How to Be Free: Shaka Senghor, Oprah Winfrey, Ben Horowitz

0:01Today, we're sharing a conversation from the Oprah podcast with author, Shaka Senkor, about his new book, How to Be Free. He and Oprah talk about escaping life's hidden prisons, the power for 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 it to it. 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?

0:55What 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? I'm here with best -selling author, Shaka Senkour. Welcome back to the T -House. I'm so excited to be here and thank so much for having me. Ten years. Ten years at our 10 -year anniversary. Yeah, I think you're right. Let me tell everyone listening and watching that shock 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. Yeah. When I first met Shaka's in -core, it had been about six years since he got out of prison after serving 19 years.

1:44Many 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 trouble life that led to that hateful day. You just had an aha there. There. Yeah. Yeah. What Shaka has achieved in this decade since that conversation is truly extraordinary. His book, Writing My Rongs, 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.

2:30What's your advice to anyone who is stuck needing to forgive or be forgiven? 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? is that one of the core things that we all are striving for? And what made you write this?

3:19Because 10 years ago, you wrote a book called Writing My Wrongs, which I just loved 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, decide a freedom. And to be able to live this experience is really what inspired the book. Mm -hmm, yeah. 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.

4:05Yeah. 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. And so when I got out and I started... Okay, so let's start with that. You were incarcerated before you went into prison.

4:39Absolutely. Tell us what that means. Yeah, so the mindset that I embraced this narrative that my life can only have two outcomes. I would be dead on 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 that environment. And then when I had this awakening, You know, I was doing journal and it was just really trying to ask this question like, how do I end up here? And what's next for me? And this was how many years into your imprisonment and your incarceration?

5:18This was roughly about eight or nine years and I was in solitary confinement and really coming to terms with like what my life had become. And I started journal and it just asked me these higher questions, how do I end up here? And what I discovered was that all these things had happened early in my childhood, the trauma of the abuse, the violence, and more importantly, was the narrative that I embrace. And also the choices that you made as a result of that narrative. 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 start to live my life with those outcomes in mind?

5:59Because you could really physically see that for yourself You're journaling and solitary confinement. You have a lot of time. Yeah, yeah. And you were able to absolutely go through the patterns that had put you exactly where you were. Absolutely. Yeah. Yeah, and it was steps. And it was steps like any other thing that you want to build out, their steps you have to take. And I took steps that led me to prison. So I was like, what are the steps necessary to leave me out of it and leave me up into the greatest sense of what it means to be free? and that journaling really opened up all the possibilities because I fell in love with my mind.

6:34Ooh, I love that. I fell in love with my mind. And so long before you were actually let out of the walls of the prison, you felt that you had liberated yourself within the walls of the prison. Tell us about that. Yeah, what I discovered in that space was that that I can go wherever I wanted to go in my mind. And they could take me to places far beyond the prisons. But more importantly, what it did is it showed me that there's still possibility. You still have a life left. And if you can dream, you can actually achieve it. Like it was really like, even though it's one of those things we hear all the time, you know, conceive it, dream it, believe it, and it'll happen, it really became a mantra for me.

7:20And I just 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've, you know, I encourage people to journal, but it's also active journaling. What are the steps that I'm gonna 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 journal is I had never completed anything. I never graduated high school. I had never followed up going to the military. I always started things but never finished anything.

7:53So 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. And what I said to myself, when I wrote it down, if I finished this book in 30 days, my life can be anything that I imagined it to be. And I did it. And that's how writing my wrongs came. That was the beginning of my writing journey. Yes. That's the writing my wrongs, actually. Yes, yes, yes. And so I want to say that I think that this book, How to Be Free, a proven guide to escaping life's hidden prisons, is it's a guide.

8:36Yeah. For anybody looking to tear down their own self -imposed barriers to getting free, and you write on page four, How to Be Free, that prison, you say, prison is designed to break you. The walls, you say, 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 are 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 -doubt. So is that why you wanted to write this book? Absolutely. You know, on my journey, when I put it right in my wrong side, people would come up this sure stuff for me That they said they had never shared before a Child who committed suicide of this functional marriage of failure at job and They would say something about having a conversation really opened them up and liberated them And so I started this kind of interior game this idea of like what keeps people locked in place and these things just cut coming back grief shame, anger and forgiveness.

