At Large

Yes, and … and Tom

By Published On: May 29th, 2026

There’s a fairly standard line in detective shows scattered across the stream-o-sphere. “There is no such thing as a coincidence.” It usually arises when the writer needs to insert an inflection point in the script. This past weekend was not a detective show. So its events were either a coincidence … or a “cosmic intersection of realities.” Take your pick.

Over the years, I have had many chances to collide with performers, thought leaders, and celebrities while working behind the scenes to build events. There were always the mandatory photos … the “grip and grin” moments backstage when the event photographer felt compelled to memorialize the meeting of the headliner and the person behind the curtain. Those were moments gone in a flash. With great resolve the smiling faces in those images knew that should we meet again, there would be no recognition, which was fine. We were doing our job … and they were doing theirs.

And, Tom

So, it was mildly amusing when on a recent weekend two of the names and faces from my past created an inflection point that caused a bit of head scratching followed by a wan smile. As Harry Chapin (who was not one of the participants in this moment) sang so eloquently – “All my life’s a circle.”

The sound track for this life lesson was, in fact, delivered by a revered, resilient singer-songwriter who has been writing and performing for 65 years. Yes, Tom Rush is a man of the “elder persuasion,” but when he takes the stage, humor, wisdom, and talent continue to radiate from his mustachioed face. The man “has game.” Music lovers of a certain age may remember his appearance under the tent on the Berkshire Theatre Group parking lot in Pittsfield, MA when artistic director Kate Maguire managed an impossible miracle during the COVID epidemic and brought music and theater to carefully placed, masked audience seating … and brought hope out of darkness to patrons. Tom will be performing at the Guthrie Center in Great Barrington, MA at the end of the summer, and truly, “the juice is worth the squeeze.”

And, Kelly

The second force in the moment was a legend in improvisational theater – Kelly Leonard – currently titled vice president, creative strategy, innovation and business development at The Second City in Chicago. That may be the kind of title that requires a gate-fold business card, but Kelly’s bona fides deserve the recognition. As producer of The Second City troupe, he brought a few notables to the stage: Steven Colbert, Tina Fey, Amy Poehler, Keegan Michael Key, and Seth Meyers to name a few.

It was a re-read of the book Yes, And (New York, Harper Collins, 2015) written by Kelly and Tom Yorton, also a Second City alumnus, after producing a podcast with him that was the underlayment for the weekend’s “Aha!”

We’re not sure Rush and Leonard have ever met. It’s certainly possible, but neither has mentioned it in their resumes. Cosmically, however, they seem to run on parallel tracks. The moment of connection is at the often-baffling moment when spontaneity becomes improvisation becomes the way forward through the perpetual fog of aging.

From Yes, And:

“While no one is ever capable of being in the moment twenty-four hours a day, seven days a week, it is essential that we recognize the moments in our workday when we must make our full selves fully present. In short, if you are in a space where you are expected to bring your creative voice it is vital that you stay in the moment.”

Tom Rush, 86 years old for his Guthrie Center performance, was “in the moment.” He had the audience with him for every song lyric and every guitar lick. He was following Kelly’s mandate, and the crowd rose to meet him.

Growing old is not easy. That bit of hackneyed wisdom comes as no shock. The encouragement – from both Kelly Leonard and Tom Rush, however, is quite simple. As you age, be “in the moment.” After all, there is no such thing as a coincidence. •

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