Kicking Conformity’s Ass – An Unconventional Interview With Chris Guillebeau and a Contest

Today’s post is going to be unusual, in a really great way. 

A few years ago, I stumbled across the blog of Chris Guillebeau.  I read his free 279 Days to Overnight Success and then quickly read everything else he had written.

I was so inspired with Chris’s story that the very next day I decided to turn Nerd Fitness, a domain I had sat on for a few years, into a blog and start helping people get in shape.

On top of that, In late 2010, it was Chris’s travel hacking advice that helped me create my $418 adventure around the world that really put Nerd Fitness on the map.

Chris recently released his second published book, The $100 Startup.

His work has inspired and pushed me to become a better and more adventurous person, so I wanted to help him spread the word and maybe even inspire you to do the same!

Join me as I interview Chris about his transformation from a risk-averse, generally shy guy…to a risk-averse, generally shy guy that does awesomely inspiring things.  Enjoy!

The Interview

 Steve: Hey Chris!  Thanks so much for taking the time to hang out with the Rebellion today.  A few years back, you made the decision to visit every country in the world before you were 35. Why pick such a crazy goal?

Chris: In some ways, the goal picked me instead of me picking it. I had been to about 50 countries (mostly through volunteer work) when I set the goal of visiting 100. Then I realized that going to a set number of places would always be an easily achievable goal, since you can pick and choose among countries and therefore avoid the hard ones.

That’s when I decided, what the Hell, let’s go everywhere!  Every good goal has a deadline, so I picked April 7, 2013—my 35th birthday. It’s coming up in less than a year now, but I officially decided on it way back in 2006.

Steve: Great point on the deadlines. Now you do a lot of traveling and go on almost all of these adventures alone.

Are you naturally an outgoing, risk-taking person? Or do you have to kind of force yourself while traveling to be more adventurous and risky?  It takes guts to visit Eritrea without a visa!

Chris I’m not naturally outgoing or pro-risk at all; I’m both introverted and conservative by nature. In the beginning, there was indeed a bit of forcing myself to become more comfortable with adventure.

In almost every case, though, I realized that adventure was worth it. And when it comes to risk, I also came to see that the greatest risk was to avoid making important choices. Once I decided that I didn’t want to miss or regret anything, it got a lot easier. I’ve increased my tolerance for risk, and that feels good.

Steve: You inspired my Epic Quest of Awesome, as I’ve found it more fun and much easier to find success when I always have something to be working towards. How important was it to have a goal like “visit every country” in the world?

Chris: You nailed it—having measurable goals and specific deliverables helps a lot. When I was first thinking about these things in 2004 or 2005, I made a list of “5 Year Goals.” This list included things like run a marathon, earn a Master’s Degree, visit 30 specific countries, and so on. There were maybe 30 or so goals on the list, and most of them were fairly significant.

However, I learned that once I had merely identified the goals and put them in an active verb, specific outcome format, I achieved them much earlier than expected. In fact, I was done with most of the five-year goals within less than two years.

I don’t think this is because I was superhuman or somehow special; I think it’s because I had specific outcomes and knew what I was working toward.

Steve: Great point – determine your level 50, and then work every day towards that. So, you only have a few countries left at this point; back when you set the goal, did you believe it was possible?

Or did you pick the goal specifically because you thought it was impossible?

Chris: I thought it was somewhere between possible and impossible.

In other words, I thought of it as a huge challenge—something that could be done, but would almost certainly require a lot of work and sacrifice. Once I set the goal, I began the process of deconstructing it: figuring out step-by-step what each part would involve, how much it would cost in terms of time and money, and slowly beginning to schedule visits to various parts of the world.

I encountered numerous challenges along the way, but I knew to expect them. (I wasn’t necessarily sure what they would be in advance, but I knew they’d be there.)

Fortunately the time required to overcome the challenges has not exceeded the amount of time left to achieve the goal. At least so far!

Steve: This being Nerd Fitness, I’d love to change gears and talk about how you stay in shape while traveling.

I know you enjoy going for a run in each new country, and recently you’ve even started beating yourself up with Crossfit. How important has exercise been throughout your adventures?

Chris: Fitness helps me do everything else, so it’s critical. I have fond memories of long runs (for me, this means approximately 10 miles or more) all over the world, in interesting places such as Ghana, Liberia, Brunei, Poland, and Cuba.

That said, I often get behind and I’m not able to exercise as much or as regularly as I’d like. I once said I was on the “two-weeks-on, two-weeks-off” fitness regimen. I’m home in Portland, Oregon, roughly half the time, and during that time I usually do some form of exercise almost every day.

But then I do things like go on book tour to a different city every day, and it’s honestly tough to get in any gym time when I’m constantly speaking at events in the evening, getting back to the hotel late, and checking out early the next day to go somewhere else.

(Note to self: The “Vodka-and-Clif Bar” diet that comes along with a book tour probably isn’t helpful either.)

Steve: Along with guys like Brett McKay and Tim Ferriss, I’d consider you one of my Yodas – somebody I look up to when it comes to living a life that matters and building a business that helps people live better lives.

Who are your yodas?

