I've worked at multiple startups sub 50 to >1000 (unicorn status) and have founded and sold my own company. I've also worked at a few of the FAANGs. This is common advice, especially among VCs since it's one of the key benefits used to pitch prospective employees on giving up that fat FAANG salary, but in my personal experience, it's not so cut and dry.

Working in a startup will brand you as a startup person and help you meet VCs which may make it easier to raise. It'll also show you the problems that that particular startup faces and give you n=1 degree of pattern matching. On the flip side, something like YC can give you the same benefit or just shipping a for-profit side project on the side. Additionally, given how poorly run most startups are today, I'd posit that you're actually in more danger of learning the wrong lessons than the right lessons by joining a startup. At the end of the day, the truth is likely to be Peter Thiel's observation that joining the right, highly successful, high growth startup as a very early employee is a great way to learn exactly 1 method of starting a successful company--the way that company did it. But if the startup you join isn't that rocketship, you've only learned how to (or how not to) achieve that particular path of failure or mediocrity.

Not particularly great advice though, because then the challenge becomes identify those startups. And if you could do that reliably, I'd suggest you switch careers into VC instead :)

sounds like the beginnings of either burnout, depression or both. I'm in a job that's not quite demanding enough at the moment and it caused me to fall into a depression. It's good to catch it in time to do something about it.

Yeah. It's less like stress and more like a depressive void and a limbo where you have to work and at the same time not.

Somehow this pace of low energy, zero initiative and low motivation also crushes your motivation for personal project.

I naively thought that the likes of Stripe existed in order to abstract away this issue. Sort of like how TransferWise will give you a US, UK, EU, and others, account number. If I want to send Euros to GB, simply pay the local EU account number for free, then cash out in the UK for a minimal TransferWise fee (up to hundredths of the fee for sending it via the banks themselves).

So stripe here would charge an EU card from its EU entity, US from the US, GB from GB etc etc, regardless of where the merchant is actually located. Maybe there is something fundamentally different with the workings of Visa / MC payments and clearing though that means this is not possible?