Reboot Podcast Episode #179 – The Work of Getting Free: Redemption, Gratitude & Hope – with Shaka Senghor

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

#179 // September 10, 2025

Guests

Shaka Senghor

Shaka Senghor

Author & Thought Leader

View Bio

Episode Description

In this episode of The Reboot Podcast, Jerry sits down with Shaka Senghor, author, mentor, and leading voice in criminal justice reform, for a tender conversation about transformation, freedom, and what it truly means to be redeemed. 

Together, Jerry and Shaka explore what it means to be free. They discuss how the deepest forms of imprisonment are not always physical, but are instead forged in our minds—made of grief, shame, anger, and old stories. Shaka shares how his path of healing, reading, and a practice of gratitude helped him reimagine his life, and how his writing became a discipline of self-emancipation.

Shaka reflects on the obstacles he continues to face as a returning citizen, and the quiet oppressions that persist even after release. Yet, through gratitude, storytelling, and mentorship, he lights a way forward; not just for himself, but for all who seek to break the cycles of suffering and step more fully into their lives. 

Show Highlights

Memorable Quotes:

“I was incarcerated before I ever stepped foot into a prison cell because I bought into a narrative that had very limited outcomes. And I believed it based on my surroundings, based on my older siblings and the older guys in my neighborhood who had followed these two pathways, dead or in jail.” – Shake Sengor

“How did I end up in a prison cell? You know, I wanted to be a doctor, I wanted to be an artist, I wanted to help people, I wanted to bring beauty into the world.” – Shaka Senghor

“And I just thought about like, man, what are the seeds I’m planting in my own mind? And then I was struck by this idea that I just didn’t know enough about my own life. And that’s when I began to think that, hey, I do have some agency over the rest of my life. I may not be able to control the past. I may not be able to control all the traumatic events that happened to me. But I can take responsibility for my contribution. I can be accountable for how I want to live the rest of my life. And I can create some form of agency even in an environment where you’re stripped of nearly all agency. And that agency was I can choose how I think about my circumstances and how I think about the future.” -Shaka Senghor

“I’ve explained to people that there’s a difference between solitude and solitary confinement. And within solitary confinement, I had to find solitude because that environment is extremely chaotic and barbaric, and inhumane.” – Shaka Senghor

“If you live long enough, you’re gonna offend, hurt, damage, disrespect, dishonor, someone along the journey, and sometimes it’s yourself. And so we’re constantly in a state of repairing. And if you’re aware of it and you’re conscious of it, you’re less likely to cause intentional damage or harm to others. But as we know what it means to be human, no one is exempt from causing harm.” – Shaka Senghor

“We want people to be punished indefinitely. And, you know, the reality is that over 90 % of people will get out of prison at some point. And we have a choice as a society to determine, you know, how do we want people to come home? Do we want them to come home healthy and whole, or do we want them to come home so damaged that they are no longer even able to contribute in a meaningful way?” – Shaka Senghor

“I went into prison at 19, and you know, I’ve been out now for 15 years, and there are still parts of my life where I still find myself maturing. It’s a full-blown adulthood.” – Shaka Senghor

“If you suffer from grief at an early age that you don’t free yourself from, you’ll be stuck at that age. Like there’ll be things about you that you’re suffering arrested development, as if you actually went inside a prison and didn’t come out until you were physically or biologically an adult.” – Shaka Senghor