Chris: Thanks man! I’m honored to be a small part of the big Nerd Fitness world. As for who I look up to, we probably know and respect many of the same people who are online personalities. Many of those people are great and I’ve learned a lot from them too, especially my LifeRemix colleagues such as Jonathan Fields, Gretchen Rubin, and J.D. Roth.

However, I also think it’s important to get out of the bubble a bit and look for inspiration from people who are doing other things. In my case, I continue to be inspired by several of the aid workers I knew from my days in Africa.

None of them have popular blogs or thousands of followers on Twitter, but they’re making a huge difference in the midst of challenging circumstances.

Steve: Great call on finding inspiration from all over!  Now, not everybody can build an online business and travel the world.

What would you say to the guy who works in a cubicle, has a husband/wife and kids, paying off a mortgage, and trying to get healthy, but wants to add some excitement and adventure into his/her life?

Chris: Forget about what you can’t do and take responsibility for what you can! That guy or woman in the cubicle is ultimately who it’s all about.

I’m a big fan of small changes – the idea that 10 minutes of exercise is a lot better than no exercise, for example.  The same is true with anything else—you don’t have to head to Bali for adventure (although it’s a nice enough place). What can you do now, and what can you work toward in the future?

I also think it all starts with motivation. What do you really want? What are you trying to be, do, or achieve—and how does your daily work relate to that? Yes, we all have to do some things out of obligation, but one definition of success is “continuously improving your circumstances.”

You can adopt that perspective and make real changes no matter what your situation is.

Steve: Love it – small changes, every single day, that ultimately result in big changes over time. Like Optimus Prime!

Okay, so let’s say a nerd fitness Rebel reads your article today, scours your blog, and decides that he/she wants to follow in your path – go on epic adventures while running their own tiny business….but right now, they’re currently stuck at a job they don’t love.

What’s the FIRST step they should take towards leveling up life?

Chris: First up, don’t quit your job right away, unless you’re comfortable taking a big risk.

(Steve’s note: I waited almost two years after starting Nerd Fitness before quitting the day job, and even that was a huge risk!)

As you mentioned earlier, not everyone can do that. But I do believe that almost everyone can take matters into their own hands one way or another.

To start leveling up, you’re going to need some kind of source of additional income. Don’t think about a traditional startup or some kind of huge business that you probably won’t be able to start while working a day job. Instead, think about something you’re good at that is also useful to other people.

This is the formula we looked at for The $100 Startup: Passion + Usefulness = Success.

Next, do whatever you can to get that project up and running within 30 days, without spending a lot of money on it. Get a website, even if it looks terrible. Pay $10 for a domain. Put a PayPal button up and draft a description of a service you can provide. If you don’t know anyone else, tell your friends and family about it.

The sooner, the better.

Steve:  So just get started – no more collecting underpants.  Onto the “nerd” portion of the interview!  Everybody’s a nerd in some way – what kind of nerd are you?

Chris: I’d probably be a travel hacking nerd. I know hundreds of airport codes and entire route maps for probably a dozen airlines. Whenever people tell me they’re taking a trip, I ask a clarifying question or two and then try to guess their entire itinerary.

It’s a fun party trick I can perform with 80% accuracy—or at least, I think it’s a fun party trick. Though I’ve always wondered why people keep walking away while I’m still explaining all the different connection options…

Steve: You’ve turned me into a full-blown travel hacking addict as well – thanks for that.  If you could have any superpower in the world, what would it be?

Chris: Of course I’d choose to fly! Isn’t that #1 for everyone?

The ability to become invisible at will would be a close second.

If I couldn’t have either of those, I’d like to have the superpower of always knowing what to do next. Everyone is always busy, but “I have so much to do!” is a much better problem than “I don’t know what to do next!”

I wish I always knew what to do next in order to keep working on the things that matter.

Steve: Lord of the Rings or Star Wars?

Chris: Uh… undecided.

Steve: Fence sitter!  Do you have a favorite movie?

Chris: I don’t watch a lot of films, but I saw Restless on a recent Turkish Airways flight to London and it made me cry.

Yeah, it was awkward. I’ll try to see it again sometime in the comfort of my own home or hotel room.

Steve: Quote to live by?

Chris: “Once in a while it really hits people that they don’t have to experience the world in the way they have been told to.” -Alan Keightley

Steve: Thanks Chris!  Really appreciate you taking the time.  Good luck on the last few countries on your list.  Readers! Make sure you check out Chris’s new book, the $100 Startup (or on Amazon).  I’ve built my business by following Chris’s example – this book shows some great examples of others who have also created fun unique businesses with little to no start up money.  It doesn’t need to be expensive to be effective people.

What’s your big goal?

Chris’s big, giant, ridiculous goal is to visit every country in the world by the age of 35.

My big, giant, ridiculous goal is to one day own my own tropical island.

What’s your big, giant, ridiculous goal?

Nothing is off-limits or too ridiculous.

