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

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.

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)

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.

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’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.

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.

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!

  * 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

$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.

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!

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.

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.

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"

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.

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!

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.

> 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 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 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.

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.

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!

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.

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.

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

No. Took me 5 years to do so.

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.