How The Happy Nomad Tour Rolls – Winging It

Many people have asked me how I could just leave my job and seemingly travel perpetually. How can I afford it? How do you find places to stay for free all the time? How do you find places to volunteer? All questions I’ve received by email, and now I’m sharing the secrets in a series of posts about how The Happy Nomad Tour Rolls and what things are like behind the scenes.

Winging It

I have the ability to be very organized and on top of things. That’s how my first 28 years on this planet went. But that can also be a curse when it comes to traveling.

In normal life you can draw a line at what is normal and what is obsessive-compulsive. But when traveling, there’s almost no end to what level of detail you can research a new place and everything that goes along with it.

Back when I was working for the evil oil company, I’d often have to take vacation at a moment’s notice because something would get screwed up offshore (like dropping 10,000 feet of wire in a well 15,000 feet deep) and I’d instantly have a week of vacation.

You’d think maybe I’d have plans ready to execute.. like ok, if I have a week off then I’ll go here, stay at this place, visit these monuments and museums, etc.

No.

The first instant vacation came in 2005 when, after my African safari, my boss said I could stay on vacation for another week and I caught a flight to Istanbul some hours later.

I remember the taxi driver being speechless when I asked him if the big mosque to our left was The Blue Mosque. It is probably the biggest tourist attraction in Istanbul so it’d be like asking a taxi driver in Paris if the thing to the left was the Eifel Tower.

I showed up knowing almost nothing about Istanbul and had an amazing four days exploring. I learned a ton, had no preconceived notions, and by learning through experience I remembered and felt more.

And that became the way I traveled thereafter.

In 2006 my dad came to join me on a  vacation. We went to Spain, Morocco and Italy together. I had a yellow folder with all my planning materials. I wanted to make sure he had a good time so I planned everything for when we were together, even getting intercity bus schedules ahead of time. But when he left from Rome, all I had left were my hostel reservations in Beijing, Shanghai, Seoul, Taipei, and Bangkok.

Well, on The Happy Nomad Tour I try to stay one month ahead in planning. That usually just means knowing where I’ll be over the coming month, where I’ll be sleeping, and where I’ll be volunteering. But sometimes that planning window dwindles down to a few hours for one reason or another.

In Colombia and Ecuador some opportunities came up because my brother decided not to visit me in Colombia, so I added Venezuela to The Happy Nomad Tour and totally changed my plans in the course of an hour. In Ecuador I got set up on a Toxy Tour (which fell through). In both cases, my flexibility to go wherever opened up new opportunities. It also meant I criss-crossed both countries.

Although in a zoomed out map it may not be so obvious, you can see in the case of Colombia that going to the coffee zone was an un planned addition or it would have made more sense to go from Medellin to the coffee zone and then to Bogota. Also, on my way out, it was too long of a journey to go from Popayan, Colombia to Quito, Ecuador. So I stopped in Pasto, Colombia for three awesome days.

Ecuador was a similar story. My route is kind of a mess. But, for example, had I not gotten the opportunity for the Toxy Tour in the east,  I wouldn’t have gone there.

So, lots of stuff on this trip have happened on a whim. And things like adding Venezuela, rappelling down a waterfall, and unexpectedly going to The Philippines have been great unexpected experiences.

I don’t think I could always live whimsically. But it’s been nice getting to know and embracing the whimsical part of me I never would have known existed had it not been for traveling.

In the end, life is about rolling with the punches and embracing all that happens with a smile on your face. And that’s how I’ve decided to travel.