The term “pen pal”—sweetly alliterative and quaint—may evoke images of doomed summer camp relationships, international exchange student assignments, and 1950s schoolgirls writing letters to soldiers with fountain pens. But in this country, which locks up more than 2.4 million people and enjoys the title of most incarcerated nation in the world, the practice of pen-palling takes on a pragmatic purpose: It links those behind bars to the outside world.

Over the past eight years, I’ve corresponded with a couple of dozen pen pals in prison. The “use” of pen-palship has made itself visible in small and large ways over the course of these loosely threaded friendships. Sometimes, a piercing phrase will spring up out of the envelope—a truth that will never leave my mind. At other times, a prisoner will contribute a vital bit of information that proves unavailable anywhere else. Often, though, the “use” of pen-palship is not in the particulars of what is being communicated, but in the act of communicating.

Prison is built on a logic of isolation and disconnection. Letters between pen pals are almost always exchanged for the opposite purpose and with the opposite effect: connection.

The act of pen-palling mirrors the mindset shift that will be necessary to rethink how our society “does justice” on a much larger scale. My conversations, correspondences, and relationships with prison-torn families have taught me that separation breeds more separation, that the coldness and isolation of prison breed the coldness and isolation of violence. And I think about how the one-on-one relationship, in which the prisoner emerges as a person (with thoughts, a personality, a history, hopes, dreams, nightmares), might serve as a model for the beginnings of a person-based, connection-based justice system.

In early 2006, I began working on a piece on prison-based activism for the music and politics magazine Punk Planet. I wanted to write about action happening on the inside, action that might not be getting any attention beyond the walls, and I began writing to people in prison to find out what they were thinking. I soon developed an ongoing correspondence with my first prison pen pal, Steven Michael Woods, who was on death row in Texas. Steven was leading a hunger strike to advocate for more humane—or, at least, marginally tolerable—conditions. Addressing the envelope (“Polunsky Unit,” death row) scared me. My image of Steven was murky and amorphous, a silent symbol of the media label routinely slapped on death row prisoners: “worst of the worst.” However, the day I received my first letter from this man, I came to the jarring, thudding realization that he was human. Not Inmate No. 1267, but the person, Steven Woods.

Steven was 26, two years older than me. (He was arrested at 21.) He worshipped nineties underground rock and had played bass and guitar for “beer party punk bands” in past days. His politics were passionate—and, incredibly, more hopeful than mine: He wrote of his belief in the power of nonviolent resistance to “help our fellows rise above their chains,” even in the direst of circumstances.

The day I received my first letter, I came to the jarring, thudding realization that he was human.

To top it off, he’d been an avid Punk Planet reader before he was locked up—he could name cover stories from 2001. He claimed he was innocent: His co-defendant, whose fingerprints were found on the weapons, had confessed to being the sole shooter in the murder. No physical evidence against Steven was ever discovered, although he did acknowledge being at the scene of the crime. (I neither questioned nor affirmed Steven’s innocence throughout our correspondence, but I did go online and read, over and over, flooded with grief, anger, and confusion, the gory details of the murder he was said to have committed.) Now, he woke each morning sweating uncontrollably, hit with the stark inevitability of his impending death.

In his first letter to me, Steven shared that he was working on a zine—a handwritten, self-produced magazine filled with rants and comics—entitled “The Continuing Struggle of a Nail in My Coffin.” The point? “To educate and entertain!” Steven wrote me. “Sitting idle while the world wallows in ignorance and apathy just isn’t for me.”

In my letters to Steven, I didn’t talk much about my own life (though I answered his questions about the music scene in Chicago, where he’d once lived). It felt absurd to blather on about my bland day job, lunchtime trips to Noodles & Company, and watching television marathons on DVD. So I asked what life was like in Polunsky, what protest actions he had planned for the future, and whether he had any appeals left to fight his sentence. “One more,” he wrote.

My string of questions began wearing itself ragged. I was repeating myself, struggling to avoid the one topic that burned at the forefront of my mind and the tip of my pen. Our letters grew further apart. I tried to send him copies of Punk Planet; they didn’t get through inspection. We “chatted” about protest behind bars. He wrote, “The biggest part of being an activist is reaching out and instilling the spirit of revolution and resistance in our fellows, to break the herd mentality…you place us into a situation where all the fuel is already there, and all it needs is a spark.”

