I've always made regret minimizing career decisions, optimizing for what I was passionate about instead of the NPV of the expected outcome. While this has led to many moments of perceived failure, I’m happy where I've ended up and I'm proud of the decisions I made along the way

Yes, failing sucks, and it's often the most likely outcome. But succeeding (or failing) doing what you love is so much more gratifying than succeeding in a way others value but you don't. And ironically $$ have worked out better than I ever expected or strived for.