Chris Guillebeau: Embracing an Unconventional Life & Finding the Work You Were Born to Do


Best known for his best selling books, $100 Startup, Art of NonConformity, Happiness of Pursuit, and now Born For This, Chris Guillebeau is an impressive guest on so many levels. He's also one of the most humble humans I've ever met.

As anyone who attends one of his events can see, the foundation of Chris’ work is connection and community.  A question that he’s always asking himself is, “How can I be a part of someone else’s life?”  He enjoys connecting with people who are already excited and motivated but who might lack a tool, resource or accountability. 

He’s all about practically helping motivated people to become more awesome or to find another expression of their awesomeness by giving them what they might be lacking, and that's why we connected on his recent book tour, and he's now gracing The Bold Life Movement Podcast with his unconventional view on the world.

Chris’ most recent book, Born for This is an essential tool for anyone who is looking to find the work they were born to do. One idea that I loved was this concept of resigning from your job every year.  Since we often get stuck in a situation, neither too bad nor too good, that we don’t attempt to get out of, this is a great rest to ensure that we're always intentionally choosing our own circumstances.  This is a beneficial because now you can look forward to the coming year knowing you’ve actively made the best decision for you.

As a child Chris found much inspiration from his father.  Nowadays he draws inspiration from people in the community that are doing awesome stuff and are on a journey or a project of their own.  These inspirational people are just regular folks who do the work because they’re committed to it.  Their sacrifices and struggles are what truly inspire him.

One of the things that attracted me most to Chris, is that [he too] has always had an issue with authority and is generally a non-conformist.  He began to see this as a gift for himself, which since has led to extensive world travel and many great life experiences.  His entrepreneurial journey started as a search for freedom at first, but has evolved into a life purpose, became a way to serve the world.  He's constantly looking for ways he can add value to others.

Chris’ message reaches such a broad audience, and he actually goes as far as to say that you don’t have to niche-down for success.  “Who you are is much broader than any niche.”  Whether you go broad or focus on a niche, though, the message you deliver is critical.  Your message is your beliefs, and you’re putting them forward as an invitation or a challenge to those who resonate with it. The message is not optional, his advice is to focus on this more than anything else.

To Chris, being bold is taking risks, being afraid and doing hard things that lead to good things in life.

Once you go down the road of adventure, you don’t always know where you’ll end up. You may get where you’re hoping to get but you may get even further or to a totally different, interesting and exciting place.

Chris has made tremendous impacts in the lives of thousands, and he’s a man of much humility with a powerful message to share.  It was so surreal and humbling to connect with someone whose message and whose story is so empowering.


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  • What is one example in Chris’ life where he was bold and tenacious in pursuit of his goals?
  • Will his next quest be related to the work he’s doing on his inner self?
  • What skills is Chris actively learning right now or in the near future?
  • In terms of book writing, or planning for projects, how does he combine his planning/incubation process with the concept of “start before you’re ready”?
  • What advice does he have for people not wanting to target a small niche?


  • How Chris’ is coping with feelings of anxiety, and why these can still be present with high levels of success.
  • Some tips for getting clear on the work you were born to do.
  • Why deadlines and accountability are crucial to success.
  • The one person Chris would love to have as a speaker at the World Domination Summit.
  • What Chris asked me once we had stopped recording.
  • Plus much more…