December 28, 2011
3 Comments

After this cartoon went out in the newsletter earlier this year, we received a number of emails from people asking for female version. Here it is!
I think the Buddhist in me came out in this one. So much human suffering is tied to hanging on to things; material, emotional, or otherwise.
I believe that happiness comes from inside us - We often forget that, and spend a lot of time blaming other people for our unhappiness.
The commentary on the original image read:
“If you’re unhappy, nine times out of ten it’s because you’re clinging onto something.
Nine times out of ten, happiness and letting go are synonymous.”
Exactly.
[You can buy the print here etc.]
September 12, 2011
No Comments


Hewlett Packard is kicking off its cybersecurity conference today, HP Protect 2011, and they kindly hired gapingvoid to design some posters for them.
Basically, I wanted to draw something kinda cool n’ fun, something that computer security people wouldn’t mind taking back home and hanging on their office walls.
To the uneducated, the cartoon might seem trivial, but actually, it’s not. Like Lennie Bruce famously said, “Humor is serious business”.
Fred Wilson is right, we are indeed in the middle of a major, long-term, global trasformation, and Obama (or anybody else who wants his job) is NOT, REPEAT NOT going to save us.
So what IS going to save us? The SAME DAMN THING that has ALWAYS saved us:
That’s right. The Play Ethic. Creativity. All that good stuff Sir Ken talks about. All that good stuff that gapingvoid hopefully represents.
All serious work begins with serious play first. AND NOT the night before, but FIRST thing in the morning.You think Jony Ives works for a living? Hell, no, he plays for a living. So do I. So do my friends, Charles Hope, Seth Godin and others like us.
And YES, you can bring that sense of play anywhere– to a conference on cybersecurity, for example. Don’t get me wrong; cybersecurity is also serious business. Our collective safety and our livelihoods as citizens depend on it, and companies like HP work to help protect our culture’s critical infrastructure systems and generally keep us out of trouble.
It’s a nasty, dangerous world out there, after all…
That being said, security nerds are also people who like to play and get paid for it, more than most. They like to have FUN, at conferences and anywhere else, of course they do. Who says the good guys cannot be sweaty and unshaven? News to me. To PLAY means to HACK something. Hacking is INHERENTLY playful. Of course it frickin’ is.
[Note to non-Nerds: the reason that nerds don’t spend a lot of time on their personal appearance is because they’d rather spend their brief time here on Earth, working on something that actually matters to them, not spend it on something that matters to the usual crowd of clueless, superficial, hipster knuckleheads.]
Thanks to Hewlett Packard for giving gapingvoid the opportunity to live in a place it hasn’t yet i.e. the complex and mysterious world of cybersecurity i.e. the world where the hackers live and thrive happily. It’s good to know that some of them are on our side. So far, it’s been a blast. Rock on.
[Bonus Link: The ever-brilliant Ben Hammersley gave a great talk to a bunch of high-level UK cybersecurity nerds recently. A wonderful read.]
[The “Hire Hugh” page etc.]
August 31, 2011
3 Comments

[Buy the print here etc.]
NEVER GO MAINSTREAM
Back when I was a kid and aspiring to be a professional cartoonist one day, I had this dreadful fear hanging over my head:
That the only way to become successful as a cartoonist, was to go mainstream. Cute and cuddly, warm and fuzzy. In the world of the big money cartooning, there was little room for “Edge”.
Check out the traditional US Sunday comics section of any newspaper, and you’ll see what I mean. Utter, cutey-pie dreck.
I just couldn’t see myself doing it. My stuff was just too “out there”, and when I tried to reign it in, it just made it worse.
Of course, that was before the Internet came along and changed everything…
Anybody who courts the mainstream deserves everything they get. There’s far more action in niches.
March 31, 2011
5 Comments
Everybody wants to be on the winning team.
Some people don’t care what team they’re on, to paraphrase Bob Dylan, so long as they’re winning.
I’ve been around those people all my life. Most were forgotten, by me and everybody else.
Some people don’t mind if they win or lose, as long as they don;t get hurt.
Some people don’t mind losing, so long as they get to play the game they want to play.
And then there’s the people who want to win, and win big, but ONLY if they somehow manage to improve the game overall.
Not just raise THEIR game, but raise THE game altogether. Even if when they’re losing, they seem to manage it.
Those people have the most fun. They’re also the most fun to play with.
And they also seem to win the most, over time.
March 30, 2011
9 Comments

