Those of you who have followed this process know what I hoped this book might become: a love letter to the people who supported me, challenged me, and occasionally caused me to go home and stare quietly at a wall. But it is also meant for people who have spent years performing the version of themselves that seemed safest—at work, at home, at church, or at the Thanksgiving table—and who may be wondering whether there is still time to become more fully themselves.

I do not imagine that my story supplies anyone else’s answer. I hope instead that it offers companionship, a little courage, and perhaps permission to ask the questions we become very skilled at avoiding.

Looking through my files, I discovered that the first chapter was written in 2004. At the time, it wasn’t a memoir; it was catharsis. To my 2004 self, it described the most devastating period of my life. It was the period when I had finally said aloud what I had spent years repressing, and then had to live through the ordinary consequences: an apartment that did not yet feel like home, the fear of disappointing people I loved, and the feeling of guilt and loneliness associated with making the right decision while realizing that, at least temporarily, you had ruined everything. Eventually, as I took notes focusing on the years surrounding my coming out, it became the backdrop for the larger book.

About six years later, after giving several Juneteenth talks, I began to understand how many young adults were carrying similarly private struggles. In one-on-one conversations, people told me how impossible it felt to contemplate disappointing parents, disrupting careers, or acknowledging an identity that might change the shape of their lives. They would lower their voices, even in rooms where nobody else could hear them. One time, while a friend of mine and I were seated and chatting in a bustling breakfast establishment, he confessed that “My parents would plotz if they knew how much I am hating medical school, but I knew they wouldn’t want all my schooling to go to waste if I went into nursing.” He whispered and glanced around nervously as if this admission might cause the waitress to drop her coffee pot, summon his parents, and have him escorted directly back to anatomy lab. I began to think I might have something useful to say.

I sent that early chapter to my friend Dr. David Nichols, then president of the American Board of Pediatrics, expecting him to skim it and say something kind about my cute little chapter. David did not skim. David apparently regarded a personal essay the way some people regard an unattended buffet: as an invitation to go back for more.

“Tell me more about how this realization made you feel.”

“I suspect you didn’t just realize you were gay all at once. Readers will want to know when this began—and what it cost you.”

“How did compartmentalizing your life affect your childhood?”

“You must have had a strong relationship with your parents. What did they give you that enabled you to take the risks you took?”

His questions kept coming. More importantly, they opened questions I had never fully asked myself. He was right to ask. My parents had given me more than love; they had given me a sturdy, almost inconvenient belief that I was capable of hard things. It was the sort of belief that is comforting right up until life presents you with something hard. A memoir, it turns out, is less a matter of remembering your life than discovering how much of it you had filed under Do Not Open Until Further Notice.

Fast-forward to now: there have been hundreds of emails from people like you—people who, in the spirit of this Substack’s original name, influenced how I came to understand and tell this story. Some wrote to tell me that a piece of the story sounded like their own. Some remembered a teacher, a parent, or a friend who had changed the direction of their lives. And some simply wrote, in one form or another, “Keep going.” For a writer, this is the emotional equivalent of being handed a snack and a map at the same time. Thank you for that.

The working title, The Influencers, once felt both clever and true to my brand. Then it became an overused word, attached to more books, blogs, podcasts, and people offering discount codes for supplements than I could count. It was time for another title. I needed the writing to be more immersive and to have a faster pace. I needed to inject humor, and, most importantly, I needed to “show” more than “tell” the story.

Fortunately for me, I was awarded a great honor: The Rockefeller Foundation selected me to join a cohort of amazing people for a month-long residency in Bellagio, Lake Como, Italy.

Thanks to The Rockefeller Foundation, I had time to work on this project while also learning and writing about artificial intelligence and health equity. Chapters became my weekend pastime—sort of an amuse-bouche to cleanse the palate before the next week of interviews and presentations.

Once I’d accomplished that complete rewrite, I knew it was time for a new title.

After trying on several possibilities, two finalists remained: Weirdo and Misfit. Naturally, I asked GPT for an opinion.

Its answer was Misfit—and, annoyingly, it was right. A weirdo may simply be eccentric. A misfit is someone for whom the available rooms were not designed, who eventually learns not merely to enter them, but to help remake them.

So we are off and running with my first book: Misfit!

Stay tuned for more posts about the second phase of this journey!

I wrote it because, for a long time, I was certain it wasn’t.

There is a particular kind of silence that settles over a person who has spent years believing they arrived by accident — in the room, in the role, in the life, in the version of themselves that somehow kept showing up and being allowe…

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Legacy arrived for me on a weekday afternoon, served with wine and charcuterie.

