Speedrunning NYC

what I’ve learned from 9 sublets in 5 years

The three most important decisions in life are what you do, who you marry, and where you live. These three elements of experience—work, relationship, and place—shape the contour of our lives, while friends, family, and hobbies fill in the spaces. In the past, these choices were relatively fixed. You likely stayed in your hometown, married someone in your village, and did the same type of work for your entire life.

Personally, I’ve kept my marital views intact—still hoping for a long-term, monogamous partnership (no sister wives, and with any luck, no divorces either). But when it comes to work and residence, I’ve embraced something more fluid. Like many others, I’m learning just how much agency we actually have over both our careers and where we live.

Work, in particular, has seismically shifted.

Decades of questioning the default path have culminated in quiet quitting, sabbaticals, and portfolio careers. AI is automating knowledge work while humans are craving more meaningful work. I’ve written about my own winding path, from quitting tech to sabbatical to career transition to an integrative approach that remains open-ended.

But this post is about another pillar of modern life that has opened up: place. While I’ve spent a lot of time exploring work and the inner terrain of self-discovery, I’ve also poured just as much energy into experimenting with where (and how) I most feel at home.

Lately, after signing a lease and putting down roots, I’ve had time to reflect.

The past few years have felt like an emotional rollercoaster with flips, corkscrews, and surprise drops—all on 2x speed. I’ve experienced the intensity and fullness of speedrunning a decade’s worth of adventures into three. I’m not married and I don’t have kids (or even a dog) and yet, I feel oddly contemplative. I’m 28, with a healthy mind and body, so it’s strange to feel like I’ve already lived a full life even though I’m still at the beginning.

I attribute this to pursuing life at full speed, made possible by the lack of a lease and the willingness to wander off the default path.

Over the past 5+ years, there’s been a lot of movement, both figuratively and literally.

Although the bulk of these winters have been spent skiing, NYC has been a central pillar throughout. I first arrived in NYC in 2020, and since then, I’ve spent anywhere from one to five months a year in the city.

I’ve become an expert at the tactical game of hunting down sublets and a student in the softer art of understanding how my environment shapes me, and how to create a feeling of home wherever I go.

I’ve wanted to revisit my experience of living in NYC because I just know that there is so much richness to mine for.

I’ve lived in neighborhoods across boroughs, from new luxury buildings that use an app to unlock the door to borderline illegal apartments that require earplugs and an eye mask to fall asleep.

I have lived multiple lives all on the same urban soil of NYC. I’ve slept in $10M penthouses and also stayed in rooms that could be confused for Shaquille O’Neal’s shoebox. One chapter came with an Equinox membership in Hudson Yards and an Amex Platinum card. And then the sabbatical version. Quieter, simpler, filled with home-cooked meals and public park hangouts.

Each sublet revealed a new neighborhood, and a new version of me.

A Tour of NYC, Sublet Edition

This series of sublets has taken me to every corner of NYC, with each stranger’s home offering a new lens into the city, and into myself. Across nine neighborhoods, I experienced the city in nine distinct ways.

There was the grimy hustle of the Lower East Side and East Williamsburg. The baby strollers and landmark parks in Park Slope and the Upper West Side. The immigrant communities of Chinatown and Sunset Park, where the food felt like home but the language still felt somewhat foreign. And the polished pace of Dumbo and Flatiron, where wealth, speed, and ambition saturate the streets.

a map of my NYC sublets

In between these stints, I wove in time in ski towns like Tahoe and tropical paradises like Hawaii. Each new setting required me to recalibrate, recreating new routines and expectations to match the environment. The stark contrast between places forced me to prioritize what I needed in each season. Each time I returned to NYC was a choice: a conscious swap of quiet mountains and slow beaches for chaotic concrete.

I wasn’t aware of it at the time, but the city was acting as one giant mirror, reflecting and amplifying whatever was going on inside me.

With its sheer scale and constant motion, the city met me exactly where I was at. In the early years, that meant hustle and overstimulation. I chased belonging and recognition. I filled my schedule with work and social plans, staying busy enough to quiet the anxiety, at least during the day. At night and in the early morning, it would always reliably return.

But things started to shift.

