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This powerful conversation brings together two men who discovered true freedom within the confines of prison walls. Shaka Senghor, who spent 19 years incarcerated including 7 in solitary confinement, and Christian Howes, Lewis's brother and an award-winning jazz violinist who served 4 years, share their parallel journeys of transformation. (02:26) Both men learned that the most powerful prisons aren't made of concrete and steel, but are built from grief, anger, shame, trauma, and self-doubt. Through journaling, music, mentorship, and confronting their deepest wounds, they found liberation before their physical release. Their stories reveal how anyone feeling trapped - whether physically, mentally, emotionally, or spiritually - can break free and create a life of purpose and meaning.
Shaka Senghor is a New York Times bestselling author, internationally recognized speaker, and leading voice on resilience and redemption. He spent 19 years in prison, including 7 years in solitary confinement, for second-degree homicide before transforming his life through writing and self-discovery. His books include "Writing My Wrongs," "Letters to the Sons of Society," and "How to Be Free."
Christian Howes is Lewis Howes' brother and an award-winning jazz violinist, composer, and educator. After serving 4 years in prison for drug trafficking, he transformed his musical career by learning jazz, blues, and various musical styles from fellow inmates. He has visited nearly 1,000 orchestra classrooms across the United States and created the film "Redemption Time" with poet Jimmy Santiago Baca.
Shaka discovered his path to freedom through journaling while in solitary confinement, asking himself "How did I get here?" (03:28) This practice allowed him to unpack layers of trauma, shame, and inherited narratives that had led to his incarceration. Journaling became his tool for disrupting negative thought cycles and finding the "beautiful human being" beneath the cloud of pain. The practice revealed that if negative mindset worked to manifest destruction, then positive mindset could work to create transformation. This isn't just therapeutic writing - it's archaeological work on your own psyche, digging through layers of conditioning to find your authentic self underneath.
Both men learned that shame erases our victories and keeps us trapped in old narratives. (30:25) Shaka realized that when he experienced a work failure, instead of letting it define him, he needed to remember all his successes, innovations, and the wisdom colleagues sought from him. The key is being intentional about writing down and acknowledging these victories rather than letting shame convince you that "this season doesn't count." This creates a new scorecard based on present reality rather than past failures, allowing you to give yourself the clean slate that professional athletes get each season.
True forgiveness isn't about the other person changing or being receptive - it's about freeing yourself from carrying the weight of past hurt. (1:08:02) Shaka learned this when he received a letter from the man who shot him at 17, and later when he had to truly forgive his mother. Forgiveness with conditions isn't real forgiveness; it's a transaction. Real forgiveness means letting go completely, which allows you to show up differently in relationships and stop carrying "this albatross around your neck" that keeps you trapped in cycles of resentment and pain.
Both men learned to see their younger selves with compassion while maintaining accountability. (25:25) Shaka realized his 19-year-old self was "a kid who had experienced more trauma than is almost humanly possible" and that his actions were "a traumatic reaction to a life full of trauma." This doesn't excuse the behavior, but it provides context that allows for both justice and healing. Understanding this prevents you from being trapped in shame cycles and allows you to address root causes rather than just symptoms.
Some of the most powerful mentors come from unexpected sources and know how to "set the table" for transformation. (47:54) Shaka's prison mentors didn't try to scare him straight - instead, they challenged his intellectual rebellion by engaging him in debates about books and ideas. They became "master teachers" who taught research, argumentation, and critical thinking while feeding his need for intellectual stimulation. The key is finding mentors who understand your language and can translate complex concepts into accessible wisdom, whether in prison, at work, or in life.