Inside Out and Outside In

Exploring the possibilities—and the pitfalls—of immersion projects

When I was twelve years old and starting to break competitive-swimming records, I read only books about athletes. I started with Lance Armstrong’s It’s Not About the Bike: My Journey Back to Life. After that, Laura Hillenbrand’s Seabiscuit, biographies of Olympic gymnast Carly Patterson and Olympic swimmer Mark Spitz, and a tale of Shoeless Joe Jackson, the Major League outfielder whose career was ended by his alleged involvement in fixing the 1919 World Series. Convinced of Shoeless Joe’s innocence, I went so far as to send a letter to The Shoeless Joe Jackson Society, outlining all the reasons he should be inducted to the Hall of Fame.

I think I was attracted to these sports books for the same reason my mother always thumbed through the shiny gossip magazines in checkout lines: I wanted the inside scoop. Like the tabloids, these books depended on an inherent division between the subject and the reader, but they also promised access, the chance to get a little closer to the athletes I idolized and, maybe, to become less of an outsider. Carly Patterson, Mark Spitz, and the others represented greatness, athletic excellence—at times, even the sport itself. Those narrators (and ghostwriters) pronounced, with an almost God-like air: Reader, I invite you to put your faith in me, and all your questions will be answered.

My swimming career ended rather unceremoniously when I graduated from college. I’d grown sick of swimming and had wanted to quit years earlier, but I couldn’t imagine being on the outside of something that had defined me for so long. In graduate school, I joined one of the most prestigious roller derby teams in the world. I couldn’t even skate. As uncomfortable as my foray into the sport was, the visceral experience of being an outsider fueled my first several essays. Here, reader, they seemed to say. I’m just like you—clueless. Laugh at me. Watch me fall.

A few times during graduate school, I was referred to as a sportswriter, a term that never felt completely accurate. My impression was that sportswriters had to be either experts in the field (that is, athletes themselves) or devoted spectators with press passes and little pads into which they scribbled notes for tomorrow’s news. Broadening my understanding of the way in which sports, and other subcultures, could be addressed was essential to my growth as a writer—particularly because I spent so much time skirting the hazy territory between insider and outsider perspectives.

Illustration by Anna Hall


One of my professors, Edward McPherson, wrote an immersive history of the card game bridge called The Backwash Squeeze and Other Improbable Feats: A Newcomer’s Journey into the World of Bridge. The title clues us in to the fact that McPherson’s perspective is that of an “outsider.” His outsider status is the main source of tension throughout the book; it’s also his greatest bargaining chip.

Being an admitted newcomer allows McPherson to identify with an outsider audience. It can be a gentle approach to writing about a subculture because it allows him to anticipate questions we may have about the bridge scene, since these very questions occurred to McPherson himself, and integrate them without distracting from the book’s forward motion. It is also important that McPherson found an insider—a Virgil, he often called him in class—to guide him through the subculture. McPherson’s priority then became to funnel and shape experiences while gathering credible information.

Much of my thinking about the insider/outsider phenomenon has been influenced by McPherson, who taught me it can be refreshing, and even a little intoxicating, to write about a world with which you’re unfamiliar. This is why it’s important to ask:

What is your main purpose for wanting to write about this particular subculture?

Roller derby attracted me because it seemed fresh and feminist and urgent. Who wouldn’t want the lowdown on one of the only sports in the world that isn’t male-dominated? Who doesn’t love great pun-names like Betty White Trash and She-Kill O’Neal? I was also enticed by the idea of using my immersion in the sport as a container for research and a brief history of flat-track derby’s punk roots.

How will you ensure your “outsider” work does not exploit, appropriate, or exoticize?

My identity as a queer woman and former college athlete granted me immediate access into the underground world of derby. Still, I had to be careful not to perpetuate the misogyny and oversexualization that were a big part of derby’s history. It was crucial not to fall into cliché or generalization.

To write about a group with less power from a position of privilege can lead to specific challenges. Timothy Kurek’s “outsider” book The Cross in the Closet came out in 2012—a year before I did. The premise is reminiscent of John Howard Griffin’s 1961 Black Like Me in that Kurek poses as a gay man in order to understand how a lack of tolerance among his Southern, Christian peers affects queer people.

