Q&A With Chris Guillebeau

I am honored to be doing this Q&A with author, entrepreneur, speaker and blogger Chris Guillebeau! Chris’s books are nonfiction, and their titles are The Money Tree, 100 Side Hustles, Side Hustle: From Idea to Income in 27 Days, The Art of Non-Conformity, The Happiness Pursuit, Born for This, The $100 Startup, Gonzo Capitalism, & Chris’s recent release Time Anxiety. All of Chris’s books are on the New York Times Bestsellers List! 

Q: Chris would you please give a brief description of your books beginning with your recent release Time Anxiety?

A: “Time Anxiety explores our complicated relationship with time – that feeling that we’re running out of it or not using it well enough. It offers practical strategies to overcome the ‘illusion of urgency’ and live more intentionally. My previous books focus on entrepreneurship and creating meaningful work: The Money Tree shows how to create additional income sources, Side Hustle provides a structured approach to starting projects, and The $100 Startup demonstrates how to turn passions into businesses without large investments. Books like The Happiness of Pursuit and Born for This explore finding purpose through quests and career alignment.”

Q: How do you choose a topic for each book & how long does it take you to research and write a book?

A: “My book ideals usually emerge from observing patterns in my community and then conducting a lot of independent research. Time Anxiety came from noticing how many people expressed the same fears about time running out or never having enough. When I wrote a blog post about it, the response was overwhelming. Most books take me about two years from concept to completion – six months of research and interviews, then twelve or more months of writing and editing. I’m always collecting stories and observations.”

Q: What drew you into writing, entrepreneurship, blogging and speaking? What wisdom do you have for anyone wanting to do all 4? I know I am always open to learning new ways of making my blog financially successful. 

A: “I started blogging to document my goal of visiting every country in the world, which unexpectedly created a community interested in unconventional living. Writing books, speaking, and courses followed naturally. For anyone pursuing these paths: focus on serving an audience before monetization, be consistent with content creation, and don’t try to do everything at once. Pick one platform to master first, then expand. The most successful creators solve specific problems or fulfill particular needs rather than just sharing personal updates.”

Q: What lessons do you hope readers remember after reading each of your books?

A: “From Time Anxiety, I hope readers realize they have more control over their relationship with time than they think. From The Happiness of Pursuit, that pursuing a quest can bring meaning and purpose. The common thread in all my work is empowerment – showing people they have more options than they realize and encouraging them to design lives aligned with their values.”

Q: If you are currently writing your next book now, what will the topic be about this time?

A: “Right now, I’m fully focused on getting the message of Time Anxiety out. This book addresses something affecting so many people – that feeling that time is passing us by, and the constant worry about whether we’re spending it well. The research revealed how widespread these feelings are, and I’m committed to helping people break free from the ‘illusion of urgency.’”

Q: Would you like to provide your blog & social media links for my readers to follow you and your work? 

A: Sure! 

ChrisGuillebeau.com

yearofmentalhealth.substack.com

IG: @193countries

FB/LI/etc.: Chris Guillebeau

Q: Congratulations on your books reaching the New York Times Bestsellers List! Does it feel so surreal knowing that your books are New York Times Bestsellers? 

A: Accolades are nice, but mostly I’m happy that readers seem to enjoy the books. 😊