Working at a startup is overrated, both financially and emotionally

GGGP here.

I probably could have skipped my 5th startup, but psychologically, I couldn't see myself as retired. Startup #4 was, for a time, the most stressful job I've ever had. My part was distributed, and I was dealing with all the gotchas that entails, and these gotchas were being uncovered at a high rate, thanks to a stellar system testing guy.

And then, suddenly, the last serious distribution bug was solved, and the system was working, rock solid. And I glided, through the acquisition, and then for a couple of years with our new corporate parent. Interesting new development stopped, and it was all about maintaining a working system. They knew they couldn't keep people there with interesting work, so they threw money at us. And it worked for a lot of people. Me too, for a while, until startup #5 came along, and it was really interesting. So I left.

But #5 was poorly conceived, and had other difficulties, and it burned me out after a few years. A really deep burnout -- I was angry all the time, and couldn't get myself to focus on work. I figured that 25 years of startups was enough, I was able to retire, so I did.

I do sometimes struggle to keep myself occupied. I've done a couple of minor software projects, but it is difficult to motivate myself to do something that has already been done, and that nobody really needs. I have also found it difficult to motivate myself to get into new (to me) areas, e.g. machine learning. There is some amount of depression going on, for sure.

I did consider going back to BigCo, but: I really enjoy having the freedom to travel where and when I want, the lack of stress, and all the other obvious benefits of not working. But the major reason is this: If I am bored and don't know how to fill my time, that is a fundamental problem. Doing some random task for BigCo doesn't fix that problem, it masks it. I need to figure out what it is I want to do.

I did find one fun project: I decided that I really needed something that didn't involve sitting in front of a keyboard. So I decided to build a sailboat. Having no experience with woodworking, I opted for a kit that includes pre-cut wooden pieces, and it's up to me to glue, and sand, and varnish, and paint. Sort of like building a model, like when I was a kid, but on a bigger scale. Surprisingly difficult, for me at least.

I think software engineering as a profession would be a lot better off, and a lot of people would be happier, if more people made sure they got some real variety in their first ten years or so. Work at a startup and at a FAANG (if you can). Work at a company that needs software developers but don't have that as their primary business. You'll be miserable and probably not last long, but it will give you perspective. Work at a hardware company. Try different markets, different technical specialties, different roles, different stages of development. Careers are long. You might be surprised at which combination ends up appealing to you, then you can spend the majority of your career being happier. Between greater ability to focus and all the contacts you made earlier, you'll probably climb higher in the end too.

First of all, of course the number of A-team engineers willing to work for half the pay is small.

But staying out of FAANG means more than just 50% less initial total compensation.

FAANGs offer career growth, including pay growth, that simply doesn't exist in startup world. Even if reality won't hit you when you just accepted a $200k startup job when your college friend with the same experience got $400k, it will hit you 4-5 years later, when you're hunting for your next job for $200-250k while that friend is making $500-600k+ because your startup fizzled out or got acquired for peanuts while his FAANG just kept growing and carrying his career up with it.

Or it will hit when you try to get into your next startup and realize that startups are the first to look up to FAANG engineers. That engineers with FAANG experience get all the interviews, and are lavished with the best offers and most senior positions in startup-land. While the only reward you get for staying in startupland is... being considered a B-player.

Finally, let's profile the "FAANG-hating" engineer willing to work for startups for half the pay. As you said, this engineer is sacrificing most of their pay for a work environment in which they feel more comfortable. Is that great for the employer too?

Would that engineer agree to sacrifice other aspects of their comfort, such as WLB, to make the startup succeed?

Of course not. Their equity stake is negligible, they're unaligned with the company's goals. They work there for the fun, and once that fun stops, there are dozens of other startups waiting to hire them at the same (low) comp package.

Startups today don't just underpay - they completely fail to align their senior employees. The combination of minuscule equity stake, no career growth prospects, high risk and constant job-hopping means as a senior engineer you will not be rewarded for good performance. Much as we love to disparage "sclerotic big tech", I've seen more mission alignment there because employees expect ample reward - in pay and long-term promotions.

In fact the typical profile of an "A-team engineer who'd rather work at startups" is someone who spent several years in FAANG, acquired FU money there, and now looking at startup work as fun CoastFIRE if not a harmless retirement hobby that pays a bit of money as well.

On top of all this, let's not forget that even if you're absolutely obsessed with working at a small "non-sclerotic" company, there are still options for you, including unicorns and plenty of small successful shops that aren't startups.

Not sure where you're getting the idea a procurement person is making any sort of buying decisions for enterprise products within a business.

Really interesting perspective. Thanks for sharing.