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79 essays

1. WORK

   Navigate using the links on the left or view any of the posts below. Learn to think like an entrepreneur, even if you have a job.

2. 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

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. To Be More Creative, Schedule Your Work at 80% Capacity

   I’m fortunate to work with great partners, including a wonderful design studio right in Southeast Portland called Jolby & Friends . I was recently with the Jolby crew on a site visit, and o

5. How to Stand Out in Any Job

   Regardless of what kind of work you do, it’s usually not difficult to set yourself apart by going beyond the status quo of being average.

6. The Art of Radical Exclusion

   Here’s the idea: we make time for what’s important to us. If I fail to fulfill a commitment I’ve made in a timely manner, it’s because of a conscious choice

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. The Starving Artist Solves the Problem

   Paul was an artist, painting in several mediums and styles. He lived in a Northwestern city known for its love of the arts, if not always its ambition.

9. How to Make Money on the Internet

   When it comes to working online and making money on the internet, most discussions tend to look at specific tactics. How do you set up a mailing list?

10. The One-Page Career Cheat Sheet

    Originally posted March 8, 2012 — Are you happy in your job? This fun resource—a one-page, “career cheat sheet”—from Sarah K.

11. 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.

12. Climb the Right Ladder

    Originally posted on March 25, 2013 — Over the weekend I heard a talk and short performance piece by Stephen Kellogg, an independent musician who was

13. Worth It All

    Sometimes it’s hard to know if it’s all worth it. You’re out in the woodshed, slaving away on this thing you love, night and day.

14. The Crunch

    You’ve been here before. The weeks and months have gone by, and now you find yourself at the point where something big is due.

15. Consider the Dominoes

    It’s not that you’re too busy, or that you’re doing too much. You’re known for taking on challenges and doing the impossible. You know your metrics.

16. Personal Responsibility and Showing Up

    To be truly awesome, you have to go above and beyond the efforts of those around you, look for alternative solutions, and refuse to back down from the truth.

17. Rest and Recovery

    Back home in Portland, I went to my first yoga class in several weeks and immediately noticed that something was different. This class is kicking my ass!

18. Forward Motion

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

19. “There’s plenty of time.” (But what if there’s not?)

    I’ve been working on a new, non-profit writing project that I’ll share tomorrow. Here’s a preview of the concept—for more on the project itself, see the note

20. 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.

21. Life In the Tower, Somaliland Edition

    Many thanks to everyone who has been reading or supporting the launch of The Tower, my new manifesto.

22. Small Things Can Keep Us from Big Things

    Lately I’ve felt that I’m doing well at the small things, but failing to plan for more involved work.

23. The Goal

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

24. Jackson Pollock’s Overnight Success Was a Lot Like Most People’s

    Despite claims made and repeated for decades, Pollock did not paint his epic Mural canvas in one great, glorious burst of nonstop creative fervor.

25. Why Artistic Compromise Makes for Better Work

    Once in a while (thankfully not often), I look back at some of the posts and articles I wrote in the early days. What in the world was I thinking?

26. Thoughts on Working from the Drugstore

    The drugstore in my neighborhood has a deliberate policy of wasting every customer’s time.

27. 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.

28. The Craft of Editing a Very Short Story

    Lydia Davis, an author of “very short stories” for more than 40 years, described her editing process in feature for The Atlantic.

29. Do You Have to Take a Terrible Job Just Because You Went to College?

    I often enjoy the Ethicist column by Chuck Klosterman. A recent column posed an interesting question: “Do I have an ethical duty to find a better job even if

30. 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

31. Checking Your Bank Accounts Will Not Make More Money

    Seems obvious, right? We wouldn’t expect that driving past the gym will make us any healthier.

32. How Valuable Were Your Last 40 Minutes?

    Q: What are your tricks for time management? “The simple answer is to attempt to avoid, at all costs, situations that waste people’s time.” “Regarding my

33. How to Run a Business and Still Care for Your Family

    I met a guy who was a busy executive at a startup in Silicon Valley. His family, a wife and three young kids, lived several states away.

