May 6, 2023

How I Got Everything I Ever Wanted by Walking Away from Everything I Ever Wanted.

This is a story about how I spent 12 years building a thrilling and fabulous life in New York City, filled it with an endless kaleidoscope of friends, music, comedy, theater, nights on the town, and a thriving career.

Then burnt it all to the ground.

And moved to—Tulsa, Oklahoma.

Why the hell would I do that?

Funny, a few hundred friends have asked the same question.


First, let’s talk about the life I had before I decided to set it on fire.

I grew up in Maine and Vermont, living in small towns, going to small schools, just being an outdoorsy kid. I never had any ambitions of living a “big city” life.

I became an English teacher at a small town boarding school after college, but at 25, I found myself longing for a little more stimulation. Quiet New England life was putting me to sleep. Maybe it was time to join my college friends who had moved to cities like Los Angeles, San Francisco, and Boston. So I quit teaching and launched a new career in advertising. It was all big cities from there: Atlanta, Portland, Seattle, Boston, LA, and eventually NYC when I took a job at BBDO New York.

At first I thought I’d find NYC too cramped and chaotic. But it soon brought out in me a hunger I never knew I had: a bottomless desire to connect with new people and learn their stories.

I spent most of my 12 years there living in the West Village on Perry Street, surrounded by the city’s best restaurants, jazz bars, comedy clubs, and art galleries. Just steps outside my tiny apartment lay an endless parade of artists, street musicians, actors, entrepreneurs, architects, designers, writers, financiers, dancers, cinematographers, and gorgeous couples making out under streetlights.

It was a nonstop river of inspiration. And I breathed it in like oxygen.

After work each day in the ad world, I’d head to a local bistro where the bartender knew my name, spending my nights chatting with local creative types, volleying ideas back and forth about culture, art, and entertainment, then go see one of the hottest comedians in town, then maybe bump into famed writer Malcolm Gladwell on my way home, and end up having a 30-minute chat about our love affair with cars. On weekends, I played live music as a singer/ songwriter at clubs like the Bitter End and Rockwood Music Hall, surrounded by friends and fellow musicians.

I truly felt like I’d found my “tribe.”

My writing career was hitting an all-time high, and at one point, I penned the ad campaign that launched the groundbreaking NYC CitiBike program, all based around my tagline, “Unlock a Bike, Unlock New York.” My writing was now seen on every street corner in New York, and I was winning awards left and right. On Halloween, I saw a woman dressed up as a human CitiBike, so I chatted her up. Turned out it was 80s model Brooke Shields, whom I’d heard lived nearby. Yes, Brooke Shields was dressed up like my ad campaign. We chatted, shared a few laughs, and I swore right then,

…I’ll never leave this town.

And it was inspiring moments of connection like these that kept me in love with New York for years.

It seemed like I finally had all the stimulation and excitement I never had growing up in Maine.


Until something in me shifted.

(And don’t worry, dear reader, I won’t say, “But I wasn’t really happy…” You’d have to be an asshole to not be pretty happy living in the West Village.)

But a few events in my life made me see things differently.

The first was that my father died rather suddenly, and as I worked through the heartache, I thought of what else I wanted to do in my life. Then I somehow had my slowest year ever finding ad work, despite having won more awards than ever.

It all added up to one painful realization: it was hard to feel like I really “mattered” to New York. In my year of personal crisis, the city couldn’t have cared less. Here, I was just another cog in the machine.

Suddenly, the tectonic plates in my heart started to shift: when was I going to publish the books I’d been toiling away on? Was I ever going to own a house? Or save any money? Would I ever get married?

Funnily enough, the newest single I’d released as a songwriter was titled, “Start a Landslide,” about my decision to abandon teaching to become a writer. Something within me sensed it was time to start a landslide once again—although I wasn’t sure what form that might take.

Miraculously, in 2019, my advertising career rebounded. and I had my best year ever. My income hit an all-time high, and I even produced two huge campaigns for Pepsi. But it felt just like a lucky draw of the cards. New York was a blackjack table, and I’d seen how a bad hand could nearly ruin me. So, in January of 2020, I gave notice on my apartment with zero idea of where to go next.

