How 4 days in Greece turned into 1 year around the world

Until a little over a year ago, I really didn’t get traveling.

I had never done any extensive traveling outside of North America, so I didn’t see what all the fuss was about. Instead of wanting to eat tapas in Barcelona or drink Hefeweizen in Berlin, I opted to spend my money and vacation time in Vegas for three consecutive summers (no regrets, but also a lot of regrets).

Travel was always one of those things that I thought was for “other people”, but not for me.

Who were those lucky bastards?

  • My friends in college who were able to go on those incredible study abroad trips to Italy and Spain while I was making chicken caesar wraps and sweating my ass off in the A/C-less snack bar of the pool I worked at
  • Most girls on Bumble — you know, the ones with *~*WaNdErLuSt In ThEiR VeInS*~*, who are ALWAYS down for adventures, and have pictures of themselves sitting next to probably the same poor drugged up tiger (in fairness, I’m sure that the bros do this too)
  • Those people you’re Facebook friends with but you’re not real friends and somehow they always seem to be eating gelato in Rome while wearing a fedora or are on some fancy yacht in the Mediterranean

In short, they were everyone but me, or so it seemed.

Travel was so not on my radar that I was putting plans into motion that were going to squash, or at least seriously delay, my travel dreams before I even knew that I had them. I was going to get a dog and had already put a deposit down in January for a future litter in the fall (I like to plan, okay!?).

Before I made that commitment, I figured I might as well try to take advantage of an absolutely incredible perk my company had — a two week exchange program where employees propose a project idea and, if accepted, got to work on said project in an international office for two weeks with travel and accommodation expenses paid. Pretty sweet, right?

Long story short, my project got accepted and I was heading off to London for two weeks in July to begin my first international travel jaunt.

Assuming that this was probably going to be my last opportunity for international adventure for possibly ever, I added two weeks of vacation after my project in London was over.

One of my best friends, Seth, and I planned a trip that would take us backpacking through Amsterdam, Berlin, and Barcelona. Seth would leave me after Barcelona and I would finish the tour with four solo days in the Greek Islands.

I almost exclusively credit those four days in Greece to my being on Remote Year today.


By the time my redeye flight landed in Santorini, I was three and a half weeks into a trip of many firsts — my first time in Europe, my first time backpacking, my first time being responsible for planning an entire trip, and now my first time traveling solo.

I was absolutely exhausted and was was physically incapable of opening my eyes and wiping the scowl off of my face.

Seth had left the day before, so now everything was on me. I was responsible for deciding where to eat, what to do with my free time, and for not being known as the Steven Glansberg of the hostel.

I was actually jealous of Seth because he was probably almost home by now. At the time, nothing sounded better to me than stumbling into my apartment and star fishing in my comfy bed for the next 12 years. Alas, that was not an option, so I would have to settle for the questionable hostel bed instead.

When I was told that check in wasn’t for four more hours, I wanted to lose it. But that would have required energy that I didn’t have. I opted to kill time by hanging out in the common area outside and crossing my fingers that nobody would try to talk to me because I was in a foul mood.

There was already a group of people sitting down who I assumed knew each other based on the fact that they were talking to each other. Why would so many random people be acting so friendly if they weren’t traveling together?

I chose to sit across the room by some outlet so that I could “charge my phone” when in reality I just felt too awkward and vulnerable to go sit with them and engage in their conversation without my social crutch, Seth, with me.

After about five minutes of eavesdropping on their conversation, I found out that they were all from the US and did not, in fact, know each other. They actually had just met that day. I was also starting to feel conscious of the fact that I was Glansberging for an awkward amount of time. I had to do something.

Despite every bone in my body wanting to sit in solitude, I decided to bust out a trick that my sister, Jess, who had been working and traveling solo for a couple months, had prepped me with before my trip.

If you want to start a conversation with someone but aren’t sure what to say, ask them if they know what the wifi password is — regardless of whether you actually need it.

It’s kind of genius.

I waited for a pause in the conversation, picked the most approachable looking person, and asked her for the wifi password, even though I was already connected. Within maybe a minute of small talk, I was invited over to join their powwow where we traded names, hometowns, and travel plans.

They were planning on heading to one of Santorini’s many beaches in the next twenty minutes for some gyros and cliff jumping and told me to join them. I was so close to saying no and justifying it by saying how tired I was, but then I had one of those internal conversations you have with yourself — the ones where you recognize that your ego is trying to talk you into something that your gut knows is dumb.

I recognized that this was a pivotal moment for me.

