Lessons from — How to Fail at Almost Everything and Still Win Big

Lessons from — How to Fail at Almost Everything and Still Win Big

How did I get to this book? I got interested in it after watching an Tim Ferris interview with Scott. Happy I am that I did pick it up. Not that I agree with everything in the book, far from it, but there are a few gold nuggets which I really liked. After all, that’s what reading is about, picking up the things we value. I don’t understand people who talk trash about a book just because they disagree with one bit of it. Anyways, let’s get into some more details.

One of the reasons I got interested into Scott’s book is because he talks about how affirmations helped him. I’m always on the look for new strategies to help get an psychological edge, and affirmations were never really something I paid attention to. His story seemed interesting so I decided to at least give it a shot. Here are some of the lessons learned.

Passion Is Overrated, just move

Follow your passion is great if you have one. But like most people, I don’t really have a single obvious passion. So naturally, my view on this topic isn’t quite as narrow as the popular quote goes. I think most people need to discover their passion, which is what Scott talks about in this book. He says that Passion is Bullshit because many people are delusional or not self-aware enough.

My boss, who had been a commercial lender for over thirty years, said the best loan customer is one who has no passion whatsoever, just a desire to work hard at something that looks good on a spreadsheet.

Scott argues that passion isn’t really a good benchmark because when things go well, we are passionate about almost anything we do in that moment. When they don’t, we aren’t.

It’s easy to be passionate about things that are working out, and that distorts our impression of the importance of passion.

So sometimes passion is simply a by-product of knowing you will be good at something.

Instead of “following our passion”, the author claims, we should build better systems and more energy. If I have more energy, I will do more things, try out more stuff. Basically, I will keep moving and expose myself to the world so that luck can find me. Let’s look into what personal systems are.

Systems VS Goals

The problem with goals is that we tend to feel bad if we don’t achieve them. Not only do we will likely feel discouraged more than once because achieving our goals right from the get is hard, we will also not know what to do next once we achieve them. What if instead, we just had a system? Something we execute every day, a routine. This routine will automatically take us on a road to achieving our goals. But we won’t feel bad if we don’t achieve X. Because we simply execute our system and just that fact makes us feel good.

For instance, exercises and meditation are two of the best habits you can build to be happier and more energized. With more focus, you will be better at everything else you do. I noticed a big rise in my productivity once I started meditating for about 2 hours per day.

Systems people succeed every time they apply their systems, in the sense that they did what they intended to do. The goals people are fighting the feeling of discouragement at each turn. The systems people are feeling good every time they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction.

How Affirmations can give you an Edge

Let me just dismiss your worry in case you already wear a tinfoil hat. Affirmations are just a trick to rewire our thinking. More focused thoughts lead to more focused action. At least that is the effect which seems so obvious to me.

I don’t know why there has to be such polarization of opinions of this topic. On the one hand, you have the wu wu people and on the other side the hardcore skeptics. I’m a skeptical and analytical person and that is the reason why I just acknowledge that I can just ignore the wu wu stuff and recognize that there is some practical benefit to this technique. Doing otherwise would just be arrogant and biased I think. Anyway, let’s get to the book.

Scott used affirmations to get a job working on his passion coff..eh..pardon, hobby as a cartoonist. Let me just quote the chapter where Scott accounts his road to become a famous cartoonist. It is paved with so much lucky coincidences that I think, without using affirmations as a way to stay motivated and focused, he might just have given up before it happened.

I decided to revive a long-lost interest and try my hand at cartooning. But it was an unlikely dream, given my complete lack of artistic talent and the rarity of success stories in that business. So I decided to try something called affirmations, which I will describe in more detail later in the book. I bought some art supplies, practiced drawing every morning before work, and wrote my affirmation fifteen times a day: “I, Scott Adams, will be a famous cartoonist.”

