How A 32-Year Sentence Sparked Real Freedom + Resiliency with Jesse Crossen (Part 1)

One bad chapter doesn’t have to be the last, but what does it actually take to believe that when the consequences are real? We talk with Jesse Crossen, founder of Second Chancer Foundation and author of The Best Part of Prison, about the uncomfortable truth behind transformation: it often starts after the collapse, when you can’t run anymore.

Jesse shares how a lifelong sense of not being “enough” pushed him to search for relief in all the wrong places, until cocaine turned a gap year into a fast spiral that ended in robbery, a shooting, and a staggering 32-year prison sentence. We dig into the moment prison became a strange doorway to agency, the daily choices that rebuilt self-respect, and the mentorship that changed everything including his story of helping a man called Big Baby earn his GED and, in the process, learning what persistence really looks like.

We also follow the re-entry journey after a conditional governor’s pardon in 2021: decision fatigue, learning how to make choices again, and using storytelling to connect with people who feel trapped in “mental cages” even without bars. Jesse explains how his non-profit keeps iterating based on what works, from early re-entry programs to a bold new idea: a re-entry video game for prison tablets that lets people practice high-stakes life skills in a low-stakes environment. If you care about resilience, addiction recovery, criminal justice 

The Quiet Gift: A Journey of Self Worth and Resilience is now available for download as an audible.  Check it out!

Transcript

A Question About Feeling Depleted

SPEAKER_00 0:06

All of us reach a point in time where we are depleted and need to somehow find a way to reignite the fire within. But how do we spark that flame? Welcome to Reignite Resilience, where we will venture into the heart of the human spirit. We'll discuss the art of reigniting our passion and strategies to stoke our enthusiasm. And now here are your hosts, Natalie Davis and Pamela Cass.

SPEAKER_03 0:42

Welcome back to another episode of Reignite Resilience. I am your co-host, Natalie Davis, and I'm so excited to be back with all of you today. And joining me, of course, is your co-host Pam Cass. Hello, Pam. How are you?

SPEAKER_02 0:53

I am good. Good to be here.

Meet Jesse Crossen And His Work

SPEAKER_03 0:55

I don't even know what day of the week it is, but it's another day in paradise. It is another day in paradise. That's what it is. Exactly. And one that I kind of like planned my day around our recording session because I am on the road today and it's everything else is like folded by the wayside of like I just need to be in a spot planted in order to record on time. That's all I need for the day, and all is well in the world. And it happens. Here we are. We made it. We did it. I love it. I love it. Oh my gosh. Well, we have a wonderful guest joining us today. And I am so excited to dive in and have his story shared with our listeners. So, Pam, I'm gonna turn it over to you. Why don't you let our listeners know who's joining us today?

The Insecurity That Fueled Addiction

SPEAKER_02 1:40

Absolutely. I'm excited about this one. So today we have Jesse Crossen. He is the founder of Second Chancer Foundation and author of The Best Part of Prison, Ben Bella Books 2026, a memoir about transformation, resilience, and unexpected gifts found in life's darkest moments. A governor's pardon recipient, turned advocate. Jesse now speaks, writes, and builds programs that help at-risk youth and returning citizens rewrite their stories. He is the voice behind a growing movement, providing that your worst movement, proving that your worst chapter doesn't have to be your last. So excited to have you here with us, Jesse, and just excited to hand it to you to kind of share your story with us. Thank you for having me. And you started with so much energy.