[Don’t get me started…]
You may have already noticed, I’ve been doing a lot of rapid-fire cartoon postings lately.
It goes to a point that came up when I was recently talking to Doc Searls on the phone…
“The Web works best when it’s spontaneous, creative, irreverent and slightly anarchic”.
With that in mind, I decided to do something about it. The Web had been feeling kinda stuffy of late…
So when I draw a wee business-card cartoon, at Starbuck’s or whatever, I simply take a snapshot of it then and there on my iPhone, then instantly post it on the web via Instagram… which automatically feeds onto Twitter, this WordPress blog, Facebook and my Posterous page.
Simple, fast and fun.
Art is more interesting when it’s liberated from its own self.
Not unlike human beings…
Spontaneous. Creative. Irreverent. Slightly anarchic.
Exactly.
March 21, 2011
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My second cartoon for a Rackspace customer is for Posterous, the photo-sharing, proto-blogging site.
Basically, Posterous is a site that makes it easy to upload and share photos. It’s simple and straightforward. It doesn’t need a lot of explaining, really.
And nor should it have to. Talking to their CEO, Sachin Agarwal on the phone the other week, it’s apparent they want their service to have mainstream, mom n’ pop usage, not just something for the geeks…
As for the cartoon, well, I was determined NOT to draw yet another one of my cute-sy “monstercritter” cartoons [I was already doing a lot of them for Rackspace already], but in spite of my best intentions, this Posterous one just stuck, somehow… the humanity of it.
We know the point of photos is to document the seen world, capture memories and all that. But a big a part of that is the social and emotional– the creation of what I call “Sharing Devices”- social objects that allow us to share ourselves with others.
i.e. Posterous’ value comes not from the actual photos per se, but from a very human need that was around long before photography (or cave painting, for that matter) was even invented.
[Check out my other Rackspace cartoons here…]
March 7, 2011
2 Comments

I just drew this wee cartoon for one of my favorite brands, Laughing Squid.
Laughing Squid aka my good friend, Scott Beale, GETS it. Really, really gets it. Very few brands seem to be able to truly understand both the Art and the Internet so well. The only other guys I know who come close are Boing Boing.
I think it’s so cool that when Scott talks to people at parties, he’ll often talk to somebody who LOVES Laughing Squid, KNOWS Laughing Squid well, but still has no idea that web hosting is what Laughing Squid actually does for a living.
To be so great, you don’t evern need to tell people about it in order for it to work.
That is rare. That is a gift. That is THE gift. To be able to do that. That is what inspired the cartoon. Yes, exactly.
But that’s not the only reason I’m writing this. Full Disclosure: My client, Rackspace, recently commissioned me to draw a “Cube Grenade” cartoon for one of their favorite customers. A “social gesture” from them to say thanks, as it were. They gave me a shortlist, Scott’s name was on top. I was delighted to find him there.
Secondly, Laughing Squid is also one of Rackspace’s oldest customers. We’re talking REALLY early days. That isn’t common knowledge, I only just found out. But I was delighted to learn that; I really was.
So thanks to Scott, Laughing Squid, Rackspace and everybody else who “gets it”, who truly knows and truly feels the love.
Yes, you know exactly what I’m talking about. Godbless.
[Check out the other Rackspace cartoons here etc. Check out the Cube Grenade homepage here etc etc.]
March 2, 2011
2 Comments

