Episode Summary What happens when a top strategist at some of the world’s largest tech companies walks away from the known? In this reflective episode, Glenn DeVore joins Allie to talk about the slow unraveling of his corporate identity, the radical power of not knowing, and the healing that emerged from silence. From strategy decks to Vipassana retreats, Glenn shares the moments that cracked him open and the writing practice that helped him reassemble with greater presence and purpose. Along the way, they explore the tension between agency and acceptance, the healing power of inner child work, and the life-changing practice of learning how to pause. Key Themes: * Leaving a high-level corporate role to pursue a life of greater meaning * Vipassana meditation, inner child work, and identity reformation * Writing as a spiritual and psychological practice * Moving from external validation to inner fulfillment * Embracing uncertainty without collapsing into fear Books & Thinkers Mentioned: * Transitions by William Bridges * Comfortable with Uncertainty by Pema Chödrön * Constellations by David Whyte * Determined by Robert Sapolsky & Free Agents by Kevin Mitchell * Teachings by Joseph Goldstein and Kamala Masters * The concept of cetana (Pāli for volition/intention) Where to Find Glenn: Newsletter: Falling Into Place Book project: Light: A 5-Day Memoir Into Stillness (coming soon) Bio For over 25 years, Glenn DeVore shaped strategy at some of the world’s largest tech companies – work that unfolded alongside a growing inquiry into self, consciousness, and agency. A lifelong student of philosophy, systems thinking, quantum physics, psychology, and theology, his most recent inquiries have turned inward, toward the patterns and perceptions that shape how we make meaning of our lives. Today, Glenn is a writer and poet whose work explores transition, identity, and the emotional architecture of becoming. Drawing from Eastern mindfulness practices, Western philosophy, and both cognitive and physical sciences, his writing invites readers to slow down and attend more fully to what arises. He writes regularly at Falling Into Place , and is currently serializing his first book, Light: A 5-Day Memoir Into Stillness , along with other forthcoming books. Glenn believes that attention, when paired with awareness, discernment, and presence, becomes our most sacred form of agency. It is how we shape experience, choose meaning, and meet the world with intention. We may not always choose what arises, but we do choose how we attend to it – and the story we make of what remains. Music thanks to Mutual Benefit! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit alliecanton.substack.com