The experiment seems well-intentioned. Kurek stated that his goal was to increase compassion and empathy in his community by “coming out” to his parents and living as a gay man for one year. I read Kurek’s story during my own disastrous coming out—a process that is never really over—in the hopes that it would help me speak to religious, conservative family members about my sexuality. On some level, the book did change the way I thought about Christianity and homophobia—but it was hard to get past the fact that Kurek’s “coming out” was essentially an elaborate practical joke. The very construction of the book relied on pretense; I don’t think there was any way Kurek could’ve avoided exploiting and appropriating from queer folks in the process of “living” as a gay man—unless he realized he actually was gay.

Is your intended audience inclusive to the “insiders” about which you’re writing?

Would it have been helpful for Kurek to coauthor his book with a queer Christian—someone who wasn’t afforded the privilege of “un-coming out” at the end of the story? It certainly would have made the book more palatable and authentic to me. But then, that raises the question: 

What does your “outsider” point of view bring to an essay that couldn’t be written by an insider?

Maybe, the privilege of Kurek’s true identity granted him a broader audience. In that sense, the project was a success. A straight, white Christian going undercover as a gay, white Christian and discovering for himself how bad things are for queer people in the South is inherently more interesting (and, unfortunately, granted more credibility) than an actual gay Christian’s story about his lived experiences. That’s a story we’ve all heard before—and one the bigots have been ignoring for decades.

My project relied on my outsider status to attract readers, too. Being an outsider to derby allowed me to connect to an audience who may be fascinated by the sport but—for whatever reason—would never try it themselves. I became the intermediary for readers who remembered watching derby on TV and may have wondered, What if that was me?

Do I have a willing insider who can serve as a guide?

I often think about what McPherson said about finding a Virgil—a guide. To his credit, Kurek did have a fake boyfriend, an actual queer man who shepherded him to safe places around town and provided a shoulder to cry on. I’m lucky that my “Virgil” was assigned to me through a new skater mentorship program. Her name was QuickSandz, and as soon as I became her “mentee,” she started calling herself my derby mom. She was gracious enough to answer all my questions and became an essential character in my work.

What is the real story?

Every semester, I urge my creative nonfiction students to go out into the world and craft an “outsider” piece for our literary journalism unit. They’ve returned with spectacular essays about the local burlesque scene, the Church of Scientology, and a local swingers café. They’ve attended ghost tours, participated in a ritualistic bath at Bathhouse Row, and gone “undercover” at a crisis pregnancy center, one of the many women’s healthcare clinics that is quietly anti-abortion. 

These students are praised in workshop. I hand back their essays with comments like Thank you for taking such a risk! but we’re often left with a fundamental question: why?

I prefer that writers speak during their workshops, and we often ask questions until we identify some essential bit of missing scaffolding. The woman who investigated the crisis pregnancy center was still processing the abortion her mother had had. The ghost-tourer had neglected to mention a formative and fascinating childhood experience of the supernatural. The communal bather told us that being cleaned by another woman was a way of honoring and grieving for her late mother.


In college, I kept one book on my bedside table. It was called Mind Gym: An Athlete’s Guide to Inner Excellence. The authors, Gary Mack and David Casstevens, compiled inspirational lessons and anecdotes from forty prominent athletes who could speak about mental toughness directly to other athletes.

Insider books with an insider audience tend to have a specific focus: often they take the form of guidebooks. However, assuming you want to write an insider story for the broadest possible audience, it helps to consider these questions:

Will you embrace the challenge of writing for an audience of outsiders? 

The synopsis of Lynne Cox’s Swimming to Antarctica: Tales of a Long-Distance Swimmer professes, “Cox started swimming almost as soon as she could walk.” Cox is definitely an “insider”; there’s no question about her role in the sport. She writes from experience about competing in thirty-eight-degree water without a wetsuit and all the precautions she took to avoid shark attacks. She writes about becoming the first person to swim the Bering Strait, in 1987, and how the accomplishment helped ease tensions between the United States and the Soviet Union. I was fourteen when I read Swimming to Antarctica. I swam competitively, but I had never competed in open water and had no basis for understanding the challenges of Cox’s athletic pursuits. Yet, I felt completely comfortable navigating the waters of Cox’s story. She eased me in slowly, introduced me to the landscape with which she’d been raised, and explained in detail her training schedule and the methods she used to stay warm and safe in the water.

How will you ensure that your piece is inclusive of outsiders?

