For well over a decade, I’ve been lucky to call Chris Guillebeau a friend. He’s one of those people who seems to operate on a different wavelength, consistently living out the very advice he shares with the world. Long before we had terms like “creator economy” or “side hustle,” Chris was quietly and methodically showing people how to build a life on their own terms. His core message has always been a powerful one: you don’t have to live your life the way others expect.
From his early quest to visit every country in the world (all 193 of them) to founding the legendary World Domination Summit, Chris has built a career around curiosity, adventure, and questioning conventional wisdom. Through bestselling books like The Art of Non-Conformity and The $100 Startup, he gave a generation of creatives and entrepreneurs a practical blueprint for turning their skills into sustainable, independent careers. His work has always been a field guide for the unconventional, proving that the most interesting paths are the ones we carve for ourselves.
Our paths have crossed many times over the years, built on a shared belief in empowering creative people. I was honored to speak at his groundbreaking World Domination Summit, an event that became a magnetic hub for talented and collaborative people from around the globe. Chris has also been a recurring guest and friend of our show, sharing insights from his many projects, including his most recent book, Gonzo Capitalism. These collaborations are a testament to the community and ideas we both champion: that your creativity is your most valuable asset, and you have the power to design a life that truly aligns with who you are.
Chris has a unique talent for distilling complex ideas into actionable principles. Here are a few concepts from our conversations and his work that you can apply directly to your own creative journey.
1. Escape the Average System
Chris argues that the systems of the world—in finance, careers, and education—are built for average results. They have to be, in order to function at scale. But if you want exceptional results in your life and work, you can’t follow an average path. You have to find a way to do something different. As he says, “If you want average results, follow an average system.” To be exceptional, you must create your own.
- Audit the “rules.” Look at the conventional advice in your field. What are the accepted steps to success? Ask yourself which of these rules actually serve you and which are simply outdated traditions.
- Identify your unique contribution. What can you offer that is uniquely yours? It could be a specific skill, a quirky perspective, or a new way of combining existing ideas. Miss Excel, who Chris mentions, combined dance videos and spreadsheet tips to create a massive business. The twist is what matters.
- Start small. Escaping the system doesn’t mean you have to upend your entire life overnight. Start a small project, a side hustle, that allows you to test your unconventional ideas with low risk.
2. Hunt for Asymmetrical Risk
One of the most powerful ideas for any creator or entrepreneur is to seek out opportunities with asymmetrical risk. This is where the potential upside is massive, even unlimited, while the potential downside is small and manageable. Instead of betting the farm, you make small, smart bets on ideas that could pay off in a huge way. The real risk, Chris says, isn’t that one of these bets will fail; it’s remaining stuck because you never tried at all.
- List low-cost experiments. What are three things you could try in the next month that would cost you less than $100 and a few hours of your time? This could be starting a newsletter, launching a simple digital product, or creating a TikTok channel around your niche interest.
- Measure the true downside. For your next big idea, ask yourself: “What is the absolute worst-case scenario?” Often, the “risk” is just a little bit of wasted time or a minor hit to our ego. Once you realize the downside is survivable, it’s easier to act.
- Look for leverage. How can you use existing platforms and skills to create something where the potential return is far greater than your initial effort? Think of the creator who spends ten hours making a YouTube video that gets millions of views and generates revenue for years. That’s leverage.
3. Build the Skill of Self-Inquiry
In a world that is constantly changing and full of noise, the ability to know what you truly want is a superpower. We often get so caught up in what we should be doing that we forget to check in with ourselves. Chris suggests a simple but profound practice to cut through the confusion and connect with your own internal compass. It starts with just two questions.
- Start a simple journal practice. Each morning, ask yourself: “How am I feeling?” and “What do I want?” Don’t overthink it. Just write down the first things that come to mind. Connecting your feelings to your wants makes the process more grounded and honest.
- Translate wants into actions. Once you identify a want, no matter how small, figure out one tiny action you can take toward it. If you want to feel more connected, your action might be to send a text to a friend. If you want to feel less stressed, it might be to go for a ten-minute walk without your phone.
- Trust the process. This isn’t about finding a single, grand life purpose overnight. It’s about building a continuous, honest conversation with yourself. Over time, the small answers will point you toward the big ones, helping you make choices that are truly aligned with who you are.
PS – If you’re looking for a guide to help you build the life and career you’ve always wanted, the Seven Levers for Life is a free 7-day email course on just that.
