In this episode, I sit down once again with my friend Barry Taylor, and what begins as a check-in about life after loss unfolds into one of the most honest, surprising, and wide-ranging conversations we’ve had yet.

Barry opens up about the recent passing of his mother—what anticipatory grief prepared him for, and what it couldn’t. We talk about dementia, family histories that leave their mark long after childhood, and the strange psychic shift that happens when both of your parents are gone. What does it mean to feel like an orphan as an adult? What does it awaken in us? These questions guide us into deeper territory about identity, childhood wounds, and the ways our parents’ unlived lives ripple into our own.

From there, the episode widens into a meditation on originality, artistic risk, and the forces that try to shape us into echoes rather than voices. Barry shares stories from his upbringing—poverty, neglect, and that unforgettable school report calling him “original, but not brilliant”—and reflects on how those early experiences shaped his lifelong commitment to curiosity, nonconformity, and following the edges of things.

We explore parenting, ambition, risk, the cruelty of imposed optimism, and the ways culture pressures us toward safety rather than authenticity. Barry talks about why he’s drawn to singers who don’t “fit,” why dissonance matters, and how discovering one’s voice is a lifelong unfolding rather than a singular moment.

And, in true Barry fashion, the conversation moves fluidly into theology, mysticism, pessimism, and the philosophical terrain of thinkers like Eugene Thacker and Camus. We discuss the mystery of subjectivity, the limits of knowing, and how beginning from meaninglessness might paradoxically open us up to a more grounded joy.

This episode is raw, intimate, wandering, and deeply human. It’s two people thinking out loud about how we become who we are—through grief, through rupture, through risk, and through the beauty of not fitting neatly anywhere.

If you’ve ever wrestled with your past, your voice, or your place in the world, there’s something here for you.