For this podcast episode, I decided to invite my good friend and fellow traveler, Tim. I met Tim back in 2011 while living in Medellin, Colombia. We continued to stay in touch and have met up in different parts of the world throughout the years including Miami, Copenhagen and Estonia, just to name a few.

Tim used to have a rather unusual job with an unusual schedule: he worked for five weeks straight (16 hours per day) and then traveled for five weeks straight. The job paid extremely well (upwards of $1,500 per DAY and more). The money he made from working for five weeks allowed him to pretty much travel anywhere he wanted and do it in style, without a constraining budget. Some friends and I called him the “overpaid traveler.”

Nevertheless, the lucrative job came with many challenges that weren’t obvious at first.

Here’s what we discuss:

  • What made Tim get into this line of work
  • How he manages his relationships on this bizarre schedule (with friends/girlfriends)
  • How traveling changes you
  • What’s it like to work on an oil rig and live with a bunch of different dudes for 5 weeks straight
  • The craziest experiences he’s had abroad
  • How he plans his travels
  • Why Tim never documented his travels
  • Tim’s advice to his 22-year-old self
  • Why Tim no longer travels as much and what he’s doing instead


You can follow Tim’s adventures here:

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James Maverick

James Maverick

James Maverick used to work in a cubicle as a code monkey in Silicon Valley. Then, in 2007, he quit his job and a one-way ticket to Brazil. Ever since, he continued to travel, visiting over 85 countries and living in more than a dozen of them. He loved his location-independent lifestyle and has no plans to live in America.

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