21 Years of Full-Time Travel with Wandering Earl

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Derek Earl Baron, aka Wandering Earl, left home to go on a 3-month trip in 1999 shortly after graduating from university…and he never stopped. He has now traveled all over the world for 21 years straight. He worked on cruise ships, taught English, wrote eBooks, successfully blogged since 2009 and started his own tour company that runs unique, small-group trips to some of his favourite countries. He has been featured by publications such as Time Magazine and The New York Times and is frequently invited to speak at events and on podcasts in order to share the stories, insights and adventures from his traveling lifestyle.

In this interview, we discuss Derek’s last 21 years on the road, how remote work is changing the economic landscape globally, productivity tips and traps, the dangers of over-planning, and he shares some of his travel adventures from over two decades on the road. 

Jump right into my Awesome Interview Series videos on YouTube here – and please give it a thumbs up, leave comments and subscribe!

Derek has also been featured on my site here:
How 8 Digital Nomads Survived the Pandemic
A Week-In-The-Life of Wandering Earl, in the Middle East

What it's Like to Travel and Work Remotely for 21 Years!

How (and Why) Do You Travel Full-Time for 21 Years?!

Derek puts my 12 years of full-time travel to shame, and leaves me in awe. How on earth do you travel full-time for 21 years and not burn out? Variety and self-reflection are key. We touched on topics like: 

  • Wandering Earl’s many different styles of travel (including backpacking, working on cruise ships, teaching English, leading tours, and much more). 
  • How he was spurred on to keep traveling because of the people and the relationships he made along the way. 
  • How to keep up connections with people and deepen friendships without a home base. 
  • Where Derek has returned to over the years. 
 Derek Earl Baron aka Wandering Earl in the desert

The Digital Nomad Lifestyle 

Derek sagely says the digital nomad lifestyle is not what most people expect it to be…nor is returning to “normal life”. We talked about: 

  • Why long-term travelers who get home bases sometimes end up giving those bases up to hit the road again. (See also: Pros & Cons of Being a Digital Nomad vs. Having a Home Base
  • Lifestyle design, and why many digital nomads bounce around between bases like Mexico, Portugal, Bali, Medellin, and Chiang Mai. 
  • The social traps of these digital nomad hubs. (See also: Chiang Mai’s Nimman – An Unapologetic Bubble)
  • The unexpected work involved in being a digital nomad, and how it ultimately affects your pace of travel. 
  • Why it’s important to remember that when you travel as a digital nomad or remote worker, you still work full-time! 
  • How the lifestyle is awesome – but also not what you think it is. 
Wandering Earl, founder of Remote Club, hanging out with the locals

How Remote Work is Changing the World (For Better or Worse)

Our conversation took a left turn when Derek made some observations about how remote work is changing the global landscape in some ways that I’d not considered, such as: 

  • How remote work is creating possibilities for people from all around the world to travel as a lifestyle.
  • Why the days of going to cheap destinations are almost over, and how currency arbitrage is on its way out. 
  • How short/medium-term accommodation costs are changing, especially in digital nomad hubs. 

Burnout! And Travel Lifestyle Choices

Burnout is real, and most digital nomads and remote workers who travel long-term have experienced it in one way or another. Knowing some of the things we talked about can really help: 

  • Burnout! And why it’s so common, and how to avoid it. 
  • How the travel lifestyle inadvertently erodes productivity. 
  • The importance of having mini home bases along the way. 
  • Why you need to be in one place more than you’ll likely anticipate. 
  • How people consistently underestimate the tasks of daily life on the road. 
Wandering Earl with his luggage traveling full-time for 21 years

How Remote Club Helps Remote Workers Hit the Road

I’ve followed Remote Club from its infancy, and I’m loving it more and more as it grows. It is a rich resource that dramatically reduces the research and time required to get set up in a new location. Some highlights we discussed include: 

  • How Remote Club helps the new wave of remote workers reduce their learning curve and arrive at a destination ready to hit the ground running. 
  • Why AirBnB is often not the best option for finding accommodation. 
  • Preparing vs. Planning vs. Over-Planning. 
Derek with his guides in Yemen on Wandering Earl Tours

The Many Ways Wandering Earl Has Wandered (and Continues to Wander)

One of the keys to Derek’s longevity in travel has been variety. Here are some adventures he shared: 

  • How Derek has also managed to travel fast (like, 60 countries in a year) despite all our talk of slow travel and home bases being necessary. 
  • Derek’s experience working on cruise ships. 
  • How “ship life” was good preparation for becoming a travel content creator and ultimately a tour operator. 
  • Wandering Earl tours: how he got started, and what they’re like. 
  • How he landed a speaking part in a Bollywood movie (and why I’m jealous). 
  • How to land a part in a Bollywood movie yourself, should you so desire. 
  • Wandering Earl’s newsletter, and why I love it. 

Catch our Awesome Video Interview Here! 

Click here to watch our entertaining talk on YouTube (and please, give it a thumbs up and leave a comment! It really helps the video get discovered), or watch it below: 

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