Oprah & Shaka Senghor on How to Escape Life’s Hidden Prisons

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? I'm here with bestselling author, Shaka Senghor. Welcome back to the Tea House.

I'm so excited to be here and thanks so much for having me.

10 years.

10 years, our 10 year anniversary.

That's incredible.

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. 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 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. What'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. Isn't that one of the core things that we all are striving for? And what made you write this?

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.

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.

Yeah. Yeah.

Yeah, 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. Yeah. You were incarcerated before you went into prison.

Absolutely.

Tell us what that means.

Yeah, so the mindset that I embrace, this narrative that my life can only have two outcomes, I would be dead or in jail before I was 21. And so I live 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 this journaling

and just really trying to ask this question of like, how did I end up here? And what's next for me? And this was how many years into your imprisonment, into your incarceration? This was roughly about eight or nine years in. I was in solitary confinement and really coming to terms with like what my life had become. And I 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.

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. Absolutely. When you're journaling in 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, there are steps you have to take. And I took steps that led me to prison.

So I was like, what are the steps necessary to lead me out of it and lead 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.

Ooh, 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 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. And 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, you know, 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. And what I said to myself when I wrote that down, if I finish 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 which led to Writing My Wrongs eventually.

Yes, yes. And so I wanna say that I think that this book, How to Be Free, a Proven Guide to Esca escaping life's hidden prisons is, it's a guide.

Yeah, absolutely.

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 aren't the ones made of concrete and steel, but they're 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 writing my roms our people would come up to share stuff with me that they said they had never shared before. A child who committed suicide, a dysfunctional marriage, a failure at 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 more-

Forgiveness. And forgiveness, and 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, you know, we come with these narratives where we think we got other people's lives figured out. Oh, they're successful, so they can't have problems. 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.

And that everybody is just here doing the best they know how at any 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 wrongs, the 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, Sherrod. 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, 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. So, it was carrying 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 in my own life. And 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 gonna be confronted with the work.

You're always gonna have a thing to challenge you to think broader about what it is that you're sharing 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 carrying around this ball of anger, this grudge, this need to revenge, you release it. So it doesn't mean you now wanna go sit and have a meal with the man who shot your brother. It means you're able to find some peace in it. Absolutely. Yeah

Yeah, cuz I mean that was the gut reaction was the anger, you know The gut reaction of my family which is natural to be upset to be yeah heartbreaking. We want to get broken Yeah, and so now it's like okay. Do I want to carry that for the next 20, 30 years? Do I wanna show that as I move through life? I have a young son, I have mentees, I have people who look up to me. How do I navigate that?

For me, it's a 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. 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 saw this 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 haunted me all these years and how he came about even knowing who I was.

But 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. And when I got that letter, I bristled up. My body just tensed up with all the anger.

Where were you?

What was going on in your life?

I was actually home. I was at home in LA. And I was outside in. I was at home in LA and you know, I was outside and it's beautiful sunny Mm-hmm, and you know, I opened the letter and I was just like whoa Like in 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 he's still in prison and Just seeing his face like it felt like the weight of the world came off my shoulders

Really because I was able to humanize this guy and he was no longer this boogeyman that just kind of hid in the shadows of my past.

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 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

Yeah incident that changed their life. That's right because that incident caused you to start carrying 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. And I think that's one of the things about forgiveness. 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 forgive and build deeper relationships with? And he wasn't one of them. And I'm okay with that. You know, I've forgiven 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 writing that 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 appreciate it.

Because you didn't even realize how haunted you were by not knowing. Yeah. Because he really is then the boogeyman. Yeah, he's really a ghost.

He's just like a phantom. And just to having the courage to say, I'm sorry, I imagine in an environment that he's in, because I've been there, it's not the easiest environment to be apologetic or to say you was wrong about something

and you know, 32 years later. Would you admit anything? Yeah, yeah, because it's not even encouraged in that environment. And so I thought I was 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'm gonna say I'm apologizing to this guy who can potentially do me harm.

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, I actually wrote my mother a letter. And it was-

So he wrote you a letter and then you thought you write your mother.

Yeah, I wrote my mother a 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 learned most about forgiveness is grace.

Yes, I just want to share with this audience, I'm going to bring it up because it is in the book. It's certainly in Writing My Wrongs, that that seminal moment for me was when you walked into the kitchen as a nine-year-old boy with your report card and your mom throws a pot of whatever she was cooking at you. And in that moment, everything changed for you, you know?

Yeah.

