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

Habits interview with 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.

Why the Issues that We Ignore Often Come Back to Plague Us.

Novelist Paul Auster wrote a memoir, Hand to Mouth: A Chronicle of Early Failure.

He writes, “By the end of 1977, I was feeling trapped, desperate to find a solution. I had spent my whole life avoiding the subject of money, and now, suddenly, I could think of nothing else.”

This reminded me of a thought-provoking interview I did with personal finance expert Zac Bissonnette a few years ago. I’ve never forgotten a story he told:

A few years ago – when I was in high school — my dad was going through a ton of financial problems that culminated in him living at a friend’s house.

My dad was born in 1948 and is a classic hippie; He lived in a tree-house in a state park for a while in the early 1970s, he’s a carpenter, and he is probably the coolest, most loving person I know.

But he’s never really given much thought to money. He always said that it wasn’t important to him and that it didn’t matter. So I was sitting on the couch with him at his friend’s house watching the Red Sox…and I asked him, just off the top of my head: “Who do you think thinks about money more? You or Bill Gates?”

And I’ll never forget his response: “Without a doubt, me. I spent my whole life thinking I was above money and that it didn’t matter and now it dominates my life and is all I think about. It’s like money is exacting its cruel revenge on me.”

I interviewed you [meaning me, Gretchen] once for a piece and you told me that “Money affects happiness primarily in the negative” and that’s exactly right. When it comes to happiness, the less money matters to you, the more careful you need to be with it. If you don’t like thinking about money and don’t pay enough attention to it, it will one day become all you think about.

I think this is true about money, and I think it’s true about habits. All too often, the areas of our lives that we decide to ignore can become the areas that dominate our lives, later. And not in a good way.

Perhaps this happens most with health.

Habits allow us to put a behavior on automatic, so we don’t have to think about it or make decisions related to it anymore. In this way, habits can free us from the things we don’t want to think about.

For instance, if you hate to think about money, you might decide to follow the habit of never carrying credit cards, so that you can’t impulsively buy things that you can’t really afford.

My sister told me, “Now I’m free from French fries.” Not everyone would use habits the way she did, to get free from French fries — the Strategy of Abstaining doesn’t work for everyone — but habits can bring freedom.

This idea, of how habits can be confining but how we can use them to feel free, is a big theme in my forthcoming book about habit formation, Better Than Before. If you want to hear when it goes on sale, sign up here.



“A Rush of Superiority Which Afflicts All Those Who Are Astir Earlier Than Other People.”

“He looked up at the grey house; all the blinds were down, and he instantly despised his guests for being still asleep, in a rush of that superiority which afflicts all those who are astir earlier than other people.”

— Vita Sackville-West, The Edwardians

I’m an early riser, and I love getting up early — and I also definitely feel a bit smug about it. But I’ve also noticed that people who stay up later also feel a rush of superiority.

Perhaps this helps to explain why people are so reluctant to turn off the light earlier. I talk to people who are chronically exhausted, but who reject indignantly the notion that they might go to sleep earlier.

Partly this is because for many people, the last few hours before bed are their free time, and they hate to give up their free time.

I hadn’t realized it until I read this passage, but I do think there’s also a feeling of superiority, or of getting away with something, of getting more life out of the day, or having a secret world that most people don’t see.

How about you? Do you feel a “rush of superiority” if you’re awake while others are asleep?

Before & After: “Odd Days, I Do Everything I Can for Mom. Even Days, for Me.”

I’m writing my next book, Better Than Before, about how we make and break habits– an issue  very relevant to happiness. Each week, I post a before-and-after story submitted by a reader, about how he or she successfully changed a habit. We can all learn from each other. If you’d like to share your story, contact me here.

To hear when Better Than Before goes on sale, sign up here.

This week’s story comes from Penelope Schmitt, who, as she notes, lives with her 90-year-old mother.

Bureaucratic, medical, and business tasks take up more and more time for those who are older. Doctor appointments abound, and business management goes on and on. I hate these tasks, and have been finding that doing things for TWO people that I hated doing even for one person, and that myself, was pretty burdensome. Last week, I hit on this blindingly simple idea:


ODD days: I do everything I can to complete business that needs to be done for Mom, shopping or doctor appointments or whatever. I don’t think I’m even going to care if I sound like a nutcase asking for appointments on calendar days with odd dates. ODD days are her days, and I have a special commitment to go the extra mile for her on those days–to make her life pleasant, as well as to take care of her business. 


EVEN days: I do everything I can to complete business that needs to be done for ME. I do something special that is fun for me alone (like a manicure, or a walk at the mall). I do not have to do one single non-emergency bureaucratic task for anyone else but me. 


In one week, this has resulted in me having the fortitude to address dreaded tasks for her, because after all, tomorrow is MY day. And it has also resulted in me getting my own business done, because tomorrow I won’t be able to. I feel more free to enjoy the things that I am doing to make my own life feel better, and I feel that the ‘indefinite sentence’ of taking care of her business has been lightened by 50% because I do not have to address it (or choose to ignore it) every day. It is only my job every OTHER day. 


What a revelation. 

There are a few things that I think are worth noting about this Odd/Even approach.

The Strategy of Treats: it’s a Secret of Adulthood for Habits: When we give more to ourselves, we can ask more of ourselves. By specifically acknowledging that her needs were just as important as her mother’s, and finding time do the things she wanted to do, Penelope was able to be happier, and also more helpful to her mother.

The Strategy of Scheduling: for most of us, there’s a magic to seeing something on the schedule; if it’s on the schedule, it happens. So, especially for people who have trouble saying “no,” the Strategy of Scheduling can be very helpful–they can schedule time for themselves. Scheduling allows us to make time for everything that we value, by putting it on the calendar.

The Strategy of Clarity: when we know exactly what we’re asking of ourselves, and exactly what we want, it’s easier to keep a habit. This Odd/Even approach is very clear. It makes decision-making and planning easy. It eliminates a lot of hesitation and uncertainty. Making decisions is very draining, and one of the chief benefits of habits, generally, is that they eliminate decisions.

This idea is so simple, and so appealing. Have you ever tried anything along these lines?


Secret of Adulthood: Don’t Believe Everything You Think.

Further Secrets of Adulthood:


Agree, disagree?

This reminds me of the ten categories of loopholes. With a lot of loopholes — especially those in the Questionable Assumptions category — if you look at them closely, you realize that you don’t really believe what you think.

I have a chapter on the Strategy of Loophole-Spotting in Better Than Before, my forthcoming book about habit formation. (Sign up here if you want to hear when the book goes on sale.)

I love all the habit-formation strategies, but I have to say, Loophole-Spotting is the funniest strategy. I get a real kick from identifying loopholes. There are a lot of loopholes.