I met Chris Guillebeau in the first minutes of a networking event I didn't want to attend. We hit it off immediately, traded books, and stayed connected. Chris has written nine books, hosts Side Hustle School, writes The Art of Non-Conformity, and has visited every country in the world. Obviously, I had to make him my friend.
His latest, Time Anxiety explores escaping urgency culture with practical steps for managing time guilt, deadline dread, and chronic rushing. After devouring it, I knew I needed to talk with Chris about maintaining productivity and ambition without falling into hustle culture traps and burnout.

What inspired you to write Time Anxiety?
For years, I wrestled with a constant feeling that time was slipping away and I couldn't get a handle on it. When I wrote a blog post about this experience, the response was overwhelming—I got a ton of comments and emails from people saying "I thought it was just me" or "This is the defining problem of my life."
I realized we were all dealing with the same issue but rarely talking about it. What began as personal research to solve my own problem evolved into this book when I saw how common the struggle is.
Can you define the two different types of time anxiety?
There are two main forms: existential and day-to-day. Existential time anxiety focuses on big-picture concerns—feeling like time is running out in your life, ruminating on past decisions that "wasted" time, or fearing you'll never find your purpose. Day-to-day time anxiety centers on the immediate—feeling there's not enough time in the day, constantly "switching between tasks," or rarely feeling satisfied after completing something.
Most people experience both types, but lean toward one or the other. What's fascinating is that these worries affect people of all ages, from teenagers to retirees. The fear of "being too late" for something important is remarkably universal.
What do you think we get wrong about productivity?
“Get up one hour earlier every day….” (What if you’re already getting up early?)
“We just need to prioritize…” (What if your priorities exceed the amount of time you have?)
“Stop being lazy…” (Your laziness may be learned helplessness, or just feeling overwhelmed)
In short, the biggest misconception is that productivity will solve time anxiety, when it often makes it worse. We get better and better at doing the wrong things!
Any tips to get out of the frenetic state of urgency many of us are stuck in?
Start with what I call "time decluttering." Look at your calendar for the next few weeks and challenge yourself to remove a few items. Most likely you can find some commitments that seemed important when you added them but now feel less essential.
Next, make time more visible in your life (especially if you experience "time blindness"). Place clocks where you'll notice them regularly. Use timers and alarms rather than trying to keep track of time in your head.
Finally, ask yourself regularly: "How valuable were my last 40 minutes?" This simple check-in helps you assess whether your time is aligning with what you truly value, or if you're caught in urgency traps that don't serve your deeper priorities.
How do you make decisions about how to invest your time and what to say yes or no to? Is there a criteria you follow?
Here’s an idea: our future self has perspective that our present self often lacks in the moment of decision. So what if we could call on this future self somehow?
Before saying yes to anything, I like to ask: "Will my future self—three months from now, perhaps—thank me or resent me for this decision?"
The beauty of this method is how it cuts through the immediate emotions—the people-pleasing, FOMO, or status-seeking that often drives our decisions—and connects us to what truly matters.
I've also learned to distinguish between what's truly urgent and what simply feels urgent. Most of what comes our way isn't as time-sensitive as it appears, so it can be helpful to pause before responding to requests rather than automatically agreeing.
How have you been able to pull off being so ambitious, productive, and successful without burning out or going mad?
It’s kind of you to use those adjectives! But I really do most of what I want, most of the time. I think this is the only enduring productivity hack: to craft a life around things you enjoy and find meaningful. When you do this (and it’s a long term process, of course), everything else is easier.
You advocate for building a tolerance for incomplete to-do lists and the inevitability of disappointing people. Where to begin if this sounds absolutely terrifying (my hand is up!)?
Haha. Okay, so how about this: Choose one low-stakes situation where you can practice letting something remain unfinished or saying no to a request. Notice the discomfort, but also notice that the world doesn't end.
Remember that your to-do list is infinite by design—it's not meant to be completed. The goal isn't to finish everything but to choose wisely what deserves your attention. As for disappointing people, it's inevitable. The question isn't whether you'll disappoint others, but which disappointments you're willing to live with.
Why do you recommend thinking about death daily?
Thinking about death can help us live better. It helps you distinguish between what feels urgent and what's truly important. It shifts your perspective from "I don't have enough time" to "How do I want to spend the time I have?" This subtle reframing transforms how you make decisions about your days.
The goal isn't to live each day as if it's your last—that's exhausting and unrealistic. Rather, it's to live with the awareness that your days are numbered, allowing that knowledge to infuse your choices with intention and meaning.
What three simple steps can help people break free from the "trance of busyness"?
Put a brick in your inbox - Limit the ways people can access your attention. Turn off notifications, delete social apps that drain your time, or set specific times for checking messages rather than being constantly available.
Give yourself more time than you think you need - For appointments, projects, and transitions between activities, add 10-15 minutes to your estimate. This buffer reduces the chronic rushing that fuels time anxiety.