Robbery, Shooting, And The Arrest

The Day A 32-Year Sentence Lands

Choosing Agency Inside Prison

SPEAKER_04 2:33

I was worried. I was like, am I gonna be able to keep up? Am I gonna be able to step into this? Because it was a very long night. But thank you. You know, I get sometimes uncomfortable when people describe me as like a voice or a leader in a movement. And I think that's been one of my issues all along. As a kid, I never really felt like I was good enough or like I was deserving or I was I was right. I always felt like everyone else knew something that I needed to know. So I always felt like I was behind. And I was kind of searching for the answer, for community, for permission, for all these things. And I searched in a lot of places. I searched in relationships and I searched in sports and I searched in academics. And then the first time I did cocaine, I was like, oh, this is it. This is what I've been looking for my whole life. And it felt like an answer to my problems, but I didn't realize just how much of a problem it was going to create. And in a matter of three months, I went from a kid who was taking a year off before college who was lost, but you know, kind of finding his way to completely out of control and unrecognizable. And just the addition of cocaine to my life, I became a feral animal. It was just like running around responding and afraid and angry and just full of fear. I committed two crimes. I committed a robbery to try to get more money for drugs, and I committed a shooting because I had gone to meet these guys and they ended up chasing me. It was very much like I contributed to this. It wasn't just a self-defense. And I was incredibly lucky that they both lived. Like I was incredibly lucky that I didn't take lives that day. And that was the stopping point. The police arrested me, I was sitting in the jail, and I remember that the joy that I felt actually was when they served the charges on me was that it wasn't murder charge. It was malicious moaning, that I had like shot people, but they had lived. And up to that point I didn't know if that was the case. But that stop, that you know, handcuffs going around my wrist, sitting in the jail with nowhere to run from these feelings and these thoughts and these insecurities that I'd been hiding from for a long time, you know, that was in some ways the hardest part, but it was really the best part. It was exactly what I needed. It was the only thing that could slow me down and stop me because I didn't know how to stop myself before that. And, you know, sitting in that jail, I had just turned 18 and I thought my life was over, but I thought, okay, maybe there's a way forward. And people believed in me, both people in the jail and people on the outside. Uh went through a whole thing, met with my attorney, and he was very frank. And he said, Jesse, you did some really bad stuff. And the the state sentencing guidelines called for between eight and 13 years, and you're gonna have to probably spend that midpoint of 10 years in prison. But like you did some bad stuff, you just need to own up to it. And in a weird way, that was exactly what I needed. I needed somebody to say, You did something wrong, here's what you can do about it. Because I wanted to make amends, I wanted to make things right, I just didn't know what to do, and I thought, okay, if I do this time, that will somehow make up to the people that I've harmed, that'll be a start. The day of sentencing, the first thing that happened was the Commult's attorney or the prosecutor here in Virginia made a motion to modify the sentencing guidelines. And after we didn't object, the guidelines went from eight to thirteen years to ten and a half to sixteen and a half years. So now I was looking at a midpoint of 13 and a half years, but in my mind I said, look, I'd already accepted 10 years, I'm gonna deal with this, like I'm responsible, I was guilty, I pleaded guilty, let's just get this over with. We went on, and the judge read out a list of terms, in the end didn't actually know the total he had sentenced me to, but then sentenced me to serve 138 years with 106 suspended, uh, or an active sentence of 32 years in prison. And I remember sitting in the courtroom and just like every was dead silent, except one woman, I think it may be my mother, just kind of like wailed like this grief. And I turned around and I turned back to other people and just tried to smile because I was actually trying to comfort people in the room because I could see distress on their face, and I was like, oh, it's gonna be okay, it's gonna be great. You know, not realizing that on the inside I was just kind of slowly collapsing. And when I finally got back to the jail, they actually put me on suicide watch because they said they didn't trust that I wouldn't hurt myself after receiving such a long sentence. And that was when I kind of broke. That was when I just completely collapsed into myself, and it all became even more real than it had all those days locked in in a cell, all those days like facing the fears and facing the memories, and and I didn't know what to do. I I just really and truly thought that my life was over. But I think like many people, that moment of collapse was what I needed. That moment of collapse gave me the kind of clarity and it gave me a place to start. Because up until then, I was always trying to run and respond and manage things and manage outcomes and just doing this unsustainable juggling act on a unicycle while riding down a hill. It was just it was crazy. But when I lost everything, when I was finally stopped in my tracks, I had no choice but to face what I had done, where I was, and the options that were in front of me. And in some ways that was a relief because I was no longer trying to manage or juggle all these things, and I could focus on what was right in front of me. I could, you know, help this person who was studying for his GD, or I could do push-ups, or I could read, or I could go to sleep and feel sorry for myself. And just recognizing the clarity of all those options, I definitely had moments where I felt sorry for myself. I definitely threw a couple pity purties and put a little hat on my head and ate a honey bun, but I chose to go in a direction that was what I wanted to do. Because for the first time, rather than just responding to things, I was actually choosing the path that I was following. I was actually making my own way and acting like I had agency. And that was liberating. So ironically, I found freedom or I found agency inside a prison cell.

