What I Won’t Regret

Chasing dreams, facing setbacks and discovering the deeper purpose in the relationships and legacy we leave behind.

Photo by Osama Madlom on Unsplash

Once upon a time, I wanted to be a professional tennis player. I worked hard going into my senior year at the high school level, getting into the best shape of my life. My coach slotted me near the top of our team’s meets, but as I faced other number one or two players, I lost most of those matches, only winning one of nine matches that year.

Undeterred, I practiced with my college tennis team but was never good enough to break the top eight (only the top eight got to play matches against other schools). Still undeterred, I played in a handful of tournaments around the Midwest after college and often lost in the first round.

Finally, after losing a close match in St. Louis, I realized I would never be good enough to play at a high(er) level, but I could still play and love the game recreationally. I watch it more than I play it these days, but I don’t regret my time in the sport.

Once upon a time, I grew my hair long, wrote ten songs and shared them with heavy metal band members who toured my area. I even learned how to play guitar, well … kinda. I was never very good. I didn’t consider getting into music to be my dream, but it was fun to disappear into it for a while.

“Many people die with their music still in them,” Oliver Wendall Holmes said. “Too often it is because they are always getting ready to live. Before they know it, time runs out.”

I’ve probably had the opposite experience, spending more time dreaming than getting ready to live. I've chased passions with abandon, not always knowing whether they would lead anywhere, but I was unwilling to let them go untried.

Over the past twenty-plus years, I’ve pursued writing. It’s been an honor to have been published in many magazines, newspapers and websites. And I’ve written twenty books. Some of my work has gained a faithful following. But mostly, I write in obscurity. And I’ve settled comfortably into that reality.

I won’t die with my music still in me. I will have played decent tennis, made bad (but honest) music and written articles and books that have left a small mark on the world. But I’m not sure any of those pursuits are actually my “music” in the sense that Holmes wrote about.

My music, as I would define it, will be the spiritual legacy I will leave on my nieces and nephews. It will be in the deep connections I’ve had with friends. And it will be in the way I have cared for others. I will never regret any of those.

If I hadn’t gone hard after tennis and writing, and if I hadn’t let myself get lost in music for a while, I might have had small regrets at the end of my life. But if I hadn’t loved people well, that would be my ultimate regret.