One time I was coming home from school and I was like the smart kid in the 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 now. I'm not sure yet. Like, I came in and she was at the kitchen sink watching this is, and I was like, you know, ma I got this score on my test.

And she rolled around and threw a pot with, like, such force that it broke the tiles on the wall.

That's a life-shattering moment when you think about it.

Yeah, devastating.

That'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 over the years. It took her 17 years to come to visit you when you were 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 sat down to write the letter, I thought I had forgiven my mother. You know, my mother came to see me on that visit. I was like, you know what, ma, I forgive you, I've moved on. But what I realized is that I was holding on to this idea that my forgiveness would somehow change 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 can change that and it wasn't this is such a good point that you're making

Yeah, 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 with my older brother We were talking and he just said to me, you know, I forgave mama and then she did this again and I forgave her and it just struck me. 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 going to get to this deep sense of forgiveness, I just got to 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. Yeah, 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? They're our heroes.

Yeah, we just say, we say this term, hurt people hurt people, but you don't realize what the hurt was like for those people.

Yeah, 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 assaults on her body. And she was willing 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 letting her know how much I appreciated her opening up in that way. And it just allowed me to see her. And it kind of reversed the kind of dynamics in our relationship where I feel more parental.

I feel more like I want to protect that little girl that didn't get protected, who became that woman that hurt her own kids. And so, you know, that's the power of like what real forgiveness is. And when you remove all the expectations that someone will become different or that somehow it's 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.

So that's really the meaning of unconditional.

Absolutely.

Meaning I'm going to forgive you I'm gonna love you regardless of what you do. Yeah, and you have to just hard. That's hard

But you know why it's hard is because the hidden part of it is we still have these conditions, right? And the conditions are I'm gonna do this. What I want is you to change. Yeah, and if you don't 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. Yes. Because it's just your parents, you know, or your children. And that means that old things can be brought up over and over, they can be triggering.

But once I release the things, the things that used to trigger me, I'm just like, that's hurt. That ain't got nothing 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.

Yeah. Absolutely.

Isn't it? Yeah, and I mean, joy is one of the great markers of freedom.

That's right.

It's like, how do you really show up in your life? And, you know, what are the things that feel pleasant in your spirit and in your being? And you can't have that if you're holding on to anger and you're holding on to anger and you're holding on to shame 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. Absolutely.

Yeah, I mean, you think about how we got here. Like, we were born through a resilient effort. The biological makeup of how a sperm reaches an egg, like there's a fight there. Yeah. 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. And 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 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 going to take a stance on something we believe or care about.

But it's so spiritual. And it's the thing about life, as I just mentioned, you don't get to the other side of these things without having to work for it. Forgiveness, I had to work for that. That idea that people are redeemable, the Creator said, you know what? Let's see how much you really believe that.

I'm going to 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 very tough. And the opposite of that is I could have went right back into the anger. I 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 is Ben Horowitz. Yes. 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.

Hi, Ben.

Hey Oprah, how are you? Good to see you, good to see Chaka.

Hey, bro.

So Ben, I'm gonna ask you to tell the story of how you and Chaka first met. I think I have something to do with that actually.

Yeah, 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 to interview 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 back to you. Yeah, 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. He just got out of prison. 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. That people can be redeemed.

And so then you proceeded to tell about the interview and it was a story that you 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 then the next thing I know, she says, oh, you know, I Facebook messaged Shaka

and you know, he's gonna 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 work 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. And then actually the other thing that was very insightful to me or like shocking,

which I really wanted to know the answer to was, there's this thing about solitary confinement, which it's very bad. There's big movements against it because, you go crazy after like two or three weeks in there. He was in it for seven years.

And like, no question, he came out like better than when he went in. And I was so interested, I was like, how did that happen? Like, what happened? And it's actually the story of this book, which is, it's when he rewrote his own narrative.

It's when he finally had the time and space to do that. And that was just so, because so much of achievement and building something great is being able to get to your own truth and be comfortable with that. And his truth was so scary and dark.

I know, and to be able to use solitary confinement, that confinement to actually explore his inner world that way, and to be truthful with himself about the results is what's so fascinating. And what's so fascinating about the first book, Writing My Wrongs, and what's so fascinating now

about how to be free, that you were able to really tap into what that looks and feels like even before he was let go.

Right.

You say Ben taught you an important lesson about failure. What is that?

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 taking an 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. Failing to show up, failing to be curious, failing 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.

