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lessons

89 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. If Plan A Fails, Remember that You Have 25 Letters Left

   *My book Born for This is all about helping you find the work you were meant to do. This series explores some of these lessons. Lesson: Craft backup plans. They will allow you to take more risks and m

4. Beware the Power of Bad Advice: A Lesson in Life and Plumbing

   Holly Finch founded the LightBox Collaborative , a San Francisco-based consultancy for non-profits. Lightbox has eight “collaborators” but no employees. When I asked Holly what she should advise someo

5. How to Be a Motivational Speaker

   I recently met with a guy who’s trying to become a motivational speaker. He’s a good guy with good things to say.

6. “In spite of everything, I still believe people are really good at heart”

   From The Diary of Anne Frank : “In spite of everything I still believe that people are really good at heart. I simply can’t build up my hopes on a foundation consisting of confusion, misery, and

7. Learning How to Learn

   Long ago, I described myself as a “lifelong learner.” I never liked school much, but I liked learning.

8. The Audience Is Listening (Hopefully)

   “People used to expect companies to take care of them,” he said. “Now you’re in charge of your own destiny, for better or worse.” -From a recent article

9. The DIY Book Tour

   Originally posted on February 11, 2013 — Over the past few years, I’ve hosted more than 100 events with readers in eight countries.

10. 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.

11. The Challenge and the Opportunity

    Once upon a time I lived in the small country of Togo in West Africa. I was based on a hospital ship docked in Lomé, the capital, and the team I worked with

12. 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

13. How To Fall Down and Get Back Up Again

    This is a lesson on how to look absolutely ridiculous in front of a crowd of strangers, and how to recover as gracefully as possible.

14. Forward Motion

    I had an early-early flight, so I booked a hotel near the airport and took the train out the night before.

15. 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.

16. Lessons Learned from 11 Years of Travel

    Last weekend I had the honor of speaking to 600 people at Frequent Traveler University , a conference devoted to the world of points and miles. A longtime friend, Gary Leff , asked me to share a few l

17. 34 Things I’ve Learned About Life and Adventure

    Want to become wiser? It’s fairly simple and closely resembles Brian Tracey’s formula for being luckier: “Luck is quite predictable.

18. Worst Case Scenario: Losing It All in Europe

    When you’re evaluating a big decision, sometimes it’s helpful to ask yourself, “What’s the worst thing that can happen?” Most of the time, the worst-case

19. 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

20. How to Think About People Who Disagree with You

    And other ways of applying perspective. “Guy from Minnesota says it’s cold in the winter. Guy from Mexico disagrees, says it’s hot in the winter.

21. Service Is Free to Offer But Incredibly Valuable: Lessons from an Airport Shuttle Driver

    At the Hyatt Dulles, my shuttle driver was named Abdullai. He was extremely enthusiastic about welcoming his early-morning travelers on board for the ride to

22. 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).

23. Do You Want to Be Right or Do You Want to Be Free?

    I’ve been thinking about this question recently (thanks, Danielle). There’s a lot of freedom in giving up on a matter of principle, so you can move on with

24. Units of Momentary Happiness

    “Everything we need to be happy is easy to obtain.” -Epicurus I’ve long advocated that happiness is not entirely related to a feeling of a precise moment.

25. 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.

26. Immerse Yourself in What You Want to Become

    In reading the transcript of Bob Dylan’s speech at MusiCares, I also liked this part on the origins of his songwriting: “There’s nothing secret about it.

27. Prepare for Tomorrow by Doing One Thing Differently Today

    Here’s a trick that will help every time you do it. Work hard during the day, and cross off as many things from your list as you can.

28. A Better Approach to “Never Check Email in the Morning”

    You’ve heard the conventional wisdom: never check email in the morning. That sounds great, unless your job involves communicating with people, or if you

29. 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.

30. How Much Is Your Time Worth? This Free Tool Will Show You

    Link: How Much Is Your Time Worth? Deciding how you value your time can help you make decisions. But how do you really know what your time is worth?

31. 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.

32. Joy, Money, and Flow: The Three Qualities of Purposeful Work

    *My book, Born for This, is all about helping you find the work you were meant to do. This series explores some of these lessons.

33. Resign Your Job Every Year

    *My book, Born for This, is all about helping you find the work you were meant to do. This series explores some of these lessons.

34. The Answer in Your Inbox

    *My book, Born for This, is all about helping you find the work you were meant to do. This series explores some of these lessons.

35. 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.

36. “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.

37. Some Advice for Me, and Maybe for You

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

38. Closing the Books: A Lesson in Letting Go

    Jonathan Fields sent me this short audio story as an example for recording my own 5-10 minute one.

39. 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.”

40. 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.