Before I signed with my agent, I read another book he had worked on; I wanted to know exactly what kind of sports book this agent had helped bring into existence. The book was William Finnegan’s Barbarian Days: A Surfing Life, which won the 2016 Pulitzer Prize for Biography and was named the 2016 William Hill Sports Book of the Year. I plowed through more than four hundred pages in two days.

There were many things that astounded me about the book, namely the skill with which Finnegan—who began surfing as a child—inducted outsiders into the world of surfing. Most of the Amazon and Goodreads reviews praise his instincts in this regard. “I am not a surfer,” one commenter wrote. “I have never been a surfer. . . . Though this book is ‘about’ . . . surfing, it is written so eloquently that it could be about anything, and I would still love it.” Barbarian Days has become somewhat of a model of an insider book for me.

Are you providing enough concrete details for outsider readers to follow?

In Barbarian Days, Finnegan makes the process of reader education so delightful that I didn’t realize I was learning as I read. Much of the memoir is rooted in descriptions of the waves themselves, which could easily tip too far into the technical or become redundant. I have never surfed—never looked at a wave the way Finnegan did—and yet I fell in love with lyrical descriptions like “It was, once again, a glorious wave, with hues in its depths so intense they felt like first editions—ocean colors never seen before, made solely for this wave, this moment, perhaps never to be seen again.”

Are you employing extraneous verbiage that will resonate only among insiders?

Surfing (like roller derby) has its own extensive vernacular. It can be a challenge to integrate jargon in a way that feels both authentic and welcoming. The first chapter of Barbarian Days includes only terms non-surfers would know, and Finnegan builds the vocabulary base slowly. By the end of the book, I found I was fluent in surf-talk without necessarily remembering the process of learning.

Outside in and inside out

One of the major challenges that comes with any kind of immersion project is that the more time you spend immersed, the harder it is to remain an outsider. In the first essays I wrote about derby, I could anticipate reader questions, introduce unfamiliar terminology, and make fresh observations about my new surroundings. As the roller derby scene became my new normal, however, I gradually lost the ability to see like an outsider.

Once that shift started happening, I struggled to write essays about derby that resonated with or even interested non-skaters. My grad school cohort wrote HA! at all the funny derby names, but my original “outsider” perspective was no longer genuine. The insider/outsider tension that had fueled my early essays had fizzled out; I was stuck in the murky territory of in-betweenness.

My approach to this insider/outsider conundrum was to bring the problem into the writing. In acknowledging the way I was starting to fit into the derby world, I was liberated to discuss a range of other conflicts that were naturally arising. I wrote about the discomfort of moving from my scrappy derby world to a posh academic setting (sometimes without even having time to change clothes). I thought deeply about the relationships that had suffered as a result of my involvement in derby. I discussed how becoming a true insider in roller derby meant that I was training obsessively and eating very little—patterns that ultimately mirrored the abuse I’d suffered as a child.

Maybe the most interesting approach to immersion work is when the outsider becomes, in the process of the writing, an insider and explores the liminal space between the two. In her beloved tale Wild: From Lost to Found on the Pacific Crest Trail, Cheryl Strayed begins her hike with too-tight boots and a too-heavy sack. By the end of her 1,100-mile journey, Strayed had survived (and become somewhat of an expert in) injury, bad weather, loneliness, hunger, and predators, not all of which were wild animals. Whip Smart: The True Story of a Secret Life opens with a young Melissa Febos tentatively asking her dominatrix neighbor questions like “Is there any actual sex involved?” and “Is the money good?” After years of domming at a dungeon, Febos explains, “I was not a tourist but a member of that world, with reasons for being there similar to those of everyone else: an obsession with power, having it and having it taken away from me.” Lara Prior-Palmer’s Rough Magic: Riding the World’s Loneliest Horse Race is a tale about deciding to enter the Mongol Derby on a whim with no formal training. It ends with Prior-Palmer defying all odds to win the race. In all these cases, and in my own roller derby adventure, remaining on the outside was untenable. Yet, maybe the dynamic journey from the outside in helps us write from the inside out.

About the Author

Gabe Montesanti

Gabe Montesanti has an MFA from Washington University in St. Louis and teaches creative writing at the Missouri Eastern Correctional Center. Her first book, a roller derby memoir, is represented by Markus Hoffmann and in the final stages of revision.

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