It might sound bleak: a barely teenage girl drinking with a 34-year-old homeless veteran under a tarp. But that's not what I remember.
The deck is warm beneath my bare feet, still holding the day’s heat. We’re anchored off Antigua, the water sparkling, the air soft with salt and something faintly sweet.
A glass of Sancerre sweats lightly in my hand as the breeze moves across my skin on the deck of my client’s yacht. I’m as comfortable here as I would be in my own living room. That ease is a wonder to me, because, statistically speaking, so few ever arrive at a moment like this, let alone feel at home inside of it.
But this unlikely circumstance was born from an unlikely friendship: one that taught me the truth about humanity and belonging. I was 12 years old when I met Jimbo, a 34-year-old Vietnam veteran. At the time I was despondent, shut down and had stopped caring about anything.
, and my mother, lost in her own sorrow, struggled to care for three children: a poor family living in San Antonio, Texas, where our utilities were regularly turned off.was its own hardship, but it was the weight of unspoken grief that pressed most heavily on our home. We mourned individually, each of us learning to survive on our own.
In a cruel twist of fate, our crumbling home happened to fall just inside the boundaries of the wealthiest school district in the city. At school, what I needed most was compassion and encouragement. Instead, a culture built on reputation and appearances left me suffocated. I was a naturally bubbly child with plenty of friends, but as we entered 4th grade, the differences in our respective lives became glaring, and my confidence fractured.
While other girls arrived in designer clothes, I rotated the same few hand-me-downs. By fifth grade, my first bully appeared, holding court by loudly mocking my clothes and asking where my father was. Most damaging was the growing awareness that my life had become a subject of speculation. Questions circulated: Where was her father?
Why couldn’t her friends come over? What was happening inside her home? I was singled out not just for how I looked, but for what couldn’t be seen. The contrast between home and school was dizzying.
I would come home boiling with frustration, railing against what I experienced as a farce. The abundance of things! The absence of tenderness! A culture that looked enviable from the outside but felt totally vacant inside.
As so many wounded kids eventually do, I abandoned the effort to fit in and turned to the one path I knew I could succeed at—rebellion. I began skipping school, drinking, experimenting with drugs, and would eventually drop out altogether. My sister and I often talked about running away to Venice Beach and becoming “hobos.
” So when my sister found a man drinking a beer behind a neighborhood store and invited him back to our house for another beer and a cigarette, it made perfect sense. When I came home that day, my sister gleefully told me she had a surprise and walked me to our backyard.
Jimbo sat there in blue jeans and a black T-shirt, with one leg languidly crossed over the other, a lit cigarette in one hand and a Lone Star beer in the other. He beamed like sunshine with blue, twinkly eyes. With his scruffy beard, a blue bandanna wrapped around his forehead and a battery-operated boombox blasting '70s rock by his side, I felt an instant affection.
“So I was just having a smoke behind Best Buy and here comes your sister. She says, ‘Are you a hobo? ’ I cracked up and said ‘Yeah, I guess I am! ’ And then she goes, ‘Well, my sister will want to meet you, so come home with me.
’ And here I am!! ” For the next two years, Jimbo became one of my closest friends. He regaled us with stories of touring with REO Speedwagon, fighting in Vietnam and living under the open sky. We were never entirely certain which of his stories were true, but he was consistent, fully present and funny as hell.
He would laugh at my outrage, not dismissively, but with delight, as if he recognized something essential in it. More importantly, he trusted what I was telling him about the world. At the time, I thought it was us against them. The poor against the wealthy.
The troubled against the perfect. The haves vs. the have nots. Jimbo listened. He loved my indignant spirit and met me with a wholehearted acceptance and the nickname “Little Bit” for my fiery nature.
He cheered on my daily rants about the hypocrisy I saw in school: “You tell ‘em, Little Bit! ” he encouraged, part father, part partner-in-crime. Together we created makeshift camps around the neighborhood. He gave homeless hangouts amusing names—“Hoochie Man Trail” , “The Green Room” and “The Tree” .
