man clutching his head feeling guilty

The ‘Reckonings’ podcast is a safe harbor for remorse.

“Right now public apologies are seen as a sign of weakness, but what if a public apology could be an opportunity to say ‘I fucked up, I did something wrong, I feel remorse about it, and I want to change’ or ‘I’m trying to change, and this is how I’ve learned and this is how I’ve grown.'” 

This is the hope voiced by Stephanie Lepp, a former consultant turned podcaster who is fascinated by apologies. In November, Lepp launched the first season of Reckonings, her podcast whose tagline promises—and delivers on—”stories from the conscience.” 

On Reckonings, which is available on iTunes, Lepp interviews people who have completely changed how they live their lives—often with conservative outlooks metamorphizing into more liberal ones. “As someone who is interested in social justice, it behooved me to understand how people actually fundamentally change their worldviews,” Lepp explained in a phone interview with The Daily Dot. 

Guests have included Neill Franklin, a former Baltimore drug cop who is now a critic of the war on drugs; Preston Shipp, a former “tough on crime” prosecutor whose perspective on the legal system changed when he befriended a group of prisoners he was teaching; Glenn Loury, an African-American professor whose views changed from deeply conservative to progressive; and Brock McIntosh, who enlisted in the Army National Guard while still in high school and later became a conscientious objector. 

Originally, Lepp hoped to interview people such as Bernie Madoff, Donald Rumsfeld and Fidel Castro who, she imagined, might toward the end of their lives “feel some kind of remorse or regret and be more open to having a conversation about what it is they were seeking when they did whatever they did.” She quickly realized that she didn’t need to focus on that level of infamy. She could focus on “everyday people making amends with everyday regrets,” which include grappling with issues of addiction and adultery, as she wrote in an essay at Medium

The first season of Reckonings focuses on people whose transformations have been so profound that they’ve turned into new callings and careers. For example, Franklin, the former drug cop in Baltimore, is now the executive director of Law Enforcement Against Prohibition. To be a suitable guest, one must feel comfortable speaking to past mistakes and holding oneself accountable. “A good guest is someone who is willing to be emotionally honest, someone who maybe doesn’t know all the answers to my questions and is okay with that and feels okay not having a script,” Lepp said. 

As the host, Lepp said she is aware of her responsibility to both her listeners and her guests to sidestep “sensationalism” and get to the meat of why we make the decisions that we do, especially when they turn out to be the wrong ones. “I’m not trying to make [my guests] look bad,” she explained. “If anything, depending on who they are, I’m trying to shine a positive light on the fact that they are talking about something that they’re not proud of. That’s something that’s hard to do.”

Leep brings that responsibility to bear when she asks guests like Canadian Christianne Boudreau, whose son, Damian, was killed while fighting for ISIS, questions like “Do you hold yourself responsible in some way for Damian’s decision to join ISIS?” The result is the kind of conversation that we do not hear very often. Lepp’s guests aren’t simply lamenting their former actions, but explaining their origins, walking listeners intimately through their thought processes and what they’ve done to counter their past actions. 

To be sure, it’s not always an easy listen. Take, for instance, Daniel Gallant, a former white supremacist who committed acts of violence which left his victims comatose and now works to help fight extremism. In his episode of Reckonings, Gallant said, “In my experience, most of the people in the white supremacist movement, their goal isn’t just to go out and hurt people. Their goal is to be a part of righteous, something that’s good.” That is not the point of view that most listeners come from when thinking about white supremecism—yet it’s precisely the uncomfortable moments that make for powerful and, Lepp hopes, transformative, listening.

Lepp said she doesn’t have a specific strategy to draw her guests out. “The best interviews are where I’m actually just listening and being myself,” she mused. “I am a sensitive person who feels these kinds of things people say. … I react as I would with anyone I was talking to if they start crying or say something that affects me.” It is not surprising to hear Lepp gasp at a particularly shocking revelation, such as when Boudreau, the mother whose child joined ISIS, admits she hasn’t spoken to her son’s father since he passed away.

That’s not to say that Lepp is a passive listener. She just wants to stay true to the podcast’s purpose. “It’s kind of a dance between being myself and moving the conversation in a particular direction.” If she feels they aren’t truly digging as deep as they could have, Lepp admitted, “I will push them. The easiest way to do that is to say, ‘What would have changed your mind back then? Whatever that is, can you do that to other people?’ I want the people who are still actively reckoning, let’s say, to move them toward some kind of action or reconciliation.” And of course, she adapts her interview style depending on who she’s talking to, being “much more gentle” with the mother whose son ran away to join ISIS while behaving “more like a reporter” with some of the folks who have worked in criminal justice system or drug law, for example. 

While episodes of Reckonings are all in the 30- to 40-minute range, her actual conversations are much longer. They usually running from one-and-a-half to two-and-a-half hours—whatever it takes to get at the core of what the guest is reckoning with. Most interestingly, Lepp has even done several interviews that she chose not to air, because they didn’t fit her mission. One such rejected episode was with the mother of a transgender daughter, a woman “who was just too open-minded, actually,” Lepp said, meaning that she didn’t have enough in her past to make amends with in regards to her parenting. “I often tell people, If you’re not a good fit for the show, good for you!” she said. Others who aren’t a good fit for the podcast “just aren’t willing to go as deep as I want to go.”

Lepp isn’t shy about her liberal leanings but would like to have more conservative guests—if she could find a personal way to relate to them, that is: “I have never had a conversation with someone who is anti-abortion; I don’t know anyone who’s anti-gun control or denies climate change.” Yet finding the right person for Reckonings—which, remember, is a podcast about coming to terms with past mistaken beliefs—would be a challenge. She’s tried, but so far it hasn’t panned out. “I’ve only explored it for one topic so far and my judgment just went up,” Lepp explained. “I had no sympathy for the person’s point of view. I’m not going to be able to do the interview if I can’t sympathize. I would have to find a person for whom I can relate to where they’re coming from and believe in sharing their story in order to do that.”

Still, does have a wish list of the types of people she’d like to hear grapple with their consciences on Reckonings, including an executive at a company involved in the minimum wage fight, a former anti-gun control Republican who comes out in favor of “sensible gun control,” a representative of a global brand that uses sweatshop labor, or someone involved in the financial crisis or bailouts. “This is totally not realistic, but I’d love to talk to a former ISIS member or recruiter,” Lepp added.

What is clear is that Lepp puts thought into who she invites to be her guests. 

“I’m in kind of an interesting position because I have a responsibility to my listeners to bring them compelling and honest stories and I also have a responsibility to my guests because they’re making themselves really vulnerable. If all goes as hoped, they may be telling me things for the first time that they have never made public. I want to be really careful with that. I want to be super clear: I do not have the power to absolve anyone. This is not a soapbox for ‘aggressors’ or perpetrators of anything.”

Reckonings is not a soapbox, but it is a place where Lepp, in particular during the episode with the former white supremacist, has found herself being forced to flex her “compassion muscles” and ask herself, “Can you really have compassion for this person?” It’s a question that listeners will no doubt be asking themselves as well. 

 Illustration via Max Fleishman

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