I think what's so mind blowing is that you had told Felicia, this guy's a real criminal, don't invite him to the house. And now you guys are like best buddies. Well thank you Ben for joining us. Thank you for for being a part of it. Thank you. We have listeners of our podcast who have questions for you, Shaka,

because I know many people, when they hear your story and read your books, they want to know how you found freedom inside your mind. And Donny is joining us now.

Donny, tell us what's happening down there in Atlanta. Oh, hi, I'm Donnie. So I grew up in a single parent household. My dad was an alcoholic. My mom had her own business, so she was working a lot. So in many ways, I raised myself.

This allowed me to become strong, goal-driven, also a goal getter. That drive motivated me to even strong, goal-driven, also a goal-getter. That drive motivated me to even teach myself how to code and transition into tech after I graduated with my master's degree. I love my job. I love climbing the corporate ladder and I love my team. However, I see myself shrinking whenever I'm around strong personalities. I started to realize that a lot of the patterns that I noticed were from my childhood, where I would treat myself small,

I would tend to be more self-sufficient, where I would avoid conflict as well as overwhelming situations. And even though I'm in a supportive environment right now, I still feel those survival mechanisms rising up. So my question for you is, how do I get the freedom to be my authentic self

regardless of who's in the room?

That's such an incredible story. First of all, I mean, you're incredibly talented, you know, and self-driven, which is very inspiring. So your sense of self-driven, which is very inspiring.

So your sense of self-awareness is you already got like a foot in the door

because that's a big deal. A lot of people navigate through life with imposter syndrome. They're not even aware of how they're showing up. And I think there's power in recognizing that within yourself. And one of the things that I've learned on this journey is that there were two things that I attribute to success in my life now, right? Resilience allowed me to survive, but being literate about life allows me to thrive.

And what I mean about being literate about life is that you're in an environment where you're already winning by every metric imaginable.

Just because you're there. Yeah, because imaginable. Just because you're there.

Yeah, because you're there and you got yourself there.

You already won.

Yeah, you're in, I mean, you're in tech. I worked in tech for three years, and it's a tough, very competitive environment. And the fact that you taught yourself to code and now you're in that environment thriving, like, life literacy is about really understanding

where are you really winning at? And how are you telling yourself that story? And you got to just put the work in over and over. Like, I still have my own mantras to this day. Like, I get up and I'm like, go get it. I got two versions of it. I got the soft, gentle, kind of affirming conversation

that I have myself. And then I have one that's more aggressive when I'm feeling like I'm slipping back into the self-doubt. Like those narratives, they don't disappear. You just got to manage them.

And I think figuring out what is the thing that you can do every day to affirm your success and whatever it is, because those small victories really do matter. And it's easy for us to overlook them. But part of being present, part of being mindful is really leaning into what it's like happening in the moment. I mean, right now in this moment you're in,

everything that you've done led you here. And that's incredible. And somebody is going to be watching this that's being inspired. They're like, wow, Donnie taught herself to code? I'm about to go code.

And so it's a constant. It's work. You know, it takes time. But I'll say affirm yourself every day, no matter what. And in those conversations, recognize that you're not the only one that's navigating that interior conversation.

Working in Silicon Valley for years, I found that a lot of people fake it till they make it, because it is such a fast-paced, hard-driven culture.

But the fact that you're there, till they make it, because it is such a fast-paced, heart-driven culture.

But the fact that you're there, that says a lot about who you are. And you just got to continue to say a lot about who you are to yourself every day.

And also, I think, if I may add here, I think that one of the reasons why you play yourself small is because you don't realize how big you are already. So everybody knows I have a girl's school and I had that girl's school for 18 years now and I recently had a study done this past year to find out where all the girls were in their lives. So I've had 830 girls graduate from my school, 600 graduate from

college, 190 still in college. And so we, as a part of that survey, asked the girls, you know, what does success look like for them? And nobody, I guess, had asked them that question. And many of them said that when they first came to the school, they were comparing themselves to me,

because it's the Oprah Winfrey Leadership Academy, and so they thought that going to the Leadership Academy meant you had to be a leader like Oprah Winfrey Leadership Academy. And so they thought that going to the Leadership Academy meant you had to be a leader like Oprah Winfrey or Nelson Mandela, who was there to help me open the school. But as a part of the interview, they were asked, what does success look like to you now?

