A Note from James:

You know, I’ve known Scott Adams for probably 12 or 13 years. He was one of the first guests on this podcast, and he’s the creator of Dilbert, which was my favorite cartoon strip for decades. But then, starting around 2013, he started writing about his life, his opinions, his approach to life, and what made him a success. The first book he did in this genre was How to Fail at Almost Everything and Still Win Big. He also wrote another book that was very influential, called Win Bigly: Persuasion in a World Where Facts Don’t Matter. Both of these books are must-reads.

Win Bigly is the best book ever about real-world persuasion. And Scott Adams himself was kind of an—I don’t want to say he’s an amateur hypnotist, but really more like a professional—in terms of how he used hypnotism techniques for persuasion. And How to Fail at Almost Everything and Still Win Big...when this comes from the very first podcast I had with him—how his story of how Dilbert became a hundred-million-dollar success… he was failing constantly. And the story of the success of Dilbert, which he tells in this episode we’re going to show you now, is just amazing.

Scott Adams has more recently become known for his political musings. He had a daily podcast, Coffee with Scott Adams, which I regularly listen to. I would say over the past decade—or 13 years, 12 years—he has not only become a great friend, and even somewhat of a mentor to me, but we’ve talked a lot, on and off the podcast—his podcast, my podcast—and he really helped me out through some times when I was a little upset about different things. He really knew how to reframe problems so that they would become successes.

And when I first heard he was sick—this was last June—I was devastated. And of course, he prepared us all that he was going to pass away, which he did a few days ago. It was really upsetting.

And, you know, I hate when people kind of take advantage of someone’s death by saying, “Oh, I knew him great. He was my best…” blah, blah, blah. I just want to tell you: listen, put aside all your opinions. He was a great artist. He was a great storyteller. He had opinions you may or may not agree with, but he really knew a lot about the DNA of success and the real mechanics of persuasion—no BS, no academic stuff—just really how to do it.

I would really encourage you: you could better your life if you read his books.

I love this guy. I’m really sad he passed away. I’ve learned so much from him, and I want to share a little bit of that in this episode. Maybe we’ll even do another one at some point. But, you know, rest in peace, Scott Adams. And please, if you haven’t learned from him in the past—or even if you have—we had a great time whenever we talked. And here’s a piece of that.

Episode Description:

Scott Adams (creator of Dilbert) explains why he thinks goals can actually make you worse off—and why systems, energy, and probability are the real tools for building a career that lasts.

He tells the story of how he broke into syndicated cartooning after repeated rejection, and how a small nudge from a stranger kept him from quitting too early.

James and Scott talk about writing with “danger,” why people can’t reliably judge good ideas, and how persistence becomes easier once you stop expecting a perfect plan.

They also get into the emotional side of “making it”—including why success can feel disorienting when you hit a milestone you thought would solve everything.

What You’ll Learn:

Build systems instead of chasing goals, because the target will move before you get there
Increase your odds by trying many small bets, rather than staking everything on one “perfect” plan
Write with an element of risk—if you’re not at least a little scared, it’s probably too safe
Don’t trust friends (or investors) to recognize a good idea on sight—nobody can predict outcomes reliably
Protect your energy and schedule your hardest creative work when your brain is actually sharp

Timestamped Chapters:

[03:04] A Note from James: why Scott mattered, and why this still holds up
[06:50] Scott’s new book, Dilbert, and why “systems beat goals”
[12:26] Scott’s daily routine and how he actually creates cartoons
[15:22] The real Dilbert origin story: rejection, Jack Cassidy, and persistence
[22:12] “Danger” in writing: why safe content gets ignored
[25:01] The strange downside of success: when purpose evaporates
[30:09] Passion is overrated: why momentum beats motivation
[33:02] The math of luck: a thousand 10% chances becomes a near guarantee
[34:45] Talent stacking: combine mediocre skills into a rare advantage
[37:03] Energy as the real multiplier: sleep, food, exercise, and timing
[41:53] People can’t judge ideas: why “bad ideas” still have value
[45:13] The Spider-Man problem: responsibility after you’ve “made it”
[46:01] CalendarTree: solving a small scheduling problem well
[52:42] Why James’s biggest opportunities came from writing that felt risky

Additional Resources:

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.