Editor’s Note: As we finish writing When Fear Blinks: How to See through Your Fear, we’re interviewing people you know doing scary things. Everyone has fears, even really successful people, and learning to do things in spite of them is one element to Living the Good Life.
It’s Friday the 13th. Are you happy the weekend is almost here or nervously looking out for black cats (please don’t look to your right!)
If you think Friday the 13th is scary, try producing an international 500-person conference humbly titled the World Domination Summit on the far western edge of the US without corporate sponsorship or previous event management experience. No pressure, huh?
Chris Guillebeau is first in this series because – hello – he is the leader of something called the World Domination Summit.
Rather than picturing Dr. Evil in his underground lair stroking the hairless cat Mr. Bigglesworth, you can picture a guy who looks more like a clean-cut bike messenger. I’m pretty sure he doesn’t even own a suit, and his only vice seems to be Chipotle burritos. That’s part of his charm, and also his secret weapon. He is Everyman. When he succeeds, we realize we can, too.
(Interesting side note: he does have a sidekick cat, so perhaps this is a requirement of all masterminds, no matter what their philosophical bent. Keep this in mind as you plot your takeover.)
I interviewed Chris recently on the subject of fear, half expecting him to tell me he didn’t have any. Silly girl.
The Interview
Q: The World Domination Summit turned out to be a huge success, but you probably had some doubts and fears at the beginning about putting on an event of this magnitude. What were some of your biggest concerns, and how did you learn to work through them?
A: Yes, I definitely had some doubts and fears. Probably the biggest was… how do we do this? How do we produce an event for 500 people, many of whom have never visited Portland before?
One of the things that helped was in realizing that most of the attendees were extremely motivated to be there. They were excited to come to Portland, and they were excited to meet old friends and new friends. I think our biggest success came in thinking about how we could channel that excitement (“ride the wave…”) and make the event overtly about them, instead of a bunch of strangers coming to watch a production.
Of course, I’d be remiss if I didn’t mention that this effort wasn’t mine alone. We had a core group of WDS leaders who worked on the event nine months in advance here in Portland, and we were joined by an extended group of volunteers (“ambassadors”) for the actual weekend. Finally, the speakers and workshop leaders volunteered their time as well. So it was definitely a group effort.
Q: What impact do you think having a goal bigger than yourself has on your fear? If WDS has just been the Chris G show it would have been an entirely different beast than the “ya’ll go out and do awesome shit” show, don’t you think?
A: Yes, and it would have been terrible! As mentioned above, it was never my goal to make it all about me. The funny thing is that it’s actually easier to make it about other people and deflect some of the attention. And in the long-run, it will probably be more helpful for whatever else you’re trying to build as well.
Q: How do you think people can determine whether something is scary because the compass is pointing north and you know it is right for you or scary because you shouldn’t do it?
A: Here’s an example, since we’ve been talking about WDS — when I first had the idea to invite a million people (OK, 500 the first year and 1,000 for year two), I was immediately excited, but also scared. As I thought it through, I knew I would regret it if I didn’t make the attempt. I wasn’t sure it would be successful, but that’s another story.
I often use the same question when considering various projects and ideas: will I regret it if I don’t try? Notice that you don’t usually feel this way about things that are actually harmful to you. If I applied the same logic to putting my hand on a hot burner, I’d think: “Would I regret it if I don’t try? Nope, not really.”
Q: What are your top 3 practical tips on moving through your fears to do big things?
- Don’t pretend to be fearless. Everyone’s afraid of something, so you might as well acknowledge and work with your fear instead of pretending it doesn’t exist.
- Don’t let fear make your decisions for you. (In fact, the things you are afraid of may very well be related to the things you need to do.)
- Sometimes it helps to get to the root of the fear. What are you really afraid of? It’s often not the obvious thing, but rather something indirectly related.
For example, like a lot of people I’m somewhat afraid of public speaking. But when I think about it more, I realize I’m not actually afraid of the speaking itself, but rather all the feelings of trepidation that come before it. The actual speaking isn’t usually a problem, and when I learned to reframe it this way, it helped me get a lot more comfortable in preparing for talks.
I think the same principle holds true elsewhere: we’re not always afraid of what we think we are, so it helps to puzzle it out a bit.
Q: What are you working on next that people should stay tuned for?
A: I’m excited about WDS 2012, taking place July 6-8 in Portland again. But before that, my book THE $100 STARTUP (Editor’s Note: You can preorder now on Amazon) comes out in May. I’ll be doing a tour to meet readers in at least twenty cities in North America, and then at least a dozen other cities around the world. It’s been a while since I’ve been on the road for book stuff, and I’m looking forward to getting back to it.
