“More people will choose unhappiness to uncertainty.” – Tim Ferris

In the world of living and working anywhere, Sean Ogle is top of mind. He’s also one of the most eloquent teachers on the topic.

5 years ago in 2009, after being laid off, he launched Location 180, to explore what it meant to be location independent – to fold travel into his life in a greater capacity. Today he hones in on exactly what it takes to create a location independent lifestyle, whatever that means for you. For me, it means one that fosters a life of travel.

I’m psyched to bring him on the show to discuss his travels, what happened that inspired him to pursue a life of travel, and how he not only believes but also helps others create location independent lifestyles for themselves. Now, whatever that means for you — maybe you want to start a business, or maybe not — maybe you just want to hear his travel stories — entrepreneurship may not be for everyone, but travel in whatever form, should be.

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What We Cover:

  • Uncertainty. How to overcome it and why doing so can lead to happiness.
  • The best thing you can do right now to get started with a location independent business.
  • 2:40 – Sean’s introduction
  • 3:30 – An experience in Rio de Janeiro that gave Sean a clearer perspective of what he wanted more of in life (hint: freedom)
  • 4:30 – How Sean left his job in Portland, Oregon to travel to Thailand
  • 16:50 – The countries and places Sean’s skills as a location independent freelancer have taken him in the past 5 years.
  • 20:00 – How Sean accidentally stumbled into the skill, freelance “Search Engine Optimization”, that he could freelance and realized he perform this service for money, from anywhere. And how you can do the same, with any number of skills — both technical and non-technical.
  • 33:25 – How Sean explains to his friends who don’t understand why he travels the way he does, and how that motivates him to continue to experience more adventure in his life.
  • 35:40 – It all comes down to Happiness. Give it a shot. What’s the worst thing that can happen? “I’m only doing what I’m doing because it’s what makes me happy… take the risk because it’s totally worth it in the end.”

Words from an Explorer:

“I want to have stories. I don’t want to have stuff… Anybody can do what I’ve done. I just actually faced the fear of uncertainty and went for it.”

Explore Further:

Music Credit: Imogen Heap – Wait It Out (Artec Remix), Intrepid Journey, by Aaron Static

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I’m a lifelong international traveler, the host of The Travelers podcast, and founder of Holocene, a framework and community for writing the story of your life using travel and creativity.