TDG #022: Lessons from 12 months on the road

Some advice that may or may not be useful.

TDG #022: Lessons from 12 months on the road
A view from the Piedras Rojas in the Atacama Desert, Chile

Hello friends,

To this day, I remember my first international trip pretty vividly. It was 2017, and I had just paid off my student loans. Three years of saving damn near every penny of my paycheck - quite literally eating rice and beans most days - and offering it as a sacrifice to the U.S. Department of Education. So I wanted to treat myself.

I never really traveled abroad growing up, save for the occasional family trip to Canada (does that even count?). But for whatever reason, I had itchy feet. Maybe it was watching too much Anthony Bourdain. Perhaps it was growing up reading and watching characters like James Bond or Jason Bourne having crazy international adventures. Whatever the case, I needed an adventure of my own.

So I set up all the cheap flight alerts, which back then was having Twitter text me whenever The Points Guy tweeted out a flight deal (hilarious, right?). Then, one fateful Saturday, I got an alert about a $220 roundtrip flight from New York to Belgrade, Serbia. Within minutes it was booked. I had no idea what to expect from Serbia, but it didn't matter. And because I figured Serbia would be relatively affordable, I also used that as an opportunity to head to Switzerland to balance the cost. In my mind, Switzerland epitomized the classic European backpacking adventure.

I drank rakia. I ate street food. I saw mountains. I took trains. Though it may sound trite, that trip was truly transformational. And if I thought I had wanderlust before that trip, now it was insatiable.

Fast forward to today, and Steph and I have just crossed the 12-month mark of being on the road. 12 months, 20 countries living out of a small 35-liter backpack. Last week we picked up some nice wine to celebrate and started reminiscing about our favorite moments on the trip, of which there are many. A good problem to have, for sure.

In a way, I think I've been plotting an extended, long-term trip like this since I was on the return flight back from Serbia. But for it to actually happen is something else entirely. I feel so fortunate to be able to do something like this. Fortunate to see so many places and to meet incredible people. And fortunate that Steph was crazy enough to humor me.

Anyway, enough sentimentality (I'm not crying, you're crying!).

Lessons from the Road

Since that fateful trip in 2017, I've observed and documented some rules of being on the road. In case they might come in handy one day, here you are:

  1. If someone pours you a drink from an unmarked jug, it's probably the good stuff.
  2. People are generally kind and willing to help.
  3. Something will inevitably go wrong. When it does, the best thing you can do is not think about who is wrong or right but how you can move forward.
  4. Eating and drinking "of the place" is the easiest and most effective way to eat both well and affordably.
  5. Try to introduce as much randomness into your travel as you can. The more randomness, the more serendipity.
  6. Italian coffee is overrated.
  7. If someone looks at you quizzically and asks, "Why are you here?" you probably did something right.
  8. You can get a discount on Airbnbs, either on the platform or by haggling offline, if you stay for a month.
  9. There will be moments you feel uncomfortable. When that happens, try to ask yourself why.
  10. Restaurant reviews and "best of lists" are mostly crap. As long as you know what to order, you should be fine.
  11. Don't eat tacos outside of Mexico and the U.S., they are usually way too expensive and never worth it. Expect to continuously break this rule.
  12. Craft beer outside of the U.S. will mostly disappoint. Learn to embrace the national lager.
  13. Carry some antibiotics if you're going to be gone for a while.
  14. Finding weed abroad is easier than you think.
  15. It's worth paying more to avoid flying on a budget airline. You'll immediately forget this the next time you go to book a flight.
  16. Always pay it forward.
  17. It's ok to take some days off. Traveling is hard and can be exhausting; you need time for yourself.
  18. Sometimes a gate agent will hassle you about needing a roundtrip ticket in/out of a country. If this happens, buy one quickly and cancel as soon as you sit down on the plane.
  19. Keep a pack of playing cards in your backpack or purse.
  20. We're all humans. We have a lot more in common than sets us apart. Not the first time it's been said, but it can't be said enough.

That’s all I have for now. I’m sure I’ve missed some, but I’m out of rum (we’re in Ecuador, after all), so more inspiration might need to come later. I'm thinking about keeping this as a running list anyway, updated each year with more learnings.

What are your travel/life-related axioms? I'd love to hear about them.

Some other stuff

Brendan Leonard of wrote an essay about algorithms and choice. If you read last week's newsletter, you probably know that I feel the same way. I also found the Ezra Klein/Dave Eggers podcast he references in the article, which is also worth a listen.

He also shows us how to make a chip drink.

Noticed anything different about restaurants these days? TikTok has taken over the menu.

This is what inevitably happens to your favorite platform.

Ryanair sucks, but whoever runs their social media deserves a raise.

That's it for this week, folks.




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