Joining Remote Year: The Itch That Became a Rash

Jono Lee
Jono Lee
Nov 4, 2016 · 10 min read

It begins as a tingly sensation. Most try to ignore it at first.

Bits of salt stick to my dirt bike helmet as I barrel down the Uyuni salt flats in Bolivia at 50 mph. Condensation builds under my bandana as I breathe into it. At 12,000 ft the air is thin so I have to gas it more than I’m used to.

In every direction lie vast plains of white salt as far as the eye can see. I have a strange feeling of being on another planet. This is no place for man, but I’m here anyway.

2 questions cross my mind.

Damn, when did I become such a badass? But more importantly, how the hell did I get here?


“If you join [that over glorified islamic terror group] during it don’t come back.”

The thought of creating an Asian version of Sh*t My Dad Says crosses my mind.

“Don’t worry Dad. I’ll definitely email you if that happens.”

I figuratively wink at him. 😉

[Note: My dad is awesome, he just says ridiculous shit sometimes]

Me and my super cool thinking hat in Plitvice Lakes National Park, Croatia.

You’re faced with a decision to blow up the only life you’ve known to join Remote Year and go on an adventure across the world. What do you do?



Life is about probability. Every second you’re alive is a roll of the dice.

You’re on a flight: 0.01% chance of dying.

You’re walking on the sidewalk: 0.02% chance of dying.

You’re in a car: 0.165% chance of dying.


Combined with anecdotal evidence, it’s not a surprise people irrationally fear a lot of things and become risk averse. Just as it’s easy for people to spend idiotic amounts on lottery tickets for the $1.5 billion powerball because they imagine the life they’d have after, people are equally adept at imagining the worst case scenario for everyday life. The human mind is wonderfully imaginative in both directions.

The one thing I’ve learned though so far in my life is that despite all the irrational crazy bad things one thinks of, it is very rarely that bad. Our ability to constantly adapt, learn, and become better is what makes us human. It’s crazy but normal at the same time. I see it in other people and experience it firsthand every single day. Don’t be afraid. You’ll figure it out.

One of my favorite decision making lenses is the regret minimization framework popularized by Jeff Bezos.

Will you regret it?

If I stayed in California my entire life and never lived anywhere else, I knew with 100% certainty I’d regret it.


My view back in San Francisco.

A year ago, I sat in my cozy high rise condo overlooking the Bay Bridge in San Francisco.

Too comfortable here. There are too many ways to get around the city and too many Uber for X apps to choose from. My favorite word is “interesting”, and being too comfortable was not interesting to me.

How comfortable is one allowed to be? How can you grow as a person if you’re too comfortable? Does it mean you’re wasting your life if you’re too comfortable?

What app shall I use to order food today? Postmates? Munchery? DoorDash?

What app shall I use to drive me 5 blocks right now? Sidecar? Lyft? Uber?

What app shall I use to park my car right now because I’m a fucking lazy ass human being? Luxe? Zigit? Parkly?

[Note: These apps are great, but in a cliched nutshell — it was me, not them.]

The San Francisco Bay Area is by most measures an amazing place to live. The tech epicenter of the world with companies offering amazing benefits and high salaries. Great food scene. Great, mild weather.

But I had tech fatigue. I felt overserved. I was tired of hearing the word disruption being applied to every single word in the dictionary. The rest of the world cannot be like this.

As a designer who wants to create products people love, it automatically means I’m an anthropologist. I have to understand people.

A maker space I visited in Penang, Malaysia. Asia is bustling with opportunity.

However, within the past few years it started to dawn on me that I only understood a narrow sliver of the world. I couldn’t fully grasp what the rest of the world was like outside of California, at least not through the touristy traveling I had done up until that point nor just through reading. It bothered me. How can I and so many others in Silicon Valley portend to want to change the world but at the same time be so naive about it?

I came to the realization that while San Francisco was my home, it’ll always be there. The unicorns will continue to sparkle. What I was missing out on was elsewhere, not there.

A contemplative moment during sunrise in Barcelona.

Freedom is the defining word of my generation. We have more options and fewer obligations than ever before.

  • Calling a car with Uber or Lyft is more freeing than owning a car and having to deal with its payments, maintenance, insurance, etc.
  • Streaming shows whenever and wherever is more freeing than being beholden to a TV network’s weekly schedule on cable.
  • Swiping from an endless supply of dating options on Tinder is more freeing than actually going out and talking to people.

The world is our own damn Hog Island oyster.

However, the freedom to travel and work from anywhere and not be tied to an office desk is still a relatively rare one. Globalization and the internet have created a post-industrial society of knowledge workers that can collaborate solely online. We might not have flying cars yet, but to be able to collaborate instantaneously across the globe with someone else is pretty amazing.

Our “office” in Prague (K10 Coworking).

It’s something my parents would’ve never dreamed of. When they immigrated to America from Taiwan in the 1980’s, their options were very limited. They came with nothing so they had to work their butts off to support me and my sister, and the internet didn’t exist yet.

I know how lucky I am to even have the option to travel and work, and to not take advantage of it felt wrong. My parents didn’t work so hard to give me all these opportunities so that I could then squander and waste them.

The itch became a rash. I decided to join Remote Year.


Montevideo kicked off with the colors of Carnival.