When you practice affirmations and you happen to succeed in the area of your focus, it feels like extraordinary luck. That’s how you perceive it, anyway. The Dilbert success story is engorged with lucky-sounding events. I’ll describe some of the luckiest parts of my story so you can get a sense for how deep luck sometimes needs to run before you find success.
The biggest component of luck is timing. When the universe and I have been on a compatible schedule—entirely by chance—things have worked out swimmingly. When my timing has been off, no amount of hard work or talent has mattered. Dilbert was the best example of lucky timing you will ever see. It wasn’t a complete accident that luck found me; I put myself in a position where luck was more likely to happen. I was like a hunter who picks his forest location intelligently and waits in his blind for a buck to stroll by. The hunter still has to be lucky, but he manages his situation to increase his odds.
I did something similar. I tried a lot of different ventures, stayed optimistic, put in the energy, prepared myself by learning as much as I could, and stayed in the game long enough for luck to find me. I hoped a buck would eventually walk by, and with Dilbert it did.
Let me give you a snapshot of the luck (timing) that needed to happen for Dilbert to succeed.
For starters, I had to be born in a time in which newspapers existed and comics mattered. And I had to have the right genetic makeup for the work and the right upbringing. And it helped a great deal that I was born in the United States.
My first comics editor, Sarah Gillespie, immediately saw the potential in Dilbert when she looked over the samples I submitted to United Media. Sarah was married to an engineer who worked at IBM. When he dressed for work, he wore a short-sleeved white button-up shirt with pens in his pocket, just like Dilbert. When the other syndication companies saw Dilbert and didn’t relate to him, they sent me polite rejection letters. When Sarah saw Dilbert, she related to both the content and the writing, and she championed the strip against some heavy objections within her company. Had someone else been in Sarah’s job, I believe Dilbert would have been rejected. There were only a handful of people in the industry who were gatekeepers for new comics. What were the odds that one of them would be married to a real-life Dilbert?
For the first few years after Dilbert’s launch, we had trouble getting any large metropolitan newspaper to pick it up. You need the first big paper to get on board before the others see it as a worthy risk.
One day an employee at the Boston Globe, whose job included looking at syndication submissions and recommending new comics to senior management, went on a vacation with her husband. She was driving; he was bored. The Dilbert sales packet happened to be in the car. The husband, who was—as luck would have it—an engineer, picked it up and started laughing. His wife didn’t relate to Dilbert the same way, but she trusted her husband’s reaction and recommended it for inclusion in the Boston Globe. With that sale in the bag, many of the newspapers in the Northeast followed suit.
But sales in the western United States were comatose. I later learned that the salesperson for that region wasn’t a fan of Dilbert. So when he went on sales calls he kept the Dilbert sales packet in his briefcase and showed other comics. Then the universe got involved: The salesman had a heart attack and died in a hotel room on the road. His replacement, John Matthews, identified Dilbert as the most sellable comic in United Media’s stable. And sell it he did, to every newspaper he visited. John is the best salesman I’ve ever seen. Had he not been available for the job, or had the original salesman lived, Dilbert might have been a small comic that ran in the Northeast for a few years before fading to obscurity.
The good timing for Dilbert was relentless. In the mid-1990s the media was focusing on the disturbing trend of corporate downsizing, and Dilbert got pushed to the front of the conversation as the symbol of hapless office workers everywhere. Dilbert was on the covers of Time, People, Newsweek, Fortune, Inc., and more. I modified Dilbert to be more workplace focused than it had originally been, and it became a perfect match of a comic with an era.
At about the same time, technology itself became a celebrity. The Internet exploded, the dot-com era happened, and all things technical were suddenly fascinating, even to the general public. In the eighties, Dilbert would have been nothing but another nerd comic. In the nineties, Dilbert symbolized the type of technology geniuses who were transforming life on planet Earth. Dilbert was unexpectedly and ironically “sexy.”
I had even more luck when Berke Breathed retired his popular comic strip Bloom County and opened up hundreds of spaces in newspapers. Later, Bill Watterson, the creator of Calvin and Hobbes, retired and opened up even more space. It was unprecedented for cartoonists at the top of their game, and so young, to retire. And the timing coincided with the growing spotlight on Dilbert, making it the most obvious replacement choice. Newspapers snapped it up like candy.

I mentioned my hand problem—the focal dystonia—in an earlier chapter. My career would have been over if not for the simultaneous development of Wacom’s Cintiq product, which allowed me to draw directly to the computer with no worries. What were the odds that the problem and the solution would happen at the same time? If my hand problem had happened five years earlier, I might have retired from cartooning.
The success of Dilbert is mostly a story of luck. But I did make it easier for luck to find me, and I was thoroughly prepared when it did. Luck won’t give you a strategy or a system—you have to do that part yourself.
I find it helpful to see the world as a slot machine that doesn’t ask you to put money in. All it asks is your time, focus, and energy to pull the handle over and over. A normal slot machine that requires money will bankrupt any player in the long run. But the machine that has rare yet certain payoffs, and asks for no money up front, is a guaranteed winner if you have what it takes to keep yanking until you get lucky. In that environment, you can fail 99 percent of the time, while knowing success is guaranteed. All you need to do is stay in the game long enough.

