I sat down with Jason Feller, who went from managing private clubs for 20 years to running his own trash bin cleaning business. Tired of missing his kids' activities, Jason decided to make a change.

This as-told-to essay is based on a conversation with Burgess Heberer, a 37-year-old business owner, based in Santa Claus, Indiana. The following has been edited for length and clarity. I loved my old ...