To me, the biggest red flag in your post is "I'm starting to feel not so happy with my current route". I had started to feel like my startup ideas had run their course around 3 years in, but I doubled down on a complicated one because I can be hella persistent and kept it going for another 3 years. Big mistake. When your feelings start telling you it's time to throw in the towel, it's time to throw in the towel. I don't regret leaving the security of a big company to play the startup game, but I do regret sticking with it for so long, even when evidence had mounted that the market had turned and there wasn't really an opportunity there.
Ask HN: I'm considering taking a break from startups to join big tech
21–30 of 32 posts
Re: Ask HN: I'm considering taking a break from startups to join big tech
#22I'm the opposite right now. I had a startup then joined FAANG. Spent the last 8yr in product at Google + Coinbase, and now I have the startup itch more than ever before. Maybe the grass is always greener. What is it about your current route that is leaving you unhappy?
Re: Ask HN: I'm considering taking a break from startups to join big tech
#23It's worthwhile to have some degree of financial stability. It lets you weather other problems with some equanimity. Do it. You'll have time later. Fwiw though, the only times I ever considered this was when I was upset at my life at a startup. I'm now happy at another startup. So this is a little of do as I say not as I do. But there's no harm in 2 years of big tech. It might blunt your edge a bit but burnout will d…
How do you reason about the pay decrease joining a startup vs. joining a high paying small company or big company?
Re: Ask HN: I'm considering taking a break from startups to join big tech
#24Re: Ask HN: I'm considering taking a break from startups to join big tech
#25I have no advice, but I want to wish good luck with the change if you decide to make it [1]. I'm not sure if this is so unpopular here. Hey! I work in a free public university, that is probably the most different place than a startup (at least form size and the income sources point of view). Just in case it's useful, this is an old post by patio11 when he transitioned from working in consulting+startup to working in…
Re: Ask HN: I'm considering taking a break from startups to join big tech
#26I also spent a lot of my 20s coding for FAANG and while I am able to retire at 35, once I met my future wife and had kids I realized just how empty my life was with just work. There’s a lot of lies we tell ourselves to settle with a hobby or piece of work that causes us to miss out of the real riches of life.
Re: Ask HN: I'm considering taking a break from startups to join big tech
#27I've switched between startups and Big Tech multiple times. I worked for startups before and after college, left to found my own, ended up at a FAANG, quit to found more startups, and then went back to my previous employer. I was effectively financially independent (went back with more savings than I started with, after 6 year with no income), but I burned myself out. It's been almost 3 years since the last startup,…
Re: Ask HN: I'm considering taking a break from startups to join big tech
#28Whatever you do don't burn yourself out. Make sure you're doing what makes you happy, and not what you feel like you "have" to do for one reason or another
Re: Ask HN: I'm considering taking a break from startups to join big tech
#29It's worthwhile to have some degree of financial stability. It lets you weather other problems with some equanimity. Do it. You'll have time later. Fwiw though, the only times I ever considered this was when I was upset at my life at a startup. I'm now happy at another startup. So this is a little of do as I say not as I do. But there's no harm in 2 years of big tech. It might blunt your edge a bit but burnout will d…
How do you reason about the pay decrease joining a startup vs. joining a high paying small company or big company?
A close friend of mine actually helped. The short form is: I'm in my mid-30s, so the majority of my compensation and wealth is still in my future so long as I can keep the engine running. So I optimize to keep the engine running. Some time that may be a couple of years in big tech so you have the amount of money that removes financial anxiety from your life. The rest of the time that may be years in startups because big tech is a low productivity environment.
This may be different for you, but I don't want to stop working so so long as macro stuff stays sane, I will probably be doing things into my 60s. That means that endurance is more important than power.