Very few people were seated. The board room of the Eskind Library hummed with motion as friends stood in loose clusters, balancing small plates, or gathered around bistro tables draped in white linen. Conversations softened as my name was called.

“Kevin, come on up.”

I stood and walked toward the front of the room, quick and practiced, smiling the way you do when you know all eyes are on you. Rob and our children were there, smiling, leaning in, plates in hand. Friends from Vanderbilt filled the room and its edges. Some were chairs. Some were clinicians. Some were gay. Some were Black. Some were both. Many had no titles at all. They were simply people who had walked with me for a stretch of the road.

Dr. Jeff Balser, CEO of the Medical Center, and Dean of the medical school, stood at the podium and began to speak, setting up what would I realized was becoming an It’s a Wonderful Life moment. He reminded the room that our patients might never know my name, but that thousands had received more personal care because I chose to come to Vanderbilt. Glasses paused midair. Heads turned. I caught Rob’s eye and felt myself breathe a little deeper.

I thought I was ready for this. I had imagined the words. I had rehearsed the feeling. But Jeff had prepared more than a few remarks, and as he spoke, something familiar stirred. A tingling in my fingers. Warmth under my arms. The physical cues that always came just before emotion took over. I pushed it back. I always did.

He talked about echoes. How even after I had been gone for years, the halls still carried the imprint of decisions made under pressure. Of risks taken without guarantees. He spoke of the transition to Epic, a moment so fraught it reshaped the institution’s clinical spine. He told a story about how I had taken him by the arm during site visits, insisting we walk the process exactly as our clinicians would. No shortcuts. No abstractions.

I looked out at the faces of the clinician builders who had threaded that needle with me. Friends. Co-conspirators. People who had trusted me when trusting anyone felt risky. And there it was again. The quiet return of imposter syndrome. The same one Jeff had chastised me for when this portrait was first proposed.

I had always thought of informatics work as something like the floor of the Sistine Chapel. Essential. Beautiful in its own way. Designed to be walked on every day by people who rarely look down, let alone wonder who laid the stone.

And yet here I was, standing before a covered portrait by Jamie McMahon, commissioned to mark a transition from paper to digital, from scattered notes to shared truth. Jeff grounded the moment with humor, reminding the room that I used to have a lot more hair. Laughter loosened the air. He spoke not just of roles or titles, but of curiosity. Of art. Of media. Of film. Of mentoring. Of showing up for people who needed to see someone like themselves in rooms that once felt closed.

As he traced my path from being born at Johns Hopkins, to Dickinson College, back to Hopkins for medical school and chief residency, then through Stanford and a decade on faculty before Bill Stead recruited me to Vanderbilt, he slowed. The cadence changed. He spoke of representation. Of being only the second African American to serve as department chair in the school’s history. Of time intentionally given to recruit, mentor, and steady those underrepresented in medicine so they might find their footing sooner than I did.

I watched my children listen. I saw Rob lean in. I felt the room settle.

The portrait, as he pointed out, represented far more than my mastery of systems or strategy–or even of Vanderbilt’s desire to add dark-skinned faces to the hallowed walls in the medical school lecture hall. It was a signal that anyone could succeed, or, in the words of Chef Auguste Gusteau from the lovely movie Ratatouille, “Anyone Can Cook.” It was a direct motivator for someone who might one day stand where I was standing, balancing a plate in one hand, wondering if they belonged.

As Jeff finished, I found myself flooded with thoughts I wanted to share with this audience, as well as with my younger, more troubled self.

I’m really here. Black, gay, geeky, artistic, scientific, positive, curious me.

A kid from a hard-working, blue-collar Black family with no role models in medicine or technology ended up in this room.

The weird kid from East Baltimore — the one bullied in alleys and classrooms — learned that belonging did not require resemblance.

Loser Kevin found the courage to be out and proud, Black and nerdy, eccentric and carefree in spaces he never imagined entering.

Being seen comes with a cost — and retreating was like keeping a pristine yacht docked in a harbor, safe, but never doing what it was meant to do.

I would have relished the opportunity to tell that story. I had a story to tell.

Jeff reached for the cord.

The room quieted in the way rooms do when something is about to become permanent.

The linen fell.

There I was. Darker than I imagined they’d paint me. Older than I feel. More settled in the face than I’ve ever felt inside. Behind me, the bookshelf held the life I’d actually lived — folk art and found objects, a rooster, a painting exploding with color against all that warm brown wood. To my right, a keyboard. One hand resting on it like it belonged there. Because it did. Me straddling two worlds of information. The white coat. The badge. The name.

I knew every answer to every question that had just moved through me. I had known them for a while. I just hadn’t said them out loud yet.

This is what it looks like when the weird kid wins.

And I’m going to tell you exactly how it happened.