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I'm a writer, entrepreneur, and compulsive traveler. For ten years I visited every…
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Chris Guillebeau posted this"You must be very disciplined." A lot of us hear this and don't know what to say. The truth is messier. We're not super-disciplined; we figured out that pure discipline doesn't work for our brains, so we built scaffolding instead. Discipline is the willpower to do the right thing in the moment. Structure is the design choice that means the moment doesn't require willpower. They look similar from outside, but they do different jobs. For some of us—particularly those with ADHD or autism, or just a brain that runs differently—pure-discipline approaches break down within a month. The scaffolding approach holds, because scaffolding doesn't get tired. What scaffolding looks like is specific to you. It could be a physical environment that makes the right thing easy and the wrong thing slightly harder. Or it might be deadlines you make public to other humans. The trick isn't to be more disciplined. The trick is to design conditions where you don't need to be.
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Chris Guillebeau posted thisWhen I'm stuck on something, I sometimes do a thing that would have embarrassed me ten years ago: I have a conversation in my head with someone whose judgment I trust. The someone doesn't have to be real. It can be a writer I admire who's been dead for a hundred years. It can be an older version of myself. It can be a composite—the no-nonsense friend, the gentle aunt, the boss I once had who could see five moves ahead. Three questions I bring to the meeting: 1. What would you tell me to stop doing? 2. What am I overcomplicating? 3. What would you do first, if you were me, right now? Then I write down what I imagine they'd say. Not what I WANT them to say. What I think they'd actually say. (The first question is usually the most painful one.) If this feels too "out there" for you, try it this way: same questions, but answer them as yourself in a slightly edgier mood. Same effect, less imagination required. I do this a few times a year. Something always surfaces that I'd been hiding from myself.
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Chris Guillebeau posted this"If only I'd known this much earlier." Most of us who find out late we have ADHD will catch ourselves saying it. You'll be replaying some version of your twenties or thirties—looking at the choices, the wrong rooms, the relationships that fell apart for reasons you didn't have words for—and you'll think it: *if only I'd known earlier, things might have been different.* That sentence is true, but not the WHOLE truth. Yes, you'd have made some different choices, and some would have been better. But some would have been different mistakes—the ones you made were the ones a person without that information makes, and the ones you didn't make weren't necessarily lined up to be wins. Here's the part that took me longer to see: the person who is finding this out now is the person all those years built. They're the ones who can use the information. The earlier version of you wouldn't have been ready for it, no matter how clearly someone explained it. The grief is appropriate. Spend time there. But once it eases up—and it does, it does ease—what you'll be left with isn't a missed life. You'll be left with this one, and a clearer set of instructions for the rest of it. There are more of us than you think. You're still on time.
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Chris Guillebeau posted thisFor about a decade, I thought my main skill was working hard. It seemed like the obvious explanation. I worked more hours than most people I knew. I shipped projects. I hit deadlines. The output added up, so the input must have been the engine. Eventually I noticed something embarrassing: *a lot of people work hard*. Many work harder than I do. And most of them don't get the same kinds of results from it. So whatever was happening, "working hard" was a description of the surface, not the cause. The real skill, when I finally squinted at it, was something I hadn't labeled. I could take a vague mess of a topic and find the through-line—what mattered, what didn't, what to say first. I'd been doing it since high school. It came easily enough that I didn't count it as a skill. It felt like thinking. This is the trap with strengths. The things you're best at often feel like nothing, because you're not aware of doing them. Other people's confusion about how you did the thing is the data—but you have to be paying attention, and most of us aren't. Which matters for the question of what to work on next. Most career advice here is forward-facing. Assess the market. Find the gap. Follow your passion. All useful in their place, but all outside-in. **The other route is inside-out:** look at what you've been quietly doing well, and ask what's adjacent. The next move is almost always closer to your current strength than you think. Not the same—that's stagnation. Adjacent. A half-step over. A few questions that have helped me find the through-line: What do friends ask my advice about, that I'd give for free, on a Saturday, without thinking about it? What did I do as a kid that didn't feel like work? When I read other people's writing in my field, what do I keep noticing that no one else seems to be noticing? The answers are often quieter than you'd want. Not "I'm a visionary." More like "I notice when an explanation is off by one degree." Useful, but not obviously a career. What works is taking that quiet thing seriously. Most people skip past their real skills because they don't sound impressive enough. Then they spend years trying to develop something that sounds better—and underperforming the people who took the unsexy thing seriously a decade ago. One caveat for those of us who are neurodivergent: "what comes easy" can mislead if you've been masking. Some of us are running so much background processing that nothing feels easy, even the things we're good at. If that's you, ask instead: what do other people keep telling me I do well, that I don't believe? That's where the signal is. Your unfair advantage has been with you for years. You probably haven't been counting it as a skill. Start there!