9:44And forgiveness and the ability to forgive. Yeah. And the more I kept coming back to that, I started to see it in people from all walks of life, which was the thing that was mind blowing to me. Because we come with these narratives where we think we got people's other people's lives figured out. Yeah. Oh, they're successful, so they can't have problems. Yeah. They're wealthy, they can't have problems. They're this, they're that. And then you start to talk to people and you realize we all have it. You know, we all have things that we're working through. and sometimes we're not even aware that we're working through them.

10:13And that everybody is just here doing the best they know how at a given moment. So I know that forgiveness for you has become like a healing agent in your life. And you received it from, you write this in writing, my wrong God, mother 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, Sharad. What's your advice to anyone who is stuck, needing to forgive or be forgiven? That part of my journey has been so profound. Because when you receive forgiveness, you forget that sometimes in life, you may have to forgive someone.

10:57And it can be so complex. It's not an easy thing. 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. So there was care and the duality of guilt while trying to grieve and then reconciling that through what have I been teaching in the world, whatever I've been saying to people all along. And now it comes front and center my own life.

11:35And I think that's the power of what this book is really about is that true freedom doesn't come without the work. You're always going to be confronted with the work. You're always going to have a thing to challenge you to think broader about what it is that you're selling in the world. And I think people always miss the point of forgiveness because you really do it for yourself. Absolutely. You do it to free yourself so that you're not not carrying around this ball of anger, this crudges, this need to revenge. You release it. So it doesn't mean you now want to go sit and have a meal with the man who shot your brother.

12:12It means you're able to find some peace in it. Absolutely. Yeah. Because I mean, that was the gut reaction was the anger. You know, gut reaction to my family, which is natural to be upset, to be heartbreaking. We want to get you broken. And so now it's like, okay, do I want to carry that for the next 20, 30 years? Do I want to show that as I move through life, you know, I have a young son, I have mentees, I have people who look up to me, how do I never get that? You know, for me, and so heavy weight to carry, to have that level of anger, just hanging over your head. So when you were 17, you were shot by a man named Terrence.

12:49Yeah. And I think this is so remarkable. You write about receiving a letter from Terrence. 32 years later. What does it say about the weight or the burden that he reached out all those decades later? It is one of the most powerful and complex experiences I've ever had in my life. When I first got the letter, there was a full range of emotions that went through my mind, because I've never really sought his guy's face. That shooting was our only encounter, which was about 30 seconds. And I didn't realize that that inability to see this guy's face had horned me all these years. And how he came about even knowing who I was.

13:30But that guy shooting you is what sent you on another path, because that's when you went and got your own gun. Yeah. It was the cycle. Yeah. And when I got that letter, I bristled up my body just to start with all the work. Where were you? What was going on in your life? I was actually home. I was at home in LA and I was outside and it's beautiful sunny. and I opened the letter and I was just like, whoa. Like, and all the things that moment came flashing back and then I was like, I gotta see this guy's face. So I got on the computer and I looked him up because he's still in prison. And just seeing his face like, it felt like the way that the world came off my shoulders.

14:11Really? Because I was able to humanize this guy and he was no longer this boogie man that just kind of hit in the shadows in my face. So how did he find you and why did he write you? So he found me because another guy was reading my book in prison and passed it on to him. He started reading it and he was like, oh my god, this is the guy I shot. And here's what the outcomes of his life was as a result of that moment. And he took so much responsibility for that moment. And I still have complete agency over that decision. But I understand how he would arrive at how one incident can spiral somebody into, you know, what, incident that changed their life.

14:47That's right. Because that incident caused you to start carrying I mean, a weapon yourself and everything that resulted from that. So is it true that you've not written him back yet? So I started writing it and then I didn't finish it. And then I put it up and I was like, you know, I don't owe him a letter. You know, and I think that's one of the things about forgiveness. You know, it's not about him. It was really about me. And what I realized was like, what matters in my life today? Who are the people around me today that matter that I can't forgive and build deep for relationships with, and he wasn't one of them.

