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.

In this premiere episode of Headstone, I sit down with Derek Brandow, an instructor at University of Oregon’s School of Journalism and Communication, to explore the delicate balance between performance and authenticity. 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