I wrote, “I am so impressed with all you are doing!” I thought: “What good will any of it do? You’re dying.” We traversed light, safe, death-free discussion terrain: Chicago bookstores, my work at Punk Planet, the merits of Mountain Dew (which he loved and I hated). He wrote about the time of enlightenment that would come “after we win better conditions back here.”

I avoided the mailbox, falling toward a selfish, gutless conclusion: I didn’t want to watch Steven die. I stopped writing first.

For four years, I quit thinking about Steven, or tried. But in the summer of 2012, I combed through my letters from pen pal interviews past. There was Steven. And so I took a deep breath and googled “Steven Woods” and “Texas death row.” The Internet delivered the news: My friend had been executed in 2011. His last meal had included French toast, bacon topped pizza, chicken-fried steak, and, of course, Mountain Dew, though he hadn’t eaten a bite. His last words: “Warden, if you’re going to murder someone, go ahead and pull that trigger….I love you Mom….Goodbye, everyone. I love you.”

In early 2013, Beth Derenne from the Women’s Prison Book Project sends me a packet of thank-you letters from women who’ve participated in her book exchange. I flip through the pages, pausing on a letter from Sable Sade Kolstee, who describes herself as a book lover with a “thirsty brain.” I drop her a note to see if she’ll answer some questions for my book on prison and disconnection. She responds promptly in round, clear print: “I am 26 years old and a mother to 3 beautiful children. When you talk about disconnected—I was shut off from my children from April 4, 2010 until just this month, March 2013. My crime put restrictions on my contact with minors.”

Sable writes achingly of how she’s been severed from her three young kids, all under the age of eight. Over the course of her incarceration, Sable has missed a long list of early milestones: “first steps, concerts, growth, birthdays, holidays, and many more.” Letters, calls and visits from her children have been banned until recently, she writes: “My greatest challenge was fighting for the children. So many times counselors would say ‘I understand.’ I would look at them and tell them not to lie to me because none of you have ever gone 1 year, 18 months, 2 years without your children.”

The battle for her children won’t end upon release, Sable says. The terms of her parole will also mandate a separation from her children. And, she writes, her “separation” extends beyond contact with her kids, and even beyond the limits of the law. She’s worried about how people will perceive her. “It’s not that I think I won’t be able to make a positive contribution to society when I get out,” she writes, “but the stigma I will live with for the next 22 years will possibly make me shy or frightened of judgment. Although I want to help others and show my children that a mistake does not define you.”

At this point, I’m absorbed and pained; I feel for my new pen pal. And I’m rooting for her! But the gigantic thought bubble hanging over my brain is shouting, “What was the mistake?” What act would bar her from receiving visits from her kids—or leave her with a twenty-two-year post-release “stigma”?

I google her, of course. One cruel irony prisoners face is that while they’re behind bars, unable to speak for themselves, the internet offers up a host of third-party information about them: mugshots, court documents, personal data (age, height, weight, tattoo verbiage), past records, and often-sensational press coverage of their convictions. A couple of newspaper snippets disclose that at twenty-three she was convicted of “statutory assault”—having a “sexual relationship” with a “known minor male” over the course of a couple of months, as evidenced by text messages exchanged between the two. I write Sable for her perspective on what happened.

Asking prisoners for their “side of the story” can be an awkward affair, something it doesn’t even make sense to do unless the incarcerated person initiates the conversation. After all, the story is just one of each prisoner’s stories—the act for which they’re incarcerated doesn’t define them—and the last thing a pen pal should be doing is implying that. Perhaps I shouldn’t have broached the topic in the first place. But Sable’s very straightforward: She “did it,” she says.

In her early twenties, she was attending college and caring for her three young children, including a newborn. The kids’ father, Derrick, was in prison, and Sable, overwhelmed (she says she’d been “codependent” on Derrick), began to drink, use drugs heavily, and “sleep around with whoever.” From there, she says, her judgment slid downhill. She began dating a guy who, a month and a half in, told her he was fifteen. They fought, he left—but he continued coming around at night for a couple of weeks, and Sable, drunk and lonely, suppressed her major qualms. “I thought, hell I did this at that age,” she writes. The relationship soon ended, but Sable subsequently discussed it with a friend—who turned her in to the cops. She was charged with five counts of statutory sexual assault.

