There has to be a willingness to tolerate counterarguments, hopefully in such a way that you can truly understand and summarize the other side’s arguments at least as well as they can. And then, after all that, still have the conviction to separate yourself from the herd.

A way to prop up this kind of humility is to keep score. Use a decision journal. Write in your own words what you think will happen and why before a decision. Refer back to it later. See if you were right, and for the right reasons (think Bill Belichick’s famous 4th down decision against Indianapolis in 2009 which summarizes to: good decision,... See more