“If You’re Always Future-Oriented, It Tends To Come At the Expense of the Present Moment.”

Portrait of Chris Guillebeau

I’ve known Chris for years. I don’t remember how we met, originally, but I’m a big fan of all his bestselling books and last year, I spoke at his terrific World Domination Summit in Portland.

I’m very excited for him, because his latest book is coming out tomorrow. I love the book, and I love the title so much, I wish I’d thought to use it first: The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life.

It’s not easy to dream big, and it’s not easy to turn that dream into reality. Chris provides the essential blueprint for people for whom the happiness of pursuit—such as Chris’s crazy successful quest to visit every country in the world!—is a key part of the pursuit of happiness. If you’ve always wanted a quest, this is the book for you.

I wanted to ask Chris about how he thinks about habits. For him, I know, it’s very important to feel free and to make the choices that are right for him. Some people (e.g. Rebels) think that habits are inconsistent with a life of freedom and choice—so I was curious to hear Chris’s perspective.

Gretchen: What’s a simple habit that consistently makes you happier?

Chris: Every day I have coffee and pastry of some kind around 3 pm. I say “around” 3 pm because it doesn’t need to be 3 pm on the dot—I’m not that obsessive. But there’s a window: 2:45 is acceptable, and so is 3:30. 4 pm is pushing it.  Once in a while I have a crazy afternoon with a two-hour long meeting or something right during the window, and we get into 4:30 coffee-and-pastry time. That creates a minor crisis, but yet somehow I overcome.

This habit has made me happy for a dozen years and more than one-hundred countries. (I should make some sort of coffee-and-pastry global index.)   

Do you have any habits that continually get in the way of your happiness?

Many people who pursue quests and other long-term goals are very future-oriented. They’re always working toward something and seeking to make incremental progress. They are “strivers,” essentially. Overall, I believe this is a healthy way of life. People who have hope and look to the future tend to be healthier, have better financial habits, and so on.

But—and this is no small problem—some of these habits can indeed interfere with happiness. If you’re always future-oriented, it tends to come at the expense of appreciating the present moment, something that we know has a lot to do with happiness. Therefore, their challenge is to continue focusing on the long-term goal, while making sure to occasionally look up and appreciate their current surroundings.

I wrote this answer in relation to the people I studied for The Happiness of Pursuit, but it could just as easily apply to me.

Which habits are most important to you? (for heath, for creativity, for productivity, for leisure, etc.)

My most important habits relate to creativity and productivity. Every day I focus on outcomes and deliverables instead of time-based commitments. I try to avoid impromptu phone calls, because I find them to be disruptive to creative work. I work with a to-do list in front of me. Sometimes I go off and do something else, but I find the list to be grounding and helpful when I get off track, which is often.

Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger?

I believe we’ve had this conversation in real life! About two years ago, you said I was a mix of Questioner and Rebel, with a bit more emphasis on the Questioner side of things. (I’d question that assumption, but that would be playing to type.) [Yes, I think Chris is a Questioner with Rebel leanings.]

Do you embrace habits or resist them?

I embrace them. Routine rules my life, perhaps sometimes to a fault.  For someone who’s been to every country in the world, I’m really more of a soft adventurer. Every day I do mostly the same things, from working off the to-do list to having my coffee at set times. I’ve forged a life around these and other habits. I always want to improve, of course, but I have no plans of answering the phone more often or quitting the pastry.

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