FAQ

Ok, so I’ve been asked a few questions about my trip. 

1)      What’s your motivation?  Why go to all these (seemingly) random countries?

There’s not a lot of risk-free chances in life to take a lot of time off. 

Truth is that I really enjoy traveling.  The way some people really enjoy sports, or music, or food (although I also really like food).  This trip is kind of a like an 8 month travel binge.  In some alternative life I might have been an anthropologist or a foreign correspondent. 

Plus, for better or worse, being trained as an investor will make me see the world that way.  And given how global the financial world is becoming, I’m hoping that can’t hurt down the road.  It’ll certainly be a unique kind of education.

2)      Where’d you get the idea?

I had a hunch this was doable after spending some time in Turkey.  It turned out a few people had done it on a grand scale.

Ewan McGregor did it with his friend around the world and then down to Africa (which was shown in two documentaries).  

Jim Rogers, Soros’ old sidekick, did it twice in the early 90s and early 2000s.  

And then you realize there’s a big global community of people that love adventure motorbike travel (www.advrider.com). 

I even met a German couple at a campground that was on a Pan-American tour.  A dream of theirs was to do North and South America tip to toe.  He worked as a plumber, and she worked as a school teacher.  For years they saved money, and finally they quit their jobs, moved their stuff into their parents apartment, and were traveling from Newfoundland to the tip of South America.  To see that firsthand was inspirational.

It’s actually pretty straightforward – the hardest part is finding the time to do it!   

It’s also addictive and stopping to return to ‘civilian’ life can be hard.

3)      How did you choose where to go?

I drew a 2x2.  On one axis was “cool” and on the other was “places you won’t really want to visit when you’re 40.”

Latin America was in the right box, and so was Asia.  

Africa and parts of Central Asia are there too… if I was more adventurous I might have added those.  I know lots of people have traveled there and had wonderful experiences.  But going there solo made me nervous.

4)      Are you going solo?  Are you worried?

Mostly.  I’ll probably meet folks on the road and that friends will parachute in for a week here or there.

It’ll be liberating… and maybe tiring after a while.  

Being away from friends and family for that long in a foreign country can be tough – luckily staying in touch is easier than it’s ever been.

5)      Are you worried about getting sick or getting hurt?  Or worse?

Truth is most of the world is pretty safe. It sounds crazy, but I think I know more people who have been mugged in the South End than who have had trouble overseas.

I plan to avoid places that have a bad rap (like Colombia or Mexico).  They are both wonderful countries and I’m probably being too paranoid. 

6)      Why a motorbike? 

I sort of discovered it by accident.  One day I was abroad, and bored, so I bought a little motorcycle (150cc – less power than most lawnmowers).  Travel went from being interesting to unbelievable. 

On a motorcycle, you’re part of the landscape, the weather and the culture.  All your senses are on.  There’s the wind in your face and the exhilaration of being on two wheels and being able to go anywhere.  And there’s nothing separating you from the local culture. 

I mean – think about what it’s like to a local.  Imagine you live in some village in Bolivia your whole life, and then, out of nowhere, someone on a motorcycle stacked with gear rolls into your neck of the woods.  It’s probably the most interesting experience either you or the traveler has ever had.  It opens up doors and facilitates all sorts of conversations.  You get to pretend to be that Dos Equis guy for a little while (“Most Interesting Man in the World”). 

7)      How do you buy a motorbike overseas?

Every country is different.  Chile happens to be very easy.  

You get something that resembles a social security number, and then the process is a lot like the US.  And no, you don’t have to pay in suitcases full of peso bills!