A note before we begin: this is not a new conversation. It's the first one.

Before Headstone had a single episode in the feed, I needed to know whether the question at the center of this show—what do you want on your headstone?—could actually carry a conversation. So Derek Brandow, an instructor at the University of Oregon's School of Journalism and Communication, offered the most generous thing a guest can offer: himself, live, in front of his own class, with a room full of students watching the machine work. No safety net, no prior interviews to learn from, no idea yet what this show would become. This was the test. Everything since was built on it.

Now, with a new group of interviews on the way, it felt right to bring this one back as a warm-up—a reminder of where the show started, and a chance to hear the question asked for the very first time.

---

We often think of confidence as a gift—something innate, something you either have or you don't. But what if it's not? What if confidence is, instead, a performance? A mask we wear to navigate the world, to protect ourselves from the fear of rejection, to shield us from a deeper truth: that we're terrified of not belonging.

Derek's journey is a case study in transformation. Raised in an atmosphere of insecurity and shame, he spent years performing his way through life—loud, funny, athletic—all to hide deeper vulnerabilities. But then, thanks to an unexpected catalyst, he reframed his understanding of vulnerability and connection.

Derek's story is about how we, as humans, crave belonging and how that craving shapes the way we present ourselves to the world. Whether it's his work teaching "confidence" to students navigating an increasingly digital and divided world or his reflections on what it means to be truly seen, Derek reveals that the key to connection—and legacy—lies not in what we perform, but in how we listen, how we see others, and how we allow ourselves to be seen.

So join us as we unpack the subtle forces that shape our interactions and discover what it means to leave a legacy not in words but in the courage we inspire in others.

Links & Notes

• Brené Brown's TED Talk, The Power of Vulnerability: Watch it here
• Brené Brown's book, Braving the Wilderness: Find it here

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”

Sometimes at fifteen, sometimes much later, we finally stop running from ourselves. We sit down and ask the quiet but impossible question: Who do I want to be?

This conversation begins with a name. I first knew him as Michael — the professional veneer that felt safe, pronounceable, uncontroversial. But today he is Nachi, reclaiming the Hebrew name that always held the truer story of identity. That shift, simple on the surface, opens a portal into something tender and universal: how identity is shaped not by the roles we play, but by the courage to show who we really are.

Faith plays a profound role in that evolution. Nachi talks about Judaism not as dogma, but as structure, clarity, and purpose — a lens that helps him understand endings without fear and see value in existence itself. He points out that death, in his tradition, gives life its shape, its urgency, its meaning. Mortality becomes not the enemy but the clarifier.

We talk about rage, comfort, goodness, the pursuit of happiness versus the pursuit of pleasure, and the strange wisdom of a terminally ill teenager named Jonathan who taught Nachi how to be happy. We explore the liminal space between clarity and acceptance — how seeing ourselves honestly requires surrender to the things we cannot control, and gentleness toward the things we can.

This episode is about identity, yes. It’s about faith and behavior and clarity and death. But more than anything, it’s about permission: the permission to evolve, to reclaim ourselves, to choose again and again and again who we are becoming.

This is Headstone with Dr. Nachi Felt.