[z33k]

Worse than not trying is trying and experiencing burnout and/or destitution.

When you fail, it can be due to many things. Not everything in the world is controllable. This is one of the reasons why expecting zero ”What ifs” at the end of your post-mortem is unreasonable.

[agumonkey]

I don't think there's any absolute rule here. I'm pretty convinced that a startup would be healthier for me rather than my safe day job. The amount of churn and nascent burn out due to chasing tech debt and tickets surrounded by demotivated people is really bad.

I guess being aware of what you need and can afford is key.