Dilbert is a Choice

Your pointy-haired boss is an illusion. Free your mind.

The worldview of Dilbert is a nihilistic parasite on the white-collar worker’s mind. I still fall victim to the parasite. I have to rid my thinking of it actively when it happens.

I first found Dilbert in 2002 when I started at a cubicle job. There were copies of the comic posted around the office. It was somewhat frowned upon. Some people didn’t like what it projected to display its cynical take on office life on your cubicle walls. But I remember thinking, “How does this guy understand my life so well?” He nailed the clueless managers, the opportunistic coworkers, and the pointless meetings. And by its popularity, I presume others thought the same.

Many years before I knew the author was such a racist, Dilbert was just another comic. Even back then, I sought something deeper when I read the comic. Comedy is great. It can help you cope with a difficult situation. And it can help you understand your world through humor. But Dilbert is plain nihilistic. There is no saving grace. It is dull, Sysiphean sameness. The comic does not offer clues for navigating the white-collar world. At least The Office has an underlying logic to the dynamics that, agree or disagree, gives you a path to tread. I haven’t read the comic in years, but a quick peek shows that it hasn’t changed. I wanted to learn how to transcend Dilbert’s crummy life. But Dilbert had no answers.

It became a lot easier once I accepted my life was a Dilbert cartoon.

—A coworker succumbing to Dilbertism

This essay isn’t about the comic. It’s about the worldview the comic represents—Dilbertism, a resignation to a life of pointy-haired bosses. You see, Dilbert is trapped. He can’t escape. He has above-average intelligence and seems to want to do a good job but is constantly stymied by his manager. He is fated to a purposeless waste of life. His only consolation is one-upmanship. And that is the trap: to get comfortable proving you’re smarter but failing to live meaningfully.

My boss once told me to work on getting a system to work over the network. Great. I listed three options I could think of, each of which she shot down.

Me: We could do a client-server model.

Boss: No.

Me: Peer-to-peer could also work.

Boss: No.

Me: We could do a hybrid, I suppose.

Boss: No.

Me: Well, those are the options! What do you suggest?

Boss: No.

I walked out in a huff. Deep in the throes of Dilbertism, she perfectly fit the pointy-haired boss archetype. Asking for impossible things, denying real solutions. I couldn’t handle it. Later, after I left due to stress, I realized what we were failing to communicate: She wanted it done. She didn’t want me to brainstorm ideas with her. Her “no’s” did not mean, “Don’t do it that way." They meant, “I don’t want to have this conversation. Figuring it out is your job.” I never confirmed this with her, so it’s just my attempt to make sense of it.

Several years later, I finally saw my way out of Dilbertism. I was working at a startup. The boss was pointy-haired but also appreciated conflict. We would argue with him about how something was impossible. Once, we were trying to get him to understand how absurd his request was. One programmer said, “So you want it to see into the future?” All the engineers instantly thought it was checkmate. But the boss said, “Yes.” Another time: “You want the software to report what the user would have done but didn’t?” Boss: “Exactly.”

It’s so common. Experts say a thing is impossible. Bosses want it anyway. This popular video shows an expert designer in the grips of Dilbertism:

He is the only one who understands that what they’re literally asking for is impossible. Red lines are drawn with red ink. Seven lines perpendicular to each other are impossible (in a plane). He tries to educate them. They think he’s being difficult. It’s a Sartrean nightmare. There appears to be no solution, but there is one.

The boss I had at that startup did ask for impossible things, but he also wasn’t afraid to turn up the pressure. The pressure of that startup was a kind of crucible for me. Through repeated impossible demands, I eventually realized my way through.

Here’s the thing: Experts use technical terms. We see details others don’t. We can see logical inconsistencies within our domain. We’re super sensitive to them. It’s what makes us experts. Others don’t see them—and we can. They’re asking for something that is technically dumb. But it doesn’t make their requests any less valid on a human-to-human level. They’re asking for something. You have to look past your expert-level knowledge to help them. And when you do that, you can connect meaningfully with the other person.

For instance, in the 7 Red Lines video, it’s clear that they don’t know what perpendicular means. When the woman draws a triangle and is happy with it, that’s a clue to what they really want. When the company’s designer asks for one line to be in the shape of a kitten, the designer should have realized that he was taking the word line too literally. Instead, he dug in deeper into Dilbertism—wanting non-experts to use the terms the way he likes them used.

Experts, especially engineering types, tend to get very Garbage-In/Garbage-Out. I do it all the time. You ask me a yes/no question. I try to answer yes/no, even if it’s a dumb question. If a client asks me, “What problems do you see with the solution?” I will list problems, even if they’re minor and irrelevant, when the client wants to hear, “We can take care of everything.”

After leaving that high-pressure startup (due to stress!), I wound up at another startup. There was way less pressure, but I had all the skills I had learned at the last one. The president asked the CTO to make some slides showing how the product worked.

CTO: What do you want them to show?

President: It doesn’t matter. Just show how it works.

CTO: If it doesn’t matter, then any slides will do.

Clearly, the CTO was an expert succumbing to Dilbertism, taking the “it doesn’t matter” to logical extremes. Garbage-In/Garbage-Out. I stepped in and offered to make the slides. I drew some pretty pictures with arrows and screenshots. The president loved them! I think the CTO never realized what happened. But I felt like I had a superpower.

I really like Wes Kao’s Newsletter. She explains how to communicate better at work. By going at least one level deeper than the typical advice, she helps experts get past Dilbertism. In How to present to your CEO, Kao shows how to communicate with your pointy-haired boss by seeing how they’re not so pointy-haired. And Question behind the question seems like an instruction-manual for the poor designer in 7 Red Lines. Such a good antidote to Dilbertism.

Like I said, I still struggle with it. When managers ask for Story Points, and I (and every other engineer) say that they’re a bad idea, but they still want them, I get angry. I complain. I feel like Dilbert, stuck. But I should try to help, not by educating, but by understanding what they need and how I can provide an alternate solution. For example, at my last job, we were asked to record story points to show where the money is going, I should have presented how my team was providing value to the business. I started but never finished because I left (due to stress :).

I hope by naming Dilbertism I can help others overcome it. Whenever you’re getting too technical, frustrated by incoherent demands, baffled by the politics at work, or feeling unheard, stop. Think deeper about what’s going on. Dilbert is a choice. It is not reality. It is a convenient untruth. Free your mind from it and live a more meaningful life.