Book Summary: How to Fail at Almost Everything and Still Win Big

Table of Contents

The Book in Three Sentences

Before becoming a recognized cartoonist and publishing Dilbert, Scott Adams failed spectacularly several times. In How to Fail at Almost Everything and Still Win Big, Adams shares a framework that involves welcoming failure, embracing it, and learning from it. While this is a personal story, the book gives advice that anyone can benefit from.

Buy the Book

How to Fail at Almost Everything and Still Win Big Summary

Chapter One: The Time I Was Crazy

In 2005, Adams was diagnosed with a mental illness. Both his doctor and his psychologist agreed, the author was crazy. He’d lost the ability to speak with other people which was a problem because he was a paid professional speaker.

Chapter Two: The Day of the Talk

Adams had problems striking up conversations with people before an event. When the talk started, the author felt confident despite his difficulties. He appreciated failure which is why he agreed to do the talk in the first place. He was able to talk for forty-five minutes, but the moment he walked off stage, he lost the ability to speak again. For the next three years, the creator of Dilbert looked for a solution to his voice problems.

Chapter Three: Passion Is Bullshit

A common piece of advice is that of following your passion. Sometimes this will lead to a reservoir of energy, resistance to rejection, and determination. But passion doesn’t cause success, but the other way around. We’re more likely to confuse passion with the skills we’re good at, so we confuse passion with talent. You don’t need passion on your path to success.

Chapter Four: Some of My Many Failures in Summary Form

The author failed many times, but he encourages others to fail as well because success hides in failure. Success is elusive because if it were easy, everyone would be successful.

Chapter Five: My Absolute Favorite Spectacular Failure

While Adams was in college, he went to an interview in New York in winter. He went to the meeting with no jacket and no suit and tie. Scott was immediately rejected due to his attire and on the way back, his car malfunctioned and wouldn’t start again. He was lucky to find someone who gave him a lift back to campus and he promised he would move to California. Despite all of his mistakes, moving was one of the best decisions he made.

Chapter Six: Goals Versus Systems

Goals are no good, focus on systems instead. Goal-oriented people fail all the time and hope this is temporary. Eventually, they get used to failing and they give up. If you achieve a goal, you celebrate, but you soon realize that you don’t have a purpose anymore. System-oriented people, on the other hand, succeed every time they apply their system which means that they feel good all the time. For example, losing a specific number of pounds is an objective while exercising is a system.

A goal is an objective you either achieve or you don’t in the future. A system includes all the habits you do regularly that make you happy in the long haul. There are no deadlines for systems.

Chapter Seven: My System

The creator of Dilbert created an entrepreneurial plan: he wanted to create something valuable and something “easy to reproduce in unlimited quantities”. To do so, he used his creativity.

Chapter Eight: My Corporate Career Fizzled

Scott worked as a bank teller, but he was terrible at it. As a way out, he wrote a letter to the senior vice president and attached ideas to improve the bank, as well as a list of his qualifications. Despite not being good, Adams was promoted several times over the years. When he was fired, a phone company hired him, but he was soon fired again. He used this as an opportunity to draw.

Chapter Nine: Deciding Versus Wanting

The best piece of advice the author ever received was something along the lines of “figure out the price of success and then pay it”. Wishing something will take you nowhere. Instead, decide you’ll have the things you wish for. Deciding involves doing something because you’ve accepted the price you have to pay. To pursue success, you also need a system.

Chapter Ten: The Selfishness Illusion

Deciding to be successful requires you to balance your needs, as well as the needs of others. When talking about generosity, there are three kinds of people:

Selfish
Stupid
Burden on others

When given the choice, be selfish because the remaining options don’t help anyone. There is such a thing as doing selfishness right because once you’re successful, you benefit society. You can be selfish and still spend time with your loved ones.

