--:-- Oprah Winfrey: Today, we're sharing a conversation from the Oprah podcast with author Shaka Senghor about his new book, *How to Be Free*. He and I talk about escaping life's hidden prisons, the power of forgiveness, and what true freedom feels like. A16Z co-founder Ben Horowitz also joins to reflect on Shaka's journey and its lessons for leadership and growth. Let's get into it.
--:-- [Oprah introduces the episode]
--:-- Oprah Winfrey: Hey there, everybody. I am so glad to meet up with you here on the Oprah podcast. And it is always my great hope that the conversations that you see here or listen to here can serve to open or expand the aperture of your life. And on this episode, I really hope we do that because we're exploring this question: What does it mean to be truly free? What would that look like? And more importantly, what would it feel like inside yourself for you? And consider asking yourself, what is holding you back from pure freedom?
--:-- [Oprah introduces Shaka Senghor]
--:-- Oprah Winfrey: I'm here with best-selling author Shaka Senghor. Welcome back to the Tea House.
--:-- Shaka Senghor: I'm so excited to be here and thanks so much for having me.
--:-- Oprah Winfrey: Ten years. Ten years. Our ten-year anniversary. It's incredible.
--:-- Shaka Senghor: Yeah. Let me tell everyone listening and watching that Shaka and I first met here 10 years ago. And as we were saying coming in, a lot of living has happened with both of us since then. When I first met Shaka Senghor, it had been about six years since he got out of prison after serving 19 years, many of them in solitary confinement for killing a young man when Shaka himself was just 19. It is one of my most memorable interviews ever. We talked about his troubled life that led to that fateful day.
--:-- [Oprah reflects on Shaka's journey]
--:-- Oprah Winfrey: You just had an aha there. Yeah. Yeah. Yeah. What Shaka has achieved in this decade since that conversation is truly extraordinary. His book, *Writing My Wrongs*, became a New York Times bestseller. He landed and left a high-powered corporate job, started his own business, even collaborated with the rapper Nas on a hit song. His new book, *How to Be Free*, is a must-read for anybody looking to manifest their own vision of freedom.
--:-- [Oprah asks Shaka about forgiveness]
--:-- Oprah Winfrey: What's your advice to anyone who is stuck needing to forgive or be forgiven?
--:-- Shaka Senghor: With *How to Be Free*, Shaka has written a workbook filled with hard-earned life lessons and practical exercises that he uses. And you can, too, to liberate both body and mind. Ooh, I love that. I fell in love with my mind. I love this question of being free. So I want to dive right into it because it's your newest book, *How to Be Free*, *How to Be Free, A Proven Guide to Escaping Life's Hidden Prisons*. I saw this title and I thought, whoa, how to be free? Isn't that one of the core things that we all are striving for? And what made you write this?
--:-- [Shaka explains his inspiration]
--:-- Shaka Senghor: Because 10 years ago, you wrote a book called *Writing My Wrongs*, which I just love that title. And *How to Be Free*. You've been free now for how many years? Coming up on 15 years. So it's really amazing to even think about that part of my journey after spending 19 years to now be 15 years this side of freedom. And to be able to live this experience is really what inspired the book.
--:-- [Oprah and Shaka discuss hidden prisons]
--:-- Oprah Winfrey: And you were inspired because you have conversations with other people and you realize there are many people who are not like you. They hadn't been to a real prison, hadn't been incarcerated behind bars, but are incarcerated in their own self-imposed bars.
--:-- Shaka Senghor: Yeah. Yeah. Yes. You know, it's been one of the most incredible parts of my journey is to think about what does it even mean to be free? And obviously I had the kind of very real experience of being physically incarcerated. But what came up for me was that I was free before I ever got out of prison. I was actually free before I even knew I was getting out of prison. But I was also incarcerated before I went in. Because I had bought into a narrative that my life could only have very limited outcomes.
