Performing formalized risk assessments can provide you with insights about a risk you're thinking about taking. I think it helped me take the right risks and leave the workforce early.

Emotionally? Just* ignore them and pursue the thing that pays you the most. It's boring and it's unhealthy and it's hard and it's not romantic.

If i retired in my mid twenties I think I would still hate myself. Knowledge of algorithms doesn't feel like labor to me it still feels like a curse. I'm pretty braindead and hardly self-sufficient now but I'm glad I never took any of the big payouts I had presented to me in my youth. I still don't know what I would do with myself if I had any significant amount of money that wasn't earned off labor but instead me selling my stake in companies / projects / what-have-you.

I thought buying bitcoin to pay work off related malware infections was "too expensive" at $300 when in reality I could have purchased several thousand bitcoin, had my client reimburse me, while keeping a chunk for myself because of course I would have.

also, the idea of being not being able to get hired or fired is really a silly concern as I always did my job well and did not want to leave my "safe" job.