meta_pixel
Tapesearch Logo
Log in
The Addicted Mind Podcast

Episode 377: The Best Part of Prison: How Jesse Crosson Found Freedom Behind Bars

The Addicted Mind Podcast

Duane Osterlind, LMFT

Medicine, Health & Fitness, Mental Health

4.7655 Ratings

🗓️ 23 March 2026

⏱️ 36 minutes

🧾️ Download transcript

Summary

This is a powerful episode featuring Jesse Crosson, author of The Best Part of Prison and founder of the Second Chancer Foundation. Jesse shares his incredible journey from being an 18-year-old sentenced to 32 years in prison to becoming a leading voice in restorative justice and cultural change.

Whether you are struggling with a physical "prison" or an emotional one, Jesse’s insights on vulnerability, routine, and radical acceptance offer a roadmap for anyone looking to reclaim their life from the darkness.


🎧 In This Episode, We Discuss:

The "Ping-Pong Ball" Existence

At 18, Jesse was "running from something he couldn't name," using substances and chaos to numb a deep-seated feeling of unworthiness. He describes the "insanity" of reacting to his environment rather than living with intention—a pattern that led to a robbery, a shooting, and a decades-long sentence.


The Reckoning: Sitting with the Silence

Jesse explains how being arrested was a "blessing" because it forced him to stop running. Locked in a cell with nothing but a blank wall, he had no choice but to sit with the fears he had spent his life avoiding. He discovered that when you finally make space for the pain, it loses its power to consume you.


Redefining Guilt and Accountability

A pivotal moment in Jesse’s journey came from a prison psychologist who taught him that guilt is a signal, not a life sentence. * The Lesson: Guilt is a flashing sign that something needs to change. Once you change the behavior and step into accountability, you are not meant to carry the weight of that guilt forever.


The Power of "Second Chances"

Jesse shares the story of helping a fellow incarcerated man—a "giant" everyone feared—earn his GED. This act of service provided a sense of meaning that no worldly success could match. This eventually led to the founding of the Second Chancer Foundation, which uses storytelling to change the culture surrounding incarceration and reentry.


The "Prison" of the Mind

During a mentor session at South by Southwest (SXSW), Jesse realized that Fortune 500 CEOs and incarcerated individuals often struggle with the same "imposter syndrome" and feelings of being "not enough." He argues that we are all seeking freedom from some form of internal confinement.


✨ Key Takeaways:

  • Accountability is the First Step to Freedom: Radical acceptance of "what is" (rather than what "should be") is the only way to move in a new direction.
  • Routine as a Tool for Sanity: Transformation began for Jesse with the simple, controllable task of cleaning his cell. Small wins build the foundation for big changes.
  • Vulnerability is Power: Sharing your "why" and your struggles doesn't take your power away—it connects you to others and opens doors that logic and "professionalism" cannot.
  • Service is Redemption: We find our own healing by helping the person we used to be.


💬 Notable Quotes:

"I was running from something and I didn't know what it was... I'd run to relationships, drugs, alcohol—anything to numb that pain."

"Accountability is the first step to freedom. Radical acceptance of what is right now gives us the freedom to make different decisions."

"Your wiring may explain you, but it doesn’t excuse you."

"We are all incarcerated in some way, whether we have bars around us or handcuffs on our wrists. We’re all seeking freedom, but we don't always know how."

🔗 Resources Mentioned:


Follow and Review: We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

If you live in California and are looking for counseling or therapy please check out Novus Mindful Life Counseling and Recovery Center

NovusMindfulLife.com

We want to hear from you. Leave us a message or ask us a question: https://www.speakpipe.com/addictedmind

Disclaimer

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Transcript

Click on a timestamp to play from that location

0:00.0

Hello, everyone. Welcome back to the Addicted Mind podcast. I'm Dwayne Austerland, and I'm so glad you're here.

0:12.1

This thing I'd been running from from my whole life that I was sure was going to consume me or just destroy me was okay when I made space for it to be there.

0:22.5

Today's conversation really stayed with me.

0:24.9

My guess is Jesse Crosson.

0:27.6

Jesse was arrested just after his 18th birthday.

0:30.0

And when the judge handed down a 32-year sentence,

0:33.7

he believed what he'd always believed deep down,

0:37.1

that his life was over, that he wasn't

0:39.9

worthy of being here. But over the next 19 years in prison, he found people who believed in

0:46.1

him until he could learn to believe in himself. He made difficult choices. He built a completely

0:52.5

different life from the inside out. And it was so transformative

0:56.6

that the governor granted him a conditional pardon and he was released with just an hour and a half's

1:02.7

notice. Since getting out, Jesse founded the Second Chancer Foundation. He speaks all over the

1:08.7

country and he just released his book, The Best Part of Prison,

1:12.6

Reclaiming Life Out of Darkness.

1:15.3

We talk about what it really takes to sit with the pain you've been running from,

1:20.1

why accountability, not punishment, is the first step towards real freedom

1:24.6

and how helping others can change the way you see yourself.

1:29.3

Whether you're struggling with addiction, shame, or just feeling stuck in your own kind of prison,

1:34.9

this one's going to meet you right where you are.

1:38.0

But before we jump in, if this podcast has meant something to you, take a moment to rate

1:43.5

and review the addicted mind on Apple

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from Duane Osterlind, LMFT, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Duane Osterlind, LMFT and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.