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My boss literally told me In these words, quite directly. Senior management. We don't have any diversity in management.
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I'm scared.
Yeah, or embarrassed. The one that you say. I could, just I'd be done. It actually is a terrible feeling.
As soon as it happens.
My life purpose evaporated. You know, I wasn't married, didn't have a family at the time. I suddenly lost my entire reason for waking up. So it was actually a sad, depressing, disorienting. Saying you did a thousand things and every one of them had a ten percent chance of working, you're pretty close to a guarantee that something's gonna work. So I like to think of life as like a strange kind of uh casino with that takes you money every time you lose, it's free.
You just pull all day long.
This isn't your average business podcast, and he's not your average host.
This is
The James Alteger Show.
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You know, I've known Scott Adams for probably twelve or thirteen years. He was one of the first guests on this podcast. And, you know, he's the creator of Dilbert, which was my favorite cartoon strip for for decades, but then You know, starting around twenty thirteen, he started writing about his life and his opinions and his approach to life and what made him a success. Like his the first book he did in this genre was How to Fail at Almost Everything and Still Win Big.
He also wrote another book which was very influential called Win Bigley Persuasion in a World Where Facts Don't Matter. Both of these books are must-reads.
Thank you.
Win Bigley is the best book ever about real-world persuasion. And Scott Adams himself was kind of an I don't I want to say he's an amateur hip hypnotist, but really more like a a professional in terms of how he used hypnotism techniques for persuasion and how to fail at almost everything and still win big. 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 it of the success of Dilbert which w he tells in this episode we're gonna show you now, is just
¶ A Note from James: why Scott mattered, and why this still holds up
Amazing. And I I have to say, Scott Adams has more recently become known for his his political musings. And he had a daily podcast coffee with Scott Adams, which I regularly listen to. I would say over the past decade or thirteen years, twelve years. He has not only become like a great friend and even somewhat of a a mentor to me, we've talked a lot, you know, on and off the podcast and his podcast, my podcast, and
really helped me out through some times when I was a little uh upset about different things and and he really knew how to how to reframe problems so that they would become successes. And I really just when I first heard he was sick, like this is last June, I was devastated. And of course, you know, he prepared us all that he was gonna pass away, which he did a few days ago and
It was really it was really upsetting. And you know, I'm not I hate when people kind of take advantage of someone's death by saying, Oh I knew him great, he was my best brat blah blah. I just wanna tell you, 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 kind of the real mechanics of persuasion, like 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 book. I love this guy. I'm really sad he passed away. And
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 a a at some point. Rest in peace, Guy Adams. And please, if you haven't learned from him in the past, or even if you have, We had a great time uh whenever we talked, and you know, here's here's a piece of that.
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So Scott, I just pre ordered your latest book, Go Add Value Someplace Else. So I'm looking forward to getting that.
Yes.
And but I have to say, as much as I enjoy your Dilbert comic I enjoy even more everything else you write. Like your book from last year, How to Fail at Almost Everything and Still Win Big, kind of the story of my life, is one of my favorite books.
Thank you. I appreciate that. It hasn't gotten nearly the public acceptance that I would hoped, but the small group of people who are reading it seem pretty excited about it, so that's meaningful.
Well let me ask you a question. Given that you're read in two thousand newspapers or more now for all I know, how come this book didn't really get all out there?
You know, I think it's in a genre that uh tends to be more of a fashion type of uh uh business.'Cause it used to be the self-help books were everything. You know, everywhere there was a self-help book. Now I think you'd find that probably there are very few self help books of any type that are being sold. Part of the problem is that people figured out that you can't read a self help book and then it changes your life and everything's good.
So I I tried to make a big point in mind 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 is what turned down to Then maybe you could compare that to what you're doing and what other people are doing and find something that works for you.
Well, you know, I always say the greatest marketer ever had the exact same technique. So Buddha said
¶ Scott's new book, Dilbert, and why "systems beat goals"
Don't believe me. This is just what worked for me. Be a skeptic. You try it for yourself and see if it works for you. And that viral marketing spread, of course, all through India within years.
I wish I had a nickel for every time I've been compared to Buddha.
Maybe you'd have a dime or something by now.
That's right. Yeah, but w who who markets better than Buddha? So yeah, I I could see that.
So I really like what I really liked in this book, and I I really subscribe to this as well, this idea that goals are bullshit. You say live by systems, I call it something similar. I say live by themes. But I really think so many people come to me and say, oh, I have to find what my goal is in life. And that's just meaningless. And the idea of living by a system or a theme is much more valuable. And so so what do you mean by systems?
Well, first of all, I think that this sort of a snuck up on society because society became more complicated. So if you went back a hundred years, let's say you were a farmer and you had a goal To clear forty acres before winter. That was a simple, accomplishable goal, and by the time winter came it was probably still a good idea. So you'd be glad you did it.
Now you fast forward to twenty fourteen and you know, I have more complexity in my smartphone in my pocket than the farmer had in this entire operation. I don't know what the world looks like next year. I don't know what my industry looks like next year.
I don't know as a cartoonist, I don't know if newspapers exist next year. I mean, there are a lot of things I don't know. So if I pick a goal and say, five years from now, I want to be here, what are the odds that that's still a good place to be in five years? So rather than taking that pinpoint approach and trying to shoot at something that probably isn't even a good target to begin with,'cause the world will change before you get there.
I say do things that improve your odds in a fairly uh general way so that no matter what the future looks like, you're in a good position to take advantage of it. The most obvious and common example of that. is simply stay in school, go to college, get a degree. Obviously it matters which degree you get, but the general idea that if you become more educated, you're in a better position to take advantage of whatever opportunity, people get that.
But I think there are lots of other ways to exploit that same phenomenon, which is if you just put yourself in a position where the odds are better, you can't predict exactly how that's going to turn out, but you're probably in a better position.
Well it's interesting because I think people almost limit their odds when they are when they're goal oriented at all. So like take the example you said, like going to college, then going to grad school, then getting a job and having as a goal promotions and then eventual retirement. That's sort of like the natural path of the past one hundred years. And that path has totally destroyed, you know, millions of lives. Like more lives than war destroys. Yeah.