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Chris Guillebeau posted thisTime management: is one of the biggest myths that holds people back. For a long time I tried every variation of it. I used apps and spreadsheets. I went through a phase with a color-coded calendar. I read all the right books. I time-blocked and batch-processed. Here's what I figured out, embarrassingly late: I was managing the wrong variable. Time isn't a thing you can negotiate with. It moves at exactly one pace whether you log it or not. (Believe me, I tested this thoroughly.) What you CAN pay attention to is attention itself—sort of. And energy—kind of. And more than anything, the small daily question of whether what you're doing right now is what you'd want to be doing if you stepped back and looked at the week. Some days I get this right. Some days I lose the whole afternoon to something I won't remember when the day's done. The point isn't perfect execution; it's that the question is at least the right one. I'm not saying systems are useless. But if you've tried three of them and they all decayed within a month, the issue might not be discipline. The issue might be that you've been trying to control something that isn't controllable, and ignoring the thing that is. These days I mostly ask myself, before sitting down: "What's worth my attention right now?" I haven't gone back to the spreadsheet.
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Chris Guillebeau posted this"Just be yourself" is one of the more annoying pieces of advice, partly because it sounds like a posture to adopt. As if there's a Real You waiting somewhere, and the trick is to retrieve and display them. That's not how it works! You spend a lot of energy presenting a calibrated version of yourself for whatever room you're in. Adjusting your tone, downplaying the parts that don't land, performing the parts that do. But there's a TAX to this role-playing, and most people don't count it. The performance burns calories. Coming down from a day of it, you can be tired way out of proportion to anything you did. (Some of us know this tax intimately.) So here's another way to think about it: *notice what the performance is costing you*. If you end your day wiped out and you didn't lift anything heavier than your laptop, the answer is in the math. And then maybe—some of the time, in some of the rooms—let a few more parts of yourself through.
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Chris Guillebeau posted thisSome advice I've found useful: you can actually stop reading books before you finish them. That's right! You don't have to give a book closure or skim the last chapter. You can close it, give it to someone, and move on. The book will be fine, and so will you. I am a professional author and happy to tell you that not every book is worth finishing. I also have a small graveyard of books I'm never going to finish, and I am, somehow, still standing. P.S. This applies to more than just books.
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Chris Guillebeau posted this"I'll do it after this one quick thing." Most of us with time blindness have said some version of this sentence and not realized it was a confession. The quick thing was ... not quick. Time blindness is exactly what it sounds like: the intuitive sense most people have for how long things take, how much time has passed, how soon the future is—that sense is unreliable or absent. Five minutes and two hours feel similar inside a task. Tomorrow doesn't feel like a real time. The deadline that's three weeks out exists as an abstract until it's three days out and the panic clicks on. So what helps? In a word: AWARENESS. Tasks need to be on a list that has a chance of catching your eye when you'd otherwise drift past them. Also, use timers. Some of us run multiple alarms because one isn't enough. None of this is overkill if it works. The fix piece—the part where you're supposed to develop a "better sense of time"—that one is harder. The self doesn't grow by being scolded. Much better to just stop trying to keep track of time in your head. 🤓
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Chris Guillebeau posted thisIt's called a productivity hangover. You read a thread or watch a video about somebody's day—their morning routine, their deep work blocks, their cold plunges—and finish worse than you started. The strange part is that you didn't do anything wrong. You read a thing, that's it. But you came away with a vague new sense that you're behind on systems you weren't even using yesterday. Most productivity content does this to me, good advice or bad. I think the implied frame is always "here's what a real grown-up's day looks like, and yours doesn't." Even kind, useful advice can carry that frame, and the frame is what lingers. What helps is asking, before reading: do I want this person's day? If no, the advice won't fit. Reading it will mostly cost you. If yes, fine — read with an eye toward finding ONE THING that will actually help you.
Chris Guillebeau replied to a comment
2w
Brooke Yool I love libraries! I use the Libby app for Kindle + audiobooks all the time.
Chris Guillebeau replied to a comment
2w
John Welches It's acceptable to leave them on your bookshelf. :)
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Chris Guillebeau liked thisChris Guillebeau liked thisNever confuse effort with results. You can grind 12 hours a day, seven days a week, 365 days a year. If nothing moves, you wasted the year. Busy is not a strategy. Most businesses die here. Everyone’s exhausted. Calendars are full. The team looks heroic. And the numbers don’t budge. RevPAR doesn’t care how hard you tried. ADR doesn’t reward sweat. Occupancy doesn’t grade for hustle. Activity feels like progress because motion feels like meaning. It isn’t. Hard work is the price of entry. Results are the only receipt. Know the difference. Reward the difference. Effort is what you spend. Results are what you keep. This Assembly
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Chris Guillebeau liked thisFun job for an events person!Chris Guillebeau liked thisPlanwell is looking for our next Event Marketing Manager! This role is perfect for someone who loves details, thrives in fast-paced environments, and gets excited about creating incredible events for B2B brands. You’ll help lead planning and execution across trade shows, field events, conferences, and summits — managing timelines, vendors, logistics, and onsite execution. About the role: ✈️ Travel to places like San Diego, Austin, New York, Boston, London, and more 🤝 Work on a small, collaborative team that loves figuring things out together 👀 Looking for someone proactive, organized, and excited to grow with us We’ve got a really exciting year ahead and are looking for the right person to join the team. Apply here 👉 planwellco.com/hiring And if someone comes to mind while reading this, send them our way!