And what’s one ACTUAL step you took TODAY to get just a tiny bit closer to making it a reality?



photo source: tigersydney, book tour

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    183 thoughts on “Kicking Conformity’s Ass – An Unconventional Interview With Chris Guillebeau and a Contest

    1. My big gigantic ridiculous goal is to complete postgrad studies, my honours degree and my masters by the time I am 35. A shorter term big goal is to be fluent in Japanese by the end of the year. The most important goal is to help my children grow into strong resilient capable, welladjusted adults.
      Today I am attending my placement to finish my Bachelor of Nursing. I will spend time practising Japanese. Today I will also make sure that I spend more positive, quality time with my kids.

    2. I want to start a non-profit organization to help 100s of farmers transition from GMO-grain or animal farming to organic vegetable farming. Transitioning farmers will help prevent erosion and global warming while ensuring that people after us will actually have a viable Earth to live on.

    3. My goal is to be able to retire from work and travel the world.  I am starting towards this goal by paying off debt, taking small trips now as time permits, and getting myself into the best shape I have ever been in so that I am physically ready to go when the time and finances get into line.

    4. My lvl 50 dream is to some how make a difference in the world by inspiring others through music and to let people know that you can do anything if you try.  Today, I am going to practice my flute and compose some music.  The more I do each of these, the better I get!

    5. My goal won’ happen by age 35 as i am long past that point.  I am still striving to have my 4 boys all reach adulthood successfully.  There is no true definition of sucess, i just want them to do better than me.

    6. I would like to retire at age 45 and open a little bookshop/coffee shop on a beach in the west indies and in the quiet moments restore a little fishing boat, shawshank style. Closely associated with this goal is convincing my fiancee’ that this is something she would like to do too.

      Today’s step: I was up at 4:30am to be at the gym to get 1 step closer to my level 50 goals and now i’m going to work hard (in a job that i’m lucky enough to love) to earn the money to sustain my book/coffee shop which may or may not ever run a profit. And perhaps continue yesterday’s research into frequent flyer miles so I can explore potential coffee shop locations.

    7. My goal: Harmoniously redesign the way humans interact with nature & technology (buildings, furniture, cities, etc). Become a philosopher-warrior of physical training a la Bruce Lee. And have badboy international jet-setter, sex symbol, eccentric artist appeal while doing it. Make millions & give it all away when I die. 

      Today I worked on design for clients, worked out & meditated. 

    8. Rediculous goal? I want to do a dragon flag, a front lever, and a full planch by my 21st birthday. What have I done today? Decided on that goal and did some handstand pushups.

    9.  My big crazy goal is to bike across across canada to raise money for cancer. I’ve had numerous loved ones effected by this disease and I want to do something meaningfull to help find a cure. 

      To help this goal along, i went for a 25km bike ride today.  I still got a long ways to go but definitly my long term crazy goal!

    10. My Big Ridiculous Goal is:
      – To own and captain an ex-Imperial Star Destroyer as a goody gumdrops floating around the galaxy. (not happening any time soon)
      What i did today to get there:
      – Pretended i was flying an X-Wing in Rogue squadron whilst reading a novel about Wedge Antilles. (true)

    11. Big, ridiculous goal? See Earth from space! Today I did some ‘Research’ and watched the SpaceX launch online.

    12. Hmmm… I haven’t really thought of a big, giant, ridiculous goal. I have no idea what mine would be, all I really want is to be healthy and fit and preferably happy. Haven’t thought too much past that.

    13. My big giant ridiculous goal is to never let fear hinder me from accomplishing whatever goal I set for myself. I think by growing spiritually and striving for enlightenment is the path. One step I started was learning transcendental meditation.. I will be finishing my last class tomorrow and practicing it daily.

    14. My big goal right now is to become a professional boxer and travel the world training as well. What I did today to get closer to this? 4000 pushups. A ridiculous amount less for the body as for the mental aspect of training. I allowed myself to do any number of push ups in a set in any manner I want. I just had to reach 4000(doesn’t mean I’d go easy on myself ;-)) . A few months back I did this as everyday for 30 days. Having to get up every few minutes made overcoming the pre-workout laziness that I have go away instantly. I have become much more disciplined already. A sparring session is coming later today 😀 Hell yeah!

    15. Like most people, i want to travel the world. So what I did today was went to get my passport application.

    16. My Level 50 Goal is To Pay for Chiropractic Med School By the Time I Graduate (exactly 2 years). Today I Start Putting Together My Website and Videos for Selling Supplements online to start that cash flow!

    17.  Oh, and I have no idea how to get there. I’m torn between earning a giga-load of money, infiltrating into a space shuttler, or just wait for it to be more democratic :p
      Anyway, I’ll go there one day, probably not today, but in 50 years it should be doable

    18. I know it is way too late, but I didn’t say anything because I didn’t have a big, improbably goal. I had those goals, and decided against them. Like, I was going to open up a Quick service (think Quizno’s, Bagel chains, Chipotle style restuarants) restaurant. The catch? It was all going to be healthy. Something you could bring home every night and it would be a good thing. Then, I grew out of the food service business.

      Now, I know what I want to do. I want to go back into karate. I tried years ago to get back in, but my wrist wouldn’t cooperate. So, now I am about 120 pounds and 12 dress sizes bigger than I was. But I shall do it. I was learning a Bo kata when I left. I will go back adn I will learn that kata!

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