Chris Guillebeau is definitely an entrepreneur. More than that, he’s an entrepreneur that doesn’t believe in conformity. Chris is the New York Times best-selling author of ‘The Art of Non-Conformity,’ and the ‘$100 Start Up.’

Chris describes himself as “being self-employed for life.” His resumes boasts having worked on a hospital ship in West Africa for four years, and he traveled to every country in the world (193) by his 35th birthday.

Chris is a man who doesn’t talk the talk. He lives his message. He writes, speaks, and throws amazing conferences that help men see what’s possible. He leads by example. 

I had the honor of interviewing Chris about his new book, ‘The Happiness of Pursuit.’ Chris was gracious enough to send me an advanced copy, and in my opinion, he hasn’t lost his touch. Here’s our talk.

How can an entrepreneur keep the hope of their dream alive when they seem to be making little or even no progress towards it? 

I’m not sure the best answer is to always keep the dream alive. Sometimes dreams need to die to allow other dreams to birth and grow. Most entrepreneurs go through a cycle of many different businesses and projects over time—so you shouldn’t necessarily stick with something that isn’t working.

That said, if you do believe in what you’re doing, and it’s just hard at the moment, then it helps to focus on the long-term outcome. What are you trying to make? Will you regret it if you stop? For me, in visiting every country in the world, I thought about that a lot.

What advice would you give to the solo entrepreneur who wants to build a profitable business?

Focus relentlessly on how your work can help people or otherwise improve their lives. That’s ultimately where value is found, and hopefully profitability, too. 

You’re a New York Times bestselling author, you have a wildly popular conference, and an incredible website. Your business has exploded; do you have a team that helps you with the business? How big or small is that team?

It’s a very small team. For World Domination Summit, the annual event, we do ramp up to a bunch of folks as we get closer to production, but most of them are volunteers or other people who just believe in the experience and want to participate somehow. Aside from that, I work with a few people on specific projects, but I don’t have any full-time employees.

Chris Guillebeau
Jonathan Fields interviews the efficient traveler.
YouTube/The Good Life Project

How many emails do you get a day? Do you have s system?

A lot. Maybe 200-300 … it’s hard to say, and it varies. My system is: “just keep swimming.”

I do like a tip I learned from Chris Brogan years ago. The short version is that we all get overwhelmed and behind, so when we have that big queue of emails from many days ago, it’s a struggle to go through it and begin each message with a long apology. So his advice, and again I’m paraphrasing, is: “Don’t worry about the long apology. Just say, hey, I’m sorry but is this still current? What can I do for you?”

But yeah, I get behind. 12-hour flights help. I write a lot of emails on planes.

How do you stay productive? I realize not every day is typical, but what would a typical day look like for you?

Yeah, no day is typical, but when I’m home in Portland, Oregon I do try to follow a pretty basic routine. I go for a short run in the park and then spend most of the morning in my office. I try to complete as many commitments as possible before 11am, because then I know I’ll start to slow down. I try to reserve phone calls, interviews, and meetings for the 11am – 2pm time period, when I’m not super productive.

Every afternoon I take a coffee and pastry break. I try to read for half an hour or so, usually fiction. I might have another call or interview. Then, from 4pm-6pm, I have another work session. I take a break for dinner and then do a few more emails or something small before bed. 

What’s a valuable tip you would give to Entrepreneurs about productivity?

Just as you should focus your long-term efforts on how your work will help people, you should focus your short-term efforts on deliverables and outcomes. Always keep things moving forward. If you’re the kind of person who likes to work on multiple projects, that’s fine —don’t listen to the people who say that’s impossible. But it does require a certain skill of triage and continuously getting stuff out the door. 

Lastly, one final note: if you can find the life you want to live, be grateful and do everything you can to protect it. Such a thing is rare and beautiful. 

I want to thank Chris for taking the time to speak with me. His new book ‘The Happiness of Pursuit’ released September 9th, 2014.  The book is filled with stories of ordinary people doing extraordinary things. Life is too short to ignore the quest that’s in your heart. Chase those dreams and die with no regrets.