Nine months ago, I arrive in Montevideo, Uruguay. I know next to nothing about this country, and I’m about to meet 75 other strangers who feel similarly. Remote Year has begun.

Everything’s new. Everything my eyes see my visual cortex has never processed before. Everything I hear I’ve never heard before. New, weird dishes to eat. New people to meet. New activities to try. When does new become old? Is that possible?

I am a sponge thrown into an ocean of novelty.


“We think we listen, but very rarely do we listen with real understanding, true empathy. Yet listening, of this very special kind, is one of the most potent forces for change that I know” — Carl Rogers

While becoming a better designer was part of my reason for joining Remote Year, ultimately traveling offers so much more than any single reason one initially thinks of and it all comes down to one main thing: the people.

The motley crew of Remote Year 2 nearly halfway through in Prague.

Let me first start with the people I travel with on Remote Year. It’s a wily gang of people from all over the world, but despite our differences they are among the most open minded and good natured people I’ve ever had the pleasure of knowing. It’s certainly a huge part of what makes Remote Year so fun and worth it relative to organizing your own travel around the world, which anyone in theory could do.

It’s also the random encounters everywhere. I’ve met so many interesting people across the world:

  1. An Argentine doctor who spends half his time in the US, constantly sharing medical learnings between the two countries.
  2. My salt flats guide in Bolivia who moved from the UK after marrying a Bolivian woman and now extols the virtues of one of the world’s most interesting countries for a living.
  3. An Indian Canadian in London pursuing her fashion tech entrepreneurial dreams.
  4. A young Croatian personal trainer who dreams of becoming a YouTube fitness star.
  5. A Malaysian Chinese who taught me to how to speak “Manglish” aka removing syllables and adding “la” after everything.
“lol who let this guy travel”

I’ve always believed that two people can disagree but still both be right, and Remote Year so far has further carved that into my being. The ability to listen and understand and see that while someone else’s position may differ from your own, it’s clear that the path they took to arrive at that conclusion is still valid. It’s often easy to ignore someone’s opinion, especially in the echo chamber of sameness back home, until you truly talk to them and realize that we all have had a lifetime of experiences, valid experiences, that shape who we are today.



Arigato? Did someone just fucking say “arigato” to me?


I couldn’t help but laugh. While not malicious, to encounter overt racism like this clearly meant I was no longer in the melting pot of California. I was actually kind of proud.

Arigato, young Uruguayan teenager. Arigato very much.

Or as Luis, a fellow Asian on Remote Year, said when the same happened to him: “Wrong fucking Asian.”

One of our many travel days (this is from Belgrade to Split).

Remote Year and long term travel in general isn’t for everyone, but it’s for more people than you think. Many automatically think its unobtainable. “I wish I could do that” and “I’m jealous” are the two most common responses I get when I tell people what I’m doing, despite the fact that many of these people could do it.

I’ll admit it’s been far from perfect:

  1. I was robbed of my MacBook Pro and GoPro 3 weeks in (thief broke in through our AirBnB window when we were sleeping).
  2. I had borderline traveler’s diarrhea at a remote hostel where there was only 1 toilet for 20 people (sorry everyone there…).
  3. I was given a 60 euro fine in Berlin a few minutes after my 72 hour subway ticket expired even though I was at my last stop (c’mon man… even with my puppy eyes??? 🐶).
  4. Enduring long 3 flight 28 hour travel days is always tough (Priority Pass = major key).
  5. Packing for a whole year into just one checked luggage and backpack is tricky (benefit is you’re forced into a minimalist lifestyle).
  6. Sketchy internet in certain countries can be endlessly frustrating.

I also miss many things about home:

  1. Being able to easily hang out with family and friends whenever
  2. Amazon Prime
  3. In-N-Out
  4. Having a closet
  5. My own bed
Machu Picchu with the gang.

But the list of highs would require a post of its own:

  1. Hiking the beautiful Lares on the way to Machu Picchu with my fellow Remotes.
  2. Working out of a picturesque converted Dutch embassy in Prague.
  3. Enjoying endless pastel sunsets living a stones throw away from the beach in Split.
  4. Eating at 15 of the top 50 restaurants in Latin America.
  5. Living in London during Brexit (ok not really a high, but it was definitely interesting).
  6. Hiking in Patagonia, which is hands down one of the prettiest places I’ve ever been to.
  7. Devouring all the pintxos in San Sebastian, Spain.
Ali Pacha: an eye opening vegetarian fine dining experience in La Paz.

That’s maybe only 3% of what I could list, and I still have another 3 months.

So while not easy, it’s definitely doable and the amazing experiences you have make it all worth it and then some. Travel is inherently messy and there are challenges everywhere, but that’s really the part you want. It’s what helps you grow as a person.

I wasn’t entirely convinced of the remote work lifestyle at first and I don’t plan to do this forever, but having lived it the past 9 months I do truly believe in it. The benefits far outweigh the cons, and with the continued improvement in technologies like VR and AR and as the infrastructure of the world continues to improve the remote work trend will only get bigger.


Let’s see how itchy I am by the end of this. Or someone just buy me some damn antihistamine cream.


Go Remote

Musings from the the global Remote Year community and beyond. Inspiration and resources for location-independent professionals.

Jono Lee

Written by

Jono Lee

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Go Remote

Go Remote

Musings from the the global Remote Year community and beyond. Inspiration and resources for location-independent professionals.

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