I could stay here and nap once my room was ready, or I could go with these friendly strangers and potentially experience what it’s like to go with the flow and just let things happen — the stuff that you hear travel is all about.

It turned out to be the pivotal moment that I thought it would be.

After an afternoon of deliciously cheap gyros, cliff jumping, and beer towers, I felt like I had known these people for way longer than a couple of hours.

When we got back to the hostel and I finally checked in, I found out that two of my new friends, who were checking in for the first time too, were my roommates for the next two nights.

It was my first time realizing that seemingly coincidental stuff happens all the time while you travel if you stop trying to be in control over everything and are open to what comes your way.

The next two days were spent exploring the island, watching sunsets, eating more gyros, and going out with my new friends. We were pretty much inseparable, with the exception of an incredible sunset catamaran cruise I booked before my trip that was clearly meant for couples (I was the only person there by myself out of 17…oops).

“umm, excuse me? hi, when you two are done making out, would you mind taking a picture for me?”

After two nights, we started to go our separate ways. I continued on to the neighboring island of Ios and was a little worried that I wouldn’t be able to replicate that magic again.

Lo and behold, I instantly met a bunch of new people at the hostel pool and within two hours, I had a group to get dinner with. I ended up meeting two hilarious friends from Canada, Tyler and Austin, who were visiting Ios on the tail end of their Birthright trip. I instantly gelled with them so well. Like, weirdly well to the point where we’re trying to plan a reunion in Austin when I get back. I knew them for two days (!!).

The most vivid, impactful 💡lightbulb💡 moment I had during the entire trip was during at silent disco on Ios with Austin, Tyler, and a beautifully random mix of new Canadian and Australian friends. There was one point where everyone, including myself, was dancing like idiots without any reservations. In the middle of the craziness, I had a little out of body experience as I tried to recognize what was happening.

I am typically a pretty reserved guy in dancing situations unless I’ve had several daddy sodas. But this particular time I was fully in control of how out of control I was being. It wasn’t because of alcohol, it was because I was letting go of any inhibitions or self-consciousness that typically would have prevented me from going all out.

How is this even happening?

How do I meet people so quickly and reach this level of comfort so fast?

How has it taken me 26 years to experience this?

Those two days on Ios are some of the fondest memories I have from the past couple of years. They’re the kind of memories you don’t want to mess with. So much so that when several Remotes wanted me to plan a side trip to the Greek Islands so that they could see these places I kept raving about, I had to decline because I didn’t want to go back so soon and risk altering my memory of them.


I returned back to Austin after my four days in the Greek Islands on a post-vacation high like I’ve never had before. I left Ios energized and motivated to start planning my next trip, although I had absolutely no idea when that would be or when I would be able to afford it.

It was my first Friday back in the office. It was a slow day, so I was scrolling through Facebook when I came across an ad.

It was a video ad that showed someone throwing her suitcase onto her bed followed by some guy working from a cafe and then people at some rooftop pool. The ad was promoting a company that enabled you to travel abroad with a community of other travelers while working for your current employer.

I remembered this ad.

I had seen it months prior and recalled looking through the details and thinking that it sounded awesome, but if literally anything was meant for those “other people”, it was this.

Wait though…I literally just did this for two weeks in London.

Then I had a crazy, semi-terrifying realization that I could actually f*cking do this.

I applied that afternoon and spent that Friday night (and probably the whole weekend) scouring the internet for anything I could find about this program.

Within two months, I applied, interviewed, got accepted, became a blog cyber stalker, got my company to say yes, and paid my deposit.

Within six months, I was on a plane to Split, Croatia, ready to start my year abroad with a community of 50 strangers.

And now, here I am, writing this post from a coworking space in Kyoto, Japan barely a year later.

To say that things escalated quickly is an enormous understatement. I never ever EVER thought I was capable of doing something like this. I was very much not a traveler and I liked routine too much to do something this drastic.

However, since the moment I applied, I knew that I needed to do this. I wasn’t (and still am not) 100% sure why I felt like I needed to, but I knew that it was right.


I wonder from time to time if I would have applied had I gotten on that flight home with Seth from Barcelona instead of continuing on to Santorini.

If I’m being honest, I don’t think I would have.

Traveling together was too comfortable. While Seth and I had a hell of a time in our two weeks of backpacking, I don’t think that I had really experienced the parts of travel that compelled me to sell everything I own and move across the world for a year by that point.

It wasn’t until I was feeling down in Santorini and forced to live outside of my comfort zone that I was finally let in on the inside joke that those “other people” had been a part of this whole time.