--:-- [Shaka shares his personal journey]
--:-- Shaka Senghor: The mindset that I embraced, this narrative that my life can only have two outcomes. I would be dead or in jail before I was 21. And so I lived within this very limited belief about— That was its own incarceration. That was my own prison, the own hidden prison. And so I began to live my life through that lens, and it produced that outcome. I ended up being in that environment. And then when I had this awakening, you know, I was doing this journaling and just really trying to answer this question of, like, how did I end up here? And what's next for me?
--:-- [Oprah and Shaka discuss journaling]
--:-- Oprah Winfrey: This was roughly about eight or nine years into your incarceration. You were in solitary confinement and really coming to terms with like what your life had become. And you started journaling and just asking these hard questions. How did I end up here? And what I discovered was that all these things had happened early in my childhood, the trauma, the abuse, the violence, and most importantly was the narrative that I embraced. And also the choices that you made as a result of that narrative.
--:-- Shaka Senghor: Absolutely. Absolutely. And that was one of the most powerful things that if I can choose based on this negative narrative and create these negative outcomes, what would happen if I chose positive narrative and started to live my life with those outcomes in mind? Because you could really physically see that for yourself when you're journaling and solitary confinement, you have a lot of time.
--:-- [Oprah and Shaka discuss forgiveness and healing]
--:-- Oprah Winfrey: Forgiveness for you has become like a healing agent in your life. And you received it from the godmother of the young man that you had shot and killed. And that's what landed you in prison. You also gave forgiveness to the man who killed your younger brother, Sherrod. What's your advice to anyone who is stuck needing to forgive or be forgiven?
--:-- Shaka Senghor: That part of my journey has been so profound because, you know, when you receive forgiveness, you forget that sometime in life you may have to forgive someone. And it can be so complex. It's not an easy thing. You know, my brother was murdered in 2021. And it was heartbreaking because my gut reaction was all the negative things that come with losing a loved one. And then I thought about this person's soul, like what led him down that path. And it was really having empathy and compassion for his journey because I had my own experience.
--:-- [Shaka shares a personal story]
--:-- Shaka Senghor: So I started writing down, here's what I want to happen in my life. And I've realized that writing it down was just part of it. And I encourage people to journal, but it's also active journaling. What are the steps that I'm going to take to make this become reality? So active journaling. So give us an example. You would write down. So I wrote down that I wanted to finish something. Because what I learned during my journaling is I had never completed anything. I never graduated high school. I never followed up going to the military. I always started things but never finished anything. So one of the first things for me was you have to complete something. And that something was writing a book. And I gave myself a very defined timeline to do it. 30 days, you have to write a book. And that was the action step.
--:-- [Oprah and Shaka discuss the power of forgiveness]
--:-- Oprah Winfrey: You write on page four of *How to Be Free* that prison is designed to break you. The walls, the rules, the routine, it's all meant to just strip you down until you forget who you are. And what you discovered is that the most powerful prisons aren't the ones made of concrete and steel but they are the ones that we carry with us that are built from our anger and our shame and our trauma and our self.
--:-- Shaka Senghor: So is that why you wanted to write this book? Absolutely. You know, on my journey, when I wrote *Writing My Wrongs*, our people would come up and share stuff with me that they said they had never shared before. A child who committed suicide, a dysfunctional marriage, a failure at a job. And they would say something about having a conversation really opened them up and liberated them. And so I started just kind of interrogating this idea of like what keeps people locked in place? And these things just kept coming back. Grief, shame, anger, and the inability to forgive.
--:-- [Oprah and Shaka discuss resilience]
--:-- Oprah Winfrey: I know that forgiveness for you has become like a healing agent in your life. And you received it from the godmother of the young man that you had shot and killed. And that's what landed you in prison. You also gave forgiveness to the man who killed your younger brother, Sherrod. What's your advice to anyone who is stuck needing to forgive or be forgiven?
--:-- Shaka Senghor: That part of my journey has been so profound because, you know, when you receive forgiveness, you forget that sometime in life you may have to forgive someone. And it can be so complex. It's not an easy thing. You know, my brother was murdered in 2021. And it was heartbreaking because my gut reaction was all the negative things that come with losing a loved one. And then I thought about this person's soul, like what led him down that path. And it was really having empathy and compassion for his journey because I had my own experience.