You've got that problem that not only do you not know what the future is going to bring, but the moment you say this is my goal, then the whole point of having a goal is focus, right? And the point of focus is to tune out all the rest of the noise. Now the problem is that there might be more valuable more value in the noise.
than in the goal. And that's that's, you know, what I'm proposing here is that the world is full of opportunities. There may be plenty of things that were not your goal, not something you anticipated, that were way better than what you imagined. I mean there was a point in my life where I was dead set on becoming a corporate lawyer. I thought that's where I was at. Now had I kept that goal and been kind of laser like focused on that, I'm sure I could have accomplished that.
But would I be happy compared to how things turned out? I don't think so.'Cause I wore my pajamas all morning, you know, doing my work this today and I don't think I could do that as a corporate lawyer.
So let's talk about your day. So you woke up and you're in your pajamas and you started drawing a cartoon.
Well I I yeah, I get up round six, get my coffee and then I usually either read my email or maybe write a blog post on Dilber dot com or do something. But then I kinda get into my cartooning. Usually do about two comics on a typical weekday in rough form. I write them and I draw them in r rough form. And then sometime later at night or the afternoon when when there's some slow time, I I do the finished art when I don't have to, you know, use any brain power. It's pretty much just just uh skill.
And how long does it take to do one cartoon, you think, to to write it out and come up with the idea and so on?
Uh, it varies a great deal. So one of the things I learned when I was working my day job when I when I first started cartooning and I was getting up at four thirty in the morning and I had to be done with the cartooning by about six or you know, and I had to do one every day. I found that sometimes I'd have a good idea right away and I'd have a full hour and a half to develop it. But other days I'd have ten minutes left I had nothing.
And I would just say, okay, I I don't have any good ideas, so I'm gonna have to write down something, because it's not an option to do nothing. So I'd quickly throw together what I thought was a bad idea, and then I would wait to see how the audience reacted. And what I found is that I could not predict the good reactions or the bad reactions based on the work I'd done. In other words, I didn't have any power of prediction. And that freed me.
From thinking that if i it's only a good idea if I am dead certain it is at the moment. So rather now I say, I'm pretty sure this'll work and I put it out there and then I'm surprised.
¶ Scott's daily routine and how he actually creates cartoons
But that's a long way to say that sometimes I can knock it out in ten minutes, meaning that I got the idea and I rough out the art in ten minutes. But that's unusual. More more likely it's Mm, closer to forty minutes or an hour, I would say, to rough a cartoon. And then another Forty minutes to finish the art some other time.
And then and you started your first dil Dilbar cartoon you wrote in or you drew in nineteen eighty nine?
That's the first time it was published, yes.
And how long had you been drawing them before they got published?
Well, it was a doodle that I did in my day job. I was working at Pacific Bell, the that was then the local phone company. And probably Two or three years. It was just a doodle that I would draw on my whiteboard at work. Sometimes I'd work him into my presentations I gave at work. And then one day my manager at the time suggested that his name he didn't have a name. He said, Maybe you should call that guy Dilbert. And that's that's kind of what it all came together.
And then you started submitting it to syndicates or newspapers.
Yeah, so the process I could give you the interesting longer version or the tight short version. Which one do you like?
Let's do interesting.
Oh interesting. Okay. So one day in my corporate career, when I'd been told for the second time that I couldn't hope to be promoted because of my gender. So it was a weird little time in San Francisco when there was reverse discrimination, and my boss literally told me In these words, quite directly, I can't promote you because you're male, because we have a very imbalanced senior management. We don't have any diversity in management.
So until that gets fixed, which could be a hundred years, you know, there's no hope of you getting promoted. So I started thinking, Well, what can I do that's not in corporate America where I could do something where my talent alone makes a difference? Or better yet
moved somewhere where where uh being who I am is an advantage instead of a disadvantage. So I started thinking, well maybe I could try my hand at cartooning just on the side, because I'd always had an interest since childhood. But I didn't know how. Like how do you become a cartoonist? Wh where's the starting point?
Now the interesting thing is that just as I was thinking this, I came home one day and I was flipping through the channels on TV, and it was the end of a TV show about how to become a syndicated cartoonist or how to become a cartoonist. But I missed almost the entire show. I just caught the last few minutes and I figured out what it must have been about and I wrote down the name of the host and the you know, where it was broadcast from as the closing credits went by and I wrote a letter.
to the host and I said I missed your show, but I've got some questions about how to become a cartoonist. A few weeks later I get a handwritten two page letter from the host of the show. His name is Jack Cassidy.
¶ The real Dilbert origin story: rejection, Jack Cassidy, and persistence
And he gave me instructions on what book I should buy that tells you how to submit your materials to syndication companies and what materials you should use and a few other tips. And he gave me this advice. He said it's a very competitive industry and you're gonna get a lot of rejections, but don't give up.
So I thought, oh, this is great. I know exactly what to do now. So I bought the books he recommended. I got the materials he recommended. Put together some of my finest comics. This was before Dilbert. They were single panel comics. and sent'em off to the major magazines, Playboy, the New Yorker, the w anybody who paid the most. They came back rejected, as you might imagine. I was an unknown cartoonist and the comics were fairly terrible at the time.
But I figured, okay, I tried. I gave it my best shot. I did what I could. It was my best effort. It didn't work out. Like that's life, right? Not everything you do works out just the way you want. So I felt good about it, but I took all my materials, my drawing supplies, and I put'em in a closet. I just forgot about it, just moved on. About a year goes by, and one day I walk out into my mailbox and there's a letter.
And it's from Jack Casty, the cartoonist who had helped me with the first letter. And I hadn't even thanked him for his advice. And I felt bad about that. Um, yeah, I really owed him a thank. And I wondered why he would write a second letter a year later. And I opened it up and it said that he was cleaning his office. And he came upon in one of the piles my original samples I had sent him when I asked for advice, and he said he was just writing to make sure that I hadn't given up.
