Mark Danger Powers

4 Questions with Chris Guillebeau


When people suggest to me that I’m continually on the go, have a million things happening and seem to be everywhere at once, one person always immediately comes to mind for me: Chris Guillebeau.

We’ve both spent parts of our lives as jazzbos, both have had cats named after African countries, have both crept our way into cages with live tigers and both enjoy travel being an integral part of our work. Those similarities aside, we are also very different. The two biggest ways . . .

1. Chris is a whiskey drinker, while I prefer rum.

and 2. I stay “busy,” while Chris stays productive.

He’s regularly posting on his site, The Art of Non-Conformity … traveling tirelessly to complete his goal of visiting every single country in the world … generating stellar guides to help others conquer their own goals and businesses … maintaining his duties as kingpin of the Travel Hacking Cartel … writing bestselling books … AND coordinating one the biggest, baddest annual gatherings of creative entrepreneurs.


I don’t know how the man does it. While many of our respective goals are, and will continue to be, different, occasionally keeping tabs on what Chris is up to reminds [and inspires] me:

A) to make sure the work I’m doing is not just constantly chewing away at my time without moving me closer to my goals;

and B) that it is always possible to think bigger.

I’m guilty of often letting (as Stephen Covey would warn against) “urgent” but “not important” tasks come before the more “important” but “not [seemingly] urgent” ones. I’ve also found myself completing a project and, in hindsight, realizing that, with nearly the exact same amount of time/work/energy, I could’ve made the whole thing much bigger, more productive, more worthwhile, more valuable to myself and others.

Super quick to respond to messages, even while smack dab in the middle of his current book tour, Chris was kind enough to take a few minutes and share some thoughts on how he’s able to stay on top of so much while constantly on-the-go.


chris-guillebeau [MP] You are in and out of airports more than anyone I know. In what ways have you learned to prepare yourself and your carry-on and/or checked luggage to streamline this process (TSA, etc.) for yourself?

[CG] First up, I never check a bag— it’s always carry-on luggage, no exceptions. Next, having elite status with airlines and a Priority Pass membership helps with lounge access and (sometimes) faster screening. Also, it helps that I like airports. I don’t mind arriving several hours before a flight, since I can always catch up on work once I’m safely past the security checkpoint.


[MP] How do you manage to stay as productive as you do, amidst such a busy travel schedule?

[CG] I’m always working. Right now I’m answering these questions in the back of a cab to the Pittsburgh airport. Yesterday I had two events and an hour-long Wisconsin Public Radio show, so things got stacked up. When that happens, I triage. I did the radio show from a quiet room at the university where we had the first event. During the news break before we went back to callers, I had my laptop open and tried to work through a few things.

Then I went to the second gig, and then finally back at the hotel I spent another hour tackling stuff. Fortunately by that time it was well into cocktail hour, so I worked on my laptop from the bar with a nice Knob Creek Manhattan at hand.

I guess the greater point is that I love what I do. It’s not just about a compulsion to stay busy but rather a desire to create. I’m also fortunate to be able to earn a good living and work with interesting people all over the world. If you get a gig like that, you should treat it with the respect it deserves . . . thus you keep working.


[MP] Are there any particular personal or work rituals/routines (be they at home and/or abroad) that you regularly adhere to keep yourself on track?

[CG] Not really. But I do focus constantly on deliverables and outcomes. I’m always thinking ahead: what’s next? What can we make progress on? I get antsy when I’m falling behind or not making things.


[MP] Previous mentions you’ve made of David Allan’s “GTD” task and project organizing approach are what first led me to learn more about, and integrate, aspects of his system. It’s appears to me that you successfully apply his concept of simultaneously viewing [and pursuing] your life and work from several “altitudes.” Your continual juggling of blogging, traveling to accomplish current life goals, creating products, being a spouse, coordinating a fast-growing conference, and who knows what else, seem to be proof of this. Could you offer some suggestions on how to begin and maintain this?

[CG] Yes, I like some aspects of GTD, especially the parts about breaking down big projects into small, specific tasks and writing everything down to ensure it’s not stuck in your head. I’m not as familiar with the altitude perspective, but I guess the way I think about it is convergence. You can’t be good at everything, but you need to maintain some aspect of alignment between various projects, responsibilities and roles.

Several times a week I make a series of lists for each current project or focus. On these lists, my goal is to capture a couple of things. First, I want to capture the upcoming tasks or next steps. But I also try to note if there is anything that bothers me or I feel unsettled by. This usually relates to something I need to do or a relationship that needs more time or attention. Paying attention to how you feel, while not the only way to run your life, can be a good indicator of both your emotional wellbeing and your productive potential.


Thank you, thank you to Chris for the continued inspiration and for taking the time to share!


How about YOU? Have any of your own favorite productivity tips? Share them with the rest of us in a comment below!

(header photo by Chris Guillebeau)