Then once the pandemic came and New York was about to close down for a while, I knew it was time to pivot. Check, please. Closing time.

“Dude, you can’t give up that apartment! Are you crazy?” my friends screamed.

“C’mon, you can’t leave New York. You are New York!” another friend insisted.

“Where else are you ever gonna be happy after living in the big apple?”

I had no idea what I was gonna do. But my gut told me there was some new horizon to chase.

In my final month in New York, I stumbled across a New York Times article about people leaving big cities to move somewhere new, mentioning a program called “Tulsa Remote” that paid people to leave their cities and move to Tulsa, Oklahoma for one year.

I thought to myself, Tulsa? I mean, I’d never move there. But, hmmm…

In a moment of “here goes nothing,” I applied. I figured, “If we’re just gonna work from our living rooms for a year, let’s work from a cheaper living room.”

Soon I was accepted, and by late summer 2020 after a quick visit to check out the town, I found myself driving to Tulsa to start a new life. Most of my friends thought I was joking.

But quickly, everything in Tulsa started going my way.

I lucked into an apartment in a downtown hotel building (that was half residential) with an old Steinway piano in the lobby. Aside from having a 1000-square-foot loft that I never could have afforded in New York, I played the piano every night, sang songs for all the other residents, and soon the hotel hired me to be their weekly musician in the penthouse bar each week.

At my shows, strangers would tip me $20 without thinking twice. This never happened in NYC.

It was like the universe was rewarding me for taking the leap. Keep going, kid, we got your back.

(And I sure didn’t always feel that way in New York.)

Tulsa Remote hosted events almost every week, so I made countless friends, many of whom would come see me play my shows each week. We would all trade stories and adventures about forging a brave new life in Tulsa. I felt like I’d found a new “tribe.”

Soon, I joined a local cycling group and even rode in the 100-mile “Tulsa Tough” cycling event.

I volunteered at an Ironman triathlon and began helping out with a charity called the PencilBox.

Everywhere I turned, I felt welcome and wanted. Whereas in NYC, it seemed like I was lucky to sneak my way into the party.

And suddenly, I was getting more advertising work than ever. So I started saving every dollar I could. My bank account reached numbers I’d never seen before.

Soon. I had more than enough money to buy a house. While I’d never had plans to “stay” in Tulsa beyond year one, I suddenly realized: work was going great, I was playing more music in Tulsa than in New York, and I had a group of friends who all seemed to “get” each other. What more am I looking for?

A month later, I discovered a hilltop neighborhood filled with modern homes called “Reservoir Hill” that reminded me of both my youth in Maine and the whimsical character of Laurel Canyon in LA. At one point, I walked by a gorgeous, modern house where a married couple stood on the deck arm in arm admiring their sunset view. I thought to myself, “Damn, I want a life like that.”

Three months later, I bought their home.

How it happened involved many episodes of manifestation, chasing charm, and having conversations with people who inspired me, but eventually, a long-shot dream home just fell into my lap.

Tulsa was steadily making all my dreams come true, even if it wasn’t under the bright lights of NYC.

And not long after I moved into their home, I knew: this place is just begging for parties.

I started hosting cocktail parties and brunches on the regular, cooking for friends, playing piano, and building a new community. But here, it wasn’t just single 30-somethings; my house played home to young and old, singles and parents, teens and grandparents. All were welcome.

Suddenly, I realized I could turn my new home into a house concert venue. While in NYC, I’d been competing to perform in other venues, here I would be the venue, and host touring musicians far and wide to play in my house for music-loving Tulsans.

Finally, I felt like: here, I actually matter. I can nourish others. I can provide sanctuary to creative souls.

And that’s a feeling we all need more of.

So my larger point is: you’d be surprised where you can be truly happy.

After 20 years in big cities, I know what it’s like to define your identity by the city you live in.

But it turned out a smaller third-tier city allowed me to harness everything I’ve learned from larger cities and use it to create a richer, more connected life.

So here’s to reinvention. And the notion that maybe where we are is not actually where we’ll reach our greatest potential. Sometimes, to find your real tribe, it might just be in the last place you’d ever expect.


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