Dilbert 2.0: The Boom Years Read online

  In pre-Internet days, figuring out how to do something out of the ordinary was a challenge. In a strange twist of fate, I came home from work one day, and found myself in the right place at the right time. I started flipping through the channels on TV and noticed the tail end of a show about cartooning. As the closing credits rolled by, I grabbed a pen and paper, and wrote down the name of the host: Jack Cassady.

  I wrote a letter to Jack Cassady, asking a number of questions about starting a career in cartooning. I asked about materials, and where and how to submit comics. He responded with a two-and-a-half-page handwritten letter that was packed with tips.

  Armed with this advice, I bought the 1986 Artist’s Market book, which told me how and where to submit comics, and I started drawing. I soon learned that the New Yorker magazine and Playboy paid the most for comics. So I focused on drawing off-the-wall comics for the New Yorker, and naughty comics for Playboy. See if you can tell which are which.

  Playboy rejected my comics with a form letter. They made the right decision. The comics I submitted were dreadful. (Years later, when Dilbert hit its peak, I was the subject of a Playboy interview, and got on the party invitation list for the Playboy Mansion. But I never attended because I couldn’t imagine myself hanging out with Playmates and sweating through my pajamas.)

  The New Yorker magazine rejected me too. I think we all know they made the right decision.

  So I gathered up my art supplies and put them in a closet. I felt okay about my effort. I tried as hard as I knew how. I didn’t expect everything to work out the way I wanted. I decided to move on. I figured affirmations didn’t work every time.

  A year later, out of the blue, I got a second letter from Jack Cassady. This was especially odd because I hadn’t even thanked him for his original advice. Why would he write a second letter after so much time had passed? Here’s why.

  Somehow he knew I needed the encouragement. He saw something in my work that Playboy and the New Yorker didn’t see. In fact, I didn’t see it myself. I think you will agree that my talent was well hidden in that period. But Jack saw it. His letter accomplished exactly what he intended. I got out my art supplies and started drawing again.

  During this period I was drawing pre-Dilbert and pre-Dogbert comics on the whiteboard in my cubicle, complete with witty captions about workplace happenings. Cartoons naturally draw attention, and soon my co-workers were asking the names of my two regular characters. I didn’t have names for them, so I held a “Name the Nerd” contest on my whiteboard. My co-workers would trickle in during the day and write their ideas for names. The suggestions were traditional nerd-sounding names. None of them stood out. Until one day, my ex-boss, Mike Goodwin, walked in, picked up a dry erase marker, and wrote “Dilbert.”

  This was one of those moments when you feel as if you can see the future. I ended the contest immediately. It felt as though I was learning this character’s name, not naming him. The name Dilbert fit him so perfectly, I literally got a chill. I have a vivid memory of that moment, because it felt as if something special had just happened.

  Later, I named Dilbert’s dog on my own. I wanted the dog’s name to have some connection to Dilbert’s name. So naturally, I named him Dildog. (Yes, really.)

  At about this time, my friend Josh Libresco noticed in the local paper, the San Francisco Examiner, a contest for people who looked like their dogs. Readers were encouraged to send in photos posing with their dogs, and the best ones would get some sort of prize. Josh suggested that I send in a drawing of Dilbert and Dildog. After all, they looked sort of similar.

  In retrospect, this was a ridiculous idea, since the contest was specifically for photos. For some reason, that didn’t stop me. But I knew I had to change Dildog’s name to something more newspaper-friendly. That’s when Dildog became Dogbert. This is my letter and entry.

  For some reason, my drawing was selected for publication among a page of photos of people who looked like their dogs. In retrospect, they probably thought I was a twelve-year-old kid, based on the artwork, and figured it was cute. But the reasons didn’t matter to me.

  My comic was published in a newspaper. My co-workers congratulated me. I liked the feeling. And I wanted more.

  I knew that practice was essential. You don’t get good at something by sitting around hoping. So I started waking up every morning at 4 A.M. to work on a series of comic panels, in something of a comic book form, that featured Dilbert and Dogbert. I spent two hours every morning developing my drawing and writing skills before heading to my day job. Here is the very first comic form of Dilbert and Dogbert. At the time, I believed puns were the highest form of humor. Please forgive me.

  1988—Submitting to Syndicates

  I liked these two characters, Dilbert and Dogbert. Inspired by Jack Cassady’s letter of encouragement, I decided to set my sights high and submit my comics for syndication in newspapers. It didn’t cost much to try, except some paper and ink and postage. I put together about fifty comics based on Dilbert and Dogbert, and sent them by mail to the addresses in the 1986 Artist’s Market book. Below is a portion of my original Dilbert submission package.

  Then the rejections started trickling in. I have included a couple, so you get the general idea.

  After a few months, when I thought all the rejections had come in, I gathered up my art supplies and put them back in the closet. I had given it my best shot. I felt okay with my effort. It was time to move on.

