#43: Reverse Snowbird: my version of Seasonal Living 🐦

intentional experimentation in how to live

I haven’t had a lease in four years. While it started out not by choice (moving to NYC in March 2020 was wild), I’ve come to embrace this way of living. Although I may not have my own literal home, I’ve certainly felt at home. Not just in one particular place, but actually several (SF, Tahoe, NYC, Oahu). By accepting the additional discomfort, logistics, and uncertainty, I’ve been able to reap the rewards of this dynamic lifestyle.

Through intentional, seasonal planning balanced with spontaneous, intuitive flowing, I’ve been able to position myself in what feels like the right place, at the right time. For the past three ski seasons, I’ve lived in the mountains, often just minutes away from ski resorts. When I lived in Hawaii for six months, I could get from door to paddling out in ten minutes thanks to my trusty moped with surf rack. To some extent, where I live follows the seasons because the snow doesn’t fall year round and the south shore swell isn’t always pumping, but it’s also determined by what’s going on internally.

Now that I’m eight months into my sabbatical, I increasingly spend my time chasing curiosities and identifying work that feels aligned, rather than chilling on the beach or backpacking in the wilderness. The combination of being in NYC with the freedom to take advantage of being here has led to some cool experiences in just my first week back. Monday lunch was at an intimate Italian restaurant on the Upper West Side with my food influencer friend. The concept for the nine-course tasting menu was that every dish would be made with parmigiano reggiano. I made sure to grab some lactaid on the way over. Tuesday evening brought me to my friend’s 50th floor rooftop in Hudson Yards where we caught a near 360° sunset around Manhattan. Then we hooped in his apartment’s NBA size court. If you were up at 6am on Thursday, you might’ve seen me on the A train heading to surf Rockaways. Where you live shapes what you do and who you’re with which by extension permeates into who you become. And when I’m in NYC, I become the most ambitious, creative, and often overwhelmed version of myself. It’s good to be back.

It might sound counterintuitive, but this evolving untethered way of living has resulted in more family time. In recent years, I haven’t gone more than three months without seeing my family. After a big trip, I always stop by to unpack and repack before the next adventure. Instead of owning furniture, I have a gear closet filled with skiing and backpacking gear. Visiting family was already something to look forward to, but it becomes even more aligned when you can live rent-free and enjoy home-cooked meals together.

I never know what to say when people tell me “I’m so jealous. I wish I could do that.” because the truth is they can. To be clear, some corporate in-person jobs require them to stay rooted in one place, but for the majority of my friends, it’s rarely ever financial constraints that get in the way. Last year, I stayed in places ranging from $250 per night to ski Jackson Hole to many free nights at home, on friends’ couches, and in my tent. My average monthly rent for 2022 was $1,550. My lavish ocean view Honolulu apartment from April to July and $3,100/mo Manhattan studio from October to December were offset by 92 nights of rent-free living. While $1,550 is certainly not cheap, it’s also not expensive compared to living in a major city on a 12-month lease.

I think the main culprit of all the unborn memories and never-happened adventures is double rent. When you have to continue covering your lease while you travel, it becomes unrealistic (psychologically and financially) to be gone for more than a week or two at a time. Given rent is the largest living expense, avoiding having to pay for two of them enables far greater possibilities, especially when combined with flexible work. Last year, it was a five week national road trip while still working. This year, it was five weeks in Southeast Asia.

Through my own experience and observing others who live this way, money is never the primary blocker. Circumventing financial constraints requires the tolerance of physical discomfort of constantly changing homes and doing more with less. I’ve learned to sleep soundly with every possible permutation of bed sheet, mattress, and pillow. I don’t own any furniture, cookware, or physical artwork. Living without a guaranteed home also demands the tolerance of psychological discomfort in the form of uncertainty. The furthest future I can forecast is usually only within a few months or so. Every time I start searching for a new sublet, there’s always a bit of anxiety around the neighborhood, price, and roommate situation. It’s like spinning a roulette wheel and watching in anticipation to see which friend-of-a-friend is willing to let me sublet from them.

A Way of Living

At its core, this way of living requires openness, experimentation, and intentionality. It starts when you realize the place you’re currently living in may not be where you want to be. It’s also entirely possible that you enjoy where you live, but could also see yourself elsewhere during a certain season (ex: winter in NYC). To know what “this feels like home” actually feels like, you must actually go and live there. Daily life is made up of millions of minutia. Your own lived brief interactions with neighbors and baristas will tell you more than secondhand consuming curated IG posts and Youtube vlogs.

