TFB 023 - Going on a Bear Hunt: Facing the Past, Finding Yourself w/ Evan "Shakes" Holt

What if understanding who you've become means having the courage to revisit the experiences that shaped you?And what if understanding your past could help you rediscover parts of yourself you didn't even realize you'd lost?In this episode of The Fort Builders, I sit down with Evan "Shakes" Holt, a retired Marine Corps attack helicopter pilot, former commercial real estate professional, and author of A Boy Named Pooh, a deeply personal memoir about childhood trauma, military service, and his journey toward healing.I've known Evan for years through the real estate world. Or at least I thought I knew him.When I learned he'd written a book, we got together for coffee. What followed was a conversation I wasn't expecting. His story, his willingness to share it, and the work he's done to understand himself resonated with me in ways that connect directly to why I started this podcast.Evan grew up in a home marked by abuse and generational trauma. As a young boy, he learned to survive by disconnecting from painful experiences and emotions. Years later, he would serve 21 years in the Marine Corps, including two combat tours in Iraq flying Cobra attack helicopters.From the outside, his life looked successful. But beneath that success were experiences and emotions he had never fully confronted.Eventually, those unresolved struggles began affecting his health, relationships, and sense of who he was.Evan shares how reaching a breaking point led him to examine his past, seek help, and explore approaches to healing—including therapy, reflection, and his personal experiences with psychedelic substances.One of the most moving parts of our conversation is Evan's account of reconnecting with the little boy he calls "Pooh"—a part of himself he believes he left behind many years ago.We also explore self-compassion, breaking generational cycles, and why understanding our stories can change how we see ourselves and others.Near the end, Evan shares a familiar childhood story: We're Going on a Bear Hunt.You can't go over it. You can't go under it. You can't go around it.You have to go through it.For Evan, that became more than a childhood saying. It became a way of understanding his journey.In this conversation, we explore:Childhood abuse and the lasting influence of generational trauma.The unexpected path that led Evan to a 21-year Marine Corps career.Combat, military service, and what happens when the mission ends.The difference between appearing successful and feeling fulfilled.The moment Evan realized he needed to change.His journey through trauma, therapy, self-reflection, and psychedelic experiences.The story behind A Boy Named Pooh and reconnecting with his younger self.How understanding our past can help us better understand ourselves.Gratitude, self-compassion, and the courage to keep growing.Thank you for joining us in The Fort. And thank you for your time.About the guest Evan "Shakes" Holt — A Boy Named PoohEvan is a retired U.S. Marine Corps officer and Cobra attack helicopter pilot who served 21 years on active duty, including two combat tours in Iraq. Following his military career, he worked in commercial real estate. His memoir, A Boy Named Pooh, explores childhood and combat-related trauma and his journey toward healing.