In the grand hierarchy of public perceptions of crime, ranging from I-don’t-know-why-this-person-is-in-prison to this-person-is-despicable-scum, people incarcerated for sex offenses are categorically deposited into the “scum” pile. I’d never corresponded with someone in this position before, except for brief interview-style exchanges for articles. Honestly, if I hadn’t impulsively written Sable based on her WPBP letter, I probably would’ve looked up her conviction and, glimpsing “sexual assault,” ruled her out.

But I didn’t, and now we were friends, and—though I didn’t and still don’t pretend to fully comprehend the ins and outs of her case—when she wrote of her hunch that if she’d had money for a decent lawyer, she’d “never have seen a day in prison,” I thought, “She’s probably right.” I google “age of consent.” In Spain, it’s thirteen. In Austria and Bulgaria, it’s fourteen. In Turkey, it’s eighteen. In Costa Rica, it’s fifteen. And in Pennsylvania, where Sable was convicted, it is sixteen; the boy with whom she had sex was fifteen years old.

I thought: “What good will any of it do? You’re dying.”

I wonder: What defines a sex crime, what makes someone a sex “criminal,” and why am I so hesitant about writing to someone who’s been branded with that label? I’ve had pen pals who have pled guilty to murder. Why am I even more insecure about corresponding with a woman who admits to a statutory sex offense? How do our definitions of “human” match up with our categories of “crime”? Questioning the labeling of a “sex criminal” is not to diminish the tragedy and trauma of rape, or the pain of survivors, who are often under-recognized, ignored, or even punished in our culture. Rather, it’s about questioning the logic of a system in which a person becomes defined by one of their acts—defined as that act instead of as a person. The questions knock at my brain. Sable and I continue to write.

One day, I’m delighted to find a letter from Sable in my box, this one sent from her grandmother’s house in New York, telling me she’s gotten out. “I did have pizza my first day out—it was SO good,” she writes. She’s also enjoying the series of small decisions that comprise her days on the outside: picking out her clothes, cooking a meal, choosing to go for a barefoot walk along the nearby river…as long as she’s sure—as sure as one can be—that she will not come across a minor.

Indeed, there are many choices she can’t make. She can’t find a job, so is tethered to her “Gram” (who loves her but is prone to getting “worked up into a tizzy”). She still can’t see her kids. And her face is plastered on a sex offender registry for the next twenty-two years. Months later, I receive a short note from Sable: “Being on parole is the hardest thing ever.” I wrack my brain for encouraging things to say—but “Hey, you’re getting out soon!” doesn’t work anymore. I end up simply writing, “I’m so sorry.”

For deeper insight into the emotional and political roles of the pen pal, I turn to Rev. Jason Lydon of Boston. If there’s such thing as a prison pen pal guru, it’s Jason. His group Black and Pink focuses on helping prisoners connect directly with pen pals on the outside, building both friendships and action-based relationships that link people through the bars. Jason has been incarcerated himself, and many of his own pen pals are people he left behind in prison. He sees pen-palship as a way to “dispel myths about who’s incarcerated…it’s necessary for people to recognize that it’s human beings who are being locked up, denied access to health care, assaulted.”

I’m struck by the way he talks about the pen-pal process as active and transformative: It’s not just about making friends. And, he tells me, if you’re fully engaged in the process, it’s probably not always going to be easy. You can’t keep your pen pal in a box. (That’s not what you’re there for—they’re in a box already.)

“We need to challenge ourselves on why we’re creating certain boundaries,” Jason says, when I ask about navigating the sometimes-weird personal terrain of pen-palship. “Are we setting those boundaries to make ourselves feel comfortable, or to make ourselves feel safe? Allowing ourselves to feel uncomfortable can help us grow, and to build authentic relationships and understandings. Being uncomfortable at times is OK, as long as we’re still safe.”

I think of my own abandoned pen pals. One expressed such blatant homophobia in a letter that I couldn’t bring myself to respond. I didn’t want to start a conflict but didn’t want to implicitly agree—so I stuffed his letter in a drawer. The other, of course, was Steven Woods; I had quit writing simply because I didn’t want to face the emotional avalanche of his impending execution, and I will always regret it.

Your pen pal may call you out on assumptions and biases you never realized you had.

