Chris Guillebeau is a New York Times bestselling author, entrepreneur, and longtime advocate for intentional living. He has visited every country in the world (193 in total) before his 35th birthday and has built a career helping people break free from conventional paths. His books, including The Art of Non-Conformity, The $100 Startup, and Gonzo Capitalism, have sold over a million copies and been translated into dozens of languages.
His latest book, Time Anxiety, examines how to live meaningfully in a world consumed by urgency. He also hosts Side Hustle School, a daily podcast with over 100 million downloads, and has recently launched NeuroDiversion, a pioneering conference that celebrates neurodiversity through interactive workshops and community-driven programming.
1) I really enjoyed your book Time Anxiety. A central theme I came away with is that the privilege of spending time can be both a blessing and a curse. Time is the currency we use to make the memories that define us. Yet, it also represents all of the things we could have done (which you beautifully illustrated using Sylvia Plath’s fig analogy). In this context, what was the most surprising insight or shift in your thinking that emerged while writing the book?
I think for me, it’s this dichotomy: there’s not enough time; this is true. Fundamentally, there is a limit. It’s a hard limit. And you mentioned time being a currency, there are all these clichés about time being our most precious resource. But the contrast here is that a lot of us don’t always live that way. We treat time as if it’s renewable, when in fact it’s not. At the same time (no pun intended), time is ultimately running out. That’s distressing. It causes anxiety and angst. It makes us question how we’re spending what we do have.
If we’re able to think about questions like: What do I want my day to look like? What am I working toward? Then, we still have some autonomy. There isn’t much in life that we have complete control over, but there are some things that we do have control over. And when you frame it that way, it becomes a lot less distressing and a lot more freeing. It shifts from pressure and angst to possibility and opportunity.
That mindset has helped me worry less about things that don’t matter and spend more time on what does, or at least on what I find meaningful and fulfilling. So it’s been helpful for me. I’m glad the book is out and people are enjoying it, but ultimately, I wanted to write a book that would change me. That was the goal.
2) The principle of “unfinishing” from the book offers potential liberation from obligations that don’t suit us. Yet, I think for a lot of people (especially some who are neurodivergent), we’ve been conditioned to be hypervigilant when it comes to finishing tasks. What are some ways to practice unfinishing with self-compassion, especially for those who feel conditioned to complete what they start?
Unfinishing connects closely to another idea in the book: doing things poorly. Not everything has to be done with excellence. That can be hard to accept, not just for neurodivergent folks, but also for some neurotypicals. Especially if you’re Type A, you might think, “Why would I not do something as well as I can?” You grow up getting the best grades, and that becomes your identity. Then you carry that mindset into adulthood, trying to be the best at everything.
But in life, you can’t be the best at everything. There’s too much going on. You have to choose. You can give your all to some things, but not everything. So the idea of unfinishing challenges that old saying, “winners never quit,” because it’s just not true. Winners quit all the time. The most successful people (and often the happiest, too) are willing to take a step back and reassess their situation. Not everything you start needs to be finished. There’s a lot of power in walking away.
If you want to think about it in a low-stakes way, take consuming media. You’re reading a book, and you don’t like it. But you keep going anyway. I know people who make it a point to finish every book they start. And to each their own, but maybe that’s just a habit. Maybe it’s worth asking whether that habit is serving you.
It’s not that everything needs to be unfinished. It’s more about realizing that not everything needs to be finished. We’re just introducing another principle here. If your default mindset is “I have to finish everything,” that’s the idea I want to gently challenge.
Once you realize you have a choice. Once you realize that you can evaluate whether something is still worth doing, you might end up making the same choice you would have anyway, and that’s okay. But now it’s intentional. You’ve thought about it. And that can actually reduce anxiety. Ask yourself: What does the other side of this look like? How will I feel six months from now, or a year from now, if I don’t make a change?
3) The insight that “what got you here won’t take you there” often is a major unlock for folks who find it difficult to level up. I have followed your content for a long time now and admire your continuous learning practices and adaptive mindset. In your own evolution, how do you guard against over-systematizing or becoming too attached to accumulated wisdom that no longer serves you?
