Reflecting on 20 Countries in 2 Years

Jeff Warren Orr
5 min readJan 10, 2020

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I’ve spent the better part of the past 24 months traveling.

I started in Europe, where I based in Madrid. Moved to Mexico City to learn Spanish. Traveled through South America. Explored Southeast Asia on motorcycle. Spent time in Guatemala. At the time of writing I’m in the Philippines, coming off a two month trip in China. I’ll head to Taiwan next, then to San Francisco for the foreseeable future.

This post is a retrospective on these experiences. Written with the intent of sharing observations and lessons learned walking off the beaten path.

Travel won’t solve your problems, but it lets you look at them more objectively.

When I first started traveling, I had just shut down my first company, which was a challenging and stressful experience. I vividly remember sitting on the roof of my hostel in Mallorca, Spain. I looked over the city and for the first time in two years felt completely free of anxiety. Like when people describe near-death experiences. Floating above their bodies in the hospital room — looking down at the stress, worry, and suffering of the world while feeling completely detached. Maybe this is a dramatic analogy, but it’s really how I felt.

I think the practical note here is that travel offers a temporary escape following a challenging life event — whether that’s shutting down a company, the loss of a loved one, divorce, etc. I don’t believe traveling has the power to fix things (it wasn’t going to save my company) but it does provide a different perspective. For some reason, the act of geographically distancing myself from the US created an “outside-looking-in” view. It helped me analyze things more objectively. From there I was able to see the bigger picture, learn from mistakes, and move on in a healthy way.

Harder to feel stressed on a volcano.

You don’t have to be rich. (Time > Money)

There’s a belief, certainly in the US, that long-term travel is only for the rich. In the movie Wall Street, one of the character’s goals in life is to get rich enough to ride a motorcycle across China. The reality is you can do this trip for a few thousand dollars.

Riding a motorcycle in Ha Giang, Northern Vietnam. <$400 for a week of rental, lodging and food.

Wealth, to me, comes in two forms. There’s financial wealth (which is the standard metric in the US) and there’s time wealth. Time wealth refers to the amount of time an individual has at their disposal. Often people with high financial wealth have limited time wealth (the businessman who works 100 hour weeks but doesn’t have time for family). Conversely, an unemployed person may have lots of time wealth but less financial wealth. (Striking a balance here is for another Medium post).

You obviously need money to travel. But what’s more important is creating time. This is why people often put off traveling until they retire (and have lots of time wealth).

Awesome interview by Tim Ferriss with Rolf Potts on this here.

Meeting people is easier because you automatically share a common interest.

Meeting people while traveling is easier because (A) they’re also traveling, and you share the common interest of travel or (B) they’re local, and you’re mutually interested in each others cultures. Both of these are generally sufficient starting points for a conversation.

Fast friends in Vietnam (despite massive language barrier).

Maybe this is something I need to work on in my own country…but I just don’t feel this connection with strangers in the US.

There are good and bad people everywhere — but most people are good.

Many places portrayed badly by American media as “dangerous” have been full of the kindest people I’ve met. Scary stories are interesting, so the news often chooses to focus on them.

The reality is that danger exists everywhere in the world. My chances of being robbed in LA are similar to Mexico City if I’m being careless. The .01% of bad people in a country don’t reflect the 99.99% of good people living there.

Loneliness — being abroad has a multiplying effect.

One of the downsides of long-term (solo) travel has been feelings of loneliness. This has the highest impact on me while in Asian countries, where culture shock is generally higher, and time difference means that during the daytime, my friends/family in the US are asleep.

Ways I’ve learned to combat this while traveling:

  • Meet people → obvious but effective.
  • Exercise → a long run clears the mind.
  • Write → the fastest way to beat negative emotions is to put them on paper.

Practical Notes

  • Never check a bag if you can help it. With some planning, there’s no reason you can’t pack everything you need in 1 carry-on bag and 1 personal item (the standard free allowance on most airlines). Benefits include: saves money, saves times, minimizes risk of lost baggage. If you must check a bag, keep your essential items in your carry on.
  • Hostel bars and lounges are great places to meet people. I prefer staying in Airbnbs, but doing so means I miss out on some of the social element of traveling. A way to get the best of both worlds is to find an Airbnb near popular hostels.
  • Having a pack of cigarettes, even if you don’t smoke, is a great way to start conversations.
  • Backup chargers are life savers.
  • Cash exchanges at airports are almost always a ripoff. Pull cash from an ATM instead.
  • This is a personal thing, but even if I have a short conversation with someone, I exchange WhatsApp or Instagram info. The world is small and you never know when you’ll again be in the same place.
  • Buy a local SIM if you’re going to be somewhere for longer than a week. It will be cheaper than an international plan (in most places) and if your phone is lost/stolen, you’ll have your main SIM safe (which is harder to replace while abroad).
  • Bring two debit cards. Leave one at the hotel, keep one on you.

✌️🌏

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