The Overconfident and Unrealistic Entrepreneur
leosternlicht.com
leosternlicht.com
Doubt is healthy and normal. If you don't have doubts about whatever path you're on, you're probably not thinking clearly enough. If you truly don't have any fears about risk, you're missing a critical self-protection mechanism that comes factory-standard for even the most primitive creatures on the planet.
In particular, when I encounter people who suggest that I shouldn't have any doubt about an financial transaction, I hide my wallet and back away slowly.
The problem is, you conflate reasonable doubts with irrational outside influences. It's not as if people who want to be entrepreneurs can't also want to get a law degree. Entrepreneurial ambition is not the only kind, and there are many legitimate reasons that a smart person might want to get a professional degree, aside from "society told me to do it".
The idea that you need to commit yourself wholly to whatever path you choose is well-taken, but the notion that you must eliminate all doubt in order to act decisively is excessive (and impossible).