Oh hell yeah I would – even more so now that I know how things turned out. In fact I did just do it all over again by getting rid of all my possessions and moving down to Costa Rica. But back in 99 I had no idea how things would turn out. It was a huge jump – just a leap of faith where I got out of my comfort zone and surrendered control of my life completely. But it’s almost easier to do that because the scale of it is so unimaginable. You don’t even have one iota of an idea what to expect or what you will face, so you can’t even wrap your mind around it enough to become scared. And then I was on the road and I looked up one day and I was in the middle of it and it was like “Oh shit! I’m vibing on this energy! Holy shit what did I get myself into?!!!” Of course I enjoyed the trip but it was also extremely challenging in many ways, so I think the rewards came later, and still keep coming, in ways that were never anticipated. It’s like I took one step down the road less travelled and as time goes on the distance between that road and my past life widens more and more.
I was just a crazy, confused kid going into it, and when I came back I was a conscious man with a pinpoint of certainty about who I was and what I wanted my life’s purpose to be. But it took me a lot of years to figure out what to do with that meaning. I had no idea I would become an author or come full circle and live in Costa Rica. Hell, I had no idea about all of this even a year ago! That’s how fast everything has happened.
2. What did you need to acknowledge in yourself to take such a giant leap and decide to travel the way that you did?
I think as complicated as things get in life, we always do well to simplify them. For me it was like this – If I’m not happy with my life, then change it. That’s it. I was living in San Francisco, which I loved, but I was working a dead-end boring insurance job that just drained the life out of me. Every day I would look at the clock and wish it were five o’clock. Every day I would look at the calendar and wish it were Friday. I was 28 years old and I was literally wishing that hours and even days of my life passed me by. That hit home for me that something was wrong – life is a precious gift and I was wishing it away. So right there in my cubicle I thought to myself, if I could do anything with my life, with no restrictions or limitations, what would it be? And my trip around the world is the result of that – my grand escape plan. Looking back, I think the part where I allowed myself to dream without a ceiling, and consider it possible, was more important than all that followed.
You know the Viking warriors in their time were known as the fiercest and most committed soldiers. Retreat was just not in their vocabulary. When a Viking ship would pull ashore on far-off enemy lands and they all got on dry land and started fighting, their leaders would set their boats on fire. That way the soldiers knew there was no going back – failure was literally not an option, and the only thing they could do was commit 100% and fight forward. I think we all need to do something in our lives where we commit 100% and don’t consider failure an option – whether its chasing our dreams, being a good parent, getting in shape, starting a business, etc. No matter how big or small sometimes we have to burn our ships and fight forward with that resolve.
3. What made you decide to choose the countries that you did? What were you hoping to find in yourself in them?
My original plan was to move to Brazil and teach English as a second language. I even invested $14.95 in some Portuguese tapes (and that’s a huge purchase for me) and went to school in Boston to get certified to teach English as a second language so I could work down there. But at the same time my new basketball buddy in San Francisco, “Shane” in the book, was talking about travelling too. It became apparent that we were both serious so it morphed into travelling all over the world instead of just Brazil. We both made a list of our A, B, and C choices of the countries we wanted to visit, then we cross-referenced and crossed things out and prioritized our choices, like it was a fantasy football draft with countries. “I’ll give you Argentina because your uncle’s friend owns a bar down there if you give me Thailand because I hear they have cool beaches.” That was about as scientific as the process was! We bought special round-the-world tickets with United, which gave us something like 35,000 miles for only $2,500. The only rules were that we had to go in one direction – from East to West – and we could change the dates but not the destinations of the flights. We planned our major stops and used up those miles on paper, but from there we had literally no plan. Once we were in a theater of the world using that ticket we would just hop to other countries using local flights, buses, trains, taxis, camels, elephants, and bamboo rafts. We did no research, had no travel agent, and rarely opened a guidebook until we were in that country, preferring to just fly by the seats of our pants. One day I was in Japan and woke up sort of frustrated about how expensive and unfriendly it was, and in a split second I said “f- it” and took a taxi to the airport and asked them when the next flight out to anywhere in the Middle East was. The airline worker asked what country I wanted to go to, and I literally said I don’t care, just give me the next flight. And that is how I ended up flying 19 hours and arriving in Israel on my birthday, February 9, 2000. That sense of freedom and spontaneity was exhilarating beyond words.
4. How did you know that you couldn’t ignore this and had to make the choice to listen to your gut?
Back in 99 I felt like life was beating me down. I was trying to be “responsible” and just work hard and keep it clean, to play the game the right way, but no matter what I did I never seemed to catch a break or get ahead. If that was going to happen I sure as hell was going to throw a few punches of my own. So I decided to change the game and play by my own rules. So what could I do? What was a dream so big and audacious that it would put my stamp on this world forever? Like I’ve said before, I wanted to be the smallest fish in the biggest pond imaginable. If I failed at least I would fail with blood and dirt of battle on my face, knowing that I gave it everything I had.
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Series Two will be up next Wednesday on Motivation