SPEAKER_03 7:00

Jesse, that's wild, right? Because here you are taking what many young people do, right? They take the gap year, very common with European children and slash young adults, um, taking this gap year to find purpose, find have an understanding of what you're gonna do, where you're gonna go. And instead of like finding that independently, it it took this event, actually the sentencing. It wasn't the event itself. It was the sentencing that put you in that space where you were able to realize, okay, I have agency now. I get to choose, and I can still fulfill my purpose, whatever that may be, or at least go on this journey to find out what my purpose is.

SPEAKER_04 7:34

Yeah. I don't think I knew it was possible. And the irony is that by losing everything, by losing all these outside options, I suddenly found a path to that purpose and to that meaning on the inside.

Childhood Instability And A Caretaker Role

SPEAKER_03 7:43

Yeah, absolutely. Can you take us back to just childhood as you're leading up to this gap year? Like what was childhood like? I mean, just in terms of household and where you were plugged in, what you were involved in, what was your experience growing up?

SPEAKER_04 7:56

You know, I had one of those interesting experiences because what it looked like on the outside wasn't necessarily what was happening on the inside. You know, my parents were both very respectable professionals. They were also addicted to drugs and alcohol, and they got clean when I was younger. My dad used to have a saying, he said, if you take a drunk horse thief and you take away the alcohol, you still got a horse thief. And so what I saw was my parents had done a lot of work and they had gotten sober, but some of the underlying issues they hadn't really addressed or they hadn't had the tools to address. So I grew up in a place that didn't feel the most stable or didn't feel the most safe. They had a really tumultuous divorce that involved assault and arrest, and I didn't know what to do with that. And I really thought it was my job to take care of other people. Like I thought it was my job to kind of take care of my family. The same way as that day in court, I thought it was my job to make sure other people were okay with what had just happened rather than worrying about myself. And I got into that pattern and it felt good because it was a thing that I was praised for. Like, oh, you're such a thoughtful guy, you're such a nice guy, you care so much about other people, not realizing that the core of it, it was a trauma response. Like it was not coming from a healthy place. It was coming from that was the only way I knew to try to create safety and security in my life or in my household. So I'd say, again, on the outside, things look great in a lot of ways, but on the inside, I was constantly dealing with this insecurity and this weight and this pressure. And I don't even know if it was anyone putting that pressure on me as much as me putting it on myself, but to make sure everyone was okay, make sure everyone was happy, make sure everything was going well. And I was basically just constantly emptying my cup and depleting myself, and then waiting for someone to magically come along and make everything okay for me, you know. Watch Disney movies as a kid, that's a story. Like if you act good, good things happen, the hero comes along and they make everything better. So I kept thinking, well, if I keep acting good enough or I keep doing enough for other people, somebody's gonna come along and it's all gonna be better, and that just never happened. Yeah.

SPEAKER_02 9:33

Jesse, did you find yourself doing that same thing when you were in prison, wanting to help other people and take care of other people at your expense?

SPEAKER_04 9:41

Yeah, and it's funny because I don't know that I recognize that as clearly until I was doing an interview for the book, and somebody said, You did this thing, and like I would have been up there proud of myself and beating my chest and telling everybody, and instead you were apologizing, you hadn't done more, and I hadn't seen that pattern, like I hadn't recognized it because it's something I lived with my whole life. I felt so much guilt. You know, I was able to take college classes, I was able to have enough to buy books or make phone calls or drink coffee, and a lot of people around me weren't. So every time I did one of those things or I engaged in one of those things, rather than feeling proud of myself for getting a 4.0 or proud of myself for getting whatever, I felt shame because I was doing something that other people should be able to do and they couldn't, and somehow that felt like my fault, or it was my job to make them have that opportunity or expand it, or and you know, that happened in prison. It happened after. It's something that I've still struggled to get away from because what I found is, like I said, people praise those trauma responses. So those things that are not coming from a healthy place, but that look healthy on the outside or look giving or kind on the outside, I get all this validation for. But I don't necessarily address the underlying issues that cause it to come out in not the healthiest way.

SPEAKER_01 10:41

Yeah.

Big Baby Asks For GED Help

SPEAKER_03 10:41

You've made such a massive reference when we talk about like all of the Disney characters. And as you were talking, I was like going through and I was like, yeah, there's always an external person that comes in and fixes the thing, right? Like there's never the introspective work, there's never figuring out how to deal with it on your own. It's waiting for that external person to come in and fix it for you. You found yourself in that moment where you got your sentencing, and here it is. Prison is your reality, right? Talk to us about that season of your life. I mean, you're a young adult, your brain is still developing, no offense. But scientifically, your brain is still developing, and you're now finding this sense of purpose and fulfillment. But what is the experience? What's that season of life truly like for you?

