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Vagabonding San Francisco with Airbnb

Could you imagine living in a city long term with only a backpack, having work every day, yet still feeling more relaxed and free than any other time in your life, all while expanding your friend circle more than you ever have? Neither could I, until recently.

I grew up in Orange County, California and have always loved having…things. Possessions. I wanted to have an apartment where I could have a couch and a projector where friends would really want to come over and hang out. Tons of furniture and video games. Things.

I figured that when I graduated college, I would get a sweet place and work for some big company for a few years until I decide to start my own thing. Doesn’t every software engineer say this when they graduate? Then I realized that what I really want to do is learn. Working at companies has always made me learn a ton, but it’s generally very specific job related functions. I want to learn everything I can. In terms of software, I have no idea what that means now. I can imagine every day working on a project and having that spawn a new thing I want to learn the next day. My “Project a day” series has shown me that.

I realized that I can learn and code anywhere I can get internet. I’ve never really traveled that much and experienced other cultures, so why should I limit myself to living in a single city and working for a single company? I shouldn’t. Jay, a friend I worked with at Microsoft, and I decided that when I graduate, we are going to live wherever we want. We will start in Australia somewhere (by popular demand, this is now New Zealand). We have no idea how long we’ll be gone, or where we will go, even how long we will be there before moving somewhere new.

This requires getting rid of all my possessions. I will be bringing a 40L backpack on this adventure of mine and nothing else. Everything I buy means something else I need to get rid of. What a radical shift.

This summer has been a trial run of that lifestyle, and it has been fantastic. I had an internship at Airbnb which, if nothing else, is a fantastic culture fit for that lifestyle. lets people rent out their spare bedroom, entire place, or even more exotic places like treehouses and boats. Travelers can then rent these places as easily as they could a hotel, yet have a much more meaningful experience and relationship with their host and environment.

As interns, we received a $1600/month stipend for housing for the summer (San Francisco has the highest cost of living in the country). I interned there with Kyle, one of my friends from school, and we shared our stipends. Many of the other interns were worried about the notorious housing market that is San Francisco and booked places for the entire 3 month time they were there, some of which cost more than their stipend. My friend and I took a different approach and decided to fly by the seat of our pants.

We stayed in different Airbnb’s near the office and around the city all summer, something like 20 in all. We absolutely made the right decision. We were able to choose our housing around our activities, and that was something we had never considered before. Think about it, you pay for a month of rent somewhere, and then want to go on a weekend trip. You will now be paying to live in two places at the same time. Hopefully paying for a month saves you enough money to make that reasonable. Likely, it doesn’t.

Imagine instead, that you really want to go the fireworks show at Pier 39 in San Francisco for 4th of July. There also happens to be a BART strike that day so public transit in and out of the city is screwed. We were able to book a place two blocks from the pier that had a kitchen and pool for us to cook dinner and have people over, then leave for the 9:30 fireworks show at 9, because we chose to live near our activity that night.

Imagine it’s a beautiful weekend, you want to be able to BBQ, and just lounge out. We found an absolutely spectacular listing to stay in that had a big pool and jacuzzi, BBQs, full kitchen, and a really awesome host.

If you can part ways with your stuff, living this way is amazing. You don’t even need to travel around different cities for it to be incredibly fulfilling. Choose listings around one city, make friends with the host and their friends, yet know that you are still close enough to your friend group that you can still hang out with them. You can expand your friend circle by vagabonding around your own city. Fantastic.

While I’ve really embraced this lifestyle, there are some downsides that people might have trouble with. I’ve gone very minimal in this process.  I have a 40L backpack full of clothes and a laptop and that is pretty much it. But it’s important to realize that a lot of things you think you need, you can just use with other people. You don’t need a TV, pretty much any place you stay will have a TV. You don’t need bath towels or shampoo, you don’t need pots and pans. The places where you stay are people’s homes. They will have the standard furnishings and let you live by not needing to own them yourself. It’s much easier than people think to be minimal.

As a trial run of a lifestyle after college, this summer has been a glorious experience. I’ve been told a lot that travel makes time seem to run slowly because of the new experiences, new people, and the learning that comes with it. I now understand what that means, because my summer at Airbnb has definitely been that way. I’ve witnessed myself grow and be more open to things I’m not used to. Kyle likes to tell a story from the first Airbnb we stayed at this summer where we walked in and the entire place smelled heavily of weed. I wasn’t sure if I wanted to stay; we had a week reservation and with the roommates smoking so heavily, it made me uncomfortable. Never-the-less, we stuck through, ended up really liking the listing (it had a drum set, DJ gear, hammock and skateboard swing) and were much better for it.

I can’t justify paying long term rent in a city when I know what options really exist out there.  Companies like Airbnb completely change the game. I think it only makes sense to buy a place and settle down when you start considering a family and need a place for them to be stable. Until then, though, you’ll find me traveling, working, and experiencing a life few are willing to commit to.

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