Being accretive can be a strength, until it turns against you. When it comes to over-systematizing, I’m not sure there’s always a clear moment where you think, “Okay, this is too much.” Because systems are helpful, action creates motivation, and that’s how we build habits. Systems serve a purpose.
But the idea that “what got you here won’t get you there” really hit home for me when I started going to therapy. I wrote about this in the book. At the time, I’d had all kinds of experiences: I’d been to every country in the world, done a lot of stuff, but I was struggling. I was feeling depressed, anxious, dealing with relationship issues, and more.
In one of our first sessions, my therapist listened and then said, “Wow, it sounds like you have a lot of skills.” Which, of course, usually means something else is coming. And then she said, “But the skills that got you here aren’t the ones that will take you to what’s next.” And I thought, “Oh, okay.” That idea really landed.
It didn’t mean everything I’d done before was useless, but it meant I needed to create something new. That realization forced me to think differently. I had to accept that I couldn’t keep approaching things the same way. What had served me up to that point might not continue to serve me in the same way. I needed new parts, new approaches, so I had to be willing to explore.
That meant staying curious. Asking questions like, “Is this system, this process, this habit still serving me?” Or, “Is it time to try something else?” Things start to feel easier once we realize there is another way. Once we see possibility and get even a hint of direction, we can begin to move forward. It’s when we feel stuck and can’t see any alternatives that we tend to stay where we are.
4) Cultivating experiences that make you “feel alive” is a concept you and I explore in our respective work. I’m surprised that, from time to time, this idea is met with disdain from the sandwich generation, although I understand and respect the roots of these feelings. For those balancing deep responsibilities with a longing to feel more alive, how do you recommend honoring personal vitality without feeling selfish?
I think the first thing is understanding that wanting to do things for yourself is not selfish. Even before considering taking action, simply setting your own goals and having your own dreams and desires is beneficial. Asking yourself questions like, “If time or money were no object, how would I spend them?” There’s nothing selfish about any of this.
As you become a better, more fulfilled person, your capacity to care for others also grows. That’s not to diminish anyone’s situation, especially caregivers or those with limited time. But if we begin with the idea that it’s okay to do things for yourself, then we also recognize that everyone has some autonomy. Some people have more than others, but most of us have at least some degree of choice.
If you’re even reading this conversation, you likely have a bit of freedom. So the question becomes: What do we do with the freedom we have? How can we use it to live differently?
There’s an exercise in Time Anxiety called the “eighth day of the week.” It asks you to imagine that you get an extra day each week. Not just a one-off, but something that recurs. On this day, no one needs anything from you. You’re not responsible for anyone else. What would you do?
That kind of exercise can help people think about long-term goals. Maybe you want to learn a language or write a book. These are things that add up over time. Even small steps, taken consistently, can lead to something meaningful.
So yes, not everybody has the same amount of time. That’s important to acknowledge. But we each have a little space to work with, and how we use that space matters. Whatever gets you to a place where you feel justified doing something for yourself, I think that’s good for you. It’s also beneficial for the people around you.
5) There is a strong scientific argument that variety truly is the spice of life. I’ve coined this concept variable hedonics. However, it is also clear that the people who seem to enjoy life the most schedule things they want to do onto their schedule. What has your own experience taught you about the paradoxical nature of holding space for spontaneity while also being deliberate about how you spend time?
Most of us tend to lean one way or the other, and there is value in pulling ourselves back a little toward the opposite side when we are out of balance. Which is interesting to say, because I don’t always think balance is a helpful concept; But, in this case, I agree with you. Scheduling what matters to you and making it a priority is something fulfilled people tend to do.
However, there are also those who over-plan. They schedule themselves so tightly that they leave no room for spontaneity. If that’s you, you probably need a little more flexibility. And if you’re the opposite—if you’re all spontaneity—then you probably need more structure.
I think it helps to change things up periodically. Even if you have a system that’s working, introducing a shift or a variable every now and then can be beneficial. Then you see how it goes. You might find that you want to return to your previous system, and that’s totally fine. Or you might realize that the change revealed something you want more of. Either way, it gives you something to notice: What do I want more of in my life? What do I want less of?
There’s nothing overly strategic about this. It’s about being intuitive, and it’s also about gathering useful data. And these two things are easily accessible if you’re paying attention.