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Chris Guillebeau liked thisChris Guillebeau liked thisThe future of work is indeed here. Excited to be attending ATD Los Angeles this week. AI leadership development coaching culture human connection One thing is clear.. 👉 organizations that learn fastest and adapt intentionally (such a key factor) are the ones who will lead the way forward. Looking forward to the conversations, ideas, and connections this week around all that’s next for learning and development.
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Chris Guillebeau liked thisChris Guillebeau liked thisIt’s been a busy week… But with that said, we didn’t have a clear favourite this week. In part, it is because we are very different people with very different passions in our pro-readers team. And I find it a strength. But I’ve also noticed that, regardless of our differences, some books have the capacity to sway us all. However, let’s get to this week’s business. 👨👧 The Tired Dad. by Jon Gustin It is somewhat ironic, don’t you think, to start with a book on fatherhood on a day like this. First – it is a very unique angle. Most books on parenting talk to mothers and assume mothers as default primary caregivers. Second, I was hoping so much that there would be some worthy books on motherhood on the week of Mother's Day. But we have to face the facts – the book that got our semi-unanimous ‘yes’ was meant for fathers. On the bright side – a lot of moms would be made much happier if there were more engaged dads. 🚶♀️ Walk by Courtney Conley and Milica McDowell Walking is underrated. Don’t you think? And somewhat misunderstood. Here’s a solid book on the topic. I’m not entirely convinced why longevity has to be thrown into the mix – we are not quite there yet, with average life expectancy in the W.E.I.R.D. countries still at 80-85 years (hence, I wonder how it is being taught when it is purely hypothetical at this point). But even for the relatively young people such as our audience :)) walking is a lovely activity to boost health and well-being. ⚡ Body Electric by Manoush Zomorodi and Keith Diaz This may be a somewhat contested topic, I’m afraid. Lifestyles naturally impact people’s health and well-being. Yet, the extent and the exact mechanisms of that impact are still being researched and hypothesised about. There isn’t a consensus yet. But it is a wonderful topic to discuss. And the good thing about this book – the author and the publisher have great credentials. 📚 If you haven’t yet, sign up to our newsletter to get weekly reviews of the new books in self-help and business, and weekly interviews with the world’s best authors - https://lnkd.in/gyPm5nyX
Experience & Education
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Chris Guillebeau, Inc
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Publications
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Born for This
Penguin Random House (Crown Business)
See publicationWin the career lottery and find the work you were born to do. My new book is the culmination of years of research on people who’ve found or created their “dream job.” From the outside, it looks like these people have been lucky. But in reality, they’ve followed a process of trial-and-error to get exactly what they want.
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The Happiness of Pursuit
Penguin Random House (Harmony Books)
See publicationWhen he set out to visit all of the planet’s countries by age thirty-five, compulsive goal seeker Chris Guillebeau never imagined that his journey’s biggest revelation would be how many people like himself exist – each pursuing a challenging quest. And, interestingly, these quests aren’t just travel-oriented. On the contrary, they’re as diverse as humanity itself. Some involve exploration; others the pursuit of athletic or artistic excellence; still others a battle against injustice or…
When he set out to visit all of the planet’s countries by age thirty-five, compulsive goal seeker Chris Guillebeau never imagined that his journey’s biggest revelation would be how many people like himself exist – each pursuing a challenging quest. And, interestingly, these quests aren’t just travel-oriented. On the contrary, they’re as diverse as humanity itself. Some involve exploration; others the pursuit of athletic or artistic excellence; still others a battle against injustice or poverty or threats to the environment.
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The $100 Startup
Penguin Random House (Crown Business)
See publicationIn preparing to write this book, we identified 1,500 individuals who have built businesses earning $50,000 or more from a modest investment (in many cases, $100 or less). In nearly all cases, people with no special skills discovered aspects of their personal passions that could be monetized, and were able to restructure their lives in ways that gave them greater freedom and fulfillment.
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The Art of Non-Conformity
Penguin Random House (Perigee)
See publicationThe underlying message of Guillebeau's book, based on his popular blog, is that "You don't have to live your life the way other people expect you to." Those who are open-minded, ready to challenge the status-quo, hard-working, and personally responsible can lead lives of rare authenticity.
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