Winning The Career Lottery: My Chat With Chris Guillebeau

“Live an unconventional life in a conventional world” – Chris Guillebeau

Last week I sat down for a free-ranging conversation with Chris about what it means to find and enjoy work that you are were made for­ and to introduce his forthcoming book, Born for This, How to Find the Work You Were Meant to Do.

This inspiring man is carving a unique path through life and making a huge difference for others, on his own terms.

Chris travels the world and has interviewed hundreds of people across the globe about their careers. He is fascinated by how some people thrive and love their work while others simply tolerate it.

One of my favorite stories he shared was about an American man, and father, who was watching (younger) work colleagues quit their jobs to go to Thailand and decided that, although that was not feasible for him and his family, he would stage a series of “life experiments” that allowed him to live a more fulfilling life each day and gradually move into a larger change for himself and his family, towards more fulfillment and adventure, professionally and otherwise.

I enjoyed Chris’ imagination of writing a sequel to Robert Frost’s famous poem, The Road Not Taken, imagining that instead of there being just one path that leads to an extraordinary life, what if there were many different paths to a fulfilling existence?

His views echo Richard Branson’s views on business opportunities like buses and that “there is always another one around the corner.”

I find this interpretation to be inspiring and empowering. Indeed, what if we viewed each perceived misstep or “mistake” to be taking us closer and closer to what we truly want for our lives? How powerful that type of perspective is.

Chris has done some extraordinary things in his life, including traveling to every country in the world by the time he reached the age of 35, and starting a movement (“a small army” is what he calls it) of people who want to lead extraordinary lives of adventure and service while enjoying a strong, bonded community around them.

His manifesto for world domination led to a thriving blog and online community that led to several books (The Art of Non-Conformity, The $100 Startup and The Happiness of Pursuit, plus the forthcoming Born for This) and eventually to his launch the World Domination Summit, an incredible gathering he hosts each summer in Portland, OR that I affectionately call Burning Man for creative entrepreneurs.

Sitting down with him, I was struck by his humility, his collegial attitude, and his desire to help others move closer and closer to winning their own career lottery. I find that being around him helps me leverage my energies further in service of my goals and dreams for my life, and it is clear to see from the response I’ve received from my audience for this chat that he has that impact on others too.

I’m thoroughly inspired by Chris, so do listen to the chat and check out his upcoming new book—I think you’ll be inspired, too!