[My latest cartoon. Download the printable version here etc.]
Dear Rackspace,
You being my client and all, I thought now would be a good time to let you know my current thinking:
You love startups. You live and breathe making them happy. You live and breathe trying to be helpful to them. You live and breathe “Fanatical”.
Sure, other companies offer the same kind of hosting that you do– Amazon being the best known example.
But it’s your particular brand of “Fanatical” that permeates your culture… THAT is what makes you unique; THAT is what your competitors DON’T have; THAT is your secret weapon.
And the minute you lose that, of course, is the minute you start to die.
Not everybody reading this is going to believe what I’ve just said. Some will remain skeptical, both inside and outside your company. Frankly, I don’t care. I’ve been working with y’all long enough to know that I’m speaking the truth.
“We Love Startups.” That is your mantra. That is your line in the sand.
And now you’re going to have to live it. Now that the line has been drawn, I’m never going to allow you to take those words back. Nor will anyone else. Ever. Nor should you.
“We Love Startups.” That is what the startup community must know about Rackspace. They must know it AND believe it. All of them. That is the mission.
Alea iacta est.
[PS: Note to Rackers: If your boss will let you, feel free to use the cartoon in your email signature. Spread the love etc.]
[See more Rackspace cartoons here.]
February 3, 2011
17 Comments

[The EVIL PLANS print. Signed, limited-editon of 500 etc.]
[UPDATE: The offer is now closed. All 500 prints are gone. THANK YOU SO MUCH for your support! Seriously.]
As most of you already know, my second book, EVIL PLANS comes out on February 17th.
To celebrate the book launch, I’m offering a FREE, signed, 8″ x 10″ limited edition EVIL PLANS art print to the first 500 people who pre-order the book.
[Yes, you can get a signed print if you’ve already pre-ordered the book. Sorry, this offer is US-only, not international. No, Sorry, this offer is not open to Kindle buyers, hardback only etc.]
1. The first 500 people who order the book AND send their electronic receipt/confirmation number to EvilPlansBook@gmail.com will get a free, signed, limited-edition “EvilPlans” print like the one above. 8 x 10″. Limited edition of 500. Hand-signed by me.
2. Order the EVIL PLANS book from any one of these online booksellers:
3. Then please forward your receipt/confirmation number to this special email address: EvilPlansBook@gmail.com. You’ll receive a confirmation email with directions for submitting your shipping address within 24 hours.
4. This offer is limited to only the first 500 people who email us their receipts — I’ll post an update here to let you know if and when the special offer has been closed.
5. This offer is for U.S. ORDERS ONLY. Sorry, Global Sportsfans, but the logistics are just WAY too complex to ship them abroad. Long story. Ouch.
6. If you’ve already pre-ordered the book and live in the U.S., no worries, you can still get in on the deal - just be in the first 500 to send in your receipt, and I’ll happily honor it.
7. This offer is hardback only. Not for Kindle. Sorry.
8. Please do not contact me personally to get on this list — please just use EvilPlansBook@gmail.com.
9. Thanks Again, As Always, for your Love and Support!
–Hugh
February 1, 2011
5 Comments

So I drew this cartoon earlier today for Rackspace.
An idea for a greeting card. An “Apology” card. For when Rackspace screws up [ALL companies screw up occasionally].
Just a way of saying sorry. Of staying human.
It could be printed on to a card and put in an envelope. Or it could just be a digital image you put in an email or on a website.
That kind of thing…
[You can see the other cartoons I’ve done for Rackspace here.]
2 Comments

[Download the printable version here etc.]
To mark the launch of my upcoming book, EVIL PLANS on February 17th, I thought I’d do a special cartoon for my biggest client, Rackspace.
The first line in the book is “Everybody needs an Evil Plan”. This sentiment would apply to both big companies like Rackspace and, or course, the people who work for them.
So there was a natural fit. Plus I dig the red…
Hmmm… Thinking of making this one a print.
[You can pre-order the book here.]
[You can see the other cartoons I’ve done for Rackspace here.]
January 29, 2011
1 Comment

To My Groovy Clients at Intel,
I just drew this wee picture for you. Feel free to pass it around, download the high-rez version, print it out and hang it on your wall etc etc.
Yes, it’s a social object. Designed to continue a conversation that I already started online. [Yes, if you know somebody at Intel, please send this link along to them, thanks].
Whether you manufacture microprocessors, or draw cartoons like me, the question, “What is human potential?” never gets old.
Of course, you’ll never find the definitive answer. But you still have to ask the question.
And keep on asking it. Again and again.
Or else life dries up. And microprocessors and cartoons don’t get made.
Think about it.
Kindest Regards,
Hugh MacLeod
3 Comments

