I was Duped By Dilbert. Or, more accurately, Scott Adams, the creator of the Dilbert comic strip, and the author of How to Fail at Almost Everything and Still Win Big, duped me. In this latest book from geek hero Adams, all of his failures are laid bare. I admit I am a big fan. I keep up with all the comics at Dilbert.com. I read Scott’s blog, I even read his Wall Street Journal op-eds.

To truly appreciate Adams’s writing you have to get inside his head and discover the OCD, ever calculating mind, of someone who over thinks everything. In one chapter of his tell-all self-help book he describes playing out in his head the potential outcome of a trip to a restaurant and movies with his wife. By his own admission, it makes him look like a jerk but he leaves the story in because it’s funny.

The book is well worth reading. Even if you gain nothing from learning about affirmation, how to smile, and how to sit at your desk, you will pick up some tidbits that could just possibly help you achieve success. At least that is what Adams declares is the purpose of How to Fail.

The morsel I picked up is that Scott Adams is a conniving practical joker. His introduction in the book, reminiscent of Machiavelli’s two faced “I am not worthy” introduction to The Prince, reveals something I did not know about Adams:

“If you’ve ever taken advice from a cartoonist, there’s a good chance it did not turn out well. For starters, it’s hard to know when a cartoonist is being serious and when he or she is constructing an elaborate practical joke. I’ve crafted pranks that spanned years, sometimes when no one was in on the joke but me. Some of those pranks are still percolating.”

It appears I was the victim of one of those pranks and until reading his introduction I did not know it. Here is what happened.

When I launched IT-Harvest, an industry analyst firm, I had a brilliant idea for making my website “sticky:” publish a security themed cartoon every day. Adams had blogged frequently about helping beginner cartoonists launch their careers so I sent him an email.

I have to paraphrase these emails since I lost several years worth of email records, thanks to Yahoo.

From: richard
To: scott

Hi Scott: I am launching a new website and I wondered if you could point me in the direction of a cartoonist who would like to create a daily security themed cartoon? I could work out a payment scheme whereby he/she got a penny per page view.

I was quite amazed when the great man himself apparently responded to my email, although disappointed by his reaction to my idea (again paraphrased from memory).

From: scott
To: richard

Richard:  This is a horrible idea. It will never work. No cartoonist who is any good will ever work on these terms.


Talk about balloon deflating. Oh well, on to other things.

But then  a week later, on a Friday, I got the following email from Scott Adams.’

To: richard

From: scott

Richard: I have been thinking about your proposal. I have become very bored with Dilbert and have been looking for something new. I will write your security cartoon.


Wow! Pop the Champaign corks. This is HUGE!  I am embarrassed to admit that I was truly excited. Not since the first time I got an email from a friendly businessperson in Nigeria has my head spun with the possibilities. I immediately shared the good news with my wife and kids. I forwarded the email to my brother who used to be a cartoonist. I started making bigger plans for the web site.

After a weekend of cooling off I responded to Scott, accepting his offer and asking what the next steps should be. His response:

From: scott
To: richard

Richard: This is a scam, my email was hacked.


I was shaken with disappointment. I also was impressed with the cleverness of the hackers that target Scott Adams. Wow, they read and responded to his emails. That is pretty funny, even if I was the victim of the joke.

I never published this story, even though the fact that Scott Adams’s email was hacked was newsworthy. Until reading his admission that he has practical jokes that have been “percolating for years.” I am sure this was one of them! I still was falling for it eight years later because I took him at his word.

That is how Dilbert duped me.

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