Calculated bets

A framework for taking risks without being reckless

Earlier this week I shared a post on LinkedIn about how sometimes going off the beaten path can lead to outsized success. The post received a pretty big reaction from the lawyers, and there was a wide range of responses. I wanted to take some time today to explain my full thinking about the concepts in the post. Specifically: How exactly do you figure out when it’s better to follow the herd, and when it’s better to blaze your own path?

I’m going to use this graphic to explain some of the concepts below. It’s pretty basic but basically any decision you make can lead to success or failure. Green dot represents success, red dot represents failure.

Taking the safe path

For the vast majority of decisions, you’re best off by taking the tried and true path. Sometimes we call it “following the herd” which I think has some negative connotations. But I mean that’s how we deal with most decisions in life. Lawyers in particular find this approach attractive—I think because we like being informed and hate making mistakes. (I’m trying to avoid using the “risk averse” label even though it’s probably the best shorthand way to describe this type of thinking)