SPEAKER_04 11:23

There was a lot of surrender, there was a lot of depression, there was a lot of hopelessness. People see on the outside, like, oh, you accomplished these things. It's like, no, you don't know what it felt like going, you know, sometimes just putting one foot in front of the other. But there were times where I just got tired of feeling sad. I got tired of feeling sorry for myself. I got tired of paying myself as the victim. I got tired of all that, and I chose to do something. And I did it imperfectly, and I often did it awkwardly, and I often did it wrong to some degree, but I just kept doing things in a weird way. Again, taking away that outside pressure, taking away the expectations or needs of others, at least people close to me, I for the first time in my life was kind of choosing my own path. And yeah, it was not always easy, it was not always fun, but I found this great sense of satisfaction and purpose. I remember there's a story about this guy who came to me. He was this giant of a man. His name was Big Baby, but he was huge. Yep, okay. He was just like quietly strong and austere, like he people were terrified of him. And he came to me with this young humility and said, Hey man, will you help me? I want to get my GD. I've been trying for years and I can't do it. And I just remember being so struck by that because this giant, intimidating figure came and he humbled himself in front of me. And not a lot of people asked for help in prison. Not a lot of people say, Hey, you have something and I don't know how to do that, and I want your help. So I was really impressed by that. And one of my kind of earlier mentors had taught me something that was really important. And he said, if someone has never gotten something for free, don't offer them something free because they're not gonna believe it. They're gonna think it's a trick. So make them pay something, but make them pay something they can afford to pay. So at that point, he was the heavyweight boxing champ. So I said, Hey, make a deal. I will help you get your GD if you teach me how to box. And I remember he just had this little kid smile that came on his face and he was so excited. And in addition to any tutoring that happened, in that moment, he saw that he had something of value to offer. That he wasn't just this big, scary, violent guy. He was happy because he got to be what he wanted to be, which was a helpful person. He got to be a part of someone's story. And there was there was a whole long process, and there was some forward progress, there was some backward progress, but I will never forget the day that he walked back into the pod with tears streaming down his eyes, and he picked me up like a little kid and swung me around because he had passed his GED. Like it had finally happened. And that sense of happiness and joy and validation, it was the best I'd ever felt in my life. And it had nothing to do with me. Like I hadn't done anything. I had just been in a place to help someone see their capabilities and what they could do and what they could accomplish. And that was when I realized that I'd been doing this life thing all wrong, focusing on what do I need and what do I want. And all of a sudden, when I started looking externally, I said, okay, like this is much more satisfying. Like, this isn't trying to meet somebody's needs so that I'll feel okay. This is actually showing up and say, hey, what is it you want and how can I help? Not controlling the expectations, not controlling the outcome, but just showing up and giving my time in a way that ended up being ultimately satisfying.

SPEAKER_02 13:57

Jesse, what was it about you that made this giant baby like walk into your cell and baby? Like for somebody to do that, there had to have been something about you that allowed him to put down that guard to walk into your cell and say, Hey, will you help me get me get my GED? I can't imagine that's just ran a random thing.

SPEAKER_04 14:21

Right. Well, first of all, if I ever see him again, I'm gonna call him a demo baby and he's gonna look at the list.

SPEAKER_03 14:28

Can you make sure to say Pam said?

SPEAKER_04 14:34

You know, I think at that point I was lucky to be one of the few people, maybe like three or four people on the institution of over a thousand who was taking college classes. So people saw that. People saw that I had the books. You know, I was always kind of helpful, and I don't know, that had always been my role. I had always been the counselor, I'd always been the helper, I'd always been like the person, even from a young age. So I think as he saw that dynamic, because he would always sit in the corner and he was just this like silent, scary figure sitting in the corner watching everybody else. And I can't remember exactly what he said, but someday he was like, Yeah, I've been watching you, and like, you know, I feel like I can ask you. And so whatever it was, I created space for him to do that. And even so, I mean, it was still a huge act of courage, and it really impressed me. And he taught me a lot through that process. Like, I feel like I very much learned more from him than he learned from me because that GED was a small part of him teaching me what it is to not give up. He's like, I knew how to, in theory, not give up, but I watched this guy struggle with things, like struggle harder than I had ever started with anything in my life, and he got it one day. We were working on the distributive property in algebra, and then the next day he couldn't get it, and he like threw his hands down and he was angry, but then he just stopped and he said, You know what? If I got it yesterday, I can get it again. And that was it. Wow. He just made a decision to get it, to keep going, to not be frustrated. And I had never done that. I'd never seen anyone do that. So in that moment, you know, he thought that I was teaching him, but he was teaching me so much more about life than I ever could have imagined.