Uh that was the o that was the only reason he was writing. And I had given up. And I remember thinking, Well, maybe he knows something I don't know. Maybe he's seeing something with his experience that is invisible to me and invisible to the editors at Playboy and the New Yorker. And so I thought, well, I'm gonna increase my effort rather than trying to become a mere gag cartoonist for magazines, which would be good, but not the lofty level of a syndicated cartoonist.
I decided to try to become a syndicated cartoonist and then if I got rejected, I would be rejected at a higher level, which would feel like progress in a way, you know. So I followed the directions in a book called Artists Markets. It's probably still available and might be online now, I guess. And it just says where do you send your samples? And I sent my samples out to the major syndicate.
I thought most of them rejected me. I got all the the rejection letters and said thanks but no thanks. One of them ho helpful suggested that I might find an actual artist to do the drawing for me and that might work out better for me. But I thought I had all the rejections and again I said, Well, second time. I've tried, didn't work out. I put my materials away. A few months go by and I get a call out of the blue from a woman who said she was an editor for some company I'd never heard of.
Some company called United Media. And I hadn't sent my samples to anybody by that name, so I was confused that she was calling me, especially when she offered me a contract to be a syndicated cartoonist for newspapers. And now th for the viewers, the way syndication works is that if you get a syndication contract, that's your big break'cause it's the syndicate, which is a company, that sells to the newspapers, they do all the marketing and
turning things into licensed products and such. So that seemed like a big opportunity, but I'd never heard of this United Media Company. I didn't know where they got my my number from. So I was playing it kind of cautiously and I said, you know, I'm flattered by your offer, but frankly, I've never heard of this United Media Comp. Do you work with any cartoonists that have been published? Is there anybody perhaps I've heard of?
And there was this long pause, and then uh Sarah Gillespie was her name. She said yeah, we handle peanuts and Garfield and Roma Man and Nancy and when she got to about the twelfth name on the list. I realized that my negotiating position had been compromised. And so I did end up signing that contract with them. It turns out that United Media was the parent company of United Features where I was then and so I didn't recognize the parent company name. That's why I was confused.
Since then I moved to uh Universal. Andrews McNeil is publishing the books, so everything's good now.
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So you started the cartooning with United, but you still stayed at your job at Pacific Bell and you were cartooning every morning. And how long before you said, Okay, you know what? This is I'm gonna take the jump. This is it.
Uh well, that decision was made for me by my boss. When Dilber was just starting out, I had a little bit of a target painted on my back I learned later, I didn't know that, but I found out later from people in the know that the senior management wasn't happy that I was making fun of the corporate environment.
You wrote something very interesting a few weeks ago on your blog where you basically said that a writer should to have an element of danger in their writing. And I'm paraphrasing, but I I thought this was extremely valuable writing advice. Like probably now the internet is filled with top ten reasons to or top ten ways to be a better leader, top ten ways to be happy, and no one actually takes risks.
in their writing, even though there's much more writing than ever before. And you said that Dilbert there was this danger because you were essentially making fun of of the work environment that you worked in.
Yes. First of all I would say that you actually put danger into your writing, which is why I like it.
¶ "Danger" in writing: why safe content gets ignored
That's why it resonated so much with me that advice. Like I don't publish unless I'm scared.
Yeah, or embarrassed. Because when I read your writing, what I'm reading is, God, how many times did you rewrite that sentence?'Cause I know you're looking at it and saying, I don't want to say this, but I have to say this, so I'm I'm I'm feeling you. When I was first doing Dilbert, I think people sensed that I was in financial danger.
And I was. Now, it turns out that my personality is such that I tend to run toward danger. It's not a good thing. I'm not proud of that. But you you're wired the way you're wired. So I kinda naturally was attracted to the dangerous part of it. I look for that in writing that I read, but it just came to me naturally and accidentally in my case.
So you said you had a a target on your back, did they fire you eventually?
Toward the last year or so when Dilbert was getting pretty big, my coworkers came to me with an offer. In fact one of my coworkers is the real life inspiration for the character Alex. So she was an engineer at Pacific Bell and she was probably one of the best engineers and tough as nails.
So she became the Alice character, but she came to me with this offer. She said, A lot of the customers like seeing you'cause they come in and we show'em our technology in the lab and try to get people to buy our stuff. So we like keeping you around and we'll do your work for you. If you just show up to work once in a while when a customer's here.
So in the final year I worked on a deal with my coworkers and with my boss, where I said, I'll do what I can, but it's no longer my priority to come to work. But anytime you need me to leave for budget reasons or any other reason, just let me know. And one day, just for standard budget reasons, my boss said, Yeah, I think I need an employee who does real work more than I need this guy who just shows up and customers like him once in a while.
So then you were home alone essentially and now your your goal, quote unquote, was achieved. Like you're a professional cartoonist. You had no more role in the standard corporate workplace, was that like this amazingly happy feeling or were you scared?
Oh, you're asking a good question'cause I think you already know the answer to this question, which is I'll tell you the moment that's the most interesting. So I I got my first publishing deal, book publishing deal, and those tend to be if you're lucky, it's a multi book contract and it's a very big number. And the first time I got that big check, the one that you say, you know, I could stop working right now if I wanted to. I mean, if I wanted to, I could. Just I'd be done.
It actually is a terrible feeling. And I didn't I did not expect that. Because my whole life I was I was working toward that objective, you know, to have enough money that I could do what I wanted to do. And as soon as it happened, My life purpose evaporated.
¶ The strange downside of success: when purpose evaporates
Yeah, I wasn't married, didn't have a family at the time. I suddenly lost my entire reason for waking up. So it was actually a sad, depressing, disorienting Sing and what grew out of that is when I started the Dil burrito vegetarian food product that I was working at on the side,'cause I was trying to figure out some way to do something useful for the world.
So that I could get back my sense of meaning and I thought, well, the world of nutrition is a mess. If I could make a product which has all the daily nutritional needs and it was simple, then I've contributed something to the world.
Why didn't you think the strip contributed something to the world? Like basically you were you were opening up the window on what what I call corporatism is is really like as opposed to capitalism, for instance.
