In a tech career have you ever chosen the "safe" option and regretted it, or the risky startup path?

I'm at a decision point in my tech career: one option is a stable corporate role that pays well and looks good on a CV. The other is an early-stage startup that's uncertain, pays less, but I actually care about it. I know everyone faces this. I'm not looking for advice, I'm looking for outcomes.

The part that makes it hard is that both options sound reasonable when you explain them to someone else, and only one of them feels right when you're alone with it.

So for those who chose the safe tech role: did it actually feel safe after you took it, or did the regret come later? And for those who chose the startup: did it work or did you have to go back? And the harder follow up: would you make the same choice again knowing what you know now?