What Prison Can Teach Us About School w/ Jennifer Berkshire

Tomorrow, I’ll be trading Iowa for a couple days in Los Angeles, where the HRP team will be presenting for the third year at LearningInspirEd’s Student Power Summit. It’s in LA this year in partnership with Homeboy Industries, the largest gang rehabilitation and re-entry program in the world. The founder, Father Greg Boyle, is quoted on the Homeboy homepage saying, “We imagine a world without prisons, and then we try to create that world,”. And I’m really looking forward to meeting and talking with the people there to learn more about how Homeboy works. A bit of a facetious question that sticks in my head is, in the high-stakes data-driven world of schooling, what piece of content or curriculum did these guys miss that would’ve made the difference? And more seriously, what is it about the environment at Homeboy Industries that schools can learn from? I’ll have more on that when I get back.

But until we build that world wi thout prisons, there will need to be programs for incarcerated people and people in transition from prison to public life, too.

That’s where this conversation with Jennifer Berkshire came about. Of course you know Jennifer from her years of hosting the Have You Heard? Podcast with her co-host Jack Schneider, and their coauthored books The Wolf At The Schoolhouse Door and The Education Wars. But for the past couple of years, Jennifer has also been teaching journalism and education policy in the Boston College Prison Education Program at MCI-Shirley, a medium security prison for men in central Massachusetts. Recording isn’t allowed in the prison facility, but in 2025 Jennifer spoke with some of the men in her program who had been released from MCI-Shirley and were finishing their degrees on the Boston College campus, and she gave me permission to use those clips here.

As you can hear, the program was a life-changing experience for these men, and it’s been life-changing for Jennifer too.

This conversation with Jennifer was one of the most eye-opening I’ve had in a long time, and it’s always such a pleasure to talk with her. I’ve included links to several pieces of media we talk about in this episode, podcasts and articles created by inmates, books written by prison educators, and more, so check out the show notes for those links as well.

John Lennon - The Tragedy of True Crime

Ear Hustle Podcast: “The daily realities of life inside prison shared by those living it, and stories from the outside, post-incarceration”

Have You Heard #202 - College Inside, College Outside

Article - BC Prison Education Program Shatters Stigmas and Builds Better Futures

Article - In prison, I embraced the SEL skills I should have learned in grade school