As I began to untie my desires from companies and peers, I discovered new ambitions that felt more authentic and less performative. In response, the city transformed. It became a breeding ground for creativity and self-expression. My image of a “New Yorker” shifted from Manhattan magnate indulging in mainstream trends to the Brooklyn weirdo who didn’t give a shit. I wanted to feel that free in my own skin.

Eventually, I reached a new kind of confidence, but it wasn’t because of wealth or physical appearance. It came from the spaciousness of my sabbatical, allowing me to live closer to my values. As I created distance between me and my former job title, the city became a playground. Its constraints felt less like walls and more like a jungle gym: a structured set of obstacles to move through, climb on, and explore. Every credit card swipe, every RSVP became a mini-experiment: What do I really care about? What am I okay living without?

Through all this, the city’s real gift emerged: the people.

I’ve been referring to NYC as a place, but it’s really the people who showed me the many selves I could live. I sought out a wide range of characters, always curious how they lived. I met finance power couples in $8K apartments, retail workers barely scraping by, tech bros completely wrapped up in their work, and creatives who resisted being labeled by anything.

Through them, I saw the butterfly effect of my own choices. Life could look so different with just a few small bends in my path. These weren’t just people passing through my life. They were mirrors, reflecting the lives I didn’t live and the versions of myself I didn’t become.

The Intention Behind the Effort

In NYC, I learned that effort is rewarded. By effort, I don’t mean grinding late at night at the office to earn praise or avoid criticism. I mean a form of energy expenditure that comes with care.

I line up and wait for three hours, and then I savor the best pizza in the world at Lucali’s. For 14 weeks, I run four times a week, anywhere from 3 to 22 miles, and then I revel in the communal ceremony of the NYC marathon. When I’m on the verge of quitting my job, I don’t escape with a vacation. Instead, I take a week off and still go into the office, working tirelessly on personal projects.

The returns on authentic effort are limitless.

Counterintuitively, NYC taught me to value material possessions less and shared experiences more. It’s easy to assume you need to spend big to enjoy the city. And yet, I found the opposite to be just as true.

Rotating rapidly through tiny apartments taught me to live with less. The small spaces nudged me outside, to go seek others. My most vivid memories are of cozy dinners at home, long walks through neighborhoods, and picnics in parks—not shopping sprees in Soho.

Living in New York taught me that ambition alone isn’t enough. It has to be self-directed.

The city is saturated with hustle, but not all hustle is generative. I saw investment bankers grinding 80-hour weeks with no end in sight, stuck in golden cages they weren’t willing to leave. I met remote workers who spent most of their time indoors, disconnected from all the city has to offer. But I also met artists and entrepreneurs who treated the city like a chessboard, playing with curiosity and intention.

New York taught me the difference between authentic effort and blind hustle, and that anything is possible when you learn to shape your time, not just fill it.

The Anthropology of Space

Whenever I live in someone else’s home, I find myself subconsciously absorbing details about who they are. Through inhabiting their curated space, questions begin to surface:

How does this person live? Do they cook often? How much free time do they have? What do they care about? Do they like to host? What possessions do they treasure most?

Their home becomes a quiet conversation. A reflection of values, habits, and the shape of their daily life.

In turn, the space poses questions back to me:

What do I need to feel comfortable? How do I inhabit this space differently from its owner? Does it feel like home? What’s missing? What would I bring from this space into my own future home? What does this environment invite me to do—or not do? Is there space to rest, to create, to connect?

Living across all these different neighborhoods and configurations slowly revealed a few simple truths about the role of place. Paradoxically, where you live matters a lot, but also, not that much. It determines who’s nearby, and therefore who you spend time with. But in a city like NYC, it’s so easy to get around and opportunities are always in motion.

Some homes inspired me, like that girl’s one bedroom on the edge of Soho and Chinatown with the Noguchi coffee table and massive Monstera plant. Other spaces, like my cramped room in Dumbo that I shared with a stranger, didn’t—so I spent all my time outside the apartment.

When places came equipped with kitchen tools and sufficient square footage, I leaned into hosting dinner parties. When it felt burdensome, I branched outward, seeking connection in other spaces. I was in constant conversation with my surroundings, noticing what pulled me and letting that guide how I moved through the day.

Long morning walks were easy when I lived near Sunset Park, Prospect Park, and Central Park. But in Flatiron, LES, or Chinatown, I didn’t force it. Stepping outside meant immediate stimulation, so I found other ways to start the day.