And two of the girls were actually out to dinner doing the survey. And they looked at each other and said, look at us. We just came from the gym. We both have our own car. We are sitting at a restaurant that neither our grandfather nor our mothers nor our fathers

would ever be able to sit at. We are successful just because we are here in this moment, even though we're not where we think we should be, we certainly aren't where we could have been. And so, when you realize that you are there coding and taught yourself, that you were able to do that

in spite of an alcoholic father and a single mom. You know, Maya Angelou used to always say, I wouldn't take nothing from my journey now. And I will assure you, Donnie, as one who's lived longer than all of y'all, that every single thing that has happened to you,

not one of those things is wasted. And every single thing that happened, just as Ishaka shows us in his book, How to Be Free, and all of his other works, everything is happening to grow you to the next level for yourself.

Absolutely.

And you are here to meet that rising, and you are capable of doing it because you've already done it.

Yeah, yeah.

And you're here.

You've already done it. You've already done it. So stop comparing yourself to anybody because nobody has your story. Thanks, Brax. Your story is yours to claim. Nobody has your story.

So if you're looking around at what he did or she did or they did, they didn't come through what you came through. They didn't have to endure what you've endured. They didn't have the struggles you had or the sorrows or the joys or the triumphs, any of it. And so when you, when you, when you do what Shaka did, when you really do a true self-examination of how you got to be here, you will be walking around strutting.

You will look like that emoji, that emoji with the red dress on, but look at what you've been through and you're still here and still rising.

And you're hanging out with Oprah today.

And still I rise.

All right.

And Shaka. I'm not bad to hang out with.

Chaka's a great one, too. Thanks, Donnie. Thank you so much.

Thank you.

Lisa's joining us now from Seattle. Lisa, hi.

Hi, Chaka. Hi, Oprah.

Hi.

I hear you're at a big-time crossroads in your life and what's going on with you? Well, I am an only daughter of three older brothers and I grew up knowing that my family just thoroughly loved me and adored me and we had a lot of great advantages growing up and on one end it looked wonderful on the outside and on the inside there were some real hardships.

And I had two brothers that were drug addicts, and one of them had sexually abused me. And I didn't feel like I could share what was going on. There was just my parents were mitigating a lot of the crises that come with having addicts in the home.

So it was really just hard to understand how to feel safe and trust not only others, but trust myself and my decision-making. And so by the time I was in my mid-20s, I had been married and divorced and had lost my dad. And both of those brothers had died of drug overdoses.

And so it went on a real healing path. And I always knew that I wanted to help people through the experiences that I had, especially young women. Just didn't know what that looked like and what avenue. And when my mom passed a few years back, I went to a ranch in Colorado and experienced

the wonderful benefits of equine therapy. And I just thought, this is it. This is the avenue, and this is my purpose. And God has just laid the groundwork for me. A year ago, I was very fortunate to just have a horse drop into my life.

And now I have the opportunity to move to Tennessee and get some land for horses and really pursue this. And yet, at the same time, I feel really guilty because I have my last remaining sibling here that doesn't marry and doesn't have children and really relies on me significantly.

And so this leads to my question for you, Shaka, is how did you learn to trust yourself

and to follow the path that you're on? Before he answers that, you had a horse drop into your life? Horses don't drop into people's lives.

I know. I had a very miracle of a situation.

Okay, so I'm just telling you, I'm just saying a horse drops into your life. You got the horse pillow behind you. We see that horses are important to you. That is a sign. I'm a big believer in signs. Absolutely.

Let Shaka answer the question.

Yeah, that's, I mean, it's true. That's similar to where I was going. It's like, what is life showing you? And what is the divine, you know, part of your experience showing you? And it's all the signs are like there, you know, you, you, like over say the horse doesn't drop into your life.

For me, what it was, was that accomplishing the small things just to do one step right for you to even say what happened to you. That's such a thing to celebrate, that you have the courage to talk about the things that happened to you. That's such a thing to celebrate, that you have the courage to talk about the things that happened to you. And so for me, what it was is that when

I leaned into the things that made me feel afraid, and I just could say them out loud or I can write them out, I started to slowly turn that guilt into gratitude and be just thankful that I could even say it. Thankful that I can write it down and say, hey, this happened to me, but it's not who I am. And then I just started to really care

for the little boy inside. And what I would encourage you to do is think about, there's that little girl inside that you now have the opportunity to protect. You now have the opportunity to nourish, which is like the most incredible part of the gift is that you get a chance to nourish this little girl

by helping others. And, you know, to be on this journey, if you really kind of think about it from instead of like survivor's remorse or survivor's guilt, it's survivor's gratitude. Like, you're here.

I mean, think about where you're at, like, right in this moment, like, the presence, just bringing yourself to presence. You're sitting here having a conversation with Oprah Winfrey and I. That's a true testament to, like, where your path is leading you to something

that's far bigger than what your past was.