What is possible?
Well…
I draw cartoons.
And you do your thing…
All are prayer to the same god, are they not?
The trick is, of course, in teaching yourself how to see it as prayer, and not as meaningless toil.
Godspeed.
January 25, 2011
9 Comments




There seems to be a conversation happening internally at my client, Rackspace. Spearheaded by people like Robert Scoble and the guy who hired him (and who also hired me), Rob La Gesse.
“Don’t be normal”.
Who wants a “normal” job, anyway?
Who wants a “normal” employer, anyway?
Who wants a “normal” life, anyway?
Exactly.
So why not say it, loud and proud?
So I drew some cartoons on the subject.
I’m thinking they’d make great recruiting posters…
[P.S. At the time of posting this, Rob hasn’t seen these cartoons yet. He lets me post my ideas “live”, without having to go through him first. THAT IS WHY I’m psyched to be working with Rob and Rackspace. Just so you know.]
January 24, 2011
6 Comments

[Download the printable version here etc.]
““South-By” is almost upon us, and so here I am thinking up new SXSW Interactive ideas for my client, Rackspace, who will have a presence there.
We have a basic idea what we’ll be doing– I know Scoble is involved– but that’s all still under wraps.
Nonetheless, I drew the cartoon above.
As with my usual approach, the message is less about, “This is what we do and this is how much it costs”, and more about, “We hold these truths to be self-evident”.
Think about it: Rackspace is a fast-growing company. It needs to hire really good people. Lots of them.
And to do that, it has to convince a lot these really good people to relocate to their main campus in San Antonio, Texas.
Have you ever been to San Antonio? Exactly.
Now, don’t get me wrong, San Antonio is a perfectly lovely Texas town, hugely underrated compared to say, Austin, 80 miles to the North.
But still, it isn’t one of those towns where “Everybody” goes to, like New York, Chicago, Austin or San Francisco. It’s not a capital.
So in order to get some of the best brains in the country to move there, you have to offer them something else. Affordable housing, good schools, high quality of life, high standard of living etc. etc.
But you also have to offer them, as Rackspace Chairman, Graham Weston said in 2010, the chance to be on “on a winning team, on an inspiring mission.”
People don’t go to South-By in order to buy stuff, to buy Rackspace hosting. They go there to see their friends, to commune with their tribe, and yes, to look for opportunities that allow them to play on the aforementioned winning team.
THAT is how Rackspace needs to talk to people at South-By.
Doing something that matters. On a winning team. That’s why I wrote the cartoon the way I did.
Life is short. Make it amazing.
And so there y’are…
January 16, 2011
8 Comments

[Drawn at the bar of Sushi Samba. That explains the orange light etc.]
I’ve been thinking about They Might Be Giants, an indie band I’ve been following off and on for over twenty years.
TMBG have been together for nearly thirty years.
TMBG never really had major mainstream success. They’ve just done their quirky little thing from their happy little corner of Brooklyn.
They were once of the earliest bands to really embrace the whole Intenet thing. They were pioneers. They had to be, if the band was to survive.
To be small, quirky, unique, ferociously independent and still be able to survive. A true “global microbrand”. Their example has always been huge inspiration to me.
I’m glad we live in a world where folk like TMBG can be exist. A much-needed antidote to the tedious, insatiable maw that is mainstream, celebrity-driven culture.
We live in incredible times.
[Follow TMBG on Twitter.]
1 Comment

Another one of my “Cartoons Drawn On The Back of Business Cards”, created while sitting at the bar of Sushi Samba two nights ago, while doing my harmonious infusion thing etc.
This one is entitled, “Goodness And Mercy”.
As in, “Surely goodness and mercy shall follow me all the days of my life, and I shall dwell in the house of the Lord forever.”
Psalm 23.
January 11, 2011
18 Comments

The cartoon above came to me suddenly, while I was writing the previous blog post about #Intel and my recent trip to #CES Vegas.
Yes, we are incredible beings.
Yes, we live in incredible times.
And as long as there is still one person on the planet who doesn’t believe this, then there’s still work to be done.
That’s all I have to say. I hope TO GOD that you concur. Thanks.