How and Why I Travel (Part II of II)

Part I Is Here

Question MarksPeople often ask me how I am able to travel so often and to so many places. For a long time I didn’t know how to answer the question, because for me travel is as natural as any other part of life. Over time I’ve gradually learned that someone asking me how I travel is usually asking a more specific question.

That question is usually one of these:

  • How can you afford to travel?
  • How can you take so much time to travel?
  • How do you choose where to go and plan your trips?
  • How do you get visas, meet people, arrange where to stay, or any other logistical question that deals with practical details.

I’ll answer each of these questions in more detail in the future, but for now the short answers are below. Each of the answers are related. I travel because I want to, because it’s what I value, and because I’ve deliberately structured my life around it. That’s the simple answer to most questions about why I do what I do.

To break it down a bit, here’s a more detailed explanation:

  • How can you afford to travel?

The short answer is that I have no debt and I travel very modestly, usually with Round-the-World tickets that cut my average flight cost to about $300. I stay in hostels and guesthouses for about $15-30 a night, and sometimes with people for free.

I don’t take any checked luggage with me, so I’m not usually tempted to buy anything while I’m traveling except food. I do bring several books with me and slowly give them away as I finish them, thus freeing a small amount of space in my bag for new stuff.

Of course, just because it’s relatively cheap doesn’t mean it doesn’t cost money. Travel does become expensive, especially when you go off the beaten path. Visas to developing countries are sometimes $100 or more, and lots of other expenses usually cost more too.

I support myself through small business work that I have done in various forms since 1999. I’ve done everything from Google Adwords consulting to web site design, and I’ve been working on building a small publishing group since 2006. It’s not making me a millionaire by any standard, but it pays the bills and allows me a great deal of flexibility.

  • How can you take so much time to travel?

I try to structure my life around my trips. I plan to be away in 2-3 week periods, and then I just go.

The emergency travel check-list for me is pretty short:

• Do I have my Passport?
• Do I have my Plane Tickets or e-ticket printouts?
• Do I have enough Money? (I usually travel with a lot of cash to be safe.)
• Do I have my Credit Cards?
• Do I have my Journal?

Technically, that’s all I need. The secondary list is also important:

• Laptop
• iPod
• Running Shoes
• Contact Solution
• Anti-Malarial Drugs
• and this list goes on for a while…

But the point is that you really need a lot less than you think. I’ve never found myself in desperate need of something that I forgot to bring from home.

  • How do you choose where to go for your trips?

It depends. Over the long-term, I’m trying to go pretty much everywhere, so I find myself getting more systematic as time goes by. But for the past two years, it’s been more a question of going wherever I think would be cool to visit.

For example:

I went to Jordan for my first trip to the Middle East. It seemed like it would make a good introduction, and it did.

I went to each Balkan country because I was interested in Sarajevo and Belgrade, and a lot of fun places happened to be in the region.

I went to Burma because I was interested in the social fabric of an oppressed Asian country.

I went to Romania because it was the only place in Eastern Europe I could get a Delta awards ticket.

I went to Uganda and Tanzania because I hadn’t ever been in East Africa.

I went to Luxembourg because it was close to Brussels and I felt bad about missing it on previous stopovers in Belgium.

In other words, there hasn’t been a real pattern until now. I’ve just gone where I wanted to, and not stressed over the details.

  • What about logistics?

I have no great system for dealing with travel logistics. A lot of things can be handled along the way, including things like not having a visa when you are supposed to, not having any idea of where to stay, etc. But I do also plan a fair amount for most trips.

If I really need them in advance, I get my visas from I hate paying fees for things like that, but I also don’t like the idea of sending my passport off to the consulate of Tajikistan or Burundi or wherever. I also don’t like the threat of being denied boarding for a flight somewhere because I don’t have the right piece of paper in my passport.

(I’ve seen this happen many, many times to people on flights to Africa from Europe. It’s not a good situation, especially when you consider that most African countries don’t exactly have embassies all over the place.)

When in doubt, therefore, I send my passport to the service in D.C., which takes it to the embassy or consulate in person.

Lonely Planet

I have a love/hate relationship with travel books such as Lonely Planet or Rough Guides. It’s true that you end up going to the same places that everyone else does when you rely too much on the books, but on the other hand, it’s hard to get reliable info for a lot of places in the world. I usually buy the better-reviewed one for a major region, then tear out the sections I want to take with me for reference.

Lodging usually has at least one low-rent option for most cities I go to. If I head further out, I can arrange that once I’m in-country. Sometimes I just show up and find a place to stay, and I’ve learned that this strategy works better in some places than others. In Bucharest, for example, I had a hard time finding a decent place to stay when I just showed up at the airport, but in Singapore, it wasn’t a problem.

Every 5-7 days when I’m in the developing world, I try to check into a relatively nice hotel. This helps me rest up, get connected to the world through email and Skype, and generally get a good plan in place for the next leg of the journey. I get my hotels through or with Starwood Points that I earn with my credit card spending.

I’ve stayed in some really nice places along the way, although I rarely pay more than $70 a night anywhere. I feel the same way about nice hotels that I do about flying First Class—I’m thrilled when it works out, but then I look around in amazement at the travelers who pay 3-5 times what I do.


One of my professors has a deal where he gets $20,000 a year to spend on travel, however he chooses. If I ever decide to get a real job, that will be a perk I spend some time negotiating for. Until then, I’m on my own.

In the meantime, I have no such stipend, a fact that is probably for the better. I certainly wouldn’t turn down a sponsor who wanted to help out, but I also don’t want to get too complacent. Instead, I have to make things happen myself, in whatever way I can.

I read a story a couple years back about another guy who was trying to see much of the world. He was a retired dot-com millionaire, so his approach was different than mine. He spent nearly $1 million on three years of travel, staying at every Ritz Carlton in the world and chartering private planes to take him throughout Africa.

Perhaps I’m prideful, but I think my style is more impressive. I’m out there on my own, no 7 or 8-figure bank account backing me up, no one telling me what to do. One time I took a U.N. military flight from Conakry (Guinea) to Freetown (Sierra Leone) where I was the only passenger, but that’s the closest I’ve come to a chartered plane.

Resourcefulness is a good thing, and I’ve learning to maximize my life to do the things I want to do most of the time. For that, I’m truly grateful.

And that’s pretty much how I travel. How about you?


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