How to fail at almost everything and still win big
Portfolio Penguin, £14.99
What inspired you to write "How to fail at almost everything and still win big"?
I grew up in a very small town and didn’t have access to a credible mentor who could show me any shortcuts or tips for success. I had to figure it out by trial and error. After Dilbert hit big, people started asking for my secrets on success. It made me wonder if I could bottle my experience in book form.
I don’t believe in giving advice because every situation and every person is different, and the advice-giver rarely has complete information. But I do think it helps to expose yourself to a variety of success stories and observations so you can look for patterns and systems that might work for you. I wrote How to Fail for the person who has the desire to succeed and is looking for some ideas on how to get there.
Who did you write the book for?
I think young adults need this type of material the most to get them started in the right direction, but experienced folks will understand it at a deeper level. And I think some people will enjoy reading it just to learn of all the embarrassing ways I failed until Dilbert took off.
The Dilbert comic strip is enjoyed daily by 150 million people in 2,000 newspapers, in 65 countries. Would you be as comfortable with failure if you hadn’t enjoyed that kind of success?
I was comfortable with failure long before Dilbert worked, so apparently I deal with failure well. And I choose my ventures so that no matter what happens with them, I come out with new skills. I want my market value to increase no matter how well things are going at the moment. My system involves moving from a game with low odds to a game with better odds and making myself a more attractive target for luck to find me. When you feel yourself becoming more valuable it doesn’t feel like losing, even if the details of the situation argue otherwise.
You have an MBA from Berkeley’s Haas School of Business. What was the most useful thing you learned there?
The best way to explain the value of an MBA is that it tunes your brain to see the world in business terms. Some people see a flower shop and marvel at the pretty arrangements in the window. But I reflexively wonder if their profit margins are sustainable given the low barriers to entry.
A big turning point with Dilbert happened when I started including my email address in the strip. Prior to that I had no direct customer feedback about my work, and I knew from my business training that it was a huge mistake to fly blind. Thousands of readers wrote and asked me to do more comics featuring Dilbert in the workplace because they liked those best. So I quickly morphed Dilbert into a comic about work and it took off.
You say that goals are for losers and it’s better to adopt a "system". Sum up your own system.
My most important system involves continuously acquiring knowledge and skills that are complementary by their nature even if I don’t know exactly how it will play out. For example, I took the Dale Carnegie course long before I became a cartoonist and author. That training allowed me to make a fortune on the speaking circuit after Dilbert became a hit.
Likewise, I studied to become a certified hypnotist when I was in my twenties. I reasoned that I could use those skills in a wide variety of settings, from business to writing to dating. I was right on all counts.
Rather than focus on a particular goal, which can be limiting, my system involves continually improving my market value while scanning my environment for opportunities. For example, when I started blogging, my wife asked why I was doubling my daily workload for what looked like a 5% increase in income that I didn’t need. She was concerned that I had no goal. But I was working a system, and my system involved sharpening my writing skills while gaining a deeper understanding of what my readers wanted via the comments on the blog. I figured that the noise I created on the blog would attract offers, but I didn’t know what sort. My new book is the end result of that process. It’s getting great reviews because my system had already filtered the topics down to what I knew would get the best reaction.
In the book, you list some of your most spectacular failures. How do you know when to quit?
It’s easier to answer the question of when NOT to quit. The best predictor that your product or service will be a hit is that you see big demand for the "bad" version. By bad, I mean the buggy and unreliable first version. For example, the first cell phones had terrible quality and they dropped calls like crazy, yet the demand was high from the start. The same was true in the early days of personal computers, automobiles, and even television.
When Dilbert launched it was poorly drawn and the characters’ personalities had not been defined. And yet a small portion of the public was wild for it anyway. When you see enthusiasm independent of product quality, you might have a hit on your hands. You can fix the quality as you go.
How does a serial failure stay optimistic?
Some of my optimism is probably genetic. But a lot of it has to do with seeing life in terms of systems and not goals. I try to pursue challenges that will improve my market value no matter what else happens.
For example, at the moment I’m working with partners on an Internet start-up. No matter what happens, I’ll come out of it with a deep understanding of the start-up process. That will help me write Dilbert comics about the start-up world, and it will help me do another start up someday if I choose. I’ll also learn enough to make me feel more confident investing in someone else’s start-up if that ever comes up. So no matter what, I’ll come out ahead.
You talk a lot about health and personal energy. What’s your own exercise regime?
I used to exercise 3-4 times a week and dread it every time. I would exercise until I knew my body would be sore the next day because no pain, no gain, I thought. It wasn’t a good system.
Now my system boils down to this: be active every day. That might mean going to the gym, playing tennis or just cleaning the garage. The important part of the process is the "every day" part because that’s how habits form.
When I’m active every day, so long as I don’t overdo it, I get a positive lift in attitude that is addictive. I’m like Pavlov’s dogs in the sense that at about lunchtime every day my body is so trained to be active that it feels as if exercising would be easier than not. Sometimes I feel my foot start to tap as my body reflexively prepares for the daily workout.
I’m in the best shape of my life, by far, at age 56.
Where do you typically find fodder for your comic strip?
I spent 16 years in the corporate world, so I have a lot of memory to draw on for context. But the specific topic ideas come from readers’ suggestions, conversations with friends, stuff I read on the internet, and my own side projects. And don’t forget that Dilbert is a business too. On any given day I’m negotiating contracts, reviewing marketing plans, refining pricing models, designing apps, applying for patents, and that sort of thing. I stay immersed in the business world.
You say that all success is luck if you track it back to the source. Tell us about the luckiest moment in your career.
It all seems lucky in retrospect. But the first big break happened when I got a call from Sarah Gillespie, an editor at United Media (then one of the largest three comic syndicators), offering to syndicate Dilbert – meaning they would sell it to newspapers. The other major syndicators had seen my Dilbert submission packets and politely rejected it. Luckily for me, Sarah was married to an engineer who worked at IBM and could have been the prototype for Dilbert. When Sarah saw Dilbert, she instantly related to the character and championed it in her own company. If Sarah had been married to someone else, you never would have heard of Dilbert.