41. 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.

42. 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

43. 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.

44. “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.

45. “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.

46. 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.

47. Win the Way You Won Before

    When you encounter a setback and need to regroup, think back to a time when you won.

48. 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.

49. The Japanese Tradition That Encourages Us to Be Present

    More supporting evidence for my focus on units of momentary happiness: Japanese tradition tells of ichi-go ichi-e, a concept fortified over centuries of

50. The Historian Who Couldn’t Escape From Alcatraz

    In the introduction to one of the chapters of my new book, I wrote about escaping from Alcatraz.

51. There’s No School For What You Need To Do

    At one of the stops on my current tour, the bookstore host introduced me by saying in part “… and Chris earned a master’s degree in International Studies

52. Hope, Expectations, and Winning the Lottery

    Most people know that the lottery is not a good investment plan. It’s not rational to invest large amounts of money in lottery tickets, because you’re almost

53. 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.

54. Black Sheep Basics

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

55. “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

56. It’s Not My Birthday

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

57. “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.

58. The Myth Of The Self-Made Man

    Arnold Schwarzenegger on being a self-made man: I came over here with absolutely nothing. I had $20 in the pocket and some sweaty clothes in a gym bag.

59. 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

60. 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.

61. 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.

62. When You’re Stuck In A Hole, Look For Someone To Join You: A Lesson In Empathy

    Happy Thanksgiving to all, and not just those in the U.S.! Thankfulness is available no matter where you live.

63. 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

64. Uncomfortable Is Not Unsafe

    TLDR: Being uncomfortable is not the same as being unsafe. Avoid things that are fundamentally unsafe, but move in the direction of your discomfort.

65. The Three Conditions For Making Ordinary Magic

    Magic is all around you. Maybe you’ve even made some magic of your own. What you might not realize is that there’s a formula for such a thing.

66. 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?

67. The Greatest Story Ever Sold 💵

    Two weeks ago, I wrote about how money mistakes are temporary. My main argument was that unlike other kinds of mistakes, money mistakes rarely have permanent

68. 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

69. When You Need to Escape, Build Your Own Countdown Clock

    *My brand-new book, Born for This, is all about helping you find the work you were meant to do. This series explores some of these lessons.

70. Improve the Right Kind of Skills (They Probably Aren’t What You Think)

    *My book Born for This is all about helping you find the work you were meant to do. This series explores some of these lessons.

71. Winners Give Up All The Time

    *My brand-new book, Born for This, is all about helping you find the work you were meant to do. This series explores some of these lessons.

72. Three Simple Actions to Increase Your Available Options

    Even if you’re perfectly happy where you are, anything you can do to add security and increase your options will help you.

73. 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

74. Should You Perform For the Audience or Just Entertain Yourself

    Link: Sir Paul on Fans, the Beatles, and Himself When Paul McCartney goes on tour, he plays a lot of songs.

75. 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.

76. “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.

77. 9 Life Lessons From Starting a Daily Podcast

    So hey—I started a podcast! Yes, it’s true: I’m catching up to the technological age of 2005. And let me tell you: I’m having so much fun. I feel purposeful.

78. 168 Hours Time Tracking: What I Learned Tracking Every 15 Minutes (+ Free Template)

    Tracking every 15 minutes of my week — what I learned, the patterns I didn't expect, and a free 168-hour spreadsheet template you can download to try it yourself.

79. Why Ideas are Not Enough (OR: How to Sell Out Like Iron Maiden)

    Link: Perennial Seller “What if I’m not good at making ideas happen? I just like to have ideas!” Ever since I started Side Hustle School on January 1, I’ve

80. 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.

81. Is There a Hole in Your Bathtub?

    Imagine that you’re filling your bathtub for a nice relaxing soak. You’ve got the water on full blast at just the right temperature, and the soap suds are

82. Be Careful of Telling Your Origins Story Over and Over

    The time came for the interview and I logged into Skype with my headset. After a few minutes of small talk, the host pressed the record button and began with

83. 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.

84. How to Buy Plane Tickets on the Same Day of Departure

    On a recent excursion I found myself in Washington, DC, and I was ready to leave. There were just two problems: I didn’t know where I wanted to go next,

85. 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.

86. 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.

87. If You Can’t Learn Math, Maybe It’s Not Your Fault

    I dropped out of high school and never learned algebra or geometry—not for lack of trying. Here's what that experience taught me about how we think about intelligence and learning.

88. Do This When You Visit a New Place

    Pandemic life has taught many of us to appreciate moments in life that might otherwise pass us by.

89. Be Persistent and Impatient

    I’m fascinated by people who work unabashedly towards a difficult goal, especially when there’s little chance of external reward or motivation.