Be Selfishness to Serve

I think the airplane emergency instructions are a great analogy to daily life. If you first put up the oxygen mask to yourself (take care of yourself) you are in a better, more favorable situation to help other people.

If you do selfishness right, you automatically become a net benefit to society. Successful people generally don’t burden the world.

If you pursue your selfish objectives, and you do it well, someday your focus will turn outward. It’s an extraordinary feeling.

Focus on Maximizing your Energy

Just as a quick intro, try to think of a time where you built something or did something you were so passionate about, you didn’t want to stop. It seemed you suddenly didn’t need to worry about energy because you had a vast resource of it. Scott, as most of us, discovered the same thing.

For years, the prospect of starting “my own thing” and leaving my cubicle behind gave me an enormous amount of energy.

His goal was to get out of the corporate cubicle, you likely have different motivators. Whatever they are, try to maximize them.

The way I approach the problem of multiple priorities is by focusing on just one main metric: my energy. I make choices that maximize my personal energy because that makes it easier to manage all of the other priorities.

When I talk about increasing your personal energy, I don’t mean the frenetic, caffeine-fueled, bounce-off-the-walls type of energy. I’m talking about a calm, focused energy. To others it will simply appear that you are in a good mood.

Simplicity gives you focus. Simplify!

I discovered this principle before reading this book. The best results I’ve gotten often came when I just simplified and executed. I think we are all chronic over-thinkers nowadays, but that tendency to over-complicate and over-optimize things backfires. It makes taking effective action just harder.

In my career I’ve always felt that my knack for simplicity was a sort of superpower. For example, when I draw Dilbert I include little or no background art in most panels, and when I do, it’s usually simple. That’s a gigantic time-saver. I assume that other cartoonists retire early at least in part because they are optimizers, and that level of energy can be hard to sustain in the long run.

Dilbert was designed from the start to be simple to create, and I continue to streamline the process. That simplicity has paid off big-time because it frees me to blog, write books, do interesting side projects, and still enjoy life.


Exercise is something so useful to improve mood. Recently Simon Rosenbaum and his team released a lot of research in a book on the effect of exercise on mental health.

Good health is a baseline requirement for success. But I’m not talking about the obvious fact that sick people can’t get much done. I’m talking about the extra energy and vitality that good health brings. I might be getting the correlation wrong, and perhaps whatever motivates a person to succeed also motivates that person to maintain an exercise schedule. But I think it works both ways. I believe exercise makes people smarter, psychologically braver, more creative, more energetic, and more influential. In an online article about twenty habits of successful people, the second item on the list is exercise five to seven days a week.2 Other studies back this notion—physical fitness and daily exercise are correlated with success in business and in life.3

Learn to Fail and don’t be embarrassed!

This is one of my favorite lessons from Scott. He takes such an emphasis on listing all his failures in this book so that people can get over the false notion that successful people are just born that way. No special requirements to be successful! You just have to try. But you aren’t going to try if you fear embarrassment!

A lack of fear of embarrassment is what allows one to be proactive. It’s what makes a person take on challenges that others write off as too risky. It’s what makes you take the first step before you know what the second step is. I’m not a fan of physical risks, but if you can’t handle the risk of embarrassment, rejection, and failure, you need to learn how, and studies suggest that is indeed a learnable skill.1


I feel like I can improve in this one. Not that I don’t have humor, but sometimes it’s hard for me to pull up this skill at a time where it clearly could help me out.

If you see humor as an optional form of entertainment, you’re missing some of its biggest benefits: People who enjoy humor are simply more attractive than people who don’t. It’s human nature to want to spend time with people who can appreciate a good laugh or, better yet, cause one.
Take it from me when I say a good sense of humor can compensate for a lot of other shortcomings in one’s looks and personality. Humor makes average-looking people look cute and uninteresting people seem entertaining. Studies show that a good sense of humor even makes you seem smarter.1 One study showed that women seek out men with a better sense of humor because it can signal that they may be “amusing, kind, understanding, dependable.”2
Best of all, and central to the theme of this book, humor raises your energy, and that can reverberate into everything you do at school, at work, or in your personal life. The boost of energy will even make you more willing to exercise, and that will raise your overall energy even more.
Humor also transports your mind away from your daily troubles. Humor puts life in perspective and sometimes helps you laugh at even the worst of your problems.
Because humor directly influences your energy levels, it touches every part of your life that requires concentration and willpower. And for the most part, humor is free and easily accessible.

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