15:24And I'm okay with that, you know, forgiving him and, you know, I hope for the best life outcomes for him. But I didn't feel it was necessary for me to follow through with, with right now letter. But you had started to write a letter. I did start to write it. And what did you want to say at that time? Well, I wanted to say thank you for finally revealing your face. I thought that was really, really an important part of my journey and that I appreciated. Because you didn't even realize how haunted you were by not knowing. Yeah. Because he really is then the boogie man. Yeah, it's literally a ghost.

15:53He's just like a phantom. Yeah. And just to have an encourage to say, I'm sorry, I imagine an environment that he's in, because I've been there, it's not the easiest environment to be apologetic or to say he was wrong about something, you know, 32 years later. I should admit anything. Yeah, yeah, because it's not even encouraged in that environment. And so I thought it was a brave of him, you know, and that's what I would have said. I thought that was brave step to take. And knowing that, you know, he's very vulnerable to even reach out because I still have a lot of influence in that environment and he didn't know how healed I am or where I met in my journey.

16:27So just a courage to say, you know, I'm gonna say I'm a apologizes guy who can potentially do me harm. You know, I thought that was courageous. But you haven't responded to his letter, but you do say that that letter helped you in the healing process with your own mother. How? Yeah, yeah. I actually wrote my mother a letter. And it was you a letter and then you thought you were your mother. Yeah, well my mother letter and you know My mother and I had a very complex relationship, you know going back to all the things that I had written about before and What I lying most about forgiveness. Yes, I just want to share with this audience I'm gonna bring it up because it is in the book It's certainly in in writing my wrongs that That's seminal moment for me was when you walked into the kitchen is a nine -year -old boy with your report in your mom throws a pot of whatever she was cooking at you.

17:20And in that moment, everything changed for you, you know? Yeah. One time I was coming home from school. I was like a smart kid in a family. And so my grades was like the thing that I was most proud of. And so came home super excited to... How old are you? I'm probably in the fourth grade. So I'm assuming like eight, nine or not short yet. And I came in and she was at the kids of St. Washington. This is, and I was like, you know, my heart got to the floor, my chest. And she rode around and threw a pot with like such force that it broke the towels on the wall. That's a life -shattering moment when you think about it.

17:59That's a life -shattering moment when you think about being an eight -year -old or nine -year -old coming home and saying, mom, look at my grades. So you've had a volatile relationship with your mom. I was over the years. It took her 17 years to come to visit you when you incarcerated. And after you get the letter from Terrence who shot you and sent you on a spiraling path downward, you then are moved to free yourself to write your mother. Yeah, and so when I say down the right the letter, I thought I'd have forgiven my mother. You know, my mother came to see me on that visit. I was like, you know what?

18:41My forgive you, I moved on. Well, what I realized is that I was holding on to this idea that my forgiveness was somehow changed her, which would in turn change our relationships. And so that little boy part of me that just wanted to be nurtured by my mother, I thought I could change that. And it wasn't a trouble. Well, this is such a good point that you're making. And if you're going to forgive with conditions in place. It's really not forgiveness. It's really not forgiveness. Yeah. And I learned it through a conversation from my older brother we were talking. And he just said to me, you know, I forgave Mama and then she did this again.

19:14And I forgave her. And it just struck me and I was like, whoa, I've done the same thing. I put all these conditions around it without even interrogating how she even got to become the woman that she was. And so I was like, you know, if I'm gonna get to this deep sense of forgiveness, I just gotta know her story. And if she's willing to go on that journey with me, the possibilities are infinite. And so we went on that journey and we spent time together. We talked deeply and my mother shared things with me. That was heartbreaking.

19:50Yeah, just to think about what her young life was. And I don't think we do enough of that when it comes to our parents, right? There are heroes or girls. Yeah, we just say, we say this term, hurt people, hurt people. Yeah. But you don't realize what the hurt was like for those people. Yeah, and so when my mother she was willing to open up and she just shared all these things that she had went through the abuses the thoughts on her body And she was willing to to really share that with me and I thought it was one of the most powerful Things that she could ever do and so I wrote her the letter just let her know how much I appreciate it Her opening up in that way and it just allowed me to see her and it kind of Reverse the kind of dynamics in our relationship.

