[Shortly after my career tanked in 2000, I drew this cartoon. This is what failure felt like at the time.] 1. Anyone with a successful business will know this to be true: That business gets successful eventually, not by some flawlessly-executed grand vision, but by a lot of trial and error (mostly error) over a […]

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How To Be Successful

    [Sent out in the newsletter etc.] “Success” is a pretty blurry, vague, annoyingly relative construct. Asking someone to define it is just an exercise in tiresome blather, therefore I won’t bother. What I will say, however, is that if you’re doing something the genuinely matters to the world, and you’re doing it surrounded […]

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“Visceral Encounters with our Most Important Ideas”

We really admire Alan de Botton’s view on the power of art – to paraphrase his great 2011 TED Talk: It is ridiculous that art be simply for art’s sake, art should be used to remind us if what there is to love, hate and fear- art should be a visceral encounter with your most […]

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Ten Questions For Chris Anderson (2009)

[Back in 2009, as part of my Ten Questions Series, I interviewed Chris Anderson, who was then the Editor-in-Chief of Wired Magazine (he since left to work on other things, namely, a drone-making startup). Re-reading the interview recently, I was delighted to see how much of it has stood the test the time, hence I'm […]

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[Motivational Art: the Roman Catholic Church were always the best in the business...] Art was always the most enduring passion of my life. It’s what defined me since grade school, it’s what I went on to do for a living, it’s what interests me the most intellectually. First I started with cartooning as a child, […]

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gapingvoid is hiring! Social Media Manager, Full-Time.

FANTASTIC job role going at Gapingvoid! “Social Media Content Manager” A truly great full-time opportunity to work with the amazing Hugh MacLeod. You will never be short of interesting, meaningful and inspirational content to write up, develop and brainstorm. The person needs to be creative and write in a conversational style. Please send an email […]

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Get my latest e-book: “The Art Of The Entrepreneur”

Hugh’s first ever art show, “I’m Not Delusional: The Art of the Entrepreneur” features nearly 300 new and classic images that tell the story of entrepreneurship.  In Hugh’s words, WE’RE ALL ENTREPRENEURS NOW We’re  living through the greatest sociological shift since the Industrial Revolution: The Age of the Entrepreneur. No more “Jobs for Life”.  No […]

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My New Year Message for 2014: Choose your mountain to die on.

Like I said in my first book, “Ignore Everybody”, everybody was has their own private Mount Everest they were put on this earth to climb. Some people go their who lives without ever finding their Mount Everest, their own mountain. Real life gets in the way: Jobs, family, Monday Night Football, retail therapy, taking selfies on […]

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The “I’m Not Delusional” Show: Art Basel Miami 2013

[OFFICIAL HASHTAG: #NotDelusional] RSVP HERE: http://bit.ly/1jCYmeE INVITATIONS [download and print out etc].   “WE’RE ALL ENTREPRENEURS NOW” We’re are living through the greatest sociological shift since the Industrial Revolution: The Age of the Entrepreneur. No more “Jobs for Life”. No more “Business As Usual”. The combination of globalization and the advent of the Internet has put a […]

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“Space Hacking”, the new geek-chic term for “decorating”

[spotted inside facebook's manhattan offices: their logo made out of new york city metro cards. photo: businessinsider.com] So there’s a new buzzword in town: “Space Hacking”. It basically means creatively altering the space you work in, in order to make it more agreeable to your sensibilities. Yes, it’s basically another term for “decorating”, just a […]

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Hugh MacLeod is a genius.  Genius.

Seth Godin
Best Selling Author

His work acknowledges the absurdity of workaday life, while also encouraging employees to respond with passion, creativity, and non-conformity...   MacLeod’s work is undeniably an improvement over the office schlock of yore. At its best, it’s more honest, and more cognizant of the entrepreneurial psyche, while still retaining some idealism.

The New Republic
Lydia Depillis

Last year my State of the College address was 76 slides loaded with data. This year it was 14 cartoons that were substantially more memorable.

Len Schlesinger
Former President, Babson College

"There are only two daily newsletters that I look forward to opening and reading every time they show up to my inbox: Seth Godin's and gapingvoid."

Tony Hsieh
CEO, Zappos

In moments of indecision I glance at the wall [to Hugh's work] for guidance.

Brian Clark
  • Seth Godin
  • The New Republic
  • Len Schlesinger
  • Tony Hsieh
  • Brian Clark