Yeah, you know, I've had this conversation a lot. It's the question of whether entertainment is sort of a real value. All right. Now, on some level of course it is. People like to be happy. You need to manage your attitudes as well as any other asset you have. So sure, entertainment's an important real thing. But I also can't help thinking as important things go, it's at the bottom of the important list.
You know, like if if you had to downsize the important things, what would you lose first? It's always the entertainment, right?
I no, I I don't know because look at comedy in general, the world of comedy. You take a guy like Louis C.K., you know, who I would say is a similar genre to you, this observational
humor that really sheds light on things that people don't normally think about. Nor people normally just go through their daily lives without thinking of these issues like, oh, that What Scott Adams just pointed out, what Dilbert just pointed out, is something really stupid that happens in my life every day that I never would have thought about before.
Yeah, I'm not gonna say it has no value. I'm just saying that among the valuable things it's at the bottom. All right. And and may you know, maybe that's'cause I'm too close to it. You can't really see it the way other people see it if you're the one producing it. But I'm Shocked and amazed and humbled that people read it every day. I'm happy about that.
And unlike many other comic strips, people hang it up on their cubicle wall. You know, I used to work in an IT department at the you know, in the Time Warner family and every cubicle had like Dilbert cartoons hanging up in it. Like it had an effect on people. It had an effect on cubicle life.
Yeah, I hear stories all the time. This is anecdotal, so I can't put any science on it, but the number of people who say my boss was starting to roll out a program and then he caught himself and said, Uh oh, this could appear in a Dilbert comic strip and then he completely rolled it back. So I think
Management had a free pass. They could do literally any ridiculous thing and say, Oh, I read a book that says this new process, this new system is gonna change the world and they could get away with anything. But as soon as you have the threat of public mocking, And in effect I gave employees a voice because they could take my words in the comic strip and cut it out and slip it under their boss's door, you know, pre internet and then post internet they could email it to him.
And suddenly it wasn't so dangerous for them. 'Cause they're now saying this is my opinion, but obviously they're sharing the opinion or they wouldn't pass on the comic. So I think I gave employees a a voice a and it's a mocking voice, which I think does put some control on management.
You know, and the the fact that it's a cartoon as opposed to let's say an op ed in the Wall Street Journal actually puts some distance between kind of the opinion and the danger of it. So it could be both dangerous and opinionated, but hey, it's a cartoon. So people could say, hey, don't take me so seriously. But look, there is this opinion that's valid.
Yeah, and that's part of the phenomenon that the funnier something is, the more you can get away with. A related phenomenon is that there are some topics, some subjects that you you would never be able to publish in a comic because people would get too angry, unless it's really, really funny. And then you can totally get away with it.
All right, so and that and that's true with you know, making any kind of serious commentary about the world. There are things that people would jump all over you if you said non funny, but if you put it in a funny context, people are willing to absorb it.
So it seems like from the beginning the system here was there was perseverance and what I know from your book is that you were interested in cartooning when you were a little kid. So you kind of T took out these passions and we all have these passions from when we're like ten years old that we kind of leave in our ten year old history. But you took it out and you persevered with it, you handled rejection and you kept doing it until
It was...
Time to make a break. You didn't you didn't rush it. You didn't you didn't leave cartooning once you got all rejected. So there would there was a system there.
Well, you know, my background was economics. I was an economics major and then business major. So I tend to look at things in the most practical way you could go. And one of the things I reject is the notion of passion or chasing your passion.
¶ Passion is overrated: why momentum beats motivation
So that's also what I wrote about in how to fail almost every time and still win big is that uh I think passion comes from things that work. So my system was to try lots of stuff and see which ones just are gonna work on their own because it was the right time, it was the right combination of skills. I got lucky, something happened in an environment that I didn't know about, and it was just the right time.
So I tried lots of things, and that's mostly what the book is about is how many things didn't work. So if you looked at just Cartooning in isolation, and I worry that when people looked at my career, it was actually demotivating because they didn't have the context of how many things I tried that didn't work.
So if you look at
just the cartooning part of my life, it looks like I shot an arrow and hit a running rabbit at a hundred yards and like, wow, that was either Amazingly skillful or incredibly lucky, but probably both. But then he any way you look at it is very demotivating, right? Because you can shoot a lot of arrows in the direction of a lot of running rabbits and you're not gonna hit one.
But if you look at it in this context, which is cartooning is just one of the dozens of things that I tried, and all of the other dozens of things were reasonably good ideas, w and which I had the ability and resources to expect some sort of execution that wasn't terrible. But most of those didn't work out, and most of the things that didn't work out were because of bad luck, bad timing, things things just didn't come together.
But it's it's that kind of uh diversification of opportunity that creates the luck. So I don't know if you p so you play a lot of tennis and I'm sure you've had this phenomenon where you play someone in tennis and you win and they say, Oh, you just got lucky. And there's a saying in chess, so I play a lot of chess. There's a saying in chess, only the good players get lucky. It always seems like the good players are the luckiest ones.
So the same thing happens in life. It's not quite like you create your own luck, but you leave yourself open for the opportunity of luck.
Yeah, it's just math. I mean th there's a reason that people diversify their portfolio. There's a reason that buy and hold works. It's a reason the index funds work. And the fact is if you try one thing once Probably things aren't going to go your way, right? Because the odds of the any one thing working, even if you do everything right, is about 10%.
But if you did a thousand things and every one of them had a ten percent chance of working, you're pretty close to a guarantee that something's gonna work. So I like to think of life as like a strange kind of a casino with a slot machine that instead of a slot machine that takes your money every time you lose, it's free.
¶ The math of luck: a thousand 10% chances becomes a near guarantee
You just pull all day long. All right. So in that sense, you can't control when the luck happens, but you can guarantee that you get a a payoff.
I mean this also goes along with the concept that you could even be fairly mediocre at all the things you're trying. Because if you try lots of them, it's like what you said in your book. Once you actually got syndicated, you found your cartooning skills got much better because people do tend to become, let's say, more passionate at what they're good at vr as opposed to the other way around.
