When I go too long without experiencing the gut-punch of failure, I know I’m doing something wrong.

Feeling like I’m good at things feels good. It’s nice to ease into a flow state, produce work I’m proud of, and know at the end of each day that I did something worthwhile—made productive use of my time on this planet.

Unfortunately, that wonderful, comfortable, fulfilling state also suggests that I’m not challenging myself. I’m just doing more of the things I’m already good at. And while th...