A word typically used in investing, I have been thinking about is asymmetric upside.

Simply put, trying things where the upside is much greater than the downside.

For most of my life, I’ve held a conservative view on risk, tending to fixate on “what could go wrong"‘ versus “what could go right". A defensive strategy.

But now, I’ve been more curious about how to flip the script and play my chips more offensively. Focus on things that may never pan out, but if they do, it could be exponential. That includes writing more, creating more, and meeting more.

Playing to win, not playing to lose. How about you? What bets are you making that could pay out 1000 to 1?