Show Notes
In this Lonesome Conversation, Cal and I discuss a kind of loneliness that has nothing to do with being alone — the "island in your own home" feeling that comes from not sharing what you're struggling with, even with a partner who'd drop everything for you. Cal is disarmingly honest about how pride and shame, usually around money, keep him from letting his wife in, and how every time he finally does, he's met with a grace that shocks him. A tender look at how the wall we feel between us and the people we love is one we quietly build ourselves. About Cal Cal is a former trader turned seeker of truth and human potential and the host of The Great Unlearn—a podcast inviting listeners to question old narratives and reconnect with what’s real. After leaving behind a successful career in finance, Cal stepped into a more intentional life—one centered around curiosity, self-inquiry, and personal freedom. Through The Great Unlearn, he holds space for meaningful conversations with entrepreneurs, rebels, and mystics who challenge the status quo and offer new ways of seeing the world. He’s also the founder of Unlearn Ventures—an incubator, fund, and venture studio supporting bold, conscious projects that expand possibility and prioritize people over profit.
Lonesome Conversations Limited Series Lonesome Conversations is a special series from The Life Stylist, built around my new book, A Horse Named Lonesome (out November 17, 2026). Loneliness is something almost everyone goes through, and almost nobody talks about honestly. So I sat down with psychologists, philosophers, trauma therapists, teachers, and friends to find the truth about loneliness, and how we heal from it. Each episode is its own conversation, but together they walk the same ground the book maps out. (Pre-order your copy at ahorsenamedlonesome.com) You'll find new episodes alongside our regular show over the coming months.
More from The Life Stylist
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I join my brother Kyle Kingsbury for a raw conversation about the life experiences behind my new book, A Horse Named Lonesome. We trace my journey from childhood abuse and addiction to recovery and spiritual awakening, exploring how shame, trauma, and the illusion of separation can keep us disconnected from ourselves and others. We also get into forgiveness, ego death, 5-MeO-DMT, and the hard-earned lessons that ultimately inspired me to share this book with the world.
In this Lonesome Conversation, Dr. Lipton and I explore his striking claim that loneliness runs against a law of biology—that no organism, from an ant to a bee to a human, survives outside its community. He walks through why we've been programmed to feel separate by religion, politics, nationality, and sex, and who actually benefits when we're isolated and disempowered. A bracing reframe of the loneliness epidemic as a spiritual and biological crisis rather than a personal failing. About Dr. Lipton
Can a natural drug get you off drugs?
In this Lonesome Conversation, Joel and I explore his reframe that "aloneness can become all oneness" — that you can learn to connect with the earth and sun so deeply you're never truly alone, even in solitude. He shares the story of a teacher who spent 18 years alone doing shamanic practice, and makes the case that intentional solitude, far from something to fear, can be an actual lifeline. A grounding look at why most of us lack the tools to be alone well, and how they can be learned. About Joel Joel Schafer is a personal empowerment mentor and shamanic dreaming arts teacher. Through online courses, one-on-one mentoring, and in-person workshops, Joel trains people in a highly effective way to reclaim vital energy and attention utilizing the Toltec knowledge base. These are powerful, non-linear redistribution techniques that guide and support students in discovering clear purpose, increasing awareness, getting grounded, reclaiming focus, & accessing strong intent. Joel is also an excellent listener and mirror, offering practical but magical solutions to life's challenges.