How Bloggers Earn a Living: Chris Guillebeau

Customer Stories State of Blogging
6 min read

You know that friend you have who does tons of traveling and you’re always like “Argh. Why didn’t I start traveling sooner? I wish I could travel more and really live the life I’ve dreamed of but it’s just too late. Oh well, I’ll just go back to this muffin.”

Yeah, me too.

And, to be honest, I’ve always been a little envious of my traveling buddies but never really had the gumption to actually travel more. Outside of a few trips (England, Mexico, Bahamas, Canada) I haven’t been around the world much. And I thought I was doing pretty well with the whole passport stamp situation… until I met Chris Guillebeau.


Chris Guillebeau


Now you might know Chris a little bit already. After all, he’s the founder of World Domination Summit (an annual conference for remarkable people), Pioneer Nation (a smaller conference for equally remarkable people) and he’s made his way to every single country in the world. Yep. All 193 countries.

But when I met Chris that was all I really knew. He travel hacked (whatever that means) his way around the globe and has this big conference/event every year in Portland that I constantly have FOMO about. Turns out, there’s more to Chris than a 20,000 foot view from an airplane.

Chris Guillebeau wants to help you see the small things and turn them into a big impact.


inside of book


I recently asked Chris about what he means by that, how he does what he does, and what exactly “travel hacking” is anyways.


What’s your name and what do you do?

Chris Guillebeau, pronounced “gil-a-beau” or however you’d like to pronounce it. I’m a writer, traveler, and entrepreneur.

How long have you been in business?

First business: age 11, when I tried to start a shoplifting ring with three of my friends. Though the potential for recurring income seemed high at the time, an initial  market analysis proved that the endeavor was not sustainable for a variety of reasons.

A few years later I dropped out of high school and snuck into community college. From graduation onwards I never had a real job and always worked for myself one way or another (no more shoplifting—I don’t like malls).

I’m 37 now, so I suppose the direct answer is… approximately forever?  

So what is travel hacking?

Essentially it’s a way to see the world for free. There are lots of ways to do it, but the cornerstone of travel hacking is to maintain multiple accounts of Frequent Flyer miles and points. As your balances build up over time, you’ll be able to redeem the miles and points for valuable rewards all over the world.

I wrote more about the details and my experience with travel hacking here.

What is your day to day like?

Great question. I travel nearly half the time, all over the world, so there’s not really a typical day. However, I do try to keep as many morning hours open as possible for writing + connecting.

Editor’s note: read more about Chris’ morning routine – it’s the same no matter where he is! – right here.

Then in the afternoon, I’m usually in meetings (if I’m home in Portland) or out and about exploring somewhere if I’m on the road.

When I have a book out I do events in the evening in a different city each day, so much of the day is taken up with travel to the next city. But throughout the process, I’m constantly trying to both keep up and work ahead, which sometimes works well and other times doesn’t.




How many different revenue streams do you have?

There are probably 6-9 in total, but several of those are fairly small. In general I’d estimate that I earn roughly half my income through writing books (yes, some authors actually make money) and the other half through entrepreneurial ventures like events, speaking gigs, World Domination Summit, and Pioneer Nation.

Do you have a plan to grow your business more? Why or why not?

Yes and no. I’d love to grow my business more, but not at the expense of the routine I have. I don’t have a ton of employees and don’t want them.

What is your definition of success?

Continuously improving my circumstances, and continuously working to improve the circumstances of others. Put more simply, I want to “live the dream” (my dream) and help other people achieve theirs.

What advice do you have for someone starting their blog today?

Don’t look to the past to guide the future. What worked before won’t work now.

What’s happening now is very different: native social engagement (not “use social media to drive signups on your blog” but rather “meet people where they are”) is difficult to master but extremely powerful for the few who do.  

This approach won’t work for everyone, of course. But if you want to focus on what’s coming, this is it.

Also, the next big thing is small. Those who can connect authentically with a group of people who share values or goals can still be very successful. Experts have always said “it’s not about the numbers” but the reality is that most of those experts have been very focused on growing their numbers. Now more than ever, it’s really not about the numbers. It’s about the depth of the connection and the uniqueness of the message.


book on the beach


And, boy, does Chris have a message. With three books under his belt already, Chris Guillebeau is an accomplished author but that’s not stopping him. Earlier this month Chris released Born For This – the book that helps people find their very best work.

In Chris’ words:

This book is the culmination of years of research on people who’ve found or created their “dream job.” From the outside, it looks like these people have been lucky. But in reality, they’ve followed a process of trial-and-error to get exactly what they want.

You can find your best work (we promise, it’s out there) and Chris is here to be your guide. AND……

We’ve gotten ahold of 30 copies of Born For This and we’re giving them away for FREE!

All you have to do is sign up for the giveaway here.

Born For This Book Giveaway

As part of the giveaway, you’ll gain access to ConvertKit’s weekly articles of strategic advice for professional bloggers and email marketers. But hurry. This giveaway ends at midnight PST Monday April 25th.  

Chris said he would trade in all his frequent flyer miles if it would help you succeed, but the airlines don’t offer that kind of trade. I know, sad face. But he did pull together some extra bonuses to go with the book!

Enter the giveaway and if you win one of the 30 free copies of Born For This, you can register the book and get $147 worth of other resources completely free.

So don’t forget to enter the giveaway and share it with others… sharing = more chances to win!

Born For This Book Giveaway

Val Geisler

Val is a yogi, mom, military wife, and avid podcast fan. She is ridiculously obsessed with sharing and creating content that actually makes a difference in the world, connecting with her fellow bloggers, and doing more with less effort. Val is based on Columbus, Ohio (O-H!) and can often be found oversharing on Instagram at @lovevalgeisler.

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