I would often leave a sign on our front door so our band of lost souls would know where to find us. The sign would read"At the Green Room" or"See you at the TreeBut The Green Room was our haven, with room to spread out beneath the trees and nightly campfires. Someone found a green carpet in a dumpster–that became our floor. We strung a tarp above us and the trees became our walls.
There, with a ragtag tribe of lost souls, we sang songs, shared poetry, listened to music and found refuge in each other. Visitors would bring gifts of firewood, booze or whatever food might be procured. Each day, I would make us cheese sandwiches–two pieces of white bread, a slice of American cheese and a drizzle of mustard. It paired beautifully with malt liquor.
It might sound bleak: a barely teenage girl drinking with a 34-year-old homeless veteran under a tarp. But what I remember is that we laughed constantly—at the world, at ourselves, at the absurdity of it all. Jimbo liked to say, “Everything’s copacetic. ” So we dubbed ourselves the Copacetic Club.
As we approached one of our campsites, Jimbo asked us to announce ourselves so he wouldn’t get spooked by our arrival–he blamed it on his post-traumatic stress disorder from Vietnam. Everyone was assigned a number by Jimbo and we’d announce ourselves by hollering “Incoming! ” followed by our number. Jimbo said this was a phrase they used during the Vietnam War, to alert fellow troops of an impending artillery attack.
"Incoming, hit the dirt! " Jimbo was of course No. 1 and I had the great honor of being proclaimed No. 2. One of our friends could never remember his exact number, so he would announce “70-something” as he approached. For me, hollering “Incoming!
Number Two! ” was not only hilarious, but proof that I had a place, a number, a tribe. Regardless of our number, we each came with our unique struggles. Seventy-something was a teenage runaway whose father horrifically abused him.
And Jimbo, despite his light spirit, was a severe alcoholic and grieved deeply for the family he’d left behind. None of us could undo the pain, and we didn’t know how to overcome it. So, we did our best to set it all down and enjoy the kind of freedom that those with more conventional lives may never truly know: living moment by moment, sheltered by laughter, unburdened by expectation. For a time, that freedom was enough.
Slowly, after I turned 14, I drifted away from Jimbo and the Copacetic Club. I found a full-time job and eventually returned to school. The last time I saw Jimbo I was 19, in college, working in the music industry, and laser-focused on success. Driving to work one morning, I spotted him at a bus stop.
Thrilled, I pulled over. But as soon as I approached, I realized he was far gone. His words slurred, his body frail, his spirit dimmed. He was happy to see me, but it was clear we weren’t on the same plane anymore.
There was no real conversation to be had. Which one of us had changed more? Was it that he had gotten worse, hiseroding him? Or was it that I had grown up so much, unable to see him as I once had?
I told him I loved him, hugged him tightly, and drove away. Jimbo died two years after, at the age of 42. He was buried at Fort Sam Houston National Cemetery, alongside his fellow veterans. Years later, as my life expanded in ways I never could have predicted—working with the wealthy, the powerful, the widely admired—I began to notice that beneath the veneer, resources and reputations, the struggles were the same and sometimes worse: Fear.
Longing. Insecurity. The universal ache to be seen and understood. The resentment that once sharpened everything—the judgment, the need to sort people into categories—began to loosen.
Not because the world had become kinder or fairer, but because I had been encouraged to see past all façades. Those years of laughter, kindness and patience from Jimbo had shown me that wealth and homelessness are simply different costumes worn over the same fragile interior.
When I think of Jimbo now, I know he didn’t fit the part of a mentor, and I didn’t fit the part of a friend to a middle-aged man living on the streets—at least not by the standards we’re taught to trust. But the connection was real, and it carried me through one of the darkest chapters of my life—onto college, out of poverty and into a comfortability around the wealthy people I once disdained.
Unlikely friendships carry their own kind of alchemy, and they can lead to unlikely circumstances. They break open the walls we think define us—age, class, circumstance—and reveal the simple truth that love begins the moment we stop insisting on being separate. Jimbo gave me belonging when I needed it most. Even now, decades later, I still measure friendship not by its likelihood, but by its ability to bring us back to life. All views expressed in this article are the author's own.
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