The 12 Most Common Questions I Get About Traveling the World (Part II)

I’m no longer going to every country in the world (mission accomplished), but I’m still traveling at least 200,000 miles a year.

As such, I get a lot of questions over and over, both from people who want to travel far and wide and those who just want to learn a few things to make their lives easier.

This series of three posts provides some attempted As to the Qs. This is part II; part I is over here.

  • Why travel? What’s the point?

Have you ever done something that brought joy to your life, even if other people thought it was stupid or just didn’t understand it? Well, that’s what travel does for me.

At first it was about discovery. Being out in the world, I felt different. I felt alive. Something had changed and it was intoxicating. The more I saw of the planet, the more I wanted to see.

Then it was about challenge: I wanted to go everywhere! I set a quest to visit every country in the world, and I accomplished that goal in 2013.

I didn’t stop after making it to country 193 of 193, though. Now it’s about lifestyle—it brings me joy, so I keep doing it.

  • How do you manage to work from the road?

Short answer: my work is my life, and it goes with me everywhere. As a general rule, if I’m in a city where I want to sightsee or explore, I’ll work through the morning and then take off for an adventure of some kind in the afternoon. Then I usually have another work session before dinner.

I like my work, so it’s not something I need to escape from. Also, my work enables me to travel. I’m not independently wealthy, so I couldn’t travel indefinitely without producing an income—and neither would I want to.

I also take a lot of long flights, where I have 8 hours or more to catch up on neglected emails and plan the next steps for my projects.

  • Can anyone do this? 

I’m well aware that traveling is easier for those of us who have passports from rich countries (U.S., Canada, Australia, New Zealand, European Union, some Asian countries, etc.). However, this community also has a lot of independent travelers from countries ranging from India to Iran. Visas may be more of a challenge, but it’s certainly not only Americans who can venture outside their homeland.

Chances are, if you’re reading this, you can access much of the world of travel. There are plenty of people in the world who can’t do that, of course. But most of them don’t read this blog, or any blog for that matter.

  • What’s the best way to book flights? 

The best way depends on lots of factors, but here’s a simple way: use Google flights to check a whole month’s worth of options at once.


Next, use Skiplagged (more info in this post) to check on an hidden-city ticketing options.


Those two sources are decent enough to get a quick look at basic paid (cash) fares. But for more significant trips, or if the price is higher than you’d like, you should also search for award travel.

Searching for award travel is a little more complicated. If you only have miles or points in one program, that’s easy enough—you just go to that program’s website and search from there. Note that results for all available partner airlines may not be displayed online, so in that case, you’ll need to call.

If you’ve been building miles & points balances for a while (and you should be!), then you’ll have a few different options. My “go-to” award searches include:

  • (for awards on Star Alliance partners) – Earn miles through Chase Ultimate Rewards, especially the Chase Sapphire Preferred® card

  • Aeroplan (also for awards on Star Alliance partners) – Earn miles through American Express Membership Rewards, especially the Premier Rewards and the Platinum cards

  • (for awards on American Airlines and OneWorld partners) – Earn miles through AA Citi cards, BankDirect, and ongoing promotions

There are other options, of course, but searching those sites will help at least 75% of the time.


I hope that’s helpful—stay tuned for part III!


Images: 1, 2, 3, 4, & 5

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