Yes. And the horse got dropped into your life by some miracle.

Thank you.

And you now get to use the experience of the treatment that made you feel so liberated. You now get to offer that to somebody else. You now get to offer that to somebody else. You now get to gift what was gifted to you and you get to share that.

You know, I always think it boils down to, obviously, when you read Shaka's story, he was born to do what he's doing right now. And that horse coming into your life means your life has been leading you on a path to where you are right now.

And your ability to open up and do exactly what Shaka said, instead of saying, oh, I'm so guilty, say, thank you. Thank you. Thank you. Thank you for showing me in such a vivid, profound, and pronounced way that I'm headed in the right direction. And I don't know if that resolves the guilt,

but you will find a way to manage whatever other needs your other sibling has or whatever is required of you. But clearly, you're supposed to use the horse experience to share with others.

Absolutely.

Yeah.

Thank you.

Absolutely.

Yeah.

Thank you. Thank you. So I know there's a young man you want us to meet.

Yeah.

Carter is a 21-year-old sophomore joining us from his dorm room at Brown University in Rhode Island. Carter, hey. Hey, I'm his friend too. Welcome to the podcast. I hear Shaka's been mentoring you since you were a itty bitty high school? Yeah, I met him in middle school. What's up, punk? Good to see you. Hey, nephew. So was he helping you to be free? Was he helping you to be free? Oh, yeah. Oh, yeah.

Big time. Big time.

What has he said or done or shown you that's impacted your life that you think has helped you to grow in a better direction?

I think really it's been just being an incredible mentor. I've come to him in times that have been really stressful or just problematic in my life. My parents divorced my sophomore year of high school and I took it relatively rough. And, you know, I came to Shaka

and he was incredibly helpful. His ability to hold space for what I need in those moments was just incredible. He's a proud black man, a wise and compassionate mentor, and the world needs more of that.

That's great. What do you want to say about Carter?

Carter is one of the wisest young mentees I have. You know, I remember one of my favorite moments of hanging out with him. This was when we first met. He had to be around 12, and he was so curious about who I was and my life. And I asked his mother, I said,

Michelle, is it okay for me to tell him just a hard core truth? And she was like, he can handle it, you know? And I got a chance to talk to him and share my past. And he just had so many profound insights. And now what I really love is when he comes to the house, he's kind of like a big brother for Sekou,

a model, somebody he can model. And Sekou's mine, he's way cooler than his dad. So it's the sweetest thing though, just to see how those kids look up. And now he's in his sophomore year in college, doing incredible.

And I'm just super proud. You know, this kid is going to do some amazing things in the world. And to be able to pour into him and to have him receive that, because it's not always easy for young men specifically to take guidance from older men. They put us out to pasture kind of early these days, you know, so to have a young man that says, hey, you know, I'm in town. Can we grab a bite? I just got something I want to talk to you about. It really means a lot. And it just makes me feel really valued in a deep way.

That's wonderful.

Thanks for sharing with us today. So you've been out of prison now for 15 years, as we said at the beginning of this conversation. And almost as long as you were inside prison. Yeah. And I hear you recently applied for a pardon.

Yes.

For the first time. What would a pardon mean for you? Now that you are already free and you're writing books about how to be free. So what would a pardon mean?

You know, when I first put in the pardon, I thought it would just be a symbolic gesture.

Yeah.

And what I realized recently, every time that the mail comes and I'm out looking for that letter, is that I've wanted it more than I had given myself permission to believe. And what it means for me is that I'm now back part of the tribe. When you have a felony on your record, you're exiled. And even when you're as successful as I've become over this last 15 years,

there's still things that come up that's kind of like that slap-on-the-hand reminder of this is who you were, and this is who we'll always think you are. And, you know, when I was filling out that paperwork, I had delayed it for a long time. I was like, oh, maybe I get a lawyer to do it, et cetera.

And I was like, you know what, you have to do it. And, you know, I've carved out the time to do it. And so for me, it's like, just getting granted that would mean I'm back a part of the tribe.

Mm.

This is a question I probably should have asked you at the beginning of this conversation, because I think that for most people who think of someone who's been incarcerated,

and incarcerated for 19 years, who think of someone who's been incarcerated

and incarcerated for 19 years and incarcerated on, you know, been in solitary confinement, that the moment you are released from prison, you would experience freedom in a way that we can't even imagine, you know?