Fear-Blinking Strategies
You already know how it turned out for Chris in 2011. But what about 2012 – can he duplicate his success? The tickets sold out 13 minutes after going on sale 9 months ahead of the event, so I’d say he was on the right track.
His strategies work, and here’s how they can work for you:
- Will I regret it if I don’t try? I love this lesson. You don’t know this, but regret is one of the main subjects we get via email. People have regrets as they get older, or they tell us about someone who recently became ill or died without accomplishing what they wanted most in life, and it is heartbreaking. Your end-of-life regrets might motivate the people around you to do great things, but they won’t do a damn thing for you. Ask yourself this question next time you get scared.
- Rally your tribe. You don’t have to go it alone, and you’ll do more and do it better when you ask for help and feedback. Tell just one person about your idea and see how much more momentum you have to get it done.
- Examine your fears. There’s a message in there, a roadmap, a self-discovery that will allow you to propel yourself further than you imagined. I like the “multiple why” approach: keep asking yourself “but why?” and answering until you hit an uncomfortable truth. Now you’re on to something.
Many thanks to Chris for being so candid with us. Check out his website to learn more about unconventional living. Who’s next in the interview process? You wouldn’t believe it if I told you. Stay tuned…








Happy Friday the 13th!
So honored to be here - you guys are doing great work.
All the best with world domination, overcoming fear, and everything else.
Thanks, Chris. We like getting some of the behind-the-scenes info on building something great. It is incredibly motivational for people to see that very successful people still have doubts and fears - they just learn how to work through them and even use them to fuel their activities. Thanks for sharing your story.
Thanks Betsy - and Chris - for this great interview. I loved your Litmus test for taking the plunge: will I regret this later? When facing tough, scary decisions, one of my older brothers used to say that your heart’s already made a call but the brain just needs to catch up! This quick-reaction question is a great one for getting to what your heart really wants.
I’d love to share this bit from a speaking engagement I did for women business owners, called Face the Fear. It’s about how I faced down the fear that enveloped me after a near-fatal brain aneurysm. I also related this “life lesson” to your own business efforts. Enjoy! http://vimeo.com/25093750
I love this, Maria - “embrace the fact that you’re supposed to be scared because you are blazing a trail and accept the fear…Just get on with it.”
Readers, we’ll be interviewing Maria in a couple of weeks about her recovery from a brain aneurysm and what that taught her about working through her fears. For those who don’t know, Maria’s health crisis was a big instigator in our decision to change our lives. It is a powerful story, and one you don’t want to miss.
What an awesome interview Betsy! Thank you for interviewing one of the greats for your readers. It was Chris’ book that inspired us to conquer our own fears and travel the world full-time just as you and Warren are doing.
Such an inspiring and timely message. Keep up the amazing work. You’re an inspiration to all!
Hi, Marvin. We loved having Chris share his thoughts on fear unrelated to travel, since we all know he does that very well. Most people won’t start their own international conference, but we will all face personal challenges and goals that are just as big to us, and this is a great example of how to do it. Thanks for joining the conversation - we’d love to see you back here again!
Great interview! Hearing from Chris is always inspiring. It is so true that the things you fear are probably the things you need to do. It’s not always easy but I don’t think anyone ever regrets trying.
Hi, Erin. That’s a great litmus test. I remember writing about this some months ago when we interviewed Sherry Ott just before the Mongol Rally and she said her gauge for these kinds of things is the fabulous “does it scare the shit out me?” question. I like Chris’s example with the hot burner because it gives another layer of thought for those who might actually want to touch the hot burner
Great interview! I was at WDS last year and it was an inspiring and life changing weekend… and I don’t just say that. I am working on a new project that was born at WDS and I made some connections with people that have inspired me to take a different look at life. The event was ridiculously well organized and everything flowed perfectly. Through it all, Chris’ humbleness was always evident. He really is everyman and it that really does help others believe that they can do amazing things too.
I won’t be at WDS this year because we’ll be living our dream of traveling the world… I met so many others at WDS that were doing the same thing, I left feeling as thought it was the most normal thing in the world.
Kim, I can imagine this was exactly the kind of response Chris was looking for when he started the summit. And how cool to meet other like-minded people who make you think your wildest dreams are just a regular Tuesday, totally achievable and acceptable. Everyone should have that!
Great interview Betsy!
I’ve been a fan of Chris since the early days and also following you as we recently quit our jobs and have begun our own three year trek around the world by road. Letting go of fear - as well as the crap in our house - was a big part of it all. thanks for the great info.
Wendy, it is amazing how much you get back from letting go, right? No one understands it until they do it, and then it is crystal clear. Best lesson I’ve ever learned in my life. Happy travels!