Conversation with Chris Guillebeau

In Conversation, Guest, Inspiration
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Earlier this week, I had the chance to attend a lecture and book signing with New York Times bestselling author Chris Guillebeau, whose new book, Born For This, hit book stores in early April. The talk was hosted by executive coach Irina Baranov at the Impact Hub, and centered around an open discussion between Chris and those in attendance, followed by the signing.


Tell us about your new book, Born For This, and why you felt called to write it?
Born for This is all about how to find the work you were meant to do. “Calling” is a good choice of words-and over the past 10 years, I’ve had many conversations with people who’ve found or created their Dream Job. I wanted to understand what these people had in common, what they learned throughout their journey, and most important of all, how we could apply their lessons to our own lives.

It’s been said that one of the best avenues for personal growth is to work for yourself, perhaps by winning “the career lottery” discussed in your book. Would you agree?
I think that investing in yourself is always a good idea, and there’s more than one way to invest in yourself. Self-employment or entrepreneurship is a great choice for lots of people, but not all. You can also invest in yourself by starting a “Side Hustle” (where you keep your day job but do something on the side to build an additional source of income like etf investing, Exchange-Traded Funds to build on your income). It can even be something as simple as making sure you try to sell old belongings rather than throw them away when it’s time for a clear out. Every little helps when it comes to topping up that income with a side hustle, and setting up a page on a site like LeoList in order to sell your old things is a simple and easy way to go about it. Finally, you can learn to improve the kinds of skills that are most valuable in the workplace, therefore increasing your value along the way.


What do you love most and like least about winning your own “career lotto”?
I feel very fortunate to write, travel, and serve a fascinating community of like-minded people. Not every day is amazing and I certainly have struggles and shortcomings, but I can’t think of anything I like “least.”

I’ve seen successful photographers abandon their businesses, frustrated with the commercial side of things. How can aspiring photographers minimize the discomfort where art and passion meets commerce?
Well, you don’t have to do everything for money. Especially with the arts, it’s also okay to develop and cultivate your love of photography simply for love. But if you do want it to be “commercial,” there’s nothing wrong with that either. Combining love and money is a beautiful thing, and I don’t think it has to be discomforting. You’ve worked on your craft for a long time and you’re good at it. Why not get paid for it?


Working for yourself can be scary. (I speak from experience of course!) What are some ways to combat self-doubt when creating a passion-based business, not to mention still pay the bills?
I try to be very practical about these things. First, don’t spend months planning your business before jumping in to experiment. It’s very likely that your business will evolve as you go along, and as they say, “No plan survives contact with the battlefield.”

Therefore, it’s much better to start small and start quickly. If at all possible, don’t leap without a net-build a safety net first. Allow yourself room to experiment. Oh, and here’s something I’ve been saying ever since I first heard it from one of the people who’s in the book: “Don’t tell your mother.” What she meant was that not everyone understands why you’d want to work for yourself or otherwise pursue some form of creative work, so don’t allow everyone into the inner parts of it before it’s ready.

Once it’s ready, and you have the website, a means of accepting payment, etc.-then you tell them. The odds of them understanding and accepting will be much greater once you’re further along the path.

Have any resources you can share?
Sure! When people buy the book from any retailer, they can email their order receipt to We’ll give them more than $147 of free resources, including a Priority Planner (to learn how to focus on what’s important) and a Side Hustle Starter Kit (to create a step-by-step guide for their own independence). I want to make sure that people are fully supported and equipped to move forward with their goals.


What’s next?
I’m on tour to 30 cities! It’s an intensive-yet fun-experience in meeting readers and talking in more detail about how to find the work we were born to do. (And if you’re reading, I’d love to see you. Sign up for free tickets at

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Chris Guillebeau is the New York Times bestselling author of The Happiness of Pursuit, The $100 Startup, and other books. During a lifetime of self-employment, he visited every country in the world (193 in total) before his 35th birthday. Every summer in Portland, Oregon he hosts the World Domination Summit, a gathering of creative, remarkable people. His new book, Born for This, will help you find the work you were meant to do.


  1. Great interview, Holly! I saw him last Friday here in Austin and it was super fun. I met this fantastic lady who sat next to me, I think she might be me in 30 years (or at least I hope so, she was super awesome). Thank you for telling me about Chris!

  2. Holly, So glad you’re sharing this and so glad you got to see Chris! I heard him on his The Happiness of Pursuit tour here in SF. Big fan. Would you ever go to the World Domination Summit? I’ll meet you in Portland!

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