Over time, I realized how much I could shape my experience within any given place. But I also uncovered a few non-negotiables. At the top of the list: sleep. It’s the single biggest factor in how good I feel. I slept better in humble Sunset Park, on a mattress on the floor, with earplugs and an eye mask, than I did in a multimillion-dollar Flatiron penthouse where the bed was so soft that I’d toss and turn all night.

The other two essentials are fitness and food. At the start of every sublet, I’d immediately scout for nearby gyms and grocery stores. I weighed my options carefully. Affordability was nice, but I often went out of my way, financially and logistically, for a better workout or more nourishing food.

Through nine sublets, I learned that sleep, movement, and nutrition form the foundation of my wellbeing. It sounds simple, and maybe even obvious, but it took experiencing life at both extremes to truly internalize it.

On the surface, subletting is a flexible way to live lightly and save money. But at a deeper level, it taught me how to be an anthropologist of space. Instead of studying the masses through a historical lens, I was learning about individuals through immersion in their everyday environments.

By studying how others live, I’ve learned how I want to live.

Ready for Departure

During the past six years of nomadic living, I spent a lot of time carefully deciding where to live, and when. Winters were reserved for skiing, a seasonal rhythm with the dual benefit of letting me escape New York’s harsh cold. I love the cold when I’m gliding on snow, not when I’m getting blasted by city wind.

I always knew that I’d eventually want to settle down somewhere, I just didn’t know where. I spent countless hours daydreaming, vividly imagining myself living in Hawaii, Tahoe, San Francisco, and even staying in New York. The freedom to choose was also paralyzing. Every possibility came with its own set of trade-offs, making optimization a futile endeavor.

Choosing to leave New York was intentional, but also an act of surrender. I’ve asked myself "Where do I want to live?" more times than most. Over time, I’ve gotten good at sensing when a place fits. Maybe we’re not so different from other migratory creatures after all. Whales cross oceans through a mix of biological clock and environmental cues. Birds travel thousands of miles, responding to shifts in light, magnetic fields, and even the stars above.

For me, there was a similar internal signal. New York no longer felt right. The intensity that once energized me had started to wear me down. I’ve become more sensitive to my environment and more guided from within. With a clearer sense of where I’m headed, I find I no longer need billboards directing me or late-night hustle to get shit done.

Along with that shift came another realization: pure drive isn't everything. There’s wisdom in slowing down and simplifying. With fewer options comes less noise and fewer distractions, making it easier to hear what I really want.

And In the end, it wasn’t even up to me.

My girlfriend matched for residency, which decided both when we would leave and where we would go. It’s funny how after years of obsessing over where to live, my answer came not from more mental gymnastics, but from something outside my control. And yet, when the time came to find out, I wasn’t anxious or fixated on the outcome. I had already accepted that the where matters less than knowing how I want to live.

Living Well, Wherever

I still stand by the idea that where you live is one of the most important decisions in life. But my view has evolved. I used to think of a city as something that imprints itself onto you, with its culture, energy, and habits shaping who you become. Now I see it more as a relationship. It's not just about the place itself, but how you respond to what it offers and withholds.

It’s easy to believe that a new city will give you what you’re missing. And sometimes it can. But I’ve come to trust that wherever I end up, I’ll be able to notice what’s missing and move toward what matters. I’ve let go of the fantasy that any one place will be perfect. What matters more is having the awareness to observe and the intention to act.

Maybe that’s the whole thing: where you live can change your life, but it’s not everything. If you feel stuck, it’s worth asking: is it really about the city? Or is it something deeper? A certain kind of friend group? A romantic partner? A healthier lifestyle? More fulfilling work?

Moving can be the move. But often, all it takes is a subtle switch-up. A single conversation with the barista can spark a sense of belonging. A new gym can bring you closer to your people. A different apartment brings new neighbors, deeper rest, and a fresh perspective.

I still believe in experimenting with new ways of living. But if there’s one thing I’ve learned, it’s that the cliché is true: we go on the outward journey searching and searching, only to find what we were looking for was within us all along.

Speedrunning New York was a serial adventure that taught this: Where you live matters. But how you live, wherever you are, matters more.

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P.S. I’m a coach who helps people live bigger, more authentic lives, especially during seasons of change. Learn more about my coaching here.