Yeah, I had a total uh Wizard of Oz moment. If you know the Wizard of Oz, you'll know what I'm talking about. When I first got the contract to become a syndicated cartoonist my level of drawing skill went from abysmal to just a little bit terrible. I mean, for me that was a big a big increase. And I would say since then I've improved through, you know, brew force and practice to that's pretty good. That's about as good as I'll ever get. But yeah, it turns out that people are not great.
at knowing what they're good at.
You know, another thing that you point out which I believe very strongly in is the idea of combining systems. So or combining skills, yes. So so you know, like if you don't have to be great. Not everyone's gonna be the best mathematician in the world, but if you combine some skill in biology and some skill in mathematics and you become a biomathematician, then it's much easier to be the best in the world.
Yeah, so i in my case I use myself as the example of that point, which is if you look at my artistic skill, there's no one in the world who would accuse me of being a real artist, and yet that's my job. I draw stuff for a living, and I'm not a good artist. But it turns out that when you combine my mediocre drawing skills,
¶ Talent stacking: combine mediocre skills into a rare advantage
with my writing skills, which again are not Pulitzer Prize winning writing skills, but they're pretty good. You know, they're accessible. You know, my my points are usually clear, so it's good enough. Now you put those things together, still not enough, right? I I've got a little bit of drawing, a little bit of writing skills, still not enough. A lot of people have that.
But then I was lucky enough to have this corporate background and and again lucky enough that I, you know, discovered somewhat accidentally that pulling from that experience was what the the audience wanted to see. None of this was something that I had cleverly constructed as a plan years ago. It was just a combination of mediocre skills. Mediocre business, writing and and art skills. Now I would argue that
Over time, all of those skills have improved quite a bit. I would say I'm a reasonably good business person now. Not great. I mean I'm not Warren Buffett. Well I'm better than the average person who'd never put any effort into it. And you know, I draw better than the average person and I write better than the average person. But you put those three things together and get a little luck, a little timing, and it's magic.
You you are you are quite self deprecating though as well. I mean you are
I've earned all that self deprecation.
Fair enough. Fair enough. And you know, another another point you make and I'm kind of going through all the all the things that I think are also the most important is More important than passion is is energy and and you know, we're sort of allocated this amount of energy each day and maximizing what you do when you have the most energy is incredibly important as opposed to having
passion for something. And that's when you talk about nutrition and exercise and sleeping and, you know, all the things we do to maximize our energy. I think this is incredibly important. S stress is another thing too that takes away energy.
Yeah, I got lots of criticism from folks for including in a book that's about success diet and exercise. Interestingly, I guess that's just a social cultural kind of thing that people like to put that in a different box. It's like, Okay, that's just what I'm doing personally as opposed to what I'm doing to try to get success or whatever.
¶ Energy as the real multiplier: sleep, food, exercise, and timing
And if you separate those things, you've missed your biggest opportunity because Yeah, I'm I'm fifty seven. I'm in perfect health. I can work all day if I want to. I get up at six when my energy is best and I do the things which require the most energy, the creative stuff. And then I wait till later in the day when my brain is kind of mush and I do the mindless drawing and filling in the lines of my art. And if I were to just simply reverse those two things.
I wouldn't even have a career. I mean it's it's a gigantic impact. The difference between your your best moment of the day, you know, when your brain is clicking, you've got it, everything's happening, what idea you come up with then, your inspiration then. versus, you know, your dull brained three o'clock in the afternoon, I ate too many carbs, I need a nap, kind of thinking. I mean, those are it's not even the same person, you know, and there's such a difference.
You know, I I think people like look at look at the popular self help books of let's say the past fifteen, twenty years. You know, you have the secret. So people people want a secret. They w they don't want to simply be told that the magic equation is sleep eight hours a day, which is probably the most valuable thing you can do to have energy. That's what sleep is for, is to connect the re-energize the brain completely for the next day. And there is no secret to it.
Yeah, yeah. In in a sense, uh it's funny, the the two criticisms criticisms I got in the book were were opposites. One was, you know, don't include that stuff, you know, about diet and exercise and energy and in a book about success.
And another group saying, You're saying things that are too obvious, you know, we already know this but I know that they don't know that. Because you have just have to walk down the street in America and look at people and they haven't figured out the whole, you know, if I get my body working
then everything in my life is better. If your body is working, you're fit and you're healthy and all that, your social life is better, you get more job opportunities, you can work better hours, create better things. It all kind of starts with that. So if you skip over that part, are you really even trying? I would go so far as to say if you care about success and you haven't taken care of your physical tool first, you're not even trying.
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I think I think people m in many cases and this is not really a criticism of people, but I think maybe sometimes people wanna have an excuse why something hasn't worked out. So for instance, I had one person write me and said, I'm following your advice about, you know, writing down ten ideas a day and I'm I'm I'm exercising and and sleeping. And then on Friday night
I go out drinking with my friends and my friends laugh at all my ideas. And and he said, What should I do? And I wrote back and I said, Stay at home Friday night. Like don't don't go out anymore on Friday night. And I never heard from him again.
I I might have added find new friends.
Yeah, fine friend. is another one. Although maybe on Thursday night those same friends would have been supportive of him. I didn't have I don't know. I just know on Friday night they specifically were trashing a him.
Yeah, one of one of the pieces of advice I I give to people is based on my own experience. When I was first assembling my Dilbert comics to submit to syndication, I had about fifty of them in in sample form and I wanted to only send the best ones. So I would have my friends come in one at a time to help me sort my fifty comics into the good ones and the bad ones so I could just send the good ones.
And it turns out that my friends were all over the map. They couldn't tell, or they all had different opinions about what was a good one and what was a bad one. So in the end I I just said them all. But I've learned from that and a million other examples since then that people cannot tell a good idea.
All right. They're just no one is that smart. You can't pick a good stock. No one's that smart. You can get lucky, but you can't know. And nobody knows a good idea when they see it. So when you tell your friends your idea and they all laugh at you What you should be registering in your mind is not, oh my God, I guess this is a bad idea after all. The tape that you should be playing in your mind is people don't know what a good idea is.