--:-- [Ben Horowitz joins the conversation]
--:-- Oprah Winfrey: I know you believe in mentors because you are one. Absolutely. To so many people. And one of the great mentors in your life is Ben Horowitz, who is a very well-known venture capitalist in Silicon Valley and one of the founders of the legendary firm Andreessen Horowitz. And you write about his instrumental guidance in your life. Now, some of you may know Ben is the author of two New York Times bestsellers, *The Hard Thing About Hard Things* and *What You Do Is Who You Are*. Ben is joining us via Zoom. Welcome.
--:-- Ben Horowitz: Hi, Oprah. How are you? Good to see you, Chaka. Hey, bro.
--:-- [Ben shares his perspective]
--:-- Ben Horowitz: So, Ben, I'm going to ask you to tell the story of how you and Chaka first met. I think I have something to do with that, actually. You did. You did. So you were screening *Belief*. Yeah. And you screened it in Silicon Valley. Yeah, I'd done a series on religions all over the world, and I was screening it. You had been gracious enough to interview me in Silicon Valley. Yeah. So because I had interviewed you, I was terrified. Just because you're really good at interviewing. And so I thought, okay, this is, I hope she doesn't judge me. And then I got the idea of, like, you know, maybe I could ask you a few questions about interviewing beforehand and that would help me. And you said something that was really insightful. You said, you know, I always ask people before I interview them what their intention is, and then that they have to trust me to get that intention. She says, I'll give you an example. And the example was, you know, you said I just had this guy on my show, *Super Soul Sunday*. He had tattoos, dreadlocks, big muscles. He's a real scary guy. I just got out of prison after 19 years. And I asked him before the interview, I said, you know, I'll help you get your intention, but you have to tell me what it is. And he said, well, my intention is that, you know, people won't be judged by the very worst thing that happens in their life. Yeah. That people can be redeemed.
--:-- [Ben reflects on Shaka's journey]
--:-- Ben Horowitz: And I told my wife, Felicia, who you know, and she got very excited. So she reached out to your team, got the galley for his book. And so we read the book. And then the next thing I know, she says, oh, you know, I Facebook messaged Shaka and, you know, he's going to come over to dinner tomorrow night. And I was like, are you crazy? Did you read that book? I was like, that guy was in prison. He's a prison gang member. And so I said, look, we set it at a restaurant. You know, we'll go to a restaurant. Don't bring him to the house, Felicia. We could just go home. Don't invite him to the house. So then she goes, okay. And we moved it to a restaurant. And then we meet. And it was really, I'd say, a little bit shocking for me because in talking to him, he actually sounded like, you know, I worked with CEOs all day. He sounded like a really, really advanced CEO. Like he knew all about like psychology, motivations, systems how they work together how you get to the truth. And I was like wow I could learn a lot from this guy about how he thinks about these things.
--:-- [Ben and Shaka discuss failure and success]
--:-- Shaka Senghor: Yeah, so, you know, Ben and I, we talk a lot about success. And I remember asking him, what does success mean? And he said to me, it's a series of smart decisions and a step-by-step. And I ended up asking that question again recently, and he was like, it's the same thing with failure. It's a series of steps taken in the opposite direction. And I was like, whoa. Because, you know, it's like we can think about the steps toward something positive and progressive, but we don't also always think about failure as it's a series of things that you also do. Fail in to show up, fail in to be curious, fail in to follow through. All these things are steps that lead in one very clear direction. You're going to fail. And that was just, it was so mind-blowing to hear that, his perspective on it.
--:-- [Oprah concludes the episode]
--:-- Oprah Winfrey: Thank you for this book. Thank you. Thank you so much for having me. Thank you, Shaka. And thank you for being here today. Thank you, Ben. Thank you for Zooming in with us. Shaka's book is *How to Be Free*, and it's available September 9th, wherever books are sold. To all of you listening and watching, I appreciate you sharing your valuable time with us here. And let's meet up again next week. Go well, everybody. You can subscribe to the Oprah podcast on YouTube and follow us on Spotify, Apple Podcasts, or wherever you listen. I'll see you next week. Thanks, everybody.