I still think of people that I know who are on death row who haven't seen a moon and haven't seen the stars. And I would just think, wow, everything in life would just feel like freedom, freedom, freedom, freedom. And yet when I read How to Be Free, I recognize that there's so many people who are released

and are still imprisoned once they're released.

Absolutely. Absolutely.

Yes.

And, you know, for me, I still have that feeling as if I walked out the first day. You do? I marvel at life. I am so in love with life. I'm in love with the details of life. I'm fascinated by so many things. I'm curious about so many things. Anthony Ray Hinton, who wrote,

The Sun Does Shine, said that when he came out, rain meant so much to him, just to be able to feel the rain.

All the details, I love it. And I think it's part of, you know, when I wrote this book, is I want people to go back into that feeling. Because I think we get caught up in the mundane of life and we forget about the beauty of nature We forget about the beauty of a casual walk with a friend We forget about like really experiencing food not just for nourishment, but as a real experience

We forget about like what joy is, you know It's going back to being like we have these moments where we're just like dude Let's grab this vinyl and this's just listen to music and talk about the details of art that went into creating this piece of work. And so, to me, it's like every day is a day of freedom.

So for someone who's listening to us today, watching us today, and they want to begin the journey for themselves to be free, they should do what?

They should start journaling. I would say that's my number one out of everything else. Like meditation is incredible. Practice and mindfulness, those things take a little bit of work. But journaling is something that we all have access to, even with technology now.

Like if Donnie just sat down and looked at and asked a question, how did I get here?

Yes.

It's the same question that you asked. You were in solitary confinement asking it, but asking the question y'all, wherever you are in your life of how did I get here and being able to relate to your own story, like choice by choice by choice that put you here. I mean, allows you to see, look at all you've endured.

Yeah, and even keeping that gratitude journal.

Yes, I believe in that.

What is the most magic thing that's happened to me today? And that's something that keeps me so grounded and it helps me get through those tough moments, right? So when I was going through everything with my brother, I was just writing, I was writing letters to the perpetrator.

I was just writing out my thoughts. Like, how do I really feel? Like, what's living inside my being right now? And then what am I thankful for? You know, what is the thing that brought me a sense of joy today? Yeah.

You know, what does that thing look like? The payoff for that is so great, you know, especially when you come back days later, because you move through life, you can start forgetting about, like, how many things did I do this week that was amazing? It's easy to just move through those things and forget about them. But I try to take it all in.

Oh, I do too. And I write down the God winks. Because you really forget the things that other people call coincidences or serendipity or whatever. Where you just go, like, wow, how did that thing happen? If you don't write it down, you'll forget it.

Yeah, absolutely.

Absolutely.

What is one of your favorite Godwinks like? Oh, they're just like little things. Like one time I was thinking about, it was like a rainy day and I was thinking, God, this would be a really good day for a soup. Because when I grew up, there was Lassie. There was a show called Lassie.

I didn't know that. The Collie, the dog.

The Collie, the dog. It was sponsored by Campbell's Soup. And at the end of it, there would be a little thing where Timmy's mother would bring him a bowl of soup. And they would say, soup and sandwich goes together like a soup and sandwich. So I always loved this idea of soup and sandwich. I was just thinking, wouldn't it be great just to have soup and a sandwich? And I was walking through my house and my godmother was staying with us, and she had made a grilled cheese sandwich and some soup.

I love it.

And I just thought, how did you, how did you, how did, yeah, yeah, yeah.

No, it's amazing that you lean into those moments, because I think that's the magic of all of this, is like, how present are you in your own experience? Do you think you're free? I Think I'm definitely free. I feel like the most liberated After writing this book, I feel the most liberated I've felt in my life and I think I've had two iterations of it when I was when I was in solitary and I first

Really started kind of buying into this idea that my life could be different and it was really just Journaling about it, being very present and really acknowledging it. And that acknowledgement is the big piece of it. It's like, hey, I thought I had this thing fully figured out, but I still have work to do.

And that's the part of the journey part of it. It's like, the more life you live, the more experiences you have, the more things you're going to encounter that's going to challenge the way that you think about and experience life.

Reason I like the book is because, How to Be Free, it actually step-by-step teaches you how to manifest. Yes. That's one of my favorite words. How to manifest freedom for yourself in your life

and how that liberation allows you to rise to your greatest glory.

Absolutely.

Thank you for this book. Thank you so much for having me. Thank you, Shaka. And thank you for being here today. Thank you, Ben. Thank you, Lisa, Donnie, and Carter 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. I'll see you next week. Thanks everybody.