SPEAKER_03 15:47

That is huge. And the surrender piece, right? Like when you talk about him just having that humility and saying, Hey, I'd love your help in this, that too and itself is a lesson for you, right? Like in realizing I don't have to have all of the answers and I don't have to help everyone all around me.

Borrowing Habits To Build Belief

SPEAKER_04 16:02

Yeah. Yeah. I talk in the book that there's a line that a friend of mine picked out that I said, I didn't know how to do most things and I didn't know how to go forward. So I had this policy. I would find somebody I admired, I would ask them what they did or how they got somewhere or what their daily practice was. And then I would just do that over and over and over until I got somewhere. And so whether that was academic or that was for exercise or that was like building new habits, I just adapted that. And what I found was for the most part, if somebody was able to do it, I would be able to do it. I just had to do the same things they did. And that has really gotten me a long way in life. I love that.

SPEAKER_03 16:31

I think that's huge, and that's great advice for all of us, right? Like oftentimes we look at the end result, like the reward, the goal that someone has hit, and we think, oh, we want that. And we think about the goal, the objective, and we don't think about, as you mentioned, the habits that they pick up along the way. And so instead, you are like, I can replicate or take on similar habits in my own respect and still achieve what I want to achieve. Not just achieve the thing. It's absorbing and owning those habits and understanding that that's the step that you have to really knock out of the park before you hit the goal.

SPEAKER_04 17:02

Yeah. And I think people miss the point. People think like, oh, I want to be a millionaire or I want to win a gold medal or I want like all that's irrelevant. Like the end result is not what really matters. The end result is just kind of like the finality of all the work we've done and all the exploration. You know, I gave a talk at our college today talking about what education gave me was this better sense of understanding and this better sense of belief in myself because I never felt like I could do hard things. I never felt like I deserved to do hard things or deserve to accomplish anything. So as I continued to show up and as I continue to, you know, graduate from a class or eventually get a degree or get a certification or move forward, I suddenly began to believe that I could, and maybe even that I should. And really that's what the work is. It's it's all those steps that allow us to see ourselves in a different way so that we can become the person we want to be. Because the work itself, it may not be easy, but it's pretty simple. It's getting to the point that we believe we're able to or that we deserve to.

Writing The Best Part Of Prison

SPEAKER_03 17:50

Absolutely. Oh my gosh. I love that piece. The best part of prison. When did this come about in your journey and tell us a little bit about the book itself?

SPEAKER_04 17:59

So, you know, I did a lot of writing while I was inside. I had a couple articles published, but you know, mostly just wrote letters and wrote poetry and just wrote because I had nothing to do. So I'm staring at a wall and I'm kind of like dumping everything from my consciousness out onto paper. That didn't turn into the book though, but I remember right. I was this rut where I was just like, you know, even if I do ever make it out, what am I gonna do? Nobody's gonna hire me, nobody's gonna rent to me, like I have no future. And so I met this psychologist and he sent me a book, which was this career course. And it was all about finding values and keystones, basically the things that I cared about or things that were important to me, and then building a life and building a career based on that. And so I was like, all right, I respect this guy, so I'm gonna try. And I went through this whole course and I remember getting it down, and at the end, I said that if there were no barriers, I would be a writer, I would do public speaking, and I would work with people one-on-one. And then in that cell, I remember looking at this and being like, that's not a job. Like, nobody would pay me to do that. I can't even stay out of prison. Why would somebody hire me for that? And I was like, this is a great exercise, but like this isn't possibly gonna work.

Pardon Day, TikTok, And Publishing

SPEAKER_01 18:51

Yeah.

