Living Everywhere and Nowhere
The following are my thoughts on how to live amongst many different cities. From living alone in studio apartments to living with 4 other people, small beach towns to big cities, there are many different situations you can construct. Finding what works best for you is something that you must do for yourself; for me, it has been one of the biggest factors in my personal happiness. I'm young and I like to travel; currently I am moving from sublet to sublet, frequenting New York and Toronto, and loving the ride.
Making friends is very important for my enjoyment of a place. When I visit cities I always try and make as many friends as I can. When I return to that city later I get to see these wonderful people again and feel more at home. Being around people you like, and who like you is fucking awesome, it's the main draw for me to return to any city. If I don't have many friends in a city I am much less likely to return there.
Making friends is always serendipitous, it's hard to force. As your friend ecosystem grows, making friends in new cities becomes easier. People move, introduce you to their friends, make more friends of their own, etc. The whole process gets easier with time.
People who love Burning Man are everywhere, for me they create an important sense of community. No matter what city I'm in I know there are people who love the desert, the art, and the culture. There are events to go to and great people to spend time with. Whatever your community is, find it and hold onto it.
Leases & Sublets
Being a subletter is the best way to maintain your freedom to travel, it allows you to live with roommates, as well as live alone. The only downside is the constant moving, but this has the upside of encouraging you to only keep objects which really matter.
When searching for a sublet this is the order I go with: Facebook, AirBnB, Craigslist. The best sublets are from friends or friends of friends.
Of course this makes creating and storing physical art a pain in the ass—the best place I've found to store my art is on the walls of more stable friend's apartments. Don't be afraid to get storage units in strategic locations; all my camping gear for Burning Man is in a storage unit in Oakland.
If I must enter into a lease I always look for month-to-month or 6-month contracts. Each time I've been in a year long lease I've had to terminate it early and help find a new tenant (this process stinks, and only makes the whole act of moving out more teedious). Now I am of the mindset that leases are to be avoided at all costs.
I think it goes without saying that you must choose your roommates wisely. For me, the right set of roommates are those that you enjoy spending time with. People who are equally driven, socially adept, and have similar interests are pretty good bets. The people you surround yourself with affect who you are, make sure there is mutual respect and opportunities for you to better one another.
Travel as often as you can. Escaping into new environments brings with it mental clarity and new perspective. Whether just outside your city, or to a new country, the best way to assess your happiness is to remove yourself from the factors that actively influence you. Seeing how other people live also helps you asses how you live.
Picking a job that allows me to travel has always been important. I generally stick to contract work as well as startups with flexible remote-working policies. I'm sure with time I will begin to slow, I feel the desire to pick a place to settle for a bit coming on now even. Starting a company has taken me many places, as well as given me the freedom to work wherever I want.
Get to know the transit systems of the cities you frequent. Don't be afraid of buses, and don't use Apple maps.
I spent a fair bit of money furnishing my apartment in Idaho as well as various apartments in NYC, from the perfect coffee table to the right set of cutlery. It's a process which always takes time, cost money, and is ultimately discarded when I move again. Whatever you do, don't buy a bedframe until you're certain you're sticking around. Having a matress on the floor is perfectly acceptable for people on the move.
When I moved to Oakland, my lover and I exclusively found furniture on Craigslist Free. Oakland, and the Bay Area lend themselves to this tactic as it is not as densely populated as NYC or Toronto so there are more availible items. The quality of the furniture is always greater if picked up from the person themselves and not from the curb. If I ever settle down again for a period of time I will likely scour Craigslist again, as it is the most cost effective way to get started in an apartment. If you stay around long enough then it makes sense to begin purchasing new household items.
Another upside of subletting apartments is that many household items like dishes, cutlery, beds and desks are included.
When traveling I like to keep my things in one big backpack. It is primarily filled with clothing and notebooks, as well as essentials like a headlamp, running shoes, and a towel. It makes keeping dress shirts hard, but makes the act of traveling much easier. Remember, layers are the best way to be ready for any climate.
I like camping backpacks because they're less succeptible to rolling wheels falling off, or telescoping handles breaking. I have a 40 liter Deuter backpack which I recommend because it can be taken on planes as a carry on (avoiding lost baggage and waiting around).
When running around the city I usually keep everything in a smaller backpack. My computer, notebooks, toothbrush, deoderant and an extra pair of clothes for the next day; You never know where the city will take you.
It's a Platform
All this comes together for me as the feeling of being alive. Traveling, finding a place to sleep, making friends and loving them, considering what objects I want in my backpack and where to leave other objects. They are all little pieces of an overwhelming sensation. I can be "homeless" but live everywhere, the world is my home.
It's important to remember that all these living situation considerations are for a greater purpose. It creates a platform for me to execute my goals on. Learning as much as I can, creating art and finding inspiration in travel and other's work, seeing new places, and working for myself.