The Productivity Giants Series with Chris Guillebeau, Authors & Entrepreneur


Have an interest in starting a side hustle or full-blown entrepreneurship? Then, you’ve probably heard of Chris Guillebeau and maybe checked out some of his books: Side Hustle, The Art of Nonconformity, and The $100 Startup. Chris runs his personal website as “a home for unconventional people doing remarkable things.” An avid traveler as well, Chris has visited every country in the world in the past 10 years, writing the whole way.


For 10 years, Chris’ life motto has been “You don’t have to live your life the way other people expect.” It’s the value he tries to express throughout all his work in one way or another. His hope is that people will find a certain degree of recognition and belonging in something he makes, either in his podcast, books, a live event, etc.



“I’m not trying to tell people what to do, and I don’t think I ever have. What I try to do is give people tools and resources to expand their freedom and options, so that they can do what’s most important to them.”



If you consider yourself a non-conformist and want to live a non-traditional life – this interview is for you. Read on for productivity tips and more from Chris.


How often do you check your inbox?


Usually throughout the day.


Without fail, I find that the people who have “Sorry, I’m too busy to talk to you” auto-replies are the *least* productive people. I think it’s especially ironic when I receive one in response to someone who’s pitching me about something.


I don’t check email every 5 minutes but it also doesn’t bother me to go back and forth between it when I’m doing other things. Only when I’m in “monk mode” and writing a book do I really turn it off.


#1 Email tip?


I’m either very fast or very slow with email. If something slips beyond two days, odds are it will continue to slip—so I try to avoid that whenever I can.


What bad advice do you hear often?


“Never give up” or “Winners never quit.”


This is absurd advice that has somehow become entrenched in western culture. Real winners give up on plans and ideas all the time. They aren’t afraid to walk away from something that isn’t working. Maybe it was a mistake, maybe it was a learning experience, or maybe it worked for a while but now it’s time to move on—all are valid reasons for changing course.


Stick to your mission but never be afraid to change strategy or tactics.


What’s your definition of productivity?


Doing the most optimal amount of the work that makes the highest possible impact. Oh, and doing that without getting stressed out or anxious.


I added the second part because for years I only focused on the first. It wasn’t that my work was making me anxious, it was that I’d neglected some other areas of my life that contributed to all-around anxiety. So now even though I love to work and believe in working hard (I don’t take a lot of vacations…), I try to be mindful that I’m doing the right things, not just what’s in front of me at the moment.


Maybe on the last point, I try to control the environment of “what’s in front of me at the moment.” Right now I’m writing these answers and I’ve promised myself not to get up from the desk or change tabs until it’s done. Then when I’ve finished, I can cross it off my list, feel good about a small accomplishment, and move to the next thing.


What have you become better at saying no to?


“Let’s jump on a quick call…” <– this is my least favorite phrase, especially when coming from people I don’t know.


I realize that some people think these calls are more efficient than email, but:


  • Most quick calls end up taking longer than promised
  • Even a quick call is disruptive
  • For those of us who are introverts, taking calls from strangers depletes our energy in a way that email and other forms of communication don’t


Note: if you like these kinds of calls or find them effective, great! Just don’t assume that everyone does. I say no to almost every one of these requests.



Follow Chris on Twitter.