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life

128 essays

1. The Present-Day Time Machine

   “Look around at how lucky we are to be alive right now.” -Lin-Manuel Miranda, from Hamilton of course— Most of us can think of times in our lives that we’d

2. Regret is an Unreliable Emotion

   I have long believed that thinking about regret is a powerful motivator for action.

3. 36 Ways to Live Differently

   To live better means that you’ll live differently—somehow, you’ll make some kind of change. Your life will be different tomorrow than it is today.

4. Language Matters: Lessons in Editing from Mr. Rogers

   I went to see the Mr. Rogers movie last week (“ Won’t You Be My Neighbor ”) and found it as heartwarming and uplifting as I expected. If you’re able to see it in a theatre, don’t hesitate. At the scre

5. Let the Wave Crash Over You: One Year Later

   Orion image via Ryan Hallock Readers: One year ago today I lost my brother, Ken. This difficult subject isn’t relevant to everyone, but for those who are interested I’ve written about it in a fe

6. A Story of Friendship and Values

   Note: I found this in the wilds of the internet and don’t know the original source. I didn’t write it, but I liked the story. -cg Two friends were walking through the desert. During some p

7. Creating a Legacy Project

   Originally posted on February 2, 2009 — [Note: This 3,000 word article is all about creating your own legacy project.

8. Writing With Adderall: A Personal Case Study

   Here’s the whole story of my experience taking the prescription drug Adderall (the brand name for amphetamine and dextroamphetamine) to help with an increasing inability to focus . If you’re in a simi

9. If Your Life Is a Movie and You’re the Director, Why Did You Add this Scene to It?

   Imagine your life as an epic, three-hour movie. In this saga there are numerous high points and low points, and both drama and comedy. There are coming-of-age moments and passages of growing older. Th

10. What is the Bravest Choice You Can Make Right Now?

    If you want to be more courageous, you have to make brave choices. Sounds simple enough—but how do you know which of those choices to make next?

11. How To Talk To Someone Who Believes A Conspiracy Theory

    I just came from the pizza parlor that doubles as a global headquarters for child trafficking. I counted up some ballots that proved the election was stolen.

12. 9 Predictions For The Year 2050

    Nine specific predictions for what the world will look like in 2050—from the fate of American football and esports to climate change, the metaverse, aliens, and whether human lifespan will meaningfully extend.

13. Always Ask for What You Want: A Lesson in Asymmetrical Risk

    TLDR: An asymmetrical risk is one where the potential reward greatly outweighs the potential loss. Identify and take more of these risks.

14. Dreading the Holidays? It’s Not Just You.

    Do you find yourself dreading the holiday season, or just not excited about it? If so, I promise you’re not the only one.

15. Dreading the Holidays? It’s Not Just You.

    Do you find yourself dreading the holiday season, or just not excited about it? If so, I promise you’re not the only one.

16. Things Not to Worry About

    The post on unnecessary traffic lights generated a heated debate about rules, laws, and traffic cameras.

17. Leading a Horse to Water

    There’s an old story about a salesperson who was disappointed in losing an important sale. He talked with the boss about why it didn’t work out.

18. How Has Travel Affected Your Life?

    Tom asked me what lasting impact travel has had on my life. I thought it was an interesting question. After I came home from Norway (country 193/193), I did a number of radio interviews where the host

19. How to Be Unremarkably Average

    Follow These Simple Tips for a Risk-Free Life: Accept what people tell you at face value. Surround yourself with people who think like you. Don’t stand out.

20. The Decision to Be Remarkable

    re•mark•able [adjective]: worthy of being noticed, especially as being uncommon or extraordinary *** If you want to break out of the mold of average, the

21. Creating and Living by Your Own List of Values

    Most people live by an unexamined moral code—reacting to situations rather than deciding in advance what they stand for. Here's how to build your own list of values and actually use it.

22. What to Do When It’s Not Working Out

    From countless encounters with failure, I can tell you that not everything works out the way you hope it will.

23. Generous People Have More To Give

    A few weeks ago in Miami I only had a $5 bill when it came time to get out of the airport shuttle.

24. How To Be Yourself

    It’s a good idea to be yourself, not only because everybody else is taken, but because trying to be anything else doesn’t usually get you very far.

25. The Tower: A Free Report for a New Way of Life

    Greetings, friends and readers. I’m on the road as usual, and today I’m also excited to announce the release of a new manifesto, The Tower.

