The Dilbert System: Fail until you don’t

By Eli Wolfe
The definition of failure is lack of success, but for most people it means much more: Failure destroys hope, it crushes goals, it steals energy, and it strips us bare of our resources. But not everyone sees it that way.   

“I have cultivated a unique relationship with failure. I invite it. I survive it. I appreciate it. And then I mug the shit out of it.”

This sentence comes from a new book calledHow to Fail at Almost Everything and Still Win Big.” It neatly distills the philosophy of its author, Scott Adams, the cartoonist who created the phenomenally successful cartoon “Dilbert,” which appears daily in 2,000 newspapers around the world and on the refrigerators of virtually every office break room. It portrays the workaday world of hapless “engineer” Dilbert while satirizing the micro-managed, cubicle-populated world of the white-collar office. 

Adams, a graduate of Cal’s Haas School of Business, decided to write a book about failure after people repeatedly asked him the secret to his success. His book lays out a framework that he says virtually anyone can use as a career starting point to pave the way to success and happiness.

“It’s kind of a time saver that way,” Adams says.

The core of the book—and the key to his success—is a relatively simple system that involves searching for big payoffs in many different low-risk ventures. But his real trick hinges on making sure every failure yields something of value. Otherwise it really is a failure. “The system is to continually scan your environment looking for opportunities while you’re increasing your personal value by layering on skills,” Adams says.

Adams has been layering on skills for a long time. Before and while attending Cal, he worked as a teller (robbed at gunpoint twice) and in what he refers to on his web site as “a number of humiliating and low-paying jobs” at Crocker Bank.

At Haas, Adams worked toward a general career in business. “I didn’t do so well, but I did manage to hang in there through brute force and hard work to graduate,” he says. “It was a humbling experience, but I didn’t really get to taste failure.” 

Adams’s palate became quite familiar with failure while pursuing the dozens of different far-fetched enterprises he launched after business school. These included trying to patent a Velcro rosin bag for tennis players, write and market a meditation guide, become a certified hypnotist, invest in an Internet grocery–delivery service, write several computer games, and develop software as a programmer.

Although he calls his approach of layering skills common sense, he acknowledges that his method may be an ingrained stroke of luck. “I always had the impression that I was going to try a lot of things, and it just made sense to me that it would be smarter to do things where no matter what happened, I would come out ahead.”

“Dilbert” is the crowning achievement of his system, but Adams treats it like a new chemical he catalyzed through a seemingly random combination of elements. He says that’s the advantage of layering skills—you eventually unlock success in ways you can’t anticipate.

“Clearly I’m not a good artist,” Adams says. “I’ve never taken a class in writing, except business writing. It takes a lot of business skill to make a cartoon work, but I’m not the best business person in the world—in fact, if I called myself average, that would probably be an exaggeration. But the combination of those skills is unique.

“Dilbert was just the thing that worked.”

As an example, he points out how his business background led him to create a communication pipeline with his customers by including his email address in his comic strip. Their reader feedback prompted Adams to center “Dilbert” on the workplace. And presto, he hit gold.

The “Dilbert” system works well on paper, which is how Adams likes it. It’s also so bare-bone and devoid of detail that many may find it excruciatingly boring. And Adams doesn’t necessarily disagree: in fact, he argues that dullness is preferable to passion, which can pose a far greater impediment to success.

“Everyone’s just sitting around thinking, ‘well I’ll just wait for my passion, and when that kicks in, I’m golden.’ That’s a completely non-action idea,” he says. “There probably wasn’t a lot of passion about the pencil sharpener sitting on your desk—somebody just had a good idea, maybe they had a patent, they executed it, and there was a plan that probably made sense on the spread sheet.”

“It’s the grinders that work,” Adams says. “It’s the grinders that succeed.”

In his view, “goals are for losers” because they inevitably become too specific and close people off to other paths. A person who develops many skills without any dominant goal is open to numerous routes to the good life. So success turns into a more manageable numbers game. 

Nor has success in one venture compromised Adams’ faith in the system. He has consistently taken risks to expand the “Dilbert Empire” as he refers to it, most noticeably with a failed TV series. Now he’s looking beyond the borders of his empire for new opportunities.

“I’m always looking for a better job,” Adams says.

This better job may become the startup he’s been working on for the past two years. It’s called CalendarTree.com, and if it works it will create a hassle-free way to make and share online calendars. It’s still in beta, but Adams says it “has the potential to be far bigger than Dilbert.”

And if it fails?

“My ability to do a second venture after this would probably be far more likely to succeed because I’ve picked up a lot of knowledge in this process—there are a lot of things I can do now faster, better, smarter,” Adams says. “I come out the other end of this a far more valuable asset.”

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