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.

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

[+] 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...

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.

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!

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.

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.

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!

That's what's making this decision hard.

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

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.

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.

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.

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

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

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

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.

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.

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...

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

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.

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

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.

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

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.

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.

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.

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 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.

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.

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 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.

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"

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!

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 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.

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 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.

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.

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)

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.

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

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

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.

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.

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.

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.

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!

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.

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 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.

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"

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.

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.

[0] http://www.transamericacenter.org/docs/default-source/resour...

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!

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.

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.

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.

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.

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.

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

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 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!

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. :)

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 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...

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

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.

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.

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.

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.

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.

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).

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.

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.

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.

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

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.

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.

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.

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.

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 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.

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.

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.

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.

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

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.

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

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

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.