#47 Scott Adams

One my favorite books of the last two years was How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life by Scott Adams. I even linked to the story about Dilbert not succeeding until the death of a regional salesman in my notes from the Chris Guillebeau interview. Adams is on the podcast to promote his new book, Go Add Value Someplace Else, which comes out October 28th, and gives you just enough time to read How to Fail first.

To start the interview Altucher and Adams dive into why self-help books don’t work. People are comfortable in their habits and if a self-help book requires changing those, then that’s a much harder thing. Habits are a great evolutionary advantage that lets us give attention to things that are more important. Unless we get into the wrong ones. If you want to change habits two good places are The Power of Habit by Charles Duhigg or the free Tiny Habits course by Dr. BJ Fogg.

When talking about the advice he gave in How to Fail Adams says, “I tried to make a big point in mine that I wasn’t giving you a recipe, because everybody’s case is different, but rather I was giving you an example—a template, if you will—that if I did this and this was what turned out, that maybe you could compare that to what you’re doing and what other people are doing and find something that works for you.” This is the same structure that Melissa and Dallas Hartwig give in It Starts With Food, an introduction to paleo-like eating and #2 nutrition cookbook on Amazon.

After this the two dive into system versus goal thinking. Altucher says, “So what I really liked in this book—and I really subscribe to this as well, this idea that goals are bullshit. And you say live by systems; I call it something similar. I say live by themes.” Adams says much the same, in How to Fail he writes: “To put it bluntly, goals are for losers. That’s literally true most of the time. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal.” And when you do, then what? “If you achieve your goal, you celebrate and feel terrific, but only until you realize you just lost the thing that gave you purpose and direction.”
For more on the book How to Fail, check out the writings that Shane Parrish has done at Farnam Street.

Adams also talks about his system for each morning, one he’s able to do while still wearing pajamas. Like the stories of other writers in Daily Rituals, he does his most challenging work in the mornings. “I get up around 6:00, get my coffee, and then I usually either read my e-mail or maybe write a blog post on Dilbert.com or do something. Then I kind of get into my cartooning, usually do about two comics on a typical weekday in rough form—I write them and I draw them in rough form. And then sometime later at night or the afternoon when there’s some slow time, I do the finished art, when I don’t have to use the brainpower.” Researcher Daniel Levitin might applaud the use of brain power, because that implies it will run out and need recharged.

Before Adams was able to doodle in his pajamas, he did it at 4:30am before leaving for his job at Pacific Bell. While there he twice got passed over for promotions because he wasn’t a woman and that led him to think, “Well, what could I do that’s not in corporate America where I could do something where my talent alone makes a difference, or better yet move to somewhere where being who I am is an advantage instead of a disadvantage?”

Adams settled on pursuing cartooning. He saw an ad on TV and wrote the the promoter Jack Cassidy, who suggested some resources. Adams tried to write cartoons for magazines and failed. Upon this gave up, having given it a good shot. Then a year later he got another letter from Cassidy telling him not to give up. This reminded me of the letter Carl Sagan wrote to a young Neil deGrasse Tyson encouraging him to study astronomy and even inviting him to his lab. It’s amazing the power little words of encouragement can have. Adams tried his hand at cartooning again, and failed again, only better.“I I got rejected” he reasoned, “I would be rejected at a higher level, which would feel like progress in a way.”

One thing Adams rejects is the idea to follow your passion. Cal Newport is on the same page, suggesting you just get good at something. For Adams “getting good” meant redefining the pool of talent. He wasn’t great in business, but was decent was someone who could draw. Beyond that, he was a funny business man who could draw and understood a nascent internet. That specialization meant that there were very few – maybe no – people like him, and consequently made him the best. And cartooning was only one of many good ideas. “I like to think of life as like a—kind of a strange kind of a casino with a slot machine. Instead of a slot machine that takes your money every time you lose, it’s free. You just pull all day long. So in that sense you can’t control when the luck happens, but you can guarantee that you’ll get a payoff, because you just keep pulling.”

In his book How to Fail, Adams also talks about the energy that people bring into each day, something that generated a lot of feedback. “The two criticisms I got in the book were opposites. One was, ‘Don’t include that stuff about diet and exercise and energy in a book about success,’ and another group saying, ‘You’re saying things that are too obvious; we already know this.’” Sleep for example is really important. In a study reported by Jennifer Senior, parents who got more than 7 hours compared with those who got less than 6 hours had the same difference in well-being compared to those who made $90,000 and those who made $30,000.

Altucher and Adams move the conversation to what Twitter might have looked like an investment pitch, and both agree it would have been awful. Twitter has worked out so far, and reminded me of what Nassim Taleb talked about with Altucher. Taleb was marveling at the book publishing and movie industries, where the companies have realized they can’t predict what will be successful, and instead aim for a long tail approach, cashing in on one or two blockbusters.

As evidence to keep trying other things, Adams explains what Calendar Tree is. It’s hard to remember a time when times weren’t a clickable link that automatically populated in your calendar. But at one time they didn’t. David Pogue was marveling at similar calendar features in an episode of the Cool Tools podcast earlier this year.

A little later in the interview, Adams compliments Altucher about his writing, saying “the only reason that I agreed to this podcast is because I’ve read your writing. So I’m here because I’m a fan of your writing; otherwise I wouldn’t be here.” This situation is what Adam Grant would describe as a pair of Givers helping each other. In his book, Give and Take, Grant recognizes three hats people can wear; giver, matcher, or taker and he makes the case that givers ultimately succeed the most. For Adams and Altucher the explanation might be that because Altucher gives away so much of his writing without asking for anything in return, Adams is happy to help out.

Altucher goes on to praise Adams for his article, How to Get a Real Education, saying it was “hanging up near my desk because it’s so in line with how I think about education.”

The pair propose different overalls of government, most of which sound nice – and wishful. For more of this check out President Me by Adam Carolla.

The resume Scott Adams had to get to where he is is complex and varied and one of a kind. A bit like his popular character. If you enjoyed this interview I can’t recommend his book How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life enough.


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