26. What to Do About Those People Who Sidetracked Your Life

    This article doesn’t have much to do with travel hacking or unconventional work. And in fact, it will only apply to a minority of the people who read it.

27. The Goal

    1. To wake in the morning full of life and energy, awaiting the day with anticipation and purpose.

28. Your Goals Are Too Small

    1) I want you to think about something. Maybe you’re like me: coasting along, doing okay, not lacking for anything material. You have a good life.

29. Running In Your Mind

    “They say there’s no harm in daydreaming, but there is.” -Charlaine Harris When I run, I wish I could say I was fully focused on my surroundings.

30. On the Cost of Upgrading Your Fleet of Warships

    I downloaded another iPad game that was a lot like the one I wrote about in The Tower.

31. You Should Do What Makes You happy

    I liked Seth Miller’s post about flying JetBlue on his birthday for no particular reason other than the fact that it made him happy.

32. How I Deal with Anxiety

    Originally posted August 18, 2014. More recent post –> here. *** On any given day I’m anxious about any number of things. I don’t relax very well.

33. Why You Must Study Your Mistakes, and Other Rules to Live By

    Buster Benson created the fabulous 750words.com, which encourages users to cultivate a writing streak.

34. Framing Decisions in the Context of Future Regret

    The “Will I regret it in the future?” mindset can be very helpful in making decisions.

35. Tinkering on the Margins of Small Arguments

    “I had no good reason not to take it up,” he said of a big decision. “And it kind of terrified me to imagine myself spending the rest of my life tinkering on the margins of the small arguments.” Link: Embrace the Irony Image: Ed ###

36. A Better Organizational Strategy: Throw Away Everything That Doesn’t Make You Happy

    I love the principle presented by Japanese organizational expert Marie Kondo in her new book.

37. What If We Don’t Improve After a Difficult Experience?

    “One of the unspeakable things that I think might even be the most unspeakable way of carrying on is this idea of not improving from an experience, not

38. Re: “Let’s talk when you’re free”

    Productive people are never “free.” They don’t have 15 minutes on their lunch break to “have a quick call.” They don’t “kill time”—a terrible phrase.

39. A Life That Matters

    A lot of personal development writers use the phrase “a life that matters,” as in “Here’s how you live a life that matters.” But this phrase is problematic,

40. A Magic Broadcast Channel That Will Help you Reach the World

    Imagine being able to share your thoughts with anyone at any time. From this broadcast channel, you can say whatever you want … no matter how unusual or

41. Plan in Advance When You’ll Begin to Worry About Something

    Before a big talk, I used to stress out for weeks. The feeling began with a sense of being unsettled (and not the good kind).

42. 7 Alternative Ways to Evaluate Your Life Every Day

    As regular readers know, I’m all about setting goals and working toward big projects over time.

43. Waking Up at Night with Big Ideas

    Long ago, right before I started this blog and began the full-time quest to “go everywhere,” I went through a six-month period of thinking about it.

44. Everything’s Great, But Could I Get That Breakfast I Ordered?

    My hotel breakfast server was very friendly. It took a while for him to come over after I was seated, but when he did, he was all smiles and exuberance.

45. The Treasure Is Still Out There: Thoughts on Adventure and Scott Dinsmore

    A few days ago I went to San Francisco to attend a memorial service for Scott Luckey Dinsmore, who recently died in a tragic accident on Mount Kilimanjaro.

46. Whatever Happened to the Road Not Taken?

    You’ve heard the story a thousand times. Two roads diverged in the woods, and the wanderer is forced to choose.

47. One Year of Taking Adderall to Help with Writing & Focus

    Last year I shared the story of why I got a prescription for Adderall, the brand name of the psychostimulant drug that can help you better manage your

48. It’s Not How Much Email You Get, It’s the Lack of Purpose in Your Life

    If you misidentify a problem, your proposed solution probably won’t work. Let’s say you have a headache, so you decide to amputate your leg.

49. A New Year’s Wish for the Wanderer

    Originally published January 1, 2016 — Every evening the sun sets, then rises again a few hours later.

50. “Taking Risks” Is Not the Same as “Doing Hard Things”

    Recently I’ve been noticing that I haven’t been taking enough risks. I don’t want to be complacent! And I always want to be challenging myself.

51. Some Advice for Me, and Maybe for You

    Lately I’ve been thinking about forward motion, taking risks, and finding the next big thing.