  One day, the phone rang. A woman identified herself as Sarah Gillespie, an editor for a company I had never heard of called United Media. At that point I didn’t know United Media was the parent company of United Feature Syndicate, Inc., to whom I had sent my submission, and I assumed had thrown it in the trash. Sarah said she liked Dilbert, and wanted to offer me a development contract.

  Having never heard of this United Media outfit, I was flattered but a bit wary. I didn’t know how this company even got a copy of my comics. I decided to play my cards close to the vest. I told Sarah I was interested in discussing the offer, but I would feel better if she had some references. I asked if there were any comics her company had ever successfully syndicated. I made it clear I wasn’t going to take a chance on some start-up.

  There was a long pause.

  Sarah replied, “Um, yes. We handle Peanuts. And Garfield. And Marmaduke, and . . .”

  It was at that moment I realized my negotiating position had been compromised. After scraping myself off the ceiling, I said yes. And so began my twenty-year association with United Media.

  It was time to thank Jack Cassady.

  1988—Developing Dilbert

  A syndication development contract is a six-month agreement where a cartoonist works with a syndication company editor to refine the strip and make it newspaper-worthy. There was no guarantee Dilbert would ever be offered to newspapers if the development phase didn’t work out. But within a few months of the contract getting signed, United Media liked what they saw, and decided to launch Dilbert in April of 1989.

  The launch was modestly successful, and Dilbert was picked up by a few dozen small newspapers. Most papers probably didn’t run the strip in the beginning, preferring to hold the rights and watch what other papers did first.

  After a year of hard work as a cartoonist, my efforts were about to be rewarded. My first monthly royalty check from United Media: $368.62.

  It soon became clear that I wasn’t going to be quitting my day job anytime soon. The royalties grew each month, but Dilbert was not setting the world on fire; it didn’t even run in my local papers. Cartooning was a lonely job. I drew pictures all alone, mailed them away, and rarely heard any feedback from anyone who read them. The strip grew slowly, with what seemed like two cancellations for every three sales. Some readers hated it. Some loved it. Few people were neutral.

  By 1990 Dilbert was in fifty newspapers. By 1991 it hit a milestone of one hundred papers. That’s often considered the point where a comic strip has a chance of lasting. Bu
t it was a tenuous grip. By 1992 it was in one hundred and fifty newspapers, and growth was slowing. The sales people naturally moved their attention to the newer comics in their stable.

  The biggest comic strips of the day were in over two thousand newspapers. It seemed that Dilbert had hit its peak potential, and while I had a nice side job, it seemed I would never be able to quit my day job. Still, I tried my affirmations, focusing on the seemingly unrealistic goal of making Dilbert one of the top comic strips in the world.

  The Internet and e-mail were still in the toddler phase. But because of my day job I was surrounded by the vendors and engineers who were bringing those technologies to the market. One day, my business training kicked in and I noticed an opportunity that no syndicated cartoonist had yet explored.

  The problem with cartooning in those years was that you normally got no direct feedback from readers. Your friends and your family aren’t a reliable gauge for how well you are doing. They lie. I was navigating without reference points. And I noticed that every successful business had solved this customer feedback problem in one way or another. I realized e-mail could be the solution for me.

  I started including my AOL e-mail address in the strip every day. The response was huge. I started getting thousands of messages daily, and readers were all too happy to give their opinions. A clear pattern emerged: readers wanted more of Dilbert in the office.

  Up to that point, Dilbert wasn’t a workplace strip. Dilbert was usually shown at his home or about town. But as someone smarter than me once said, “Your customers tell you what business you are in.” I changed the strip to more of a workplace theme, and it took off. I credit my business training for providing me the discipline to give readers what they wanted. For an artist (of sorts), that is deceptively difficult to do.

  At about the same time, my editor suspected there might be more Dilbert lovers than the newspaper editors who were rejecting the strip believed. She suggested I write a book of Dilbert-themed comics. If it sold well, it would be a powerful message to newspapers that hadn’t yet picked up the strip. I agreed to give it a try.

  Now I had three full-time jobs: my day job, the comic strip, and writing a book. I call that period my “running years.” If I was moving from one room in my home to another, I literally ran. When I went to the mailbox, I ran. I didn’t have time for walking. I was on a mission.

  In 1994, my first book of cartoons, Build a Better Life by Stealing Office Supplies, hit the bookstores. It was a small but solid success. And it confirmed the market for workplace humor. It was also a great sales tool for selling into newspapers.

  By the end of 1994, Dilbert was in four hundred newspapers.

  1995—Dot-com Era

  At about 1995, the dot-com era began, and all hell broke loose. Dilbert was the right character at the right time. Technology workers embraced Dilbert as one of their own. The media embraced Dilbert as a symbol of the downsizing era, which overlapped with the first part of the dot-com build-up. Dilbert became shorthand for bad management, oppressed cubicle workers, and high-tech life. Readers imbued Dilbert with their own meaning, beyond anything I intended for it.