This way of living has prompted me to ponder: What’s the difference between traveling and living? Is it based on how long the trip is? Is it whether PTO is involved or not? I think the distinction comes down to purpose. When I’m traveling, I seek to understand more of the external world. The foreignness that’s present in the food, language, and culture is intentionally sought after. When I’m living (which I guess is whenever I’m not traveling), it’s more about understanding myself. Could I see myself here for years to come? What kind of person am I when I’m here?

On the surface, it may seem like I’m a digital nomad, but I’m not. Back in 2020, I think the term was fitting. I only spent a month in each location before loading up the car with duffle bags again. But since then, I’ve moved less often and stayed longer each time. Unlike digital nomads who bounce around from Bali to Lisbon to Mexico City in a never-ending quest for novelty by leveraging currency arbitrage, I’m looking to put down roots. Permanence, the quality of something lasting, isn’t the same thing as immobility. A place can feel like home and at the same time not be home all year-round. I think the reason why people still think I’m a digital nomad is because it seems like I’ve been “traveling” this whole time. Internally though, I no longer feel like I’m traveling. While I am literally moving from place to place, it doesn’t feel the same. I’m simply rotating between a few places that feel like home. Perhaps it was the casting of this wide net that’s led to the intentional whittling down of a bucket list into a handful of homes.

I often find it difficult to explain who I am to others in a concise, legible way. For example, I’ve gone skiing for 60 days in each of the past two seasons, so I might be a ski bum. But I also draw upon the creative and ambitious energy that pulsates through NYC. For me, a good day in Hawaii could include yoga, brunch at the Kaka’ako farmer’s market, and a sunset surf session. A good day in NYC often means chaotically zipping underground via subway from one event to another. You’ll never know if I’m wearing Lululemon because I practice yoga or used to work in tech. Am I wearing a Patagonia jacket because of my previous industry or because I spend a lot of time outdoors? The answer to these false dichotomies is all of the above. We’re all multidimensional beings. This way of living fits my multi-faceted identity. Living in a way that cycles between quiet nature and big city keeps me in balance. I’m back in NYC before I hit intellectual boredom. I retreat to the mountains before my nervous system collapses from the never-ending buzz.

I don’t think it’s a coincidence that I live this way and I’m also on sabbatical. In both situations, I started from a place of not knowing. I didn’t know where to live so I kept trying out potential homes. I didn’t know what to work on so I quit my job and started a bunch of projects, including this blog, my climate tech newsletter, and podcast. Although where you live and what you do for work are different, both require a willingness to try new things, practice self-awareness, and continuously reflect to ensure that where you live and what you do remain aligned with your values.

Figuring out where home is and what work is your calling demands curiosity-driven, active exploration. This may start out with the tough truth of admitting that what you’re doing now or where you’re living now may not be optimal. I understand this lifestyle isn’t for everyone. For those with kids, an in-person job, or simply a ton of stuff in their house, it could be tough. But I’m also not trying to mass convert everyone to end their lease and join me in bopping around. This is more about relinquishing the assumption that we (everyone that’s not ultrawealthy) must live in one place year-round and escape with the occasional vacation. The societal changes brought forth by Airbnb, COVID, and remote work have created a paradigm shift that has yet to be fully realized. For those who yearn for a more active flexible way of living that flows with the seasons, it is possible now. Many of us are still living a static stationary life in a dynamic moving world.

As for Me

The term “snowbird” refers to someone who escapes brutal winters by flocking down south to somewhere warm. I typically picture a wealthy, retired New Yorker laying by the beach somewhere in Florida. They’re either living in a retirement community or one of those neighborhoods that has its own golf course. As for me, I think I’m somewhat of a reverse snowbird. Through experimenting over the past four years, I’ve decided to be based in NYC and when winter comes around, instead of sunny Floridian beaches, I head to the snowy mountains of Lake Tahoe.

At first, I thought a place that tries to do it all could work, but after living in Salt Lake City and Denver, I’ve realized that for me, it’s better to be intentionally intense and go all-in on skiing or city life, rather than both at the same time. While both are proper cities with mountains in proximity, the lack of diversity and heavy traffic during ski season make them less appealing as potential places to call home. There’s also far less entrepreneurial and creative energy in SLC and Denver when compared to NYC. I’m making conscious tradeoffs instead of attempting to optimize across everything. Turning the single-home constant into a multi-home variable as a vehicle for living intentionally.

Living without a lease for four years. On sabbatical working on multiple projects. A multi-dimensional identity that isn’t easily describable.

A way of living. A way of working. A way of being.

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