Book Summaries Business

How to Fail at Almost Everything and Still Win Big Summary (7/10)

Scott Adams is the creator of the famous Dilbert cartoons. In How to Fail at Almost Everything and Still Win Big, he shares what he has learned from a lifetime of failures. He is aware that taking advice about success from a person who has failed at businesses for decades is not very wise, and neither is taking health advice from a cartoonist who admits he used to consume a dozen diet sodas a day, but Scott isn’t shy. And that’s the lesson he wants to pass on.

Most people have too many reservations despite not having anything standing in their way, but Scott had to battle through many impediments, yet he still managed to succeed. He did so because of a combination of factors that he cannot explain, but what worked for him was fearlessness in the face of social ridicule, healthy habits (systems), and staying in the game long enough to find perfect timing.

Passion is Bullshit

Successful people tell you to follow your passion because it will make you more resilient to failure, and it will give you more energy. But passion is bullshit according to Scott. When he was a commercial loan officer for a large bank in San Francisco, his boss told him that people who want loans for passion businesses should be rejected. The people that should be given loans are only those who want to work hard on something that looks good on a spreadsheet – mostly boring business ideas. The grinder is your safe bet, not the person who loves their job.

People who have achieved success cannot admit that they are smarter than the average person, this is not very humble, so they attribute their success to passion, a more egalitarian idea. Scott initially started Dilbert as another get-rich-quick project, and it only succeeded because he got good feedback, which made him more passionate about the business, which improved his work. A combination of desire, luck, hard work, determination, intelligence, and risk appetite are better predictors of success than passion.

Learn from your failures, they are opportunities that can be used to your advantage, they are resources that you can manage.

Goals vs Systems

Goals are for losers; systems are for winners. The reasoning is simple: if you have a fixed goal such as losing 20 pounds, then you will spend your time worrying about losing the weight, and not feeling good about yourself. And worse, once you have achieved your goal, you lose the sense of meaning you once had. A better way is to have systems. Exercising every day is a system. it is not dependent on results, it is a routine that you follow, no matter what. By following this routine, you will be happier in the long run, and you will rid yourself of short-term anxieties.

Scott never wanted to sell his time, he wanted to sell something that was easy to reproduce in unlimited quantities. In other words, something that was scalable. His options had to involve creating things, either inventing or writing. He failed at many businesses, and his corporate career fizzled away, but eventually, by following his system, he found success.

Deciding Versus Wanting

If you want success, figure out its price, and pay for it.

The Selfishness Illusion

The three types of people in the world are 1) selfish 2