How to Fail at Almost Everything and Still Win Big

Kind of the Story of My Life


  • On Amazon
  • ISBN: 978-1591846918
  • My Rating: 5/10

In How to Fail at Almost Everything and Still Win Big Scott Adams, the creator of the Dilbert comics, talks about his successes and failures.

I'm a bit disappointed by this book because I expected an autobiography, not a self-help book with autobiographical elements. The content is a hodgepodge of topics like public speaking, diet, the author's voice issues, and many more. Some of it I found interesting, like the discussion about goals versus systems, while other parts, especially in the second half of the book, were boring and could have been omitted.

My notes


Making comics is a process by which you strip out the unnecessary noise from a situation until all that is left is the absurd-yet-true core.

The best example of the power of simplicity is capitalism. The central genius of capitalism is that all of its complexities, all of the differences across companies, all of the challenges, decisions, successes, and failures can be boiled down into one number: profits. That simplification allows capitalism to work. The underlying complexity still exists in business, but creating a clear and simple measure of progress makes capitalism possible.

You can debate the morality of viewing profits as the top priority in business, but you can't argue that it doesn't work. At most, you can argue that some companies take it too far. But that is the risk of any tool. A hammer is good only if you stop pounding after the nail is all the way in. Keep pounding and you break the wood.

The Time I Was Crazy

Sometimes the only real difference between crazy people and artists is that artists write down what they imagine seeing.

I learned that loneliness isn't fixed by listening to other people talk. You can cure your loneliness only by doing the talking yourself and – most important – being heard.

The Day of the Talk

Failure always brings something valuable with it. I don't let it leave until I extract that value. I have a long history of profiting from failure. My cartooning career, for example, is a direct result of failing to succeed in the corporate environment.

Passion Is Bullshit

Naturally those successful people want you to believe that success is a product of their awesomeness, but they also want to retain some humility. You can't be humble and say, "I succeeded because I am far smarter than the average person." But you can say your passion was a key to your success, because everyone can be passionate about something or other. Passion sounds more accessible.

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

In hindsight, it looks as if the projects I was most passionate about were also the ones that worked. But objectively, my passion level moved with my success. Success caused passion more than passion caused success.

Some of My Many Failures in Summary Form

[...] failure is where success likes to hide in plain sight.

Success is entirely accessible, even if you happen to be a huge screwup 95 percent of the time.

Good ideas have no value because the world already has too many of them. The market rewards execution, not ideas.

All of my computer-game ideas failed, but in the process I learned enough about personal computers to look like a technical genius in those early days of computing – the eighties.

[...] timing is often the biggest component of success. And since timing is often hard to get right unless you are psychic, it makes sense to try different things until you get the timing right by luck.

My Absolute Favorite Spectacular Failure


Goals Versus Systems

He said that every time he got a new job, he immediately started looking for a better one. For him, job seeking was not something one did when necessary. It was an ongoing process. This makes perfect sense if you do the math. Chances are the best job for you won't become available at precisely the time you declare yourself ready. Your best bet, he explained, was to always be looking for the better deal. The better deal has its own schedule.

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 – if you reach it at all – feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary.

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. Your options are to feel empty and useless, perhaps enjoying the spoils of your success until they bore you, or set new goals and reenter the cycle of permanent presuccess failure.

Goal-oriented people exist in a state of continuous presuccess failure at best, and permanent failure at worst if things never work out. 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.

[...] a goal is a specific objective that you either achieve or don't sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run.

My System

It helps a great deal to have at least a general strategy and some degree of focus. The world offers so many alternatives that you need a quick filter to eliminate some options and pay attention to others. Whatever your plan, focus is always important.

My Corporate Career Fizzled


Deciding Versus Wanting

Successful people don't wish for success; they decide to pursue it. And to pursue it effectively, they need a system.

I can't change the fact that success requires a lot of work. But if you learn to appreciate the power of systems over goals, it might lower the price of success just enough to make it worth a go.

The Selfishness Illusion

The most important form of selfishness involves spending time on your fitness, eating right, pursuing your career, and still spending quality time with your family and friends.

Humans are so emotionally and societally connected with one another that often the best thing we can do for ourselves is to help others.

The Energy Metric

Optimizing is often the strategy of people who have specific goals and feel the need to do everything in their power to achieve them. Simplifying is generally the strategy of people who view the world in terms of systems. The best systems are simple, and for good reason. Complicated systems have more opportunities for failure.

