I find that the key to risk taking is to separate the things you can't afford losing from the things you're okay risking. And if by habit you always categorize

I find that the key to risk taking is to separate the things you can't afford losing from the things you're okay risking. And if by habit you always categorize any undesirable outcome (i.e. failure) in the first category, you'd never expose yourself to the upside of risk taking. To win by losing, you first have to insulate yourself from losing. When losing is fatal to further attempts (russian roulette, financial ruin, etc) it's probably not worth participating. But it's important to distinguish between truly consequential outcomes from other failures that merely harm things you're okay losing (time, some money, some reputation, career status, ego, etc).