SPEAKER_04 18:52

And I also thought, you know, at that point that I had 17 years left on my sentence. I didn't think I was going anywhere. But in August of 2021, with very little notice, like with literally an hour and a half's notice, I walked out of prison free about 10 years before I thought I was getting out because the governor granted me a conditional pardon. So all of a sudden I was in this position in the world, and now I have to find a job and I have to find someone to rent to me, and I have to find all these things. And I didn't know what that would be, and I didn't even know how to make the decisions for myself. I really struggled with this kind of like decision fatigue because for years I didn't have to decide anything. I knew when I was gonna eat, I knew when I was gonna sleep, I knew what I was gonna do, I knew where I needed to show up, and all of a sudden I am standing in front of an aisle with 500 body wash, and I'm like, how am I supposed to- I don't know what I want. But I was lucky that in a weird way being institutionalized led me to start telling stories because I had a friend who was in marketing who said, Jesse, I think you have a really compelling story and people are gonna be interested. You need to put it on social media. And I was like, I don't know what that means, but I'll do what you said. Like, I respect you. So I downloaded TikTok on my way to a hike that I've been looking forward to for years. I got to the top of the mountain and I made this video and I posted it and I shut my phone off and I went back down. And that night I opened my phone again and I had to call Katie and I was like, hey, Katie, what is a normal number of views for a video? And she pulled it up and she said, Jesse, you had zero followers and you got 10,000 views in like less than a day. This I told you people would be interested in your story. And it was COVID, so I would go to work during the day and I would go home and I would make videos and I would make responses and I would respond to comments and just interact with people, and it became my life because I didn't know what else to do. I didn't have I didn't know how to exist in the world, so I just did this thing that allowed me to fill a bunch of time. And that led to talks about a book deal, about other things. I actually got a book deal, or I was offered a book deal not long after I got out, but they wanted to use a ghostwriter and they wanted to kind of control the narrative and they wanted to tell me how it was going to be, and I just didn't feel comfortable with that. So I said, no. But the problem for me was that like I knew the story up until that point. I knew the story of getting out, which in itself was pretty extraordinary, but I didn't know how to end it. I didn't want to stop the day I got out of prison. I wanted there to be more. I wanted there to be kind of a cycle, and I was really waiting for that. And in 2023, I had this bizarre event, I don't want to kind of give it away because it is the end of the book, where it came full circle in a perfect way. And I remember I was in a relationship when I first got out of prison with a reporter who was amazing, and even though we broke up, we were still the best of friends, we still talk all the time. And I called her from this event and I was like, hey, this thing just happened. She goes, Yeah, you got the end of your book, and she just like clapped her hands and was so happy. And I knew then. I was like, okay, I have the full story, I can write it. So I finished a book proposal, and I had a friend who had been a New York Times bestselling author, and she was gracious and gave me support and connected me with her agent. Her agent took my proposal, made a couple modifications, started sending it out, and then we got a deal. We actually got a couple deals. And the reason we chose this one is because this publisher wanted to prioritize people who were incarcerated. So 500 physical copies and unlimited digital copies are going to jails and prisons across the country free of charge. So that anyone who has access to that technology who wants to read this story can do so without any barriers. Yeah, that's incredible. But yeah, it was when I started writing it, it was really me still trying to grapple with the past. How had I become this 18 year old kid who was running around causing all this harm? Like, what was I so afraid of? What was I running from? And then how would I, in a system that leaves people often broken, somehow become like more or better or more whole and complete? Like, how would I heal in a place that hurts most people? And then I wanted to figure out how to extrapolate. Those lessons so that other people didn't have to go through the things I went through to learn that or to have that experience. And I remember the reason about the people inside is I remember sitting in a prison gymnasium, just crying my eyes out. Because for years in the Department of Corrections, no one who had been released could come back in. Like maybe for visitation for an individual, but like only after certain periods of time. But the first time they let someone come back in, we were all crying because this guy who had fought like hell to get out of prison for more than 20 years decided the most important thing he could do with this day was to come back into prison to tell us that we still mattered and that we had a future if we took the right steps. And I don't know how to describe how much that touched me and everyone around me. Like I said, we were all in tears. You see our prison gymnasium full of people crying, like something's going on, it's something special. And so I wanted to write this book for people who were still inside. And that's why this book deal was so important to me because I wanted to, to whatever degree possible, create for anybody who read this the same experience I had in that gymnasium when he came back in and said we still mattered.

