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

[tsetse]

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?

[poof131]

Avoid drastic moves. The older I get the more I realize most “drastic move” stories are bs PR pieces. Think how you can move in the direction you want to go in steps. Move to a cheaper location: see if you can move to a satellite office or work remote. No, then look at other jobs you could interview at in the area you want to move to. Translate your FANG experience into a career jump. Then you will have experience and connections in the area, so if your business flounders you have options to fall back on and aren’t starting cold. Starting your business: find a job with better work life balance and lay the foundation for the jump in your spare time. Focus on the some money path vs. the a lot of money path. See if there are people in the area you move to who can help. Take steps and avoid jumps. But it sounds like you should start moving in this direction now so you don’t get so fed up at work that you make the move in a reactionary fashion. Good luck and godspeed!

[tachyonbeam]

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

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

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

[Ritjert]

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

[lacker]

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

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

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

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

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

TLDR Do it!

[justonepost]

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

[derekp7]

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

[Trundle]

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

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

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

[mykull]

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

[WheelsAtLarge]

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

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

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

[fulafel]

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...

[watwut]

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

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

[herbst]

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.

[cjbprime]

(deleting)

[fusiongyro]

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

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

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

[chrisherd]

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

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

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

Would love to discus more, drop me a line if interested: [email protected]

[CyanLite2]

This!

[bsvalley]

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

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

[tonyedgecombe]

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.

[throwaway93192]

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

[scarface74]

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.

[haser_au]

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

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

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

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

Life is short. Live it to the full.

[maxwin]

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

[GoldenMonkey]

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

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

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

[tsetse010]

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

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

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

[ganeshkrishnan]

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

[DubiousPusher]

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

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

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

[JBlue42]

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

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

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

[ryandrake]

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

Here’s some blunt feedback: get some perspective.

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

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

[rebaco]

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

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

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

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

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

[soneca]

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

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

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

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

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

[piotrkaminski]

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

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

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

[j32fun]

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

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

Good luck.

[ApolloRising]

a rare spouse that would do that

[andymoe]

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

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

(36, two young kids)

[AstralStorm]

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

[jasonkester]

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

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

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

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

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

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

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

[tsetse]

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

[kvz]

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

[kvz]

/Translation/Transition/

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

[drawkbox]

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

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

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

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

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

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

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