It it's really true. Like uh do you know do you know the story of the very beginning of Twitter?
I might refresh my memory.
So so it was a company initially called Odeo and they were setting up software for podcasts, ironically, given that we're on a podcast. And it wasn't really working out. So they worked on this project on the side, which people sending messages back and forth and 140 characters. And they decided, look,
This is getting interesting. We have ten thousand users or whatever. Let's devote ourselves to this. So Ev Williams, who was the CEO, he went to all the professional venture capitalists that had invested in Odeo and he said, look, Odeo's not working out, but you're welcome to stay in.
¶ People can't judge ideas: why "bad ideas" still have value
And we're gonna focus on this other little project that we've been working on, or I will take you out completely at cost. You won't lose a dime and it's up to you. And a hundred percent of these professional investors all took their money out of Twitter.
Well, so yeah, there could not be a better example because if you had come to me and said, I'm gonna develop this thing that lets you send the message to people, I'd say, Stop, already exists. We have something called email. You go, No, wait, wait, it's better than that. It really limits how much you can write to an annoyingly small amount. And I'd be like, Bass. How can I get my money out? I'm outta here. I mean there's nothing about that that on the surface would make sense.
And you can go right down the line and find so many examples of things that you would not have predicted or that you predicted wrong.
And yet this this doesn't stop you from pursuing ideas, of course. As you mentioned, you've opened restaurants, you did the Dil burrito, you've done other things that, you know, you've had other ideas that you thought were good.
Yeah, lots of other ideas, but w I find value in the idea. So one of the things that I'm pretty serious about is that bad ideas have value. In other words, if I give you ten bad ideas, those probably didn't have any value. But if it made you think of one that was good, it's like, oh, those ten ideas were bad, but that makes me think of this idea.
So the way you get to good ideas is through bad ideas. All right. There's almost never a time when somebody just sits there in a blank room and says, Ah, good idea. You don't go from here to there. You go through the bad ones first. So uh the more bad ideas the better as long as they're well explained. And I try to do that on my blog in particular. I make no claim that anything I write it even makes sense, or it's a good opinion, good for the world, or anything else.
But
I do explain myself clearly. And in that process, I think people say, I don't agree with that, but you're making me think differently than I was before, and maybe that leads to something good.
You know, and also the thing about, let's say, a list of bad ideas is it could be w what I call idea sex. The two two bad ideas put together, it actually could be the case that negative one plus negative one equals three. Yeah.
Yeah. I mean I c can't think of an example of that right off hand, but I feel like I should be able to.
I can't think well a hundred forty characters plus the internet. I don't know. Maybe that turned out to be a good idea. Now You've you've been doing this you've been doing Dilbert for twenty five years or more. Is this is this gonna continue forever? Do you ever think about like, okay, I'm gonna take a break, I'm gonna stop?
I think about that literally every day. And I have mixed feelings about it. I mean e since it isn't hard to do, it would be hard for me to stop because first of all, a lot of people depend on the things I do. And y this is one of those top one percenter problems, which is that I'll call it the Spider Man problem, you know, that with great power comes great responsibility. I I'm in this weird situation where if I spend an hour of my time working, I produce more economic
¶ The Spider-Man problem: responsibility after you've "made it"
activity and value, I guess, than the average person working an hour. And it's a lot more because of, you know, I'm in this lucky position. So I feel like this responsibility to continue to be productive, both as in a role modeled way, I don't think there could be anything worse than getting rich and quitting. Like I I
Yeah, like what would you do?
What would I do? Yeah. So I may have mentioned before that now I'm involved in a startup called Calendar Tree, Calendartree.com.
And I signed up for it.
Thank you. All that does is solve a universal common problem. Which is if somebody sends you a schedule of a long, you know, bunch of events for some sport or activity or whatever organization, you don't want to have to retype it manually into your computer.
¶ CalendarTree: solving a small scheduling problem well
So instead we turn it into a link a calendar tree and then you can use the link to add it to the calendar you already have. So it solves a very small problem, but I found that very satisfying because it's a real problem and there's not a other solution. So we took that out and solved it, and that's meaningful to me.
And also in a world where people are moving towards solo preneurship, you know, one or two man startups, everybody's got different calendars. So everyone that you're trying to schedule with has different calendars and the fact that you're sort of a calendar independent is valuable.
Yeah. So it's a complicated world and we just build one little product that simplifies just this one little part of it. Now we hope to expand to solve a bunch of related problems in the scheduling field. But for now it feels good that we've done this one thing, people are using it and they're happy.
And how many users do you have?
It's in the low thousands right now. We're we're in the process of you know rewriting the code from from the bottom up to make it more scalable now that we've discovered that people like it and they work. So we're gonna wait for a big push until that's done and we hope in another month or two.
Well, do you have it as an app, like for uh I'm assuming for mobile you ha you have it all set?
Uh right now we don't have an app because the most popular use for it would be you'd create a schedule that you're sending out to someone. So it works if you're the receiver. You can receive it onto your smartphone and just click the link and add it to your calendar. But if you're the one creating it, you probably don't want to create a long schedule on a phone. Because it would just be too tedious. So at the moment it's just a web app, but someday we'll have a mobile app.
Or if I'm receiving though, I could be re like let's say I'm on a bus and I have my phone and I'm receiving a calendar request, uh
Well I guess.
Would I be receiving it on Calendar Tree or what if somebody sends me a Google Calendar uh request?
Oh so the way calendar G works is that if the organizer creates a schedule, they can turn that into a link that they can send out any way you can send a link. So I could send it through social media, Twitter, Facebook, or email. Email is the most common. So on your bus example, you would check your mail and it'd be an email and say, Somebody you know has sent you this, click here to add it to your calendar. And then you just click and
Say I'm a Apple calendar or I'm a Google calendar or I'm an Outlook calendar and it adds it. So it was for multiple events. Obviously if somebody sends you one event, you don't really need anything.