SPEAKER_03 22:53

That's huge. Oh my gosh. Wow. And congratulations. And I love that you were able to work with a company that saw had that as a focus and a priority to get the books back into the prison and sharing that again, aligning with what you discovered when you did the career visioning course, right? Like you did this career course. And Jesse, what I think is so interesting, like I what we call like synchronicities or these moments in life where things just line up. I think about like that moment that you had where you're doing this career visioning course or this career course, and you're like, I want to speak, I want to write a book, and and I want to, what was the third thing? I want to write the book, I want to speak.

SPEAKER_04 23:28

Work with people one-on-one.

SPEAKER_03 23:29

Work with people one-on-one. And in my mind, like I feel like you just you'd like you just put the key in the door and you unlocked it. And then it's like, and let's make that happen then, right? Like you realize. And it was truly that search for purpose and meaning that you were looking for prior to going into prison in that moment that unlocked, but you had no idea how it would ever come to be.

SPEAKER_04 23:50

No. And it's like it was saying before, is so often it's just showing up, and if this person has gotten to that place, I'm gonna do whatever they did. And so so often I'm doing things that I don't see the end result of. Like I don't see this as being possible. I don't know how we're gonna get there, but I'm gonna keep trying. It's one of my favorite books as a kid was The Phantom Tollbooth. And in the end, they realized they had done something impossible only because they didn't know it was impossible. And that's really how I've tried to approach things. You know what? This may be impossible, but I'm gonna try it anyways. And you know, I've failed far more than I've succeeded. I've been told no far more times than I've been told yes. But I realized just if I keep asking, eventually I'm gonna get a yes or I'm gonna succeed. Yeah, yeah.

SPEAKER_02 24:24

But you have such a defined why, which is to help other people, which it sounds like has been kind of your why your entire life.

The Cages We Keep In Our Minds

SPEAKER_04 24:30

And so it really has. Now you're doing it. So what's so interesting about this book is again, I was imagining this would be for people who are incarcerated or the families of people who are incarcerated. I was just at South by Southwest and did an author reading, but then also did a mentor session, which feels bizarre for someone to come in and ask me for mentorship. I'm like, what do I know? But this guy came in, this incredibly successful, incredibly wealthy, incredibly everything, and he said, When I read your book, I see myself in it. Like that same search for meaning, that same feeling like I'm not doing enough, like I can never do enough. But maybe if I keep trying, maybe one day I'll be enough. And it made me realize that, you know, I was thinking of prison as this external thing, but that so many of us are just walking around caged in our minds, in our hearts, or maybe we've even made outside, but we're like that tiger who's just pacing inside the cage where it used to be, because in our minds it's still real. And that was when I realized that if I want to help people be free, it's not just about people behind bars, it's about people who are living in those cages, whatever their situation is.

SPEAKER_01 25:22

Yeah, and I think there's more than any of us can imagine.

SPEAKER_03 25:25

Oh, yeah. Absolutely. Absolutely. Especially those that are willing to like take on the failure that you talk about, Jesse, right? Like you failed many of times as well. And yes, you have a fabulous story and a gift that you're sharing with other people, but there were failures along the way. There's so much fear around that. Like, people don't want to experience that. They just want the highlight real. They want what you share on TikTok, right? Like the good things that are shared online only without the failure piece. And that's part of it. That's what gives us the lessons for us to continue to grow and build on along the way.

SPEAKER_04 25:53

I agree. I remember sitting in in that jail cell when I was first arrested and just I had been running from things for my whole life. And I felt like if I stopped, if I was a shark, I would, I would die, or if I stopped, it would somehow consume me or destroy me. And the blessing was that by being forced to stop, I saw that like I could survive it or I could keep going. I remembered while I was incarcerated, I was a mentor in a mental health program. And there was this individual who was very much in the same place, very much addictive behavior, a lot of trauma, like an insane amount of trauma, and he just couldn't stop. And so I finally sat down with him one time and I said, Okay, let's try an experiment. I want you to just stop for one second, literally just one second. We're gonna do it on the clock, we're gonna do that. And then I said, Okay, you made one second, let's try five seconds. We eventually got up to one minute, and I could watch his breathing deepen, I could watch him relax. And he looked at me and he goes, I've never been able to do that before. And I said, Well, no, you have, you just didn't know it because you were trying to stop for your whole life. You weren't trying to stop for five seconds or for a minute. And that was what I realized that we have to learn that we can endure the things that we're running from. We have to learn that we can survive the things that we're afraid of. And that failure was definitely something I was afraid of. I think we were all afraid of. But by losing everything, by being clobbered over the head, I had the blessing of having to start fresh because I didn't have anything left to lose. So what did I care? Yeah, very powerful.

