I listened to a founder share his thoughts on initiatives he chose to pursue. He considered both the probability of success and the size of the potential payoff. The ones he green-lighted weren’t the ones most likely to succeed—they were the ones with the biggest potential payoff. He knew some were long shots with only a 50% chance of succeeding, but if they did succeed, the payoff would be enormous. He was comfortable with a 50% chance because the payoff would be game-changing for his company.

I love this founder’s thought process. Most people look for a sure thing, or close to it. This founder understands that most things in life aren’t certain. There’s always a chance that things won’t go as planned. He’s thinking about the probabilities in conjunction with the upside. Said another way, he wants initiatives with a potential reward that’s orders of magnitude larger than the risk.  

Thinking about more than the probability of success is hard to do when something is risky, but it can lead to outsize outcomes!