Ask HN: How do I get over constant failure?

After a couple years I hit the big time and got a job at a tech startup that was blowing up. There was one really successful project I worked on, and otherwise I didn't really accomplish much - the whole organization I was in was very dysfunctional and we churned through management and new projects really quickly, but nothing really landed. During this time our stock price went crazy, and I sold all my stock to make a down payment on a house and max out my retirement savings. Eventually the mismanagement got to me - every project seemed doomed to fail, and I was paralyzed with indecision daily. They promoted me to the level where I was supposed to propose and run projects, and I hated it.

To try and get back to building things, I joined a small startup around the time the pandemic started. Everyone there gave me great feedback, but there was no product focus, very little management, and ultimately it still felt like the things I was working on didn't matter or lead to anything. The product itself was hard to use and had so many problems that I couldn't imagine trying to untangle them all, so I left after a year.

At this point I was terrified that I just couldn't work in tech anymore. I had developed medical problems from stress, and took months of time off to try and recover. There was nothing else I wanted to do for work, but the thought of sitting down and building anything was terrible.

Fast-forward to today - I applied for and got my dream job, working at another very successful startup that has a lot of high-performing people. They get things done, and the product is great. It's been a couple months and I have achieved nothing. Not a single PR merged. I came in with all the momentum from my unemployment, all the enthusiasm and energy I could muster, and proposed a bunch of projects. Nothing landed. My manager left a few weeks after I started, my onboarding buddy has been absent, and the fear has started creeping in again that I'm alone and can't hack it in this high performing team. If I can't work in the tech industry it would completely upend my entire life.

Does anyone have any advice from a similar situation? I think I need more support and guidance but my experience has been that tech companies don't really offer that, and also that everyone seems happy and successful regardless.

Startups are naturally chaotic. Most fail. Until they mature it’s complete chaos.

If you don’t like this life and it’s causing you stress, you should join a bigger, more mature company. It’s hard to tell from what you wrote if you like the fast pace of a startup or if you hate it. If you hate it and the uncertainty, then join a bigger company with more stable processes.

If you think that’s too boring and too slow, then keep joining startups but embrace uncertainty and chaos. There’s nothing wrong with either, but understand the nature of the company you’re joining and don’t have unrealistic expectations.

When I was searching for my new job I knew I didn't wan small start-up chaos - my current role and the other big startup both have > 1000 engineers. "Startup" is kind of a loose term, but that seems big to me? I guess the alternative is like an actual enterprise company?