Chapter Eleven: The Energy Metric

We chase many things. But time spent chasing a desire is time you can’t spend chasing another desire. To organize your limited time, you should use your energy as a metric. To maximize your energy, eat right, exercise, avoid stress, and sleep well. Additionally, you need to do something that gets you excited to get up in the morning.
To maximize your productivity, match your mental state to the activity. For example, use mornings or late nights to work on activities that are creative, fun, and relaxing. Use afternoons to exercise, and use evenings to do mindless tasks. If you don’t have a flexible schedule, make up your own by going to bed early and getting up early to focus on creative projects.
There are two kinds of people: simplifiers and optimizers. Simplifiers look for the easiest way to do things, even when they know that going the extra mile leads to better results. Optimizers look for the best solution even if it leads to problems. Optimizing is tiring and leads to stress. Different situations lead to either simplification or optimization. Communicating with others requires simplification. Doing something on your own requires optimizing. Optimizing is best when you have specific goals. Simplifying is best when you need a system because the simpler the system, the more likely you are to succeed. Simplification also frees up time and energy.
Sitting down is a position that most people associate with relaxing, so train yourself to sit in a specific position to encourage concentration. Also dedicate a space specifically for work.
Tidiness affects your energy. Messy environments are distracting and optimized environments make you feel energetic. If you don’t feel motivated to organize, invite someone regularly and you’ll be inspired to tidy up your space.
Sometimes you can’t achieve success unless you acquire a specific skill. When you don’t know how to do something, you can usually figure it out easily and if you can’t, you can also hire a professional. You can find the information you need for free and in a simplified manner.
You can corrupt other people’s energy by being irritating, selfish, arrogant, or mean-spirited. So don’t dominate conversations, don’t brag, don’t cheat, and don’t be cruel.
Think of your priorities as an archery target. The center represents you, which is your highest priority because if something happens to you, you won’t be able to focus on all the other priorities. Your second priority is the topic of personal finance, which includes your job, investments, your house, and so on. The final priority is your local community, your country, and the world. Priorities may overlap and conflict with each other, so don’t avoid problems. Always choose the path that will lead to less stress.

Chapter Twelve: Managing Your Attitude

Your brain studies the environment, your thoughts, and your health to create your attitude. If your attitude’s good, you’ll produce better work and enjoy life. Controlling your attitude instead of letting the environment do it for you is a superpower. To elevate your attitude, focus on exercise, food, and sleep.
Smiling is a way to feel better immediately. Acting happy makes you happy.
Being successful at something will affect other things as well. This happens because success requires you to develop good habits and once you develop good habits for unimportant things, you’ll start using them on important things as well without realizing it. This helps you in several ways. First, you won’t abandon something because you know it takes time to be good at it. Second, you’ll be energized by winning and this will encourage you to keep going.
We have flawed assumptions which include superstitions and misconceptions. Although irrelevant, they boost our confidence and can influence our chances of success. Tell yourself any story you want as long as it helps you do your job.

Chapter Thirteen: It’s Already Working

If you made it this far, you’ve proven to be a seeker of knowledge. When you read a book, you associate yourself with the people who also read books. Those people have more chances to succeed because they studied the mechanics of success. Doing certain things, redefine your identity, and change you. Our attitude remains the same, but we adopt new skills.

Chapter Fourteen: My Pinkie Goes Nuts

Early in his career as a cartoonist, Adams was diagnosed with focal dystonia, a condition common in people who do repetitive tasks with their hands. Doctors advised him to stop drawing because the condition can’t be treated. The creator of Dilbert tried hand exercises, drawing with his other hand, and strapping his finger. Ultimately, he decided to hack his brain to draw using a different motion and it worked. When the condition came back years later, he bought a computer monitor for drawing.

Chapter Fifteen: My Speaking Career

At some point in his career, Adams was offered to give a speech in Canada. He didn’t know how much to charge for his services, so he asked a friend and settled on five thousand dollars. Soon, the author received more and more requests, so he kept raising the price. When possible, overprice yourself and see what happens.

Chapter Sixteen: My Voice Problem Gets a Name

Months after losing his voice, Adams didn’t know the origins of this problem. He decided to give a name to this condition and found out that this pinkie problem and his voice problem were related. The cartoonist had spasmodic dysphonia, a condition that causes the vocal cords to clench, preventing people from speaking properly. He went back to a specialist and the doctor told Adams that there was no cure. The creator of Dilbert decided to find a solution.

Chapter Seventeen: The Voice Solution that Didn’t Work

To Treat spasmodic dysphonia, patients get a shot of botox through the front of the neck. The painful treatment became less effective over time, so Adams stopped doing it.

Chapter Eighteen: Recognizing Your Talents and Knowing When to Quit

If you excel at something, you probably know it, but this is rare for most people. You can, however, combine ordinary talents that have extraordinary results. To identify talents, pay attention to your interests and how you spend your time. In Outliers, Malcolm Gladwell said that achieving an “expert” level in something requires ten thousand hours of practice. When you do this, notice your tolerance for risk. If you’re willing to put yourself out there when it comes to a specific skill, it probably means you’re good at it. The more skills you can learn, the more chances of success you have.

You have to know when to quit too. While persistence is a good quality to pursue, bad ideas will get you nowhere. To know when to quit, notice certain patterns. Bad ideas start bad and continue that way. Good ideas start with good potential from the beginning, they have an x-factor of sorts. Having a small following also predicts success. When your work inspires excitement and action (when people share your work, tweet about it, print your articles, and so), you’re up to something.

Chapter Nineteen: Is Practice Your Thing?

We all know practice is important. The difficult part is knowing what to practice. Use your natural inclinations that have economic value. Juggling balls for a few seconds, for example, has no economic value. But practicing jump shots does. To practice, you first have to determine if you’re a natural “practicer” or not.

