I did it a couple of times in my past (with the intention of starting my own thing), and it never played out quite as well as I envisioned in my mind beforehand

I did it a couple of times in my past (with the intention of starting my own thing), and it never played out quite as well as I envisioned in my mind beforehand. If you do it, and then you end up needing to get another job because the runway ends, then it's always more difficult and stressful vs. getting a job while you already have a job/paycheck.