Keep in mind that every time you wonder how to do something, a few hundred million people have probably wondered the same thing. And that usually means the information has already been packaged and simplified, and in some cases sold.

Managing Your Attitude

Show me someone who you think is always in a good mood and I'll show you a person who (probably) avoids overexposure to sad forms of entertainment.

[A] benefit of having a big, world-changing project is that you almost always end up learning something valuable in the process of failing. And fail you will, most of the time, so long as you are dreaming big.

The next time you're in a gloomy mood, try smiling at a stranger you pass on the street. You'll be surprised how many people reflexively return the smile, and if you smile often enough, eventually that cue will boot up the happiness subroutine in your brain and release the feel-good chemicals you desire.

Once you become good at a few unimportant things, such as hobbies or sports, the habit of success stays with you on more important quests. When you've tasted success, you want more. And the wanting gives you the sort of energy that is critical to success.

You can control your point of view even when you can't change the underlying reality.

It's Already Working

When you define yourself as a member of any group, you start to automatically identify with the other members and take on some of the characteristics of the group.

My Pinkie Goes Nuts


My Speaking Career


My Voice Problem Gets a Name


The Voice Solution That Didn't Work


Recognizing Your Talents and Knowing When to Quit

One helpful rule of thumb for knowing where you might have a little extra talent is to consider what you were obsessively doing before you were ten years old. There's a strong connection between what interests you and what you're good at. People are naturally drawn to the things they feel comfortable doing, and comfort is a marker for talent.

The smartest system for discerning your best path to success involves trying lots of different things – sampling, if you will. For entrepreneurial ventures it might mean quickly bailing out if things don't come together quickly. That approach might conflict with the advice you've heard all your life – that sticking with something, no matter the obstacles, is important to success. Indeed, most successful people had to chew through a wall at some point. Overcoming obstacles is normally an unavoidable part of the process. But you also need to know when to quit. Persistence is useful, but there's no point in being an idiot about it.

People tend to say what they think you want to hear or what they think will cause the least pain. What people do is far more honest. For example, with comics, a good test of potential is whether people stick the comic to the refrigerator, tweet it, e-mail it to friends, put it on a blog page, or do anything else active.

If the first commercial version of your work excites no one to action, it's time to move on to something different. Don't be fooled by the opinions of friends and family. They're all liars. If your work inspires some excitement and some action from customers, get ready to chew through some walls. You might have something worth fighting for.

Is Practice Your Thing?


Managing Your Odds for Success

Success isn't magic; it's generally the product of picking a good system and following it until luck finds you.

Another huge advantage of learning as much as you can in different fields is that the more concepts you understand, the easier it is to learn new ones.

The great thing about reading diverse news from the fields of business, health, science, technology, politics, and more is that you automatically see patterns in the world and develop mental hooks upon which you can hang future knowledge.

The Math of Success

The best way to increase your odds of success – in a way that might look like luck to others – is to systematically become good, but not amazing, at the types of skills that work well together and are highly useful for just about any job.

Children are accustomed to a continual stream of criticisms and praise, but adults can go weeks without a compliment while enduring criticism both at work and at home. Adults are starved for a kind word. When you understand the power of honest praise (as opposed to bullshitting, flattery, and sucking up), you realize that withholding it borders on immoral. If you see something that impresses you, a decent respect to humanity insists you voice your praise.

Quality is not an independent force in the universe; it depends on what you choose as your frame of reference.

The reality is that reason is just one of the drivers of our decisions, and often the smallest one.

It helps to remind yourself that your own flaws aren't that bad compared with everyone else's.

No matter how smart you are, educated people will think you're a moron if your grammar is lacking.

Pattern Recognition

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.





Timing Is Luck Too


A Few Times Affirmations Worked


Voice Update



If your gut feeling (intuition) disagrees with the experts, take that seriously. You might be experiencing some pattern recognition that you can't yet verbalize.

Association Programming

To change yourself, part of the solution might involve spending more time with the people who represent the change you seek.


You need to control the order and timing of things to be happy.

Happiness has more to do with where you're heading than where you are. [...] We tend to feel happy when things are moving in the right direction and unhappy when things are trending bad.




If you want to make a habit of something, the worst thing you can do is pick and choose which days of the week you do it and which ones you don't. Exercise becomes a habit when you do it every day without fail. Taking rest days between exercise days breaks up the pattern that creates habits.

Voice Update 2




CalendarTree Start-up


Voice Update 3

If you think your odds of solving your problem are bad, don't rule out the possibility that what is really happening is that you are bad at estimating odds.

A Final Note About Affirmations