Mr. Worldwide, Pt. 0: Bailtrain to Bailtown

Wherein I quit my job and prepare to leave the country

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Next: Mr. Worldwide, Pt. 1: Europe


In mid-2015 I moved to Denver, CO while continuing to work remotely at the company I had helped to found back in Gainesville, FL. Florida had been my home for my entire life, up until that point, and it felt like a change was needed. Denver was certainly a change, and ultimately I think it was one in the right direction, but it turned out to not be enough.

While in Denver I’d rented a tiny studio apartment, which over the course of two years I’d learned to live in. Living large is pretty easy; for some reason we (generally) find it more difficult to throw something away than to exert the effort to make space for it in our lives. It takes a non-trivial amount of trial-and-error to figure out a smaller lifestyle with fewer things. So minimalism is something I started to practice, and continue to practice, in the literal sense of the word, often failing at it. But I find the challenge to be worth it.

I’d always separated my work-place from my living-place, mentally. Eventually I realized that just because the two places were physically separate doesn’t mean they aren’t a part of the same thing. At the most basic level I work in order to afford basic necessities, like food and clothing and shelter. I have a dedicated home because it’s the most efficient way to keep myself fit and healthy and clean, because it allows me to having my own ammenities and routines which work best for me.

But the more I work, the more I burn out and need to recuperate at home. The more time spent at home, the more things accumulate there and the more upkeep of the home is needed, which in turn requires money which requires work. The one leads to the other, and so they are really part of the same thing. I neither want to work nor spend a lot of time at home, but that’s what my life had turned into. It was unbearable, and I had to change it.

Mr. Worldwide

In early 2016 I took a trip to Japan with some friends. It was the first time I’d been out of the US (sans a family trip to Nova Scotia when I was like 9 or something). Going to Japan might as well have been a trip to an alien planet, and yet it was also familiar. I learned that no matter how different our cultures are, the individuals of the world aren’t that different at all. By the end of that trip I felt as at-home in Japan as I did in Denver, if not more so, because of how much time I was able to spend exploring (rather than being cooped up working).

Kyoto at sunset, 2017
Kyoto at sunset, 2017

By the end of 2016 I knew I wanted to travel and see as much as possible, while working as little as possible in the meantime (except on my own ideas, as they came up and I felt like working on them). I began trimming down my life, with the aim of only having as many things as would fit into a backpack. It probably seemed to everyone like I was preparing to become a homeless person. In a way I kind of was.

My plan wasn’t that I would never work again, or never live in a home again. Vagrancy isn’t a sustainable way for me to live. But finding a life which didn’t involve spending all my energy working while also not being homeless is surely possible, I knew, though maybe I wouldn’t find it in the US. I began saving as much money as possible, and began thinking about where I might find that life.

Europe seemed as good a place to start the search as any.

Leaving Denver

By the end of 2017 I was ready to go. I had saved nearly $20k, had put in notice that I’d be leaving my job at the end of the year, and had given notice to my landlord of the same. My friends in Denver saw me off, and my friend Ibrahim gave me a small notebook to take notes in as I traveled, with some helpful phrases that might aid me along the way

Ibrahim made sure I was covered if I ever found myself in a tight spot
Ibrahim made sure I was covered if I ever found myself in a tight spot

I drove all my things back to my parents’ house in Miami just before Christmas, and enjoyed Christmas and New Year’s with them. In mid-January I grabbed my single backpack, said goodbye to my parents, and headed to the airport. It had worked out to be cheaper to fly back to Denver before flying to Europe, so I spent another day there saying hello/goodbye to everyone again, collecting some recommendations of places to go while I was there, and continued on to Europe.

The Loadout

(Wherein I give a summary of what I had with me throughout the trip, with affiliate links sprinkled in, cause money. You can skip this section if you don’t really care).

