A Beginner's Guide to Seasonal Living

How (and why) you might make multiple homes serve you over the course of a year.

(Scroll down for the seasonal living post)

Before diving into this month’s post, I want to highlight that Cabin launched its network city last week after two years of experimenting + R&D. Here’s the blogpost I helped to draft for the community.

TL;DR of Cabin’s launch:

• The original launch thread has half a million views and Balaji’s quote tweet has an additional quarter million views. Yahoo Finance, CoinDesk, and Traveling Lifestyle all carried the story. It’s further evidence that folks everywhere are paying attention to experiments in how people live.

• Cabin now has 22 beautiful properties in nature available for our community of remote workers. These properties are all over the world (Bali, Japan, Costa Rica, Portugal, Slovenia, France, etc.) and are gorgeous:

  

Let me know what you think - it’s early days and we’ll be steadily 1) improving the software and 2) adding more locations.

While the rest of this post is not about Cabin, it’s worth noting that Cabin’s network city can be an effective coordination tool for facilitating each of the examples of community-curated seasonal living that I outline below.

What is seasonal living? Why do it?

The practice of "seasonal living" refers to a lifestyle where individuals or families maintain residences in different locations and migrate among them based on the seasons or other specific patterns.

This lifestyle diverges from the usual digital nomad travel habits. Instead of quick, sporadic trips to various places without plans to revisit, seasonal living involves longer, recurring stays in 2-4 chosen locations.

The primary motivator for seasonal living is often the pursuit of ideal weather conditions year-round. However, plenty of other factors could inspire this lifestyle choice:

1. A profession necessitating regular periods in multiple places or allowing for extended breaks throughout the year, like teaching.

2. Having family or a significant other in specific locations, warranting regular visits.

3. An innate desire for variation in daily routines and surroundings.

4. An aspiration to establish a sense of rootedness/belonging in one place while still experiencing extended adventures and experimental periods in other areas.

Historically, the privilege of seasonal living was primarily enjoyed by wealthy retirees. The advent of remote work, homesharing platforms, and subscription coliving has democratized this lifestyle, making it accessible to other audiences.

It’s important that people pursue seasonal living responsibly. There are plenty of people across the world with no homes at all. My intention is not to encourage individuals or groups to further limit home accessibility by leaving perfectly-usable housing supply vacant for large chunks of the year.

Different methods to live seasonally

The rest of this post will outline six different approaches one can take to seasonal living.

Currently, I occupy the top left quadrant, meaning I do not own real estate assets and manage my seasonal accommodations independently. As I build deeper relationships and wealth, my aspiration is to transition into the bottom right quadrant - residing among a network of properties owned by me + my friends.

Asset Light

If you don’t own a home, you have high flexibility, but some instability as well. You can still live seasonally, but it requires meticulous planning.

Self-curated

Overview: You can easily rotate between places by booking a series of short term leases or booking stays on Airbnb/Craigslist.

Pros:

• You maintain extremely high optionality and flexibility with your plans.

Cons:

• Your monthly rent will be higher than most other approaches on this list.

• This can be a lonely experience.

• There’s no ROI on your time spent coordinating - you will perpetually have to plan ahead and schedule where you will be, which can cause a lot of longterm anxiety in my experience.

• Friends and connections in your individual hubs may question your long-term interest in the area.

Community-curated

Overview: You can sign up to colive with groups that arrange accommodations on your behalf. You can do this easily with Cabin, Remote Year, Selina, and other subscription coliving options OR you can put in extra work to try coordinating with your friends.

I know a group of 17 friends in San Francisco that all pay to split an 8-bed house in Lake Tahoe during ski season. Obviously, 17 people can’t fit comfortably in 8 beds, but they’re taking a calculated bet that there won’t be more than eight people at the ski house on any given weekend. For this group, it has worked without much complaint for two years in a row.

Pros:

• You’re still very flexible.

• Rent is typically not that high in these examples.

• You live alongside like-minded people and maybe make some friends.

Cons:

• You will still have to spend a lot of time planning and coordinating how to do this. Maybe even more than when you’re on your own.

• Limited supply means you can’t always guarantee your own bed at the exact time and place you might want it, because someone else might have claimed or scheduled before you.

Single Asset

If you own a home, you can leverage it to build communities elsewhere.

Self-curated

Overview: If you’re a homeowner, there’s (probably) nothing stopping you from listing your property on Airbnb or Craigslist.

Pros:

• If your renters successfully cover your mortgage + taxes each month, you are earning equity in a property while traveling at the same time.

Cons:

• You likely won’t know many of the people who stay in your home while you’re gone.

• You’ll have to spend time managing your property from afar or finding someone who can manage this for you while you’re gone. You’ll need to maintain the property physically and keep it occupied. Otherwise, you’ll lose money.

Community-curated

Overview: You can list your property in a homeswap network (like Kindred) or in a community directory (like Cabin).

Pros:

• Like before, if your renters/known home-sitters successfully cover your mortgage + taxes each month then you are earning equity in a property while traveling at the same time.

• Folks who stay in your home will be more likely to be community vetted. Communities typically have a shared set of expectations for how to leave another community member’s home.

Cons:

• This option only works if you have your own property.

• If you want to be “living in community,” a homeswap network won’t necessarily help you meet more people in the same way that using a community directory might.

Asset Heavy

For many people who live seasonally, this is the dream - to have multiple permanent homes in different locations. It’s not easy though.

Self-curated

Overview: This is reserved for the wealthy because it requires owning multiple properties around the world. Rich retirees have done this for decades - they will have one property in a northern city and flock to a southern beach for the winter (earning the nickname “snowbirds”).

Pros:

• Full control and ownership over your properties. You have little stress and can have multiple homes across the globe.

Cons:

• Not realistic for most people.

• Still not a great way to meet others.

Community-curated

Overview: How can your squad (close circle of friends or family) leverage collective wealth and time to own homes collectively? This strategy involves gathering an aligned group, slowly buying homes, and developing customized systems for managing the bookings.

This is the path least trodden. It requires high trust, high levels of coordination, patience, and still a non-significant amount of capital. There are companies and communities working on this model, but no templated approach exists yet - it’s very DIY.

I suggest rallying friends to buy the first house via an LLC, enhancing it, renting it out, and living in it for 1-2 years before buying the next property.

Pros:

• You can live with your friends in your favorite places in the world.

• You can have real ownership and equity in multiple locations.

Cons:

• Complicated to achieve.

• Requires high trust.

• Without a benefactor, this takes a long time and will require a series of iterative cycles. For me, I view this path to seasonal living as a longterm goal and will pursue the other paths along the route to making this one a reality.

Do we need multiple homes?

Probably not. But today’s world is big and interesting. Remote work, the internet, cool new tools, and the gig economy all enable more people to feel local to multiple hubs and belong to a range of communities, enriching life.

Avoid overextending the number of communities you belong to, as you may struggle to forge deep connections. That's why I recommend seasonal living with 2-4 homes, max.

There’s more than one way to skin a cat. In this piece, I outlined six paths that enable seasonal living but am curious to learn about specific approaches that I didn’t consider. Let me know in the replies :)