Ask HN: Leaving a Job at Big Tech Giants for Startup

This, pick something you really care about and would be willing to eat and breathe for a long, long time, because if you succeed at it, you're going to be doing it for a while. Don't aim for the Instagram style "exit for 1B in two years", if that's the goal the go to Vegas, it will save you a lot of time and tears.

If you don't, and if you're luckier than most, you might get stuck working on an idea or in an industry you really don't care about, just because you wanted to play startup and, like the poster above said, you read up on a bunch of success porn that's telling you that startups are the sexy, right thing for you.

Then you'll be stuck between a rock and a hard place, hating what you do for years, but not being able to leave because of all of the sunk cost, the shame of abandoning the team of people you've brought on board and convinced to chase a dream you don't really care about yourself, the reputation hit, the VCs who sunk all that cash into you, and the carrot of a potential, however tiny exit dangling in front of you. And the years keep adding up as you're chasing that carrot, still dreaming every day of getting out, but somehow that exit just never happens. If you're lucky/smart you'll find someone to replace you, but then they might kill the golden goose and you're still left with nothing, but at least you moved on, so that's a silver lining.

Fall in love with the problem and with the mission, that way, even if you fail or have a pretty rough time, at least you're working on something that truly matters to you. And "doing a startup" can't be the mission in itself, that's a recipe for disaster. It's one of those situations where even if you win, you still lose.

^ This, so true. Lot of people preaching the side hustle who either havent actually tried it OR have very lax jobs that allow for this kind of thing.

I'm in a similar situation. How are you holding up?

I did this and my advice would be “it depends”. It’s been a mixed bag. Financially I’m much worse off than I would have been staying at my 300k job (who knows what it would have grown to now?). I will say the stress of not knowing what you are doing and questioning yourself can be immense. That being said perhaps I’m not the best example as I took years off living a hedonistic lifestyle and truly adopted the YOLO mentality. I consulted here and there. It was fun but ultimately draining.

The corporate coding lifestyle can be without a doubt an existential mind fuck. It partially depends on your mindset and job responsibilities though. If you care about the purpose of your product, you aren’t some product managers code monkey, and you are making money that isn’t the worst thing.

That being said... FOR ME I have learned that the concept of retirement is a joke. It’s not all that great and at least for me people feel better having a meaningful purpose. Even if your purpose is make believe I think it’s neCessary. So I wonder about the utility of doing something you hate for 30 years just to end up “retired” and miserable anyway. That’s what I’m trying to do, I don’t want to retire but I don’t want to sit in front of a computer coding up some app UI for someone else. but I have a family on the way so we’ll see how it goes.

I think maybe optimize for that purpose you have in mind for yourself rather than starting a business just for the hell of it. If you are getting paid 500k by google to prosecute child pornographers that’s likely going to make you feel better than starting your own 1 man SaaS business running email marketing....

It depends.

I was working at Google and I'm really happy to read what's going on on Blind to be able to talk about the worst problems that are going on that you can't talk about on the internal system.

At the same time it's still a great place to work at as long as you find the right team (especially team lead).