NY Times Best Selling Author Chris Guillebeau’s Advice to Generation Y

Many people talk about their dreams but Chris Guillebeau actually lives his.

Five years ago, Chris set a goal to visit every country in the world (193) by his 35th birthday. On April 4, 2013, Chris completed his quest.

Along the way Chris created the popular blog, the Art of Nonconformity: Unconventional Strategies for Work, Life, and Travel. He’s also released the New York Times bestselling book The $100 Startup and the acclaimed The Art of Non-Conformity: Set Your Own Rules, Live the Life You Want, and Change the World.

Chris is an expert on freedom, fulfillment and success. Fortunately he dropped by FreshWisdom with advice geared specifically to people currently in their twenties through early thirties who are looking to live the life they desire on their own terms.

In your experience, what separates those who “make it” from those who don’t?

Chris: Those that make it keep trying to make it. Those that don’t become frustrated and give up.

What experience stands out directly as shaping your life direction? Why was this moment so powerful?

Chris: It wasn’t a single moment but rather the collective experience of spending four years on a hospital ship in West Africa. (From 2002-2006 he volunteered in West Africa with the medical charity Mercy Ships). It completely transformed the way I think about life, travel, and probably everything else.

What steps do you think are the most important for people in their twenties and early thirties to take now who want to find direction and experience fulfillment?

Chris: If they’re thinking about those things at that age, that’s great — many older people don’t think much about fulfillment, and people of any age rarely stop to ask themselves what they are working toward and why they do the things they do.


It costs no money to do so, and you can consider them at any point in life. Then, over time, I believe we can all work on aligning our lives to be more in tune with the vision that emerges from the answers.

Chris Guillebeau poses while in Mumbai, India during his $100 Startup Tour.

Chris poses while giving a presentation in Mumbai, India for his $100 Startup Tour. Released May 2012, the book shot to the best-sellers’ list of the New York Times and Wall Street Journal with more than 100,000 copies sold in the first three months.

Chris Guillebeau, World Domination Summit 2012

Chris presents during the World Domination Summit (WDS) in Portland, Oregon. The annual conference brings together creative and interesting people from all over the world. The 2013 WDS runs July 5 through July 7. (Sorry, tickets are sold out this year!)

Chris Guillebeau runs in Melbourne, Australia

A frequent outdoor running enthusiast, Chris Guillebeau jogs in Melbourne, Australia at NGV Federation Square while crossing off another country on his quest to visit 193 countries by the age of 35. (Chris completed his goal April 2013).

Given the changes in the economy, technology, etc., is the American Dream still available for Generation Y?

Chris: I guess it depends on how you define the dream. For a long time, the dream for many people included something about receiving job security by working for a single company over a long period of time. This is no longer reality for most people in Generation Y, but I don’t think this fact is negative.

Instead, more and more young people are choosing to go it alone and create career independence in one fashion or another. A lot of them are finding that they can create much more security by working for themselves. Therefore, the American Dream is dead. Long live the American Dream!

What “life shortcuts” have you learned along the way that helps you get from Point A (where you’re at) to Point B (your desired goal) more quickly and efficiently?

Chris: Focusing on outcomes instead of time-based schedules helps me a lot. I also try to be fairly specific about what I’m working toward. Ambiguity can cloud our thought process when we aren’t sure what we want. Figure that out, and it’s much easier to get to Point B.

At what point to you did you begin really believing you could do anything you set your mind to – even when others may have mocked your goals?

Chris: It’s always progressive. Small successes lead to bigger ones. I didn’t think I could visit every country in the world until I had been to more than 50. As I kept plugging along I became more and more confident. After awhile, it didn’t matter what other people thought because I knew I could do it. Lesson: set goals, reach them, and then set new ones. Always focus on the journey and not the destination.

Chris Guillebeau, Art of Non-Conformity Book Tour

Chris Guillebeau presents during the Art of Non-Conformity book tour. The book was released September 2010 to critical acclaim. Even 2.5 years later, the book ranks among Amazon.com’s top 5,000 books currently bought.

Chris Guillebeau, On Board Star Ferry in Kowloon, Hongkong

Truly living a life of freedom and independence, Chris Guillebeau takes in the scenery aboard the Star Ferry in Kowloon, Hong Kong, one of 193 countries he’s visited. (October 2012)

Chris Guillebeau chats on”Live Smart Show”, a South Korean talk television program.

What do most people not understand about business?

Chris: They often fail to focus on providing a solution to a problem or meeting a clear need. Sometimes people ask me, “what do you think of my idea?” My response is, “it doesn’t matter what I think, because I’m not your customer.” Therefore you should figure out who your customer is and spend time worrying about what they think, not anyone else.

Name one misconception people have about living an unconventional career/life?

Chris: That an unconventional life is somehow riskier or more difficult than a conventional one.

You can catch up with Chris as he begins his next project Adventure Capital. It’s ideal for current small business owners and those who want to create their own small business but don’t know where to begin. He’s on Twitter @chrisguillebeau where he provides real-world proven strategies and examples of how you can get to where you want to go in your life.

Chris Guillebeau, $100 Startup Closeup

Chris Guillebeau rests with a stack of his New York Times best-seller, The $100 Startup.

Don’t forget to check out FreshWisdom on Facebook and join me on Twitter at @FreshWisdomLive.  You’ll receive daily posts along with the latest Fresh content where I highlight the wisdom from those in Gen Y and older who are creating their success, freedom, and fulfillment along with information that will help you thrive.