52. The Snake in the Road: A Lesson in Fear & Perception

    Over the past few months, when I haven’t been preparing for my book launch or flying around the world, I’ve also been learning a lot more about “inner work.”

53. How Goals Change Over Time, and What to Do About It

    The other day I was cleaning out my home office, and I found some old notes. The notes were from more than eight years ago before starting this blog.

54. The 50-Mile Race vs. The Cliff Jump

    Imagine two scenarios that each require you to take on a monumental task. In the first scenario, your task is to run a 50-mile race.

55. The Light of the Oncoming Train Strengthens the Mind

    Dear Self, Your problem is that you think everything matters. The things that you do every day, the tasks that occupy your mind and draw on your energy—you

56. A Simple Thing You Can Do To Improve Any Relationship

    What if there was one thing you could do to be a better friend, partner, or spouse?

57. Don’t Make a Bucket List; Make a List of 100 Dreams

    OK, it’s kind of like a bucket list. But it’s a really big one! From Laura Vanderkam: In 168 Hours, I recommended creating something called a “List of 100

58. Sometimes It Doesn’t Work, But You Still Have to Try Anyway

    You always hear about the people who took a chance that paid off. You always hear the try, try again stories—those case studies of overcoming what seems to

59. You Can’t Live As If You Only Had Three Months to Live

    It’s a challenging thought: “How would you live if you learned you only had three months left?” Most of us would probably make some changes, or at least we’d

60. Happiness Is a Superpower

    I heard something in a dialogue recently. One character was complaining about being unhappy, and the other character replied, “You have a misguided notion of

61. The Emotional Balance Sheet

    Link: Emotional Balance Sheet I often enjoy the personal finance columns by Carl Richards.

62. Lessons in Non-Conformity from Sesame Street

    A reader sent me this fun video from a long-ago sketch on Sesame Street: I love the turning point right at the halfway mark: Dan would do everything that

63. Many Dreams Aren’t That Hard to Achieve

    Toward the end of Up in the Air, the character played by George Clooney calls up American Airlines and asks to transfer some of his Frequent Flyer miles to

64. The Game Is Rigged, So Learn to Play the Game

    You probably learned in kindergarten that life isn’t fair. You can’t always get what you want—and sometimes you might not even get what you need.

65. “What Have I Missed in My Life?” Notes on The Novels Mrs. Bridge and Mr. Bridge

    I think the message in the book is that we all have flaws we can’t resolve.” -Amazon reviewer I recently read Mrs.

66. Warning Signs That Your Life Lacks a Consistent Vision

    You don’t know what to do at the start of the day. External events determine how you schedule and spend your time.

67. Going to the Movies by Yourself

    I’m a big fan of doing things alone. I eat in restaurants alone, I go to faraway places for my birthday alone, and I generally work alone more often than

68. “Most Ambitions Belong to the Past”: Reflections on A Neurosurgeon’s Final Year of Life

    Originally published April 23, 2015 — I recently stumbled upon an essay from Paul Kalanithi, a neurosurgeon who died in 2015 at the age of 37.

69. Hate Paying Taxes? It Could Be a Lot Worse: You Might Not Have to Pay Them

    I do wish it were simpler. I was surprised last year to learn that I agreed with Donald Rumsfeld on something.

70. To Cross the Railroad Tracks, Go Against Everything You’ve Been Told

    One time, long ago, I had a hard year while living in Memphis, Tennessee. Ever since then, especially when I’ve been at events throughout the south, I’ve met

71. “If you have to ‘give back,’ maybe you took too much in the first place.”

    I heard someone say that recently. I don’t remember the context but I really liked the sentiment.

72. Sometimes Life Sucks, So You Might As Well Do Something About It

    I’ve always liked Trent Hamm‘s tagline: “All I care about is making your life not suck.” This is what good bloggers, and good people of all kinds, do well.

73. To Be Happier, Go to the Library

    If you liked the Japanese tradition, here’s another one from this side of the Pacific: Older people often draw as much happiness from ordinary experiences —

74. The Resumé Of Failures

    For every success, there are countless failures. Yet when we look at someone from the outside, especially someone who’s been particularly successful, we may

75. How To Live In Fear

    Are you tired of being courageous and fed up with bravery? Seeking an alternative to risk-taking? Not to worry.

76. When To Compromise And When To Hold Your Ground

    At some point, most of us end up settling in a major part of our life. We compromise and make tradeoffs. We can’t always get everything we want, of course.

77. Black Sheep Basics

    Be proud of being the black sheep. If everyone agrees with you, maybe you’re not being bold enough.

