Chris Schembra: The Strange Mercy of a Good Middle

This is the last conversation of my first season, and I almost didn’t finish it.

Chris Schembra came to me the way the best guests do, as a name pressed into my hand by someone I trust. Aliza Kline told me I needed to talk to him, and Aliza is rarely wrong about people. What I didn’t expect was how quickly the conversation would stop being about him.

On paper, Chris is the gratitude guy: the 7:47 dinners, the pasta, the rooms full of leaders he teaches to thank the people they have forgotten to thank. I’m fascinated by the keynote version. And I wanted to talk to the kid underneath it, the one who couldn’t hold onto his own memories, who got marched into the isolation room, who learned early that loss arrives whether or not anyone gives you permission to grieve it. We went there together, and Chris went willingly, all the way down to the tattoos and the rehabs and the version of himself he is still learning to forgive.

And then, somewhere near the end, he did the thing he does to everyone else. He turned the question on me. He asked what was coming up, and I told him about a lost friend, and from there the conversation belonged to both of us.

I sat on this recording for months because I was afraid of that stretch. I am not afraid of it anymore. If you have ever wondered what gratitude actually costs, and what it gives back, this is the one. It lands on a single word, the one Chris wants on his headstone. It’s a good one, and a reminder of what a blessing it is to be alive.

This is the season one finale, finally. I’ll see you back here for more soon.

Links & Notes

• Chris Schembra
• The 7:47 Gratitude Experience / 7:47 Club
• Podcast, Gratitude Through Hard Times
• Books: Gratitude Through Hard Times and Gratitude and Pasta
• The Anatomy of Peace, The Arbinger Institute
• Johann Hari TED talk, “Everything You Think You Know About Addiction Is Wrong”
• Tony Lo Bianco and his one-man Fiorello LaGuardia play, “The Little Flower”
• “Just a Common Soldier (A Soldier Died Today),” poem by A. Lawrence Vaincourt (basis for the Memorial Day 2015 veterans video Chris produced with Lo Bianco)
• Dr. Edward “Ned” Hallowell, ADHD author
• Curb Your Enthusiasm, “Bad Middling”

What is Headstone with Pete Wright?

A well-lived life deserves a great last line.

Headstone is a podcast about legacy—not the kind etched in marble, but the kind we carry in memory, in laughter, in the stories we tell long after someone’s gone.

Hosted by Pete Wright, Headstone uses one deceptively simple question—What do you want on your headstone?—to explore the lives behind the legacies. In each episode, guests reflect on meaning, mortality, creativity, failure, grief, and joy, finding humor and humanity in the messy middle of it all. It’s not a show about death. It’s a show about life—and the words we hope will outlast us.

Because sometimes, the story that survives you… is the best one you ever told.