

For the past two decades, John has put his big compassionate heart to work with a group called New Beginnings- Next Step which is “a peer-support group for Returning Citizens as they transition from incarceration to freedom. It is run both for, and with, ex-offenders, along with a vital and growing group of compassionate volunteer-facilitators, in order to build a community of hope, and a culture of accountability and possibility on the streets of Wilmington, Delaware.”
How would you describe the genres in which you write and perform?
I’ve never been any good at answering that genre question. Most of my airplay seems to come from folk and Americana radio if that helps.
What are some of your greatest joys?
I’ve been really lucky in my life. I still get to do what I love for a living. Plus, I have a great family. I get great joy just being at home with my wife Beth and hanging out with our kids and grandkids.
Please introduce us to New Beginnings-Next Step.
We’re a nonprofit that works with incarcerated and returning citizens in Delaware to try and help them remain free after prison.
How did you learn about the program?
I heard about it through the guy who founded it, a Franciscan friar named Brother David Schlatter, OFM.
What is your role and how has it evolved?
I originally helped run a single weekly support group at the Howard R. Young Correctional Institution with my father, Jack Flynn. The group had been sponsored by the Franciscan Center, a kind of street mission in Wilmington. I had gotten Dad involved after he retired and he was running the group with the friars back then.
The Franciscan Center closed back in 2005 and Brother David, who had become – and still is – my spiritual advisor, urged me to begin accompanying my father into prison (I refused the first two times David suggested this. By the third time, however, I figured he must have his reasons).
Unfortunately, my dad had to stop volunteering shortly after I joined him, so I was left running the group by myself for a couple years.
I wasn’t very adept at being a facilitator (at least I didn’t initially feel like I was doing much good) but I kept showing up – all the while trying unsuccessfully to get someone else to take my place.
Eventually one group a week became two groups a week and then, when some of our incarcerated guys were getting released, they asked me if I could meet them for coffee once a week on the outside. This led to the start of what we call our Next Step program which is the weekly support groups we run for returning citizens.
Little by little I began to find other volunteers to join me, and we got invited to start our groups in other Delaware prisons. Once I started raising funds to assist with some of the reentry challenges that are returning citizens faced, I realized I was going to have to start the nonprofit. So now I’m the Executive Director of New Beginnings – Next Step, Inc.
Could you have imagined, 20 years ago when you began your work as a volunteer with the program, that so many lives would have been changed, including your own?
Not at all. Like I said, almost from the beginning I was trying to get someone more qualified or gifted at this kind of thing to take over. But I knew from the start that it was too important to just walk away from it. I never thought it would become one of the great blessings of my life.
How many people has it served?
I haven’t counted. At any given moment in the last two decades –except during the pandemic – we were actively working with dozens of incarcerated individuals and these guys feed the ranks of our returning citizens groups when they’re released. I’m proud that some of our returning citizens stay involved with us long after they get out so they can help mentor the new guys coming home. A few of our returning citizens even go back into the prisons with me as New Beginnings volunteers.
What is its source of funding?
Mostly we’re funded by the folks who come to see my shows. I take up collections at my concerts and some of my fans become regular donors to support us.
What ripple effect do you see it having on the lives of the returning citizens and their communities?
If wounded people wound people, then cherished people tend to cherish people. We know that wounds are passed down generationally. Well, so is love, so is a sense of inherent goodness and dignity. I really think it’s impossible to overestimate the effect of even a single human being becoming more healthy and whole. Still, we could use a lot more of that effect these days.
How does the program help us see those who are incarcerated in a different light?
As Pema Chödrön says, we learn to stand in awe of what others have to carry instead of standing in judgment of how they carry it.
Are there particular stories that touch your heart and have remained with you?
So many. Here’s one that comes to mind –In New Beginnings we always stress the difference between reacting and responding. I remember one young man named Miguel who never believed there was much of a difference. Anyway, Miguel came into a prison meeting one night looking pretty rough because he had been beaten up that afternoon by a couple guys on the tier.
Miguel told us that, in the past, he never would have believed that he had a choice about how to respond to violence. But this time he said he actually heard a voice in his head as everything transpired. He said the voice reminded him that he had promised his seven-year-old daughter that he would attend her birthday party when he was released from prison in two months. Miguel knew that if he was caught fighting back, he was going to have his sentence extended. This would mean breaking that promise.
So, Miguel decided to cover up his head as much as he could and simply absorb the blows until someone came along to pull the guys off him. He said he knew he was going to be called a coward because of this, but he also knew that he could bear that shame easier than the shame he would feel in breaking his little girl’s heart. He also said this entire interior monologue took place in the blink of an eye.
Knowing what I did about the codes these guys lived by both in prison and on the street, what was even more astounding than Miguel‘s story itself was the fact that, when he told it in New Beginnings that night, his choice of non-violence in prioritizing his child’s happiness over his reputation was greeted with applause from all of the other men in the circle. There was a time when this would’ve been unthinkable, and I realized that real change was taking place.
And just to finish the story, Miguel attended his daughter’s birthday party. He never returned to prison. He lives in the Midwest now and is a very happy recent grandfather.
I know that Kris Kristofferson was a friend of yours who died in 2024 and together you wrote a song called Kris’s Rules. Please share the theme. I understand that the song and others will be released as a fundraiser for New Beginnings-Next Step.
God Bless Kris! I’m deeply grateful that I got to know and work with him, and for all his support over the years.
I’m really proud of “Kris’s Rules”! It was my way of trying to say goodbye. For the chorus, I got permission from Lisa Kristofferson, Kris’s wife of 41 years, to quote Kris’s personal mantra– “Tell the truth. Sing with passion. Work with laughter. Love with heart.”
When she heard the song, Lisa suggested that I add Kris’s name as a cowriter. Honestly, that’s something I would never have presumed to do. I would have simply attributed the quotations. Seeing my name next to Kris’s on a lyric sheet is one of the biggest honors of my career.
As for donating the proceeds from the song, unfortunately my songwriting royalties wouldn’t make much of a fundraising dent these days. But we are going to do a special benefit concert for New Beginnings-Next Step.

Were you inspired by Father Greg Boyle and Homeboy Industries?
Absolutely! I’m a huge fan! The Kristoffersons introduced me to Father G when we did a fundraising concert for Homeboy out in Malibu. It all started because Kris’s daughter Kelly sent me Father Boyle’s book “Tattoos on the Heart.” It’s great when you get to become friends with one of your heroes. G now falls into that category for me just as Kris did. They both continue to be big influences.
When and where is your concert in September?
September 27th at The Arden Gild Hall in Delaware.
How can people get involved if they feel called to serve the program?
You can contact me through my website at johnflynn.net. Or you can call the New Beginnings-Next Step hotline at 1-877-I GOT OUT.
John With Kris – Jayne Toohey
—
This Post is republished on Medium.
—
Photo credit: iStock