Yeah, so so that's interesting. So you basically like the business world. You write about it, you blog about it, you're starting a business, you've started other businesses. Um have you thought about raising money for this?
Well, right now we're we're adequately funded. We've started having the conversations but until we do the rewrite in a month or two, I don't want to get too serious about asking for money'cause I want people to know what they're getting and We'll have a much better thing to show them in a couple of months.
Also to get like a good one good maybe even corporate client to accept this as their calendar versus using Google calendar or Microsoft or whatever.
Well we're not a we're not a calendar replacement. We're just a way to get whatever schedules you'd like to get on calendars onto any different calendar. But yeah, we're looking at at corporate types as a way to get kind of a big footprint, right?
Or even something where they don't expect everybody to have the same software, like let's say a meetup type situation or a church or whatever where not everybody's gonna have the same calendar system.
Yeah, that's ideal. In fact, what we do right now on calendar tree dot com, we put some of the major sports schedules up there. You don't have to be a member of calendar tree. You don't have to sign up. You could just go up there, click, and add it to your calendar. We're showing that someone like the NFL, NHL, or Major League Baseball could tweet out a link and anybody who got it could say, hey, let me add the Giants schedule to my phone.
You should do a deal with um I'm sure everybody says you should do this or you should do that, but uh you should talk to a company called Ticketfly. They're like Ticketmaster, but they deal with tens of thousands of events. And they are much more savvy with social media than Ticketmaster. They're just an interesting company.
Yeah, we've talked to the uh companies that are in the events space and the ticketing space and it's pretty crowded and we're at the moment we're not going after that ticketing kind of world. I could see maybe that happening someday down the road. But right now we're going for a pretty limited problem and a full solution to a small problem.
And again, it's uh kind of combining your economic skills with probably your experiences on the internet over the past twenty years.
So You know, it it's actually interesting how much of the startup and the cartooning and the other stuff I'm doing is related because it's all creativity and it's all engineering in your mind. It's like The thrill I get from thinking of a new business model, a a way to create money and value that had not been thought of before is exactly the thrill I get when I have an idea for writing a blog post or writing a comic.
Yeah, it's interesting because I find like let's say I own a stock and the stock goes down, I'm disappointed. But if I wrote a good blog post that day, even though they're completely unrelated, like in one case I'm actually losing money, in another case it almost means nothing to any aspect of my career. But I feel so good from the good blog post that it outweighs the bad feeling of losing money.
By the way, I would argue that your blogging is a system in the sense that you don't have a specific monetary goal. You're not saying if I blog this much I get X dollars. But 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. So you thank you. So you you have increased your your odds of something good happening in some indirect way through your blogging, which is exactly why I do it by the way. So I I blog because it has produced, you know, requests from the Wall Street Journal to do things, book you know, book deals have come out of that, licensing deals. And I don't really plan any of that. Those are just the things that happen.
You know, you're you're absolutely right. And it's specifically, by the way, when I added the danger component that all my opportunities opened up. Before then I would kind of write about business or stocks or whatever, but it was very mainstream and nothing. It meant nothing to anybody. But once
I was really kind of revealing personal things and, like you say, embarrassing things. Suddenly everybody wanted to you know, uh opportunities were literally thrown at me. I had to learn how to say no. Because before I was saying yes to everything.
¶ Why James's biggest opportunities came from writing that felt risky
Yeah, you made it personal. That really made a difference.
And how p how personal is is Dilbert to you?
Well, you know, Dilbert is a big part of my personality put into the character, so these socially awkward parts, the the part of me that's, you know, half robot half the time and I tend to look at the rational side and discount the emotional, you know, magical side. So he's he's a lot of me in there. But he you know, I don't have his engineering or math skills, so you know, I'm not I'm not compatible that way.
And then the other characters have some aspect of my personality that I exaggerate because It's hard to rate someone else's personality. You have to find something about you that works for that character. You know, like there's a Right. You know, no matter how ambitious you are, you certainly can relate to trying to get out of work and being lazy. So I put that into Wally and you know. So there's always some flawed part of my personality I can capitalize on.
It seems like with your blog the way you kind of inject danger in there is not necessarily being too personally revealing, but you really play with ideas and you take ideas to an extreme and kind of see how people react to it. Whether you're talking about Israel or are we a two dimensional experiment?
or whatever, you play more with ideas and kind of test the reaction of people. And I I'm curious how much you take it to an extreme on purpose to see if you get huge reaction versus little reaction.
Well, some of it is of course theater in the sense that if it's not interesting no one's gonna read it. So Yeah, I do pick headlines, for example, in blog titles that try to draw people in. So there's a little bit of sensationalism, but I try within the body of the thing to stick to facts.
And to stick to reason and to call out when I don't know something. But what's interesting about my writing, and the thing that gets me in the most trouble, is that the world is so accustomed to people being on one side or the other side. That typically what I do that causes the most trouble is I say, Well, there's a little bit of a point on this side, there's a little bit of a point on this side, and maybe there's something in the middle you hadn't thought about yet.
And man, both sides hate you when you do that. Because
They can't handle that because unless you agree with them, you're wrong.
Yeah, it really doesn't go beyond uh just what you said. So that's the danger. And it took me a while to drive away the blog readers who couldn't handle that. But I think I have at this point.
It's interesting because I specifically do more the personal stories as opposed to the opinion stories because people just go insane. Like it's almost like you're contributing to the mental illness of society by forcing them to co to argue with you.
If my favorite in the making troubles genre was recently when I hypothesized that the stock market could go to a new permanently higher earnings multiple and stay there if you drove out the some of the risk. And the risk that I identified was the risk of all the professional advisors who were largely scammers and idiots and using luck and trying to sell it as a skill. So I mean that got me uh invited on C N B C to talk about it more. And
People can't handle that. I've written that exact topic. There'll be thousands of comments saying, Oh, he's just a loser who wishes he could make it in the stock market. Like when it's so clear I've I've actually run a fund of hedge funds investing in other hedge funds. Maybe nine out of the twelve hedge funds I invested in were shut down by the SEC for being criminals. So um yes, I'm a horrible investor in hedge funds, but also they're mostly criminals.
