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.
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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
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.