SPEAKER_03 27:04

Absolutely. You mentioned the three things, Jesse. Going back to that. You enjoyed writing, you wrote the book, speaking, and working with people one-on-one. Tell us how that has unfolded over the last couple of years.

Second Chancer And What Comes Next

SPEAKER_04 27:16

So I started Second Chancer Foundation back in 2022, and just it was a bizarre twist of fate where somebody literally gave me funding for a 501c3 organization because they didn't want me to take a job at a big bureaucratic nonprofit because they thought my talents would be wasted, is what they said. So we started working with people doing re-entry programs, essentially helping people learn the skills they need once they were out of prison. What we found was we started with a class of 14 and graduated four. Because once people get out of prison, life is pretty demanding. It's hard to say, oh, well, let me take this, you know, several hour class and let me show up to this program and you know, people need to get a second job, or they have a relationship, or they need to reunite with their kids. And so I realized we wanted to work with people while they were inside. This, by the way, is a whole litany of failures, just to let you know that it's continued even after prison. Then I thought about and I actually polled all of my friends who were formerly incarcerated who were successful. And every one of us had a mentor or a teacher or someone who believed in us and helped us see ourselves in a different way. So we started a program, this nationwide program, where we were connecting incarcerated people with mentors, where someone could write and share their experience and their perspective and kind of be a mirror to that person on the inside, hopefully helping them see that they were deserving and that things would work out. We ran this program and we had some really good, feel-good stories, but in the end, the data just didn't reflect that this was a successful use of funding and programming. And so as good as it looked on paper, and as many connections as we had made, as much we could probably fundraise, I didn't feel good about running a program that wasn't leading to results, which are that we wanted people to get out of prison and stay out and be successful. So then we kind of reflected, we're now actually working on a video game, basically a re-entry video game where we would allow people on their prison tablets to go through the reps of getting out of prison and learning the skills in a low-stakes environment to where if things mess up or they don't go as well, well, you lose your turn, you gotta start over, but it's not nearly as severe as people who get out and do that and then go back to jail or go back to prison or end up harmed or even dying. Um we're hoping that this can be one of those iterations that we can actually make an impact. On the one-on-one level, I go into the juvenile detention center. So after the college day, I had to jump right over to the juvenile detention center and I work with the kids, we bring in speakers or we bring in programs every month. And kind of like I said before about the you know, the work being not easy but simple, but the sense of deserving being the problem because when I first started bringing people in, the kids would either say to me or they would like say by their actions, they were like, Yeah, this is great, but like college isn't for me, or like this job is great, but like people like me can't get a job like that. So I started focusing on saying, okay, well, where can I get someone who looks like you? Where can I get someone who's from your neighborhood or someone who has your background who is doing all of these things? And as I've continued to bring people in, or I've continued to bring organizations in, you see that light of possibility come on in the kids' eyes where they're like, oh, like maybe I actually could do that. Maybe I actually could be a part of that, or maybe I actually do belong there. And that's the work that whether it's one-on-one or with a small group, I feel most satisfied in because I can see that light. I can see that immediate impact. And I remember what that was for me. I remember those moments where I started to believe in possibility. And if I can be a part of that, if I can be a part of that that leads to freedom, even if I don't get to see the end result, even if I don't see where they end up or how great their life is, I know I was a part of that process. And it's just ultimately satisfying.

SPEAKER_03 30:03

A light of possibility. That's huge, right? And so making sure that it's completely relatable for those kids, right? Because of course you bring a random person in, or even like bringing a celebrity in, like it's fun, it's exciting, that's great. That's not my reality. And so what does that mean to me? And then they go back to normal, regular habits and routines that we picked up before.

SPEAKER_00 30:25

Thank you for joining us today on the Reignite Resilience podcast. We hope you had some aha moments and learned a few new real life ideas to fuel the flames of passion. Please subscribe on your favorite streaming platform, like or download your favorite episodes, and of course, share with your friends and family. We look forward to seeing you again next time on Reignite Resilience.