  I was an early user of the Internet because of my day job, which involved showing customers how Pacific Bell’s high-speed data services could help them. The demonstrations took a familiar pattern. First we would demonstrate some useful business features involving control of the telephone, and the customers would yawn. At the end, we showed them something totally useless, known at the time as the World Wide Web.

  In 1993, there were only a handful of Web sites you could access, such as the Smithsonian’s exhibit of gems. Those pages were slow to load and crashed as often as they worked. But something interesting happened every time we demonstrated this technology. The customers would get out of their chairs, their eyes like saucers, and they would approach the keyboard. They had to touch it themselves. There was something about the Internet that was like catnip. At the end of every meeting, the only thing our customers wanted to know was how they could get access to this magic land of Web pages that had no practical use whatsoever.

  That experience clued me in early that the Internet was the future. United Media was reaching the same conclusion at about the same time. Once again, by luck, I found myself in the right place at the right time. In 1995, Dilbert became the first syndicated comic strip to be offered for free on the Internet. The response was huge. From that point on, when a sales person from United Media went into a meeting with a newspaper editor, the editor often said, “My readers keep asking for this one. They saw it online.” Sales started to come easy.

  At about the same time, Bill Watterson decided to retire from creating Calvin and Hobbes. That left a huge number of newspapers with openings, just when Dilbert was considered the hot new comic. By the end of 1995, Dilbert was in eight hundred newspapers, and I left my day job at Pacific Bell.

  People often ask if I quit or was fired. It was a little of both. In the final few years of my day job, Dilbert had turned me into a minor celebrity among technology workers. My co-workers found my fame useful in attracting customers to the lab to see Pacific Bell’s latest offerings. By then, Dilbert was consuming too much of my time for me to be effective in my day job. It was clear I would soon need to quit or be fired. That’s when my co-worker Anita Freeman, who was the prototype for the Alice character, suggested a deal. With our boss’s consent, she and my other co-workers in the lab offered to pick up my slack any time I needed to leave work for Dilbert reasons. In return, I agreed to schmooze customers who were Dilbert fans. As part of that understanding, I told my boss that any time the arrangement didn’t work for him, and he needed the budget for a better purpose, I would be happy to leave. Eventually he took me up on the offer.

  That year, the Wall Street Journal asked me to write a guest editorial. Someone at the Journal was apparently a Dilbert fan. So I wrote a piece introducing what I called The Dilbert Principle, in which I explained in witty prose how the most incompetent workers are often promoted to management.

  An editor at HarperCollins noticed my editorial in the Wall Street Journal and asked if I could expand it into a book. By then, hundreds of Dilbert readers had asked me to write a business book, and even suggested the form. They wanted a book that included both Dilbert comics on business themes and some extra witty text on those topics. I pitched that idea, and my publisher liked it.

  In 1996, my first “real” book, The Dilbert Principle, came out. It became a #1 New York Times best-seller, and stayed there for eleven weeks.

  Based on that success, I quickly followed it with Dogbert’s Top Secret Management Handbook. It joined The Dilbert Principle at the top of the best-seller list, ranking #1 and #2 for a brief period. (My affirmation at the time was to become a #1 best-selling author.)

  By then, Dilbert was in over one thousand papers and growing. It was approaching icon status. The phrase “getting Dilberted” entered the language, along with “pointy-haired boss,” and Elbonians. My life was a tornado of TV, radio, and print interviews. I thought I knew what media attention felt like when the comic strip was rising in popularity, but nothing prepared me for having a #1 best-selling book. It was insane.

  As Dilbert’s popularity soared, no one seemed to mind so much that my artwork looked as if it had been drawn by an inebriated monkey. In 1997 I won both the National Cartoonist Society’s Reuben Award for Outstanding Cartoonist of the Year, and Best Newspaper Comic Strip of 1997. For cartoonists, these awards are the equivalent of getting the Oscars for best actor and best picture.

  My life during that period was moving at a scorching pace. I was lucky to get four hours of sleep a night, and always worked weekends, evenings, and holidays. I was also doing regular speaking engagements for corporate events, writing more books, and starting both a vegetarian food company and a local restaurant with partners.

  In 1998 I started working on what would become the Dilbert TV show that ran on UPN during 1999 and 2000. We had a tiny o
perating budget, so I found myself doing more of the writing than I had expected. The show started out well, but in the second season the network made a strategic decision to focus on shows with African-American actors. Dilbert lost its time slot, and cancellation followed.

  The dot-com era was well underway by then. This was the hardest time to write Dilbert comics. There were so many people getting rich with Internet businesses, optimism was the dominant feeling among workers. If you weren’t getting rich, you figured it must be your own fault, because apparently anyone could start a company and become a billionaire. I couldn’t find anyone to complain about work, least of all the technology workers who were in high demand. Still, Dilbert grew. By year 2000, Dilbert was in two thousand newspapers, in fifty-seven countries, and nineteen languages. There were over ten million books and calendars in print. Then the dot-com bubble burst.