Reconsidering Career Optionality

Instead of pursuing options that cap downside while also capping upside, make bets that have asymmetric pay-offs: If you win, you win big. If not, you’ve gained valuable skills, relationships, and reputational benefits that will carry you over to your next asymmetric bet.

I think the biggest career mistake young people make is they’re afraid to look dumb, so they follow safe paths that cap their downside, not realizing that they also cap their upside.

The secret is that taking risks provides optionality as well, via learning and differentiation. If you go to an ivy league school or elite consulting firm, however, you're merely one of many. Even something as prestigious as a Harvard degree makes you only one of 315,000. If you start a company, you can truly become one of a kind—you'll be one of a... See more

The average ambitious person spends too much time accumulating optionality and too little time taking actual risks with high upside potential for themselves or the world.