Practice thought countering - When you catch yourself catastrophizing about time ("I'll never catch up," "I've wasted too much time already"), challenge these thoughts with more balanced perspectives. Label the cognitive distortion and replace it with something more realistic.
What planning system do you actually use day-to-day?
Mostly I like lists: a list of projects and associated tasks that I keep digitally with OmniFocus, and then I handwrite each day’s priorities on a little notepad.
That tool I mentioned—OmniFocus—has been helpful for me for years, but I really think any notetaking or task-management app that feels simple and intuitive can do much the same thing. In my opinion it’s far more important to find something you feel comfortable with and stick with it than it is to keep trying new tools.
What does your morning routine look like?
I run every day and I try to do it in the morning, but living on Pacific time means I do sometimes feel a little behind “business hours” compared to the east coast.
I usually try to avoid meetings or phone calls until mid-morning, so I can do some uninterrupted creative work for at least two hours first. That’s not always possible, but it’s my goal! I’m not a big fan of the “let’s hop on a quick call” thing.
Favorite app on your phone?
Instagram is probably the most-used, though I don’t use it nearly as well as you and others do. My “for you” grid has a lot of comedy and cat videos more than anything related to my work.
But is it my favorite? Probably not! I also like Instapaper, where I save long-form articles for reading on the go, or Feedly, where I read a lot of blogs and RSS-style content.
What's one tech boundary that's made the biggest difference for you?
Honestly the biggest thing is probably to accept that I can’t be everywhere in terms of social media or just mediums/platforms in general.
One self-care or wellness tip you follow religiously?
I have a 2,247 day streak of closing my Apple Watch circles. I know, I’m compulsive … but oddly I find that following the pattern provides a neat little anchor for my day. There have been a couple of times when flying around the world that I’ve worried I messed something up and didn’t get enough activity points in the right time zones, but fortunately the streak still holds for now.
When it's all said and done, what do you hope people remember about how you spent your time on this planet?
Another great question! But it also connects to a change I’ve made: I don’t really think about this a lot anymore. I used to be motivated by the concept of “leaving a legacy” and now I tend to think “well, that’s not really within our control.”
I guess if I had to pick something I’d leave them with my overall life message: “There is another way.”
Where can my readers learn more about you and your work?
Why thank you! I have a Substack newsletter called A Year of Mental Health, my main website is ChrisGuillebeau.com, and I’m on the usual social channels where I post inconsistently because I believe in doing things poorly. 🙂
Thank you for reading! You can check out Chris's books right here (they’re really good).
💬 READER QUESTION: What’s one small change you’ve made that’s had a big impact on your relationship with time? Tell me in the comments—I always read them.
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First of all, love this article and all of your content. So thank you.
Lately, a small change with big impact has been thinking about how I can help my future self. Example, don't want to put away laundry at night, but know my future (morning) self will benefit. Floss my teeth, my future self will benefit. Just doing the tiny little tasks NOW, instead of putting them on that infinite 'to do' list has been a big boost.
Thanks for sharing Chris’s ideas! Now that I’m a self-employed retired teacher, I’ve been struggling with daily time management and long-term planning, which I suppose makes sense after decades of a highly rigid daily structure and a feast and famine style work load (yes, summers off are vital for the insane mental and physical work load of teachers the other 10 months 🙂). And as a life-long procrastinator and recently diagnosed ADHD menopausal woman, I’ve done a lot of self berating over my lack of productivity!
The life coaches I know all say to use time blocking, and sometimes I do use it successfully. But I was getting myself stressed out and frustrated because I wasn’t accurately planning for how long certain to-do items were taking, so recently I did start incorporating the time buffers, like Chris mentioned. So now when I have a chunk of non-client-facing time, I try to build my schedule of time blocks with that buffer. I also build in short walks outside (my 15-year old Chihuahua’s pee schedule gets me out of the house more frequently!). Even though, or maybe because of it, I get fewer items accomplished, it feels so much better to have those little time buffers and walks built in.
I also have been using an Eisenhower style long- and short-term planner. I modified the 4-quadrant labels a little - I have Do Now (important to goals or family and urgent/timely), Schedule (important but not urgent), Delegate/Stack (things my young adult children need to take on and things I can mindlessly do while watching a movie or listening to a podcast or “stacking with something else”) and Delete. I tried writing these lists in a paper planner but am still working on implementing a paper planner in general (I’ve been a random sticky note and list person forever), so this hasn’t helped in the past.
So when I moved/downsized recently, I converted an extra large picture frame to a dry erase board for my Eisenhower chart and hung it above my desk in the living room. Each quadrant has two colored lists - one for my business and one for family/personal tasks. I’ve realized I’m definitely more of a visual person and need that chart front and center. And surprisingly, see the big to-do list doesn’t stress me out. I think it’s because of the quadrant system and because I’ve given up the stressful, for me, SMART goal system that includes specific timelines.