78. Be Realistic: Plan For A Miracle

    Be realistic: Plan for a miracle.” ―Osho Sometimes in life it’s good to play it safe. But this is not one of those times.

79. Art and Plumbing: The Indispensable Interview with Seth Godin

    It’s no secret I’m a big fan of author and change agent Seth Godin . I’ve been reading his books since my years in West Africa (2002-2006), and he continues to produce excellent work

80. It’s Time To Change The Road You Walk On

    If you don’t like the road you’re walking, start paving another one.” -Dolly Parton You could make a big change at any point in your life.

81. Even When You Aren’t Sure What To Say, Don’t Be Silent

    I recently had the honor of introducing Emily McDowell and facilitating a Q&A session with her at Powell’s for her new book, There Is No Good Card for This.

82. “Everything Is Figureoutable:” Notes from Paris to Doha

    On a recent trip, I had to get back to Doha from Paris, a 5 1/2 hour flight. I was transferring via an initial connection from Zurich, and I booked the

83. It’s Not My Birthday

    Originally published April 4, 2017 — Despite what Google or Wikipedia tells you, today (April 4th) is not my birthday.

84. “We Run Away From Desperation:” Thoughts On Pursuing A Creative Idea

    I recently recorded a Side Hustle School episode about Michelle D’Avella, a designer who spent several years building a blog before turning it into a

85. “If You Can Invest In Someone Else’s Company, You Can Invest In Yourself”

    On an upcoming episode of Side Hustle School, I tell the story of someone who obtained a patent for a special kind of mittens for runners.

86. The Movie Of Your Life, Part II

    I used to worry a lot about what people think of me. I felt that I could be damaged or even destroyed by someone’s words, or my failure to achieve an

87. Evening Rituals

    I have one or two drinks with dinner, rarely any more. Before bed I make a cup of herbal tea and take magnesium. Sometimes I have a square of dark chocolate.

88. Afternoon Rituals

    If I’ve done my job well and managed my time properly, most of the crunch time work has happened in the morning.

89. Morning Rituals

    When I’m not jet lagged from flying around the world, I have a clear routine that I follow as much as possible.

90. Going Back To A Hard Place

    Imagine revisiting a place you’d been long ago during a hard time in your life. Maybe that time was long, long ago, and the place far, far away.

91. For All The Things You Can’t Control, Remember “This Too Shall Pass”

    Just as there are some things that can’t be fixed, there are also some things you can’t control.

92. A Field Guide To Wandering In The Wilderness Of The Soul

    When you’re wandering cobblestone streets in Europe, stopping at cafes and making unexpected discoveries, it’s fun to lose your way and wander off the

93. 7 Questions to Ask When You’re Feeling Stuck

    Do you ever feel stuck? I’m pretty sure we all do at some point. Feeling stuck is like feeling afraid: it happens to everyone, but not everyone gets past it.

94. The Limits of Lifehacking: What Happens When you Approach Optimization

    I have a weird memory of my dad explaining math to me when I was a kid. I never actually learned real math, at least once it went beyond how to pocket extra

95. Under the Unseen Blue Sky in Sydney, Australia

    If you’re going through a dark night of the soul, you might as well pass the time in a beautiful place.

96. Don’t Feel Pressure to Find Your Life’s Purpose at Age 21

    I got an email from a reader who wrote in with a question I’ve heard many times in different ways.

97. All The Things You Didn’t Do

    Once upon a time, you had the chance to be brave. Your name was selected, your number was called.

98. To Every Thing, A Season

    You probably know the song, the one that borrows its lyrics from the book of ‎Ecclesiastes: to every thing, there is a season for every activity under the

99. Sometimes The Best Thing You Can Hear Is “It’s Going To Be Okay”

    I’ve had a few people write in to ask me if I’ve stopped blogging. Nope—but I’m sorry! It sure looks that way.

100. New Year, Same You

     Originally posted on January 1, 2020. — What if, instead of “New Year, New You,” you decided you were satisfied with the course you had already set?

101. The Second Best Thing You Can Do Right Now

     Wondering what to do during this time of chaos? I have a proposal. First, the best thing you can do is what you already know about: keep people safe by

102. Habits of Highly Effective Real People

     “Everybody talks about wanting to change things and help and fix, but ultimately all you can do is fix yourself. And that’s a lot.

