Several years back a colleague recommended Chris Guillebeau’s The Art of Nonconformity, which was a real eye-opener to me. The book challenges readers to think about unconventional ways of doing life and making a living, and honestly I’ve never been the same. I can draw a straight line from his book to the creation of Book Proposal Academy, for example.

Another thing I learned from Chris is travel hacking, which is the practice of traveling without having to pay for it, or at least not having to pay very much for it. Travel hacking enabled my wife and me to fulfill one of my wife’s lifelong dreams: for our tenth anniversary we went to Switzerland, flying there for less than $300.

So I owe a lot to Chris, and I’m grateful for his work. I’m particularly grateful for his latest book, The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life. Chris traveled to every country in the world, all 193 of them, before age 35. Quite an accomplishment, but it was because of this project that he became interested in other people’s quests.

This is a fun book not only because it inspires you to think about what your own quest could be. It’s also fun because of the great people you meet along the way, like a lady whose quest is to make 10,000 hand-knit hats or a guy who mastered all of MIT’s curriculum on his own in a year or another guy who ran 250 marathons in a year.

As I read the The Happiness of Pursuit, I started jotting down questions I had about how Chris wrote his book. I took a chance, sent him the questions, and he wrote back! So I’m excited to bring you this interview. I hope you find it as interesting as I did.

Chris, your first book was about doing life differently than culture’s predominant script. Your second was about entrepreneurism. How would you say your most recent book, The Happiness of Pursuit, relates to the first two?

The new book is my most personal one. It’s essentially the story of quests, including my own and many others, along with a prescriptive message: pursuing a quest or embracing a life of adventure can bring purpose and meaning to your life, no matter who you are.

Which came first: the structure and themes of the book or the stories? To what extent did you know the themes you wanted to cover even before you started story gathering?

Great question. In this case it was a bit of both. I began writing with a structure in mind, but the structure often shifts as I gather data and conduct interviews. I knew I wanted to write about the lessons of quests and adventures, but in true quest fashion, a lot of things changed along the way.

What was your biggest “Aha!” as you gathered material and wrote the book?

Many people struggle with articulating their motivations for beginning a quest. It often begins as what they describe as “a crazy idea that wouldn’t leave me alone.” But over time, as they pursue their crazy idea, they gain confidence. The confidence comes through experience; it’s not a pre-existing condition.

This is important because many people say they could never do something as incredible as some of the people I write about. But they can! They just need to start with an initial vision, even if it’s not fantastic in the literal sense of the word. Confidence comes through experience. [Tweet that!]

How did you gather the stories?

I put out the call far and wide, starting with my own community of 75,000 awesome people and eventually extending far beyond. I wanted to find a wide group of stories so that everyone could relate to someone or something.

About how much of the content did you blog in one form or another before it made its way into the book?

Very little. Maybe 5-10% maximum, sometimes for a sidebar or exercise, but always modified and edited for book publication. Writing a book is not like writing a blog.

In general, do you thinking blogging a book is a good idea?

I think it’s a terrible idea. Books and blogs are both wonderful mediums, but they are very different mediums. Most blog-to-book projects do not perform well commercially, and (perhaps more important) they aren’t very readable.

Of course there’s a lot of overlap in the craft of writing, the need to engage with an audience over time, etc. But on a blog you don’t usually have to worry about the matter of building an arc or sustaining a narrative throughout 50,000 words or whatever. And if you forget about that imperative when writing a book, it’s not going to be a great book.

What advice do you have for writers who are just getting started?

Build habits into your life. [Tweet that!] Lots of people say “Think outside the box,” but don’t do that—construct yourself a box and get in it. Decide for yourself: “I’m going to be a writer, and here’s what that looks like. Every day I’m going to write x words. I’m going to share my life online”—if you so choose, of course—”and I’m going to work toward the deliverable of my first book, my first 50 posts, or whatever I set as my goal.”

I’m sure you’re hearing a lot of people who say “Hey Chris, here’s what I’m thinking about for my quest….” and then they tell you what they have in mind. How do you typically respond?

I usually say “That’s great.” I try not to be in the pattern of offering unsolicited advice. But if prompted for advice, I’m usually interested in understanding more about how they’ve set the parameters of the quest and what the structure is. Again, structure is your friend. In writing or questing or life in general, structure will help.

What would you love to see happen as people read The Happiness of Pursuit? 

Here’s what I don’t want: I don’t want someone to read the book and say “That was a good book.” At least that’s not all I want. I want them to read it and say, “That was a good book, and it helped me think differently about something. Now I’m going to make some kind of change in my life.”

I think that’s the goal of prescriptive non-fiction: to win over the reader, take them along for a journey, and leave them in a better place than they were when they started.

Question: What’s your quest? Or what are you thinking about making your quest? You can leave a comment by clicking here.