A few weeks ago, my best friend of thirty years and I went down to Central America for a weeklong surfing retreat. We didn’t know what to expect from the organized vacation and were a bit surprised when we found ourselves grouped with five women, all between twenty-five and thirty-two. Three were other clients, and two were the guides/instructors. As nice as that was, I knew I was now going to be overthinking my every move for the week.

On the second day of the trip, we were all bouncing down a d...