Chapter Twenty: Managing Your Odds for Success

Success is the result of good systems, but schools don’t teach you that. To be successful, you must acquire skills and every skill you learn doubles your chances of success. The best part is that you don’t have to be excellent but merely good. Instead of being great at one thing, be good at two things.

The success formula looks like this: Good + Good > Excellent

Chapter Twenty-One: The Math of Success

Although you can’t control luck, you can choose to play a game with high odds of success. Finding that kind of game is harder than it seems. When you lose at something, it isn’t a matter of luck, fate, or karma. Skills increase your odds of success.

The skills the author recommends are:

Public speaking: public speaking is a brave thing to do, so be positive about it.
Psychology: knowing basic psychology makes you more effective.
Business writing: to succeed in the business world, you must be clear and concise. Get to the point and get rid of everything that’s unnecessary.
Accounting: the world won’t make sense if you don’t know the basics of accounting.
Design: nowadays, we’re all designers. Once you learn the basic rules of design, you can do anything from creating a website to organizing your office.
Conversation: being a skilled conversationalist and just talking are two different things. There are different reasons to have a conversation, both good (planning, exchanging information, connecting, and being polite) and bad (bragging, complaining). To start a conversation with a stranger, introduce yourself and ask questions until you find something you have in common. As long as you keep the conversation flowing, the stranger will be happy. You can always share a story. The basic parts of a story are the setup (it should be one sentence long), pattern, foreshadowing, the characters, relatability, and the twist. There are some topics to avoid, such as food, television, show plots, dreams, and medical stories.
Overcoming shyness: some people are naturally shy, but you can overcome it with some practice. To do this, imagine you’re acting like someone who’s more confident. When shyness tries to manifest itself, remember that everyone’s a little awkward sometimes. Also, there are two kinds of people. Thing people like talking about material possessions (technology, cars, and so on). Systems people like talking about how things work (politics, philosophy, and so on). When interacting with someone, try to determine which category they belong to. Another way to overcome shyness involves finding an outgoing person and stealing their tricks.
Second Language: learning a second language gives you more opportunities than someone who’s monolingual. Learning an additional language gives you a big competitive advantage.
Golf: golf is a universal activity that allows people to bond. While it seems boring, time-consuming, and expensive, golf gives your mind a break even if you’re not good at it.
Proper grammar: you have to have a good grasp of grammar.
Persuasion: throughout your life, you’ll spend a lot of time persuading others, so learn the subtle art of persuasion through books. Just don’t try to use the tricks to learn to manipulate others.
Technology: understand the basics of the internet, building a website, the cloud, and using devices.
Proper voice technique: use different voices for different situations. These involve breath control, tone, and mouth strategies.

Chapter Twenty-Two: Pattern Recognition

Identifying patterns in life has some benefits because noticing them shapes your thinking and this can improve your performance.

According to Stephen Covey, author of The 7 Habits of Highly Effective People, this is what makes people successful:

They are proactive
They start with an end in mind
They set priorities
They aren’t greedy
They try to understand first and then be understood
They use teamwork
They keep learning

On top of those, Adams recognizes a few more habits:

They lack a fear of embarrassment
They are educated
They exercise
They treat success as a skill they can learn

Chapter Twenty-Three: Humor

Humor makes you more attractive, influences your energy levels, attracts people, and helps you laugh at your problems. Humor is pretty much free, you can find it on the internet, in movies, with friends, and in books. You can even find humor within yourself. There are a few traps when it comes to humor:

Overcomplaining
Excessive self-deprecating
Mocking people
Puns and wordplay

Chapter Twenty-Four: Affirmations

Affirmations are phrases you repeat to yourself, signaling an intention of what you want to achieve. They can be written, spoken, or thought. The idea is to improve your focus, not to summon magic.

Chapter Twenty-Five: Timing Is Luck Too

A big part of luck involves timing. But success isn’t just luck, you have to put yourself in a position where luck is likely to take place too. Luck doesn’t give you a system, you have to figure that out yourself.

Chapter Twenty-Six: A Few Times Affirmations Worked

Adams had affirmations about being a number one best-selling author and about speaking perfectly. For every failure Adams suffered, he didn’t use affirmations. That said, he doesn’t believe affirmations led to either successes or failures because there are many moving parts to succeeding or failing.

Chapter Twenty-Seven: Voice Update

Adams was having problems interacting with others due to his voice. He tried a lot of “cures”, but nothing seemed to work, so he came up with his own system. First, he used a spreadsheet to record the possible sources of his condition. Second, he looked for the words “spasmodic dysphonia” everywhere. The first part led nowhere, but the second led him to some interesting Google results. In the meantime, he kept repeating his affirmations.