34. 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.

35. 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.

36. The Magic Button of Good Design

    At least once a week I receive questions about the design process behind the self-published work I’ve made, in particular the three manifestos I offered a

37. 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.

38. Creative Ways to Succeed in the Knowledge Economy

    Reading: How One Woman Makes $1 Million a Year on Etsy How to Make $225/hr Writing Poetry The Uber Driver Who Makes $250,000 a Year *** I enjoyed each of

39. Make Two Blockbusters for Every Arthouse Film

    Consider a successful Hollywood actor. This actor likes to make independent, arthouse films.

40. 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.

41. To Succeed in the New, New Economy, Don’t Mail It In

    Ever since I wrote about The New, New Economy, I’ve been having lots of interesting conversations with people about it.

42. My Morning Routine: Why I Do the Same Things Every Day, and How I Work from Anywhere

    I’ve been a longtime fan of MyMorningRoutine.com, which regularly interviews interesting people to learn how they spend their mornings.

43. 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.

44. The Eight-Year Escape Plan: Interview with Tsilli Pines

    It’s a new month, and time for a new profile. My friend Tsilli Pines recently quit her job to go full-time with the side business she’s been building for the past three years. Yay! Congrat

45. 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

46. 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

47. 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

48. 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.

49. 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.

50. “The Success I’m Having Now is What I Planned For Three Years Ago”

    The other day I met with a small business owner. Her business is going well, she recently had a successful product launch that brought in a lot of funds and

51. 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.

52. 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

53. 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.

54. 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.

55. Catch Pokémon For Fun and Money: Lessons in Paying Attention

    File under: entrepreneurship is everywhere. And so are Pokémon hunters. No matter where you’re reading this, you’ve probably seen them—and maybe you are one

56. Instead of Manufacturing Hype, Just Start Doing Great Work

    I got a call to do some filming for a marketing agency in Los Angeles. I had the date open and it sounded interesting, so I decided to go.

57. 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.

58. 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.

59. 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

60. Working Hard at Something That Doesn’t Matter

    “Our greatest fear should not be failure but succeeding at things in life that don’t really matter.” Last year, pre-pandemic, I went to a three-day yoga

61. How to Get Better At Saying No

    Every request you accept comes with a cost. If you want to be more effective, if you want to “get more done,” or even if you just want some breathing room in

62. The Great Resignation: If Your Job Sucks, Now Is the Time to Stop Doing It

    If you don’t like your job, what would happen if you walked away? I’ve been asking this question off and on for over a decade.

63. 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

64. 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.

65. Build a Business Where You Can’t Get Fired

    Link: Webcomic Entrepreneurs A while back, a friend of mine who worked in publishing was laid off.

66. 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

67. This “1-3-5 Rule” Can Completely Change Your To-Do List

    Do you have a cluttered and crowded to-do list? Do you try to get everything accomplished, only to burn out and end up feeling further behind?

68. What If All Your Work Disappeared At the End of the Day?

    Over the past ten years, I’ve thought a lot about building a legacy. In particular, I’ve thought about it as it relates to a body of work that you produce

69. 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!

70. 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.

71. 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.

72. 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

73. “More” Is Not the Answer to Too Much

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74. If You Want to Write A Book, Go to a Boring Place

    A friend is writing a book and asked me what I thought about taking a writing trip. “I’m going to Bali to write for a month.” she said. Big mistake!

75. Qualifications

    Sometimes people ask about my qualifications. It’s a fair question with a simple answer: I have none.

76. How to Write 300,000 Words In 1 Year

77. What to Do About That Thing You’ve Been Putting Off

    You know how there’s something you’ve been putting off? Maybe you’ve been putting it off for a long time.

78. 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.

79. Why I Became An Entrepreneur 20 Years Ago

    The best and most honest answer is that I wasn’t good at anything else. For better or worse, I learned that I was a terrible employee.