20:31I feel more parental I feel more like I want to protect that little girl that didn't get protected, who became that woman that heard her own kids. And so, you know, that's the power of like, what real forgiveness is. And will you remove all the expectations that someone will become different? Or that somehow is for them. That's true freedom. That's true freedom. And it's like, I have so much grace for her. I have so much joy whenever we're together and when we're not. I have grace and joy when it's going good and when it's not and it's fine. You know, so that's really the meaning of unconditional.

21:10Absolutely. Meaning I'm going to forgive you. I'm going to love you regardless of what you do. And you have to just say, that's hard. That's hard, chagah. What you know, I ask hard is because the hidden part of it is we still add these conditions, right? And the conditions are, I'm going to do this, but what is for you to change? Yeah, and if you'd all change, just don't hurt me again. The reality is that the people that you forgive can possibly hurt you again. And then you have to decide, okay, do I want to go back into that door again? You know, and that's the complex things with, especially with parental relationships.

21:46Yes. Because it's just your parents, you know, or your children. And that means that all things can be brought up over and over, they can be triggering. But once I released the things, the things that used to trigger me, I'm just like, that's, that's hurt. That ain't got anything to do with me, you know? Well, don't you think too, when you can't forgive without conditions being placed upon the forgiveness, that it's really challenging to experience true joy. Absolutely. Absolutely. Yeah, and I mean joy is one of the great markers of freedom. That's right. How do you really show up in your life?

22:23And, you know, what are the things that feel pleasant and you're spiraling into your being? And you can't have that if you're holding the ones anger and you're holding one to the same for things that don't even no longer exist. I think that's a great line. Joy is one of the great markers of freedom. Absolutely. And I also know that you believe, and you talk about this in how to be free, that resilience is a spiritual principle. Explain that. Yeah, I mean, you think about how we got here. Like we were born through a resilient effort. The biological makeup of how a spine reaches an egg. like there's a fight there.

22:58Yeah. Yeah, people get into this kind of comparative Olympics where they're like, well, I didn't have it as hard as you. And so I'm not as resilient as you. But I'm like, I didn't go into prison knowing I was resilient. You know, I was faced with adversity that forced me to make a decision of how do I want to live my life? Do I want to forge ahead or do I want to just quit? And what I knew was embedded in my DNA was resistance and struggle and to overcome adversity. And if we all have that, we're born with it. We, you know, sometimes we give it up. We give up agency over how we're gonna take a stance on something we believe or care about.

23:32But it's so spiritual and it's the thing about life. You know, as I just mentioned, like, you don't get to the other side of these things without having to work for it. Forgiveness, I had to work for that. You know, that idea that people are redeemable. The creator said, you know what? Let's see how much you really believe that. I'm gonna put the person who shot you, right? back in your face. I want to put the person who shot your brother right back in your face. What do you really believe? And that's the spiritual nature of like really working through something that's varied stuff. And the opposite of that is I could have went right back into the anger.

24:06I could have shrunk right back into the space that didn't allow me to be happy and joyful. And that's the hidden part of the prisons. I know you believe in mentors because you are one. Absolutely. To so many people. And one of the great mentors in your life has been Horowitz. It was a very well -known venture capitalist in Silicon Valley, and one of the founders of the legendary firm, Andrews and 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 Best Sellers, the hard thing about hard things. And what you do is who you are.

24:44Ben is joining us via Zoom. Welcome, Ben. Hi, Ben. I hate over how you get to see you. Chocoff. Hey, bro. Uh, so Ben, I'm going to ask you to tell the story of how you and Chocoff first met. I think I have something to do with that, actually. Hey, you did. You did. So you were screening belief. Yeah. And uh, you screened it in Silicon Valley. Yeah. I done a series on religions all over the world and I was screening it. Yeah. 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.

25:24And then I got, I can't wait. 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 if they have to trust me to get that intention. Jesus, I'll give you an example. The example was, 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. And I asked him, before the interview, I said, you get your intention, but you have to tell me what it is.

26:03And he said, well, my intention is that people won't be judged by the very worst thing that happens in their life. Yeah, the people can be redeemed. And so then you proceeded to tell about the interview and then it was a story that she just mentioned. That still makes me want to tear up. Yeah. 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 the next thing I know, she says, oh, you know, I Facebook message Shaka and you know, he's gonna come over to dinner tomorrow night. And I was like, are you crazy?