Chapter Twenty-Eight: Experts

When Adams was young, he had a lump in his neck. A doctor told him it could be cancer, but to be sure, the professional recommended a biopsy. After the procedure, the technician in charge told Adams that it was nothing. The cartoonist had a newfound love for life, but this also led to the belief that “experts are wrong half of the time”.

Chapter Twenty-Nine: Association Programming

Adams believes that the circle of people you surround with has an influence on you. As a way to change, spend time with those who reflect the change you want to achieve.

Chapter Thirty: Happiness

Achieving happiness is the ultimate goal in life. The problem is that while happiness seems simple, it’s extremely difficult to achieve. The formula for happiness is simple: you need a flexible schedule, sleep, diet, exercise, help others, and do something that lets you improve over time. Having too many options, on the other hand, can make you unhappy because it paves the way for a life filled with self-doubt. The solution to this is to have a routine.

Chapter Thirty-One: Diet

Have a simple diet plan. Adams’s plan is the following: “I eat as much as I want, of anything I want, whenever I want.” This plan has some caveats. Eating as much as you want involves eating healthy food. Once you eat the “right” food, you can have as much as you want. Food can determine your mood too. When you’re feeling bad, think about what you ate. Soon, you’ll start noticing patterns. Some foods made you energetic while others make you sleepy.

A problem a lot of people struggle with when it comes to a healthy diet is resisting simple carbs (white potatoes, white bread, and white rice). The author has a system for this too. He eats as much as he wants of anything he wants as long as it isn’t simple carbs.

Another difficulty the author recognizes is that eating healthy is often inconvenient, so we want healthy food to be more convenient than unhealthy food. Another obstacle is making healthy food taste better than it does. Eating healthily doesn’t have to feel like a punishment, so use condiments, seasoning, and additional ingredients to add flavor to your dishes.

Drinking two to four cups of coffee a day has its benefits: it makes you more alert, it makes you happier, and it makes you more productive. The downsides are that you might get headaches if you go too long without caffeine, it can be an expensive habit, it takes time to prepare, and it makes you urinate often.

Chapter Thirty-Two: Fitness

The author advises everyone interested in exercising to “be active every day”. This works because it’s simple. As soon as you have responsibilities in life, one of the first things you give up is probably exercise, but this can lead to terrible consequences. Exercising should be simple, therefore, you don’t need willpower.

Rewarding yourself after exercising is a good way to motivate yourself. Have a healthy snack, read articles on your phone, or have a cup of coffee. By trying these two activities together, you‘ll form a habit.

Chapter Thirty-Three: Voice Update 2

Three years after losing his voice, Adams was also losing hope. But he found a surgical procedure that successfully treated spasmodic dysphonia and he decided to try it.

Chapter Thirty-Four: Luck

All success can be traced back to luck in one way or another. Your personality is a product of chance. Without your genes, your experiences, and your opportunities, you wouldn’t be you. Once certain ideas are reinforced enough, you’ll be successful and others will call you lucky.

Chapter Thirty-Five: CalendarTree Start-Up

CalendarTree.com is a website where you can create upcoming events and share them with others so that they can add those events to their own calendar. This is the author’s latest startup and while he can’t predict how it’ll do, it’s part of his system. Best case scenario, the website’s popular and people love it. Worst case scenario, he learns several new skills and has some new jokes for Dilbert.

Chapter Thirty-Six: Voice Update 3

Adams slowly recovered from the surgery. It took him three and a half months, but he could talk again. Over time, his fluency returned as well.

Chapter Thirty-Seven: A Final Note About Affirmations

Affirmations appear to bring benefits. They aren’t magic, but a psychological phenomena similar to positive thinking, prayers, visualization, or chanting. Affirmations are powerful because of selective memory, this implies we remember the things that work but forget the ones that don’t. Also, affirmations are powerful because a lot of people who use them are liars. False memory is another reason why affirmations might work. These are the memories we remember in a certain way, but actually never happened. They might also work because optimists focus on opportunities that pessimists ignore.

Chapter Thirty-Eight: Summary

Get your diet right so that you have enough energy to exercise. Doing so will make you more productive, creative, positive, socially desirable, and better equipped to deal with life’s obstacles. Once you have energy, the only thing you need to succeed is luck. You won’t be able to control luck, but you might influence certain variables to increase your odds. Examples include learning different skills, controlling your ego, competing in a small niche, and staying in the game as long as possible.

If you have one goal in life, it should be happiness. Happiness is the by-product of good health and a flexible schedule. By working hard, you’ll be able to get new skills that lead to happiness. The best skills are public speaking, business writing, understanding the basics of technology and psychology, social skills, good voice technique, good grammar, and basic accounting. Whenever you can, simplify.

Eat well, exercise, be positive, and learn. For everything in life, identify patterns and use them to your advantage. Also, once you understand that goals are useless and that systems are important, your life will change. All successful people have a system. Failure is part of the system, so embrace it and learn from it.