go.Jimmy.go

Every once in a while, something completely unexpected makes you stop and take inventory of your life.

It happened to me recently while I was thinking back to an old blog post I wrote 15 years ago after learning of actor Jackie Cooper’s passing. At the time, I realized that someone I’d never met had nonetheless been part of my childhood.

Watching The Little Rascals after school, seeing Jackie Cooper’s endless pursuit of Miss Crabtree, and simply enjoying the innocence of those afternoons had become memories I didn’t fully appreciate until they were already decades behind me.

That post wasn’t really about Jackie Cooper. It was actually about regret.

Back then, I made a list of people I wished I’d met before it was too late. People whose work quietly became part of my life without them ever knowing it.

Fifteen years later, I realize something else.

Regret isn’t always about the opportunities we missed. Sometimes it’s about the ones we still have.

Over the years, I’ve been fortunate enough to interview many of the entertainers whose posters once hung on my bedroom wall, whether sitting across from them in person or speaking over the phone or Zoom.

One of the unexpected gifts of becoming a writer was discovering that I no longer had to wonder what I would have said to the people who inspired me. I actually got the chance to tell them. Those conversations have become some of my favorite memories—not because they were celebrities, but because I didn’t leave those thoughts left unsaid.

There are still a few people I wish I could have thanked:

I’d still love to tell Bob Ross how many afternoons he unknowingly spent painting for my grandmother and me after school. I’d still like to shake Mister Rogers’ hand and thank him for showing generations of children that kindness wasn’t weakness—it was strength. I’d still treasure a signed copy of The Cat in the Hat from Dr. Seuss. Those opportunities are gone. But countless others are not.

The truth is, we spend so much of our lives assuming there will always be another chance. Another phone call. Another visit. Another concert. Another family gathering. Another conversation. Until one day there isn’t.

As I’ve gotten older, I’ve also come to appreciate the regrets that quietly disappeared. Years ago, I regretted leaving West Chester University before finishing my music education degree. Fifteen years ago, I wondered what life might have looked like had I stayed. Today, I don’t.

Had I remained there, my life would surely have unfolded in an entirely different direction. I may never have become a writer. I may never have written a book. I certainly wouldn’t have experienced many of the incredible opportunities that followed.

I also once regretted not spending more time with my father before cancer entered his life. Looking back now, I choose to remember something different instead: those final years of his life gave us a chance to rebuild a relationship that might otherwise have remained broken forever. Ironically, they became some of our best years together.

Life rarely follows the route we carefully map out, and sometimes that’s exactly the point. Perspective has a way of changing regret into gratitude.

Today, when I hear that someone whose work shaped my life has passed away, I still feel that familiar tug of sadness. But it’s also become a reminder:

Tell people you love them while they’re still here.

Send the email.

Write the note.

Shake the hand.

Take the picture.

Say thank you.

Not because they’re famous, but because none of us are guaranteed another opportunity.

Frank Sinatra once famously said, “Regrets… I’ve had a few.” So have I.

Fortunately, I’ve also learned that many regrets can be avoided by taking a moment to let someone know they’ve made a difference.