On Seasonal Living

I have been thinking about new ways of living and, more specifically, seasonal living for a while now. Seasonal living is a term I came up with to describe a way of life that involves different ways of living throughout different seasons of the year. This can be, but does not need to be, exactly aligned with the standard seasons -- Winter, Spring, Summer, and Fall.

For example, teachers and athletes live seasonally by default. They have school-years and summers, seasons and off-seasons, respectively. Another simple example of seasonal living is the "snowbird", the typically wealthier, typically older, warm weather enjoyer who lives most of the year somewhere near New York but spends their winters in Florida or California.

Another self-made term which goes hand in hand with seasonal living is polyresidence -- having more than one place you call home. Currently, it's hard to do unless you're wealthy enough to pay for two places at once. That doesn't mean it can't be done more economically. It's just harder. For example, if you have a 12-month lease or you own a home, you have to find a way to sublet it out while you're away, unless you want to pay double rent. Alternatively, you can do the whole digital nomad thing, but to me that feels more like no homes than many. I don't want to be constantly on the move right now. I've already enjoyed seasons of that. I just want to live where I want to live, when I want to live there, affordably.

What I am looking for, fundamentally, is the best possible way of living. I am not talking about some pareto superior way of living that would be objectively optimal for everyone. That does not exist. I am simply talking about the most preferable way for me to live personally. I expect that to evolve over time, and I don’t ever expect it to be perfect, but I’m someone who believes I can always do better. So in terms of the way that I live, I believe it can always get better.

There are few things that impact your life as much as where you live – perhaps your relationships (partner, family, friends), your work, your health, and your wealth. There's not much else. Where you live includes a lot of layers – it’s your country, state or region, city or town, neighborhood, street, and of course, your home itself. We live in a world of abundant options – some might argue too many options, but great freedom brings great opportunity.

The sudden, step-function shift to remote work that resulted from the pandemic gave tens of millions of people the final and critical chunk of freedom they needed to increase their options for living by many orders of magnitude. We newly remote knowledge workers are no longer obligated to attend an office. This means we do not need to live in the one specific place where our office is located. Moreover, it means we do not need to live in one specific place at all. That single, fundamental, commonly-assumed-to-be-unchangeable constant of living near where you work has become a variable for many more than it was before.

The ability to live anywhere is obvious. The general trend favors more rural, lower cost-of-living locations, while cities like SF & NY try to stop the outflows of enterprising emigrants. The less obvious part is that you can do more than simply switch the location of your single home -- you can have multiple homes, with multiple locations. We just don't have great infrastructure to facilitate that in an economical fashion. Instead, we have traditional mortgages, 12-month leases, no sub-lease policies, digital nomadism, and Airbnbs. But I don't want an Airbnb. I want to live seasonally.

For some context, I'm 29-years-old. I’ve lived in New York, San Francisco, Miami, Philadelphia, Nashville, and New Jersey, all for at least a year. I’ve lived for at least a month in Charleston, Savannah, Brooklyn, some small towns in Georgia, Virginia, and Tennessee, and my favorite, Florence, Italy. I took a road-trip across the country from New York to California, spent a few weeks in Japan doing the nomadic thing, and spent a semester abroad traveling Europe. I’ve seen a lot of places and a lot of ways of living and I decided I don’t want just one of them. I want a few of them, every year, plus some time to try some new ones. I also don’t want to be traveling all the time. I want a home. No, I want three homes. Call me crazy -- I want three homes for the price of one.

In my ideal world, right now, I would spent 6 months in Miami (November through April), 3 months by a beach in the northeast (June through August), and the remaining three months (May, September, October) between New York, visiting family and friends, and traveling. I don’t know how that sounds to you (of course, you’ll have your own version), but that sounds absolutely heavenly to me. That's the way I want to live. And I’m working on it.

I'm working on a project with my friend Matt who shares a similar perspective. We are starting by launching a newsletter called The Subletter. Our initial focus is facilitating sublets. More broadly, we are building a community of practical idealists (like us) who believe there are better ways to live.

Quite simply, we want to help people live the way they want to. We want to help people travel more and for longer without having to pay a devilish double rent. We want to let snowbirds fly, decades before they become wealthy enough to buy multiple homes. We want to help people have three homes for the price of one! We believe we can do better than 12-month leases and landlords. We seek to live sovereignly, seamlessly, and seasonally. Join us at subletter.substack.com.

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