people while you're not working.

If you think you can repay this cost to society with volunteer work or otherwise, this might work.

Huh? You contribute with your assets. People get to use your stuff in exchange for giving you stuff.

Lending isn't productive in and of itself. There is a nice gradient stretching from freeloading rent-seeker to visionary/socially responsible investor. Not seeing the difference and condemning the former is a problem.

The difference is in how many other people get fucked along the way as the investor gets their return.

"From each according to his ability, to each according to his needs"

I thought we had got past the idea of collectivism, it just doesn't work.

Little is more naive than the broad claim "collectivism doesn't work" because the USSR and other states tried some form of it and failed.

Even if you are willing to massively oversimplify things and look at the cold war and all the real-politik business of the last century as a fair contest between the ideas of collectivism and capitalism, "which system wins in a war" is not exactly the same thing as "which system maximizes prosperity." Nor are we actually limited to picking between the two.

He already played more than other people will ever pay in taxes in their lifetime, he does not have obligation to society.

> 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.

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.

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.

(deleting)

Thank you for the response. Remote work not an option even though it's FANG (trust me I tried), college fund already established and enough money in it, not mentioned in post.

Many high paying jobs suck, but there are salary jobs positioned variously on the satisfaction-pay spectrum. You can apply tech knowledge in other places besides big tech companies and still get paid - eg NGOs, arts/culture, research, small tech consultancy doing a 4 day week with emphasis on life-work balance, etc.

Making a lot of money at miserable jobs and retiring young is a valid alternative strategy, depends on whether there are any satisfying jobs for you. But if you can't imagine one, it may be a sign of burnout...

"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.

Also, nowhere near 500K.

I think there is a huge difference if you do things that suck for the success for your own company (plus outsource that more and more) than doing the same for a company you at best have some options for shares.

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.

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

This!

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.

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.

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.

I made the assumption that the new startup would be in tech, in which case it almost certainly overlaps with his FANG employer.

The problem is that 'similar space' is too easily misconstrued. What exactly is the 'space' that Google or Amazon operates in?

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.

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.

If you’re working at a FANG company, everything you could possibly do is “in a similar space.” They will lay claim to everything you do while simultaneously employed there.

My best advise would be to start your business aside while maintaining your current job.

If the OP is struggling with the stress of his current role I fail to see how adding additional work is going to help.

I would give just the opposite advice - a man with one behind can't dance a two weddings. He has the savings, go for it. If he fails, go out and get another job.

Either decide to go all out or don't do it all. The stress of trying to juggle a full time job and a starting a business and being there for your family isn't worth it.

My point was for him to at least light up something first not to fully run a business on the side. Of course it's hard to maintain a 9-5 job and to run a business at the same time. Do you know Tarzan? It's exactly the same thing, make sure you're getting a grip on another liana when you make a move otherwise it'll hurt.

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.

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

I've seen the sabbatical option working out for some people, but in my case it won't because a number of reasons, including the fact I haven't been there long enough.

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.

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.

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.

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

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.

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.

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.

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"

Gotchya.

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!

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.

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.

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.

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.

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.

a rare spouse that would do that

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)

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.

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.

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.

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!

/Translation/Transition/

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

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

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.

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.

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.

$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.

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

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

There is a website that calculates this kind of stuff.

https://www.bestplaces.net/cost-of-living/charlotte-nc/palo-...

*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.

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.

Also, you're in a tax bracket where you're basically a golden egg-laying goose for the government.

I have lived in California and I can't think of many places in the continental US where $500k CA translates to $100k locally. And I've lived in several cities in the east coast, west coast and the Southeast

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!

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

https://news.ycombinator.com/item?id=13421078

Do you have a blog or twitter account to follow?

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.

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.

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.

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.

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"

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.

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.

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.

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...

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.

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!

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.

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.

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.

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.

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.

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.

> 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.

I think this is the case for most Enterprise

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.

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?

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!

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. :)

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

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...

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?

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.

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.

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.

> 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.

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.

> 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).

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.

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.

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.

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.

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?

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.

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.

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"?

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.

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.

> 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.

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.

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.

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.

This would be a great question for 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?

Always optimise for happiness.

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.

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.

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.

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/

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.

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

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

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.

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.

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.

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.

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.

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.

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.

Maybe you should prototype it.

https://designingyour.life/the-book/

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

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

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

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

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

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

No. Took me 5 years to do so.

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.

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.

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

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

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.

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