For #2, I can’t speak to your values. It seems unlikely you’ve never taken any risk in your life. Of course, not knowing you, I can’t say for sure, but I’d bet

For #2, I can’t speak to your values. It seems unlikely you’ve never taken any risk in your life. Of course, not knowing you, I can’t say for sure, but I’d bet you only choose to pursue “sure things”. I’ll save you the philosophy about missed gains, but instead ask—what if your “sure things” were only 99% probable? They’d be at least somewhat risky, no? Would you still do them? And, for the things you have done, how can you be certain of the outcome, any outcome, beyond that level of confidence? Maybe for someone as risk averse as you, #2 is beyond the point of diminishing returns. But for anyone who doesn’t fit that bill, I’d say #2 is critical.