Getting Discomfortable with Prison

A few months ago, I did an Instagram poll asking my followers if any of them had ever been arrested. A handful of people clicked yes, including myself. Then I asked if any of them had actually gone to prison, and only one person said yes. It was an old friend who I hadn’t seen in years. So I decided to reach out and see if I could interview him for the show, and I’m so glad I did! His story turned out to be a powerful example of the way a change in personal values can dramatically improve one’s quality of life and even lead to a sense of redemption after a “shameful” crime.

My anonymous guest went from a life of seeking personal value through power, intimidation, and money, to finding a life of meaning through love, belonging, and radical honesty. His interview is a very candid, amusing, and at times chilling look at what day-to-day life is like behind bars in a medium security prison in Canada. We cover a range of topics from prison politics, to the prison slang that will lead to an instant fight, to coping techniques both effective and misguided, even what it’s like for gay and trans people in prison. Perhaps most surprising of all, my guest actually met his now wife in the process!

We also delve into the pros and cons of prison as a system of punishment and reform, especially as it relates to privilege and the marginalized communities that are overrepresented in the Canadian criminal justice system. It’s clear that for some inmates, like my guest, prison can be useful, while for others it actually makes things worse. It seems that one of the major keys to successful reform and reintegration is the outside support that an inmate receives, which is ironic given that a lack of social support may be a big part of what causes some inmates to offend in the first place, leading to an endless cycle of recidivism.

My guest provides a surprisingly humorous, honest, eye-opening, and thought-provoking look at an uncomfortable part of our society that many of us (perhaps willfully) know very little about.

Update: when I think of this episode, the following quote from pioneering psychologist Alfred Adler comes to mind, from his book, Understanding Human Nature:

“Picture an individual who has lifted himself above the difficulties of life, extricated himself from the swamp, and learned to take bad experiences and make use of them. He truly understands the good and the bad sides of life. No one can compare with him in this understanding, certainly not the righteous ones who have seen only the good side.”

Note: this interview has been edited for privacy, clarity, and interest.