That's funny. I I've never heard that statistic, but from the the first probably week I heard the fr the phrase hedge fund, I remember my BS filter going Huh. It's a thing that's not terribly well defined, that involves a lot of money, and maybe there's some secret algorithms. Just saying. Just saying it might be bullshit.
Well that I mean I had one hedge fund where The guy specifically admitted and that the filings are all there. He stole ten million dollars from the hedge fund. He paid a fifty thousand dollar fine to the SEC and now he's on Facebook posting pictures. He's he's on the beach, he's ha having fun. Life is good.
Well I think the moral of the story is start a hedge fund. I think I might do that as soon as we're we're done with this podcast.
The Del the Dilbert five. I I have to say, ever since 2011, I've had your essay, How to Get a Real Education Hanging Up Near My Desk, because it's so in line with how I think about education, like, what do you actually People people don't realize the kind of history of the university. Back in the Renaissance, they used to have guards surround a university, but the guards would face inwards because people knew that
committed violent crimes, young men. So the guards would have to keep people in the university so they wouldn't go out and commit violent crimes. Then the university became something other than what it was then, but I still think the same the the same thing. Like What do you actually remember from college? Like you you wrote about what you learned from college. It has nothing to do with what you learned in classes.
Yeah, I mean I'm a fan of the general idea that anything you do that's kind of difficult is gonna make your brain uh more capable So from that sense, it didn't matter that I remember too much specifically from college. It just mattered that it made my brain a better instrument. But I do ask the question
Is it necessary that I learned nothing? I mean, c couldn't I at the same time, couldn't I have learned something useful? I mean, was that against the rules? So or maybe something I would remember. Yeah, so I think there's a Uh like you say, almost everything in our world right now is some kind of legacy system that if you were to uh uh uh imagine it and invent it today, it just wouldn't look like, you know, what we're living.
No, and you bring up that point too in your essay on running for president when you announced you were gonna run for president in in twenty eleven. You brought up a lot of ideas that, you know, politics is almost an incremental system. Nobody ever thinks of actual real let's start from scratch and make this better. People say, oh, let's just make a bill to reform it. And They don't actually do anything.
I'll tell you, nothing makes me crazier than hearing somebody argue, usually on the internet, that something is in or not in the Constitution.
Because
It's a piece of paper written by a bunch of guys two hundred years ago who were pooping in holes in the ground.
And own Muslim owned slaves.
Right. So the question is, what should it be? Not what somebody wrote down two hundred years ago. I don't care. I have to deal with that because that's my reality today. But why can't we talk about what it should be? Starting from scratch? Because we can start from scratch if we want to.
It's funny, last year, um, just as a spoof to market a book, I was gonna run for Congress. And I actually seriously looked into it. But my whole thing was I was never gonna go to Washington, DC. I kept trying to explain. I'm gonna stay here. And the idea is I'm not I'm never gonna go to DC. So no lobbyists can find me. And uh but I ended up not doing it. But then I made the not doing it. the marketing trick that I did for my book. So
Uh uh I I like that. You know, I and if you've read the blog you know that I've talked about lots of different governmental tweaks and ways you could fix things. But uh I have thought it would be interesting to run for president under the idea that you would just support the majority on all social issues.
Period. And when the majority changes, you'll change with them. Because, you know, it's social and the fact is the majority is going to get its way, right? So you might help argue against the majority while supporting it at the same time. I mean you might have a moral
problem with the majority, but I think as president you ought to support it, at least for the, you know, internal stuff. And then for defense stuff, of course, you've got to be a little more independent to react to, you know, immediate threats and stuff. But for the domestic stuff, Why couldn't you have a president who just says, Show me the polls, that's what I support.
Yeah. I always wonder why we're not voting on the internet. Like why why do we have to go someplace to vote now?
Well, you know, the argument is usually that it wouldn't be secure. And again, I go, Ah
Yeah.
Like first of all, like it's secure now,'cause I don't know where all those votes go to, but I'm sure it isn't like infinite monkeys with a tally sheet and a piece of paper. All that goes into a computer somewhere, right?
I mean ultimately I don't know how the system works, but somewhere there's a computer that's all going into. Now, you know, maybe you create more opportunities for problems if you make internet voting, but I would think as long as the news media could do polling in the same places that are doing the voting, that discrepancies would jump out, obviously.
I think the main thing is people are really against majority rule. They actually think that having elected officials solves the problem of how bad it could get if there was majority rule.
Well, yes, I think there was a time when majority rule would have been the worst thing in the world because you have mob rule and there's a reason that the United States is a republic and not a true democracy. But I think that the internet makes a lot of those things lesser important. Meaning that I can't think of anything that the majority is in favor of that would be awful.
Can you?
I mean,'cause there's there's no majority saying oh it l there's no uh like uh white men, you know, who are saying, Let's kill all the Ethiopians who are in this country or, you know, whatever, I'm just making up stupid examples. But You we imagine that could happen, but I don't see any signs of that happening because at this point you couldn't go public on the internet and say, I'm against. any group'cause you would be smashed.
Well, let me ask you a question. Do you think there are even more than three issues in that are domestic issues that people even care about?
Well, individually, um yeah, if you count taxes as everybody's issue and then throw in maybe abortion as the next one, yeah, you run out of issues pretty quickly.
Yeah. Taxes, abortion, and then for some small amount of people immigr for people who live in Texas, immigration.
Yeah, or gay marriage I suppose for for some people. Yeah, but yeah. It's routed three. It's a different three maybe for different people, but yeah.
Probably three.
And and think about it, all those issues don't actually affect you, like you personally. Except for maybe taxes.
Oh, so yeah, some of them affect me personally.
Well, Scott, I I really appreciate you coming on the show. It's been it's been such a pleasure. I've been such a fan for for so long of of Dilbert and all your writing and I and I'm really grateful you came on the show.
Thanks, James. This was a lot of fun and uh it was great meeting you and thanks for having me on the show.
Yeah, all right, good. I will talk to you soon.
All right, take care. Bye.
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Yeah.
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