According to Jason, the emotional avalanches are part of the point. In fact, he notes, the eruption of issues like misogyny, racism, homophobia, and transphobia may be a touchstone for important conversations, especially since, when we write to people in prison, we’re in a separate physical space. The medium of letters lends time to process words and contemplate responses. Jason tells me, “My hope is that people would be willing to extend a little more patience toward people on the inside than they would to folks on the outside, because of the amount of safety that we experience as folks who aren’t incarcerated.”

He points to situations, for example, in which white prisoners have made racist statements in letters; pen pals have sometimes challenged those statements and engaged in productive dialogues (though Jason emphasizes that people of color shouldn’t feel any obligation to “be patient” in such situations, and if safety feels threatened, it is always OK to walk away). And it’s a two-way street: Your pen pal may call you out on assumptions and biases you never realized you had.

As a former prisoner, Jason knows the value of outside ties firsthand, especially for particularly marginalized groups of prisoners, who are regularly exposed to excruciating treatment. When he was locked up in a segregated unit for queer, trans, and gender-nonconforming prisoners and repeatedly subjected to cruel treatment and sexual violence at the hands of guards, he vowed to remain in touch with his fellow prisoners upon release. “For those of us who have been incarcerated,” he says, the pen pal process serves as “a reminder to not forget folks who are left behind, that we have a responsibility to maintain relationships and compassion with those folks, to join in the healing process with them.”

Concretely, Jason says, aside from expanding our boundaries and awareness and engaging in dialogue, there are a few immediate purposes for a pen pal. Receiving letters during mail call can serve as a function that resembles the other definition of “mail”: a protective shield against potential violence. As noted earlier, it alerts guards that you’ve got contacts and advocates on the outside, so you’re less likely to be mistreated. Such “mail” is also useful when it comes to prisoners potentially harming themselves. Self-injurious behavior is common, and “having a reminder that you’re cared for and not forgotten—and part of a larger thing—can help you deal with the mental and emotional struggle that is the reality of being locked up.”

In the book Howard’s End, E. M. Forster wrote his instructions on the best way to live in two short words: “Only connect.” (E. M. Forster, incidentally, also announced on the BBC, in a fiery 1934 critique of the mechanization and industrialization of society, “Prison is no good.”)

When we reach out to a prisoner to “only connect,” we will always—to some extent—fail, because the barriers are so vast and so entrenched. But there are few cases in which a personal act that takes so little time can make such a great difference.

Before diving in, pen pals should check in with themselves, issuing a stern reminder that the act of writing a prisoner is not an act of charity. It’s about growing a unique breed of friendship. In fact, it’s one of the few contexts where you’re able to throw out a line to a stranger and say, “Will you be my friend?” It is an act that is not driving toward any clear, ostensible goal. Rather, it’s the goal-less endeavor of “getting to know” another person, which, for whatever reason, can be one of the most fulfilling, interesting, and transformative things to do in life. It’s also a primary building block for any greater political possibility that relies on connection between human beings—which, it seems, applies to every viable political possibility under the sun.

As the Illinois-based pen-pal collective Write to Win puts it: “We see individual correspondence with people on the inside as one piece of the larger struggle to abolish the prison-industrial complex and to create safe, sustainable, and equitable communities. To this end, we see our work as a way to undermine the isolation, dehumanization, and destruction of the PIC by building grassroots networks of support and solidarity between folks on the inside and folks on the outside.”

In other words, how can policy change—or, for that matter, deep systemic change—evolve, if outside activists and theorists and advocates aren’t talking to the people they’re talking about?

Lacino Hamilton, an incarcerated activist in Michigan with whom I’ve corresponded for the past couple of years, emphasizes that it’s crucial for outside audiences to listen when prisoners vocalize their struggles. “We cannot be passive recipients of the efforts of others,” he writes. “We have to be part of the work being done.”

The pen-pal journey is certainly not the endgame; it’s the beginning game. Perhaps, then, “Only connect” is not a perfect motto. Lacino’s words highlight the potential of prisoners’ connections with outside allies to build creative new models, initiatives, movements—maybe even revolutions—that cultivate a more just world.

Excerpted from Locked Down, Locked Out: Why Prison Doesn’t Work and How We Can Do Better by Maya Schenwar, published by Berrett-Koehler Publishers.