I’d already had a 40L backpacking bag which had done me well enough on a couple trips already, so I decided to try and only use that. Other homeless backpackers tend to go a little bigger, but they risk not being able to fit their bags in luggage overhead on planes. I also ended up needing a smaller day bag almost immediately, since being out and about all day necessitates bringing some things with you. The big bag/day bag combo is a classic amongst the homeless backpackers.

All packed up, one for overhead and the other for under the seat
All packed up, one for overhead and the other for under the seat
(Almost) everything, unpacked
(Almost) everything, unpacked

Most space in the bag is taken by clothes. Which clothes I actually had along changed as the weather changed and I gained and lost things. But my general clothing strategy consisted of a few key points:

  • All things need to be re-wearable, 2 to 3 days at least. This is more difficult for under layers, but wool is ideal as it’s durable, warm, and it quickly-dries (which means the fungi/bacteria, which would otherwise cause smell, quickly-die). Wool socks were easy to find on sale for $5 a pair at the end of winter. Wool undershirts (smart wool or merino) are findable on eBay with some difficulty. Uniqlo makes good undershirts to fill in when wool undershirts are too expensive. ExOfficio is worth the money in the underwear department. A pair of leggings is also super worth it for the cold.

  • For pants I went with three pairs; one beat-up pair, one casual, and one a bit nicer, and a few wool shirts/sweaters. Later in the trip, as summer rolled around, I’d pick up some shorts as well. My couple of wool shirts/sweaters were trivial to find on eBay.

  • For shoes I went with a pair of flip-flops and a pair of waterproof boots (also from eBay). The boots I chose for being able to be used in basically any occasion where flip-flops wouldn’t do (marathons excepted).

  • I really can’t stress enough how great wool is. That said, I would have died without this jacket, which was well worth the relatively tiny amount of space it took up. Same can be said for my linen towel, which struck a perfect balance between packability and being a towel.

  • Other random things which were must-haves: rubber bands (for tying up clothes), sewing kit, external phone battery, tape, super glue, umbrella, and a small package of baby wipes.

  • I also insisted on bringing a laughably small and old netbook with me, cause I get cranky if I can’t code now and then.

Even before deciding on doing this trip I had begun purging all my old clothes in favor of a much smaller set of more durable, though perhaps more expensive, ones. So a lot of these clothes carried over from that, and all that I just described is really my current wardrobe.

(Lack of) Planning

The trip was deliberately not planned out. I knew I would show up in Munich, because I have a friend who lives there as well as a distant relative. But past that I figured “show up and look around” would suffice. My motto for the trip would eventually become “plans are just lists of things which won’t happen”. From start to finish the only plans I had figured out at any moment was a general trajectory and my next destination. Rarely was my next place to sleep booked more than a week ahead of time, or my next bus or train ticket bought more than a day before.

It could not have worked any other way. For a short trip it might be viable to have an itinerary with a list of destinations/sights which will be visited and all the traveling needed in between, but the strictness of an itinerary always adds tension. Rather than spend some pre-allotted time at each sight, adding a feeling of being on a timer no matter where you are, I would rather just meander around and spend as much time as feels right at each place. There’s zero chance of seeing all there is to see, no matter how much is planned, so might as well see each thing in as much depth and detail as you feel like.

And looking back, I don’t think I did miss all that much. Each city has its notable sights, and you can know by looking around and talking to other people which ones are right for you. Start with those, if there’s time do the others, but you won’t feel like you’ve missed anything if you don’t get to them.

Much later in my trip someone would ask me and another backpacker (who’d been traveling even longer than me) if we had advice for him. The other backpacker immediately replied “Just keep your head on a swivel”. As in, just look around you, keep your eyes open, you’ll see all you want and need to. My grandma gave me similar advice before I left, when I asked her what I should do in Spain (her home country): “Oh, you don’thave to do anything. You see something you like, you go there. You see something else, you go there instead. There is nothing you have to do”.


In the next post I will actually leave and begin my adventure.

If you liked this post, consider checking out other posts in the series:
Next: Mr. Worldwide, Pt. 1: Europe