103. Start Your Resolutions on January 6th

     View this post on Instagram A post shared by Chris Guillebeau (@193countries) Resolutions can be powerful, and they don’t have to begin on any given day.

104. Money Mistakes are Temporary

     A common TV trope features someone who’s down on their luck and forced to borrow from someone with questionable moral scruples: a loan shark, the Mafia, a

105. The Courage to Change Your Mind

     Here’s a helpful filter to know when to worry: does something sound too good to be true, or does it sound so bad that people give up and stop thinking for

106. How to Win the Career Lottery

     If you won the lottery tomorrow, how would your life be different? Maybe you’d buy a new car or take a dream vacation.

107. If Your Vision Isn’t Being Understood, Never Hesitate to Change Your Tactics

     From Mike Birbiglia’s “6 Tips for Making it Small in Hollywood”: “I once heard an interview where Ron Howard said that he tests the rough cuts of his movies

108. By Any Means Necessary

     February is Black History Month in the United States, where we recognize the achievements of African Americans and honor our culture of diversity. A lot of attention during this time is focused on the

109. How to Have More Time: 8 Practical Strategies

     Want more time without sacrificing sleep? Eight practical strategies to reclaim hours in your day—including a few that go against typical productivity advice.

110. “The Beauty is That it Could Fail”: A Real-World Story of Risk

     The new host of Prairie Home Companion steps in after forty years of someone else running the show. Toward the end of the meeting at the Fort, in St.

111. What is Your Personal Moonshot?

     A moonshot, according to the ubiquitous WikiPedia, is a “is an ambitious, exploratory and ground-breaking project undertaken without any expectation of

112. Return of the Annual Review! Let’s Do This! (I mean, if you want.)

     Over the past eight nine ten! years, nothing has helped me to accomplish big goals and stay on track more than a single exercise I complete each December:

113. Opportunity Waits in the Time of Uncertainty

     Wow, what happened to the world in the past week? I’m writing to you from my sanitized desk in an underground bunker … well, it’s not quite like that.

114. The Real Imposter Is the Part of You That Hesitates

     What holds people back from making a bold choice or following a dream? When you ask, often they’ll point to the lack of knowledge.

115. What’s Something You’ve Done that Few Other People Have?

     It’s a simple question: what have you done that few other people have? Think about it.

116. Being Able To Ask “What’s Next?” Is A Sign You Are Happy In Your Work

     During the Born for This tour, people would occasionally ask how you know when you have your dream job.

117. How Do You Know If Your Idea Is Worth Pursuing?

     Creative people usually have no shortage of ideas of things they’d like to do. The greater challenge is: how do you know which ideas are worth pursuing, and

118. Pandering Never Builds a Legacy

     I’m as guilty as anyone else who says that to build a business, or a blog, it’s good to ask people what they want and then give it to them. It works!

119. Don’t Make Important Decisions Out of Desperation

     One of the best things about having more than one source of income is that it provides security when something goes wrong.

120. How to Write a Novel

     First up, thank you so much for your support of THE MONEY TREE! Despite the numerous challenges of current events, the book is getting out to lots of people.

121. How to Travel to Random Places and Work on a Project

     Greetings from the sky, on board Cathay Pacific’s longest flight. There are 16 hours scheduled for my “air world” time today, although it looks like we may

122. To Win the Lottery, Buy a Ticket and Never Check the Numbers

     I recently bought my first lottery ticket in something like 15 years. The purchase happened on a whim, as I was walking down the street in California.

123. How to Be Yourself

     It’s a good idea to be yourself, not only because everybody else is taken, but because trying to be anything else doesn’t usually get you very far.

124. What to Do When You Feel Overwhelmed

     Anyone feeling overwhelmed? It happens. The worst thing about feeling overwhelmed is the anxiety. The second worst thing is not knowing what to do next.

125. The Importance of Having a Breakdown, AKA “What Happened to the Annual Review”

     What can I say about the Annual Review process that I’ve completed without fail for more than a decade? This year, I gave up on it and walked away.

126. If Your Life Is a Movie and You’re the Director, Why Did You Add this Scene to It?

     Imagine your life as an epic, three-hour movie. In this saga there are numerous high points and low points, and both drama and comedy.

127. Writing With Adderall: A Personal Case Study

     Here’s the whole story of my experience taking the prescription drug Adderall (the brand name for amphetamine and dextroamphetamine) to help with an

128. How to Conduct Your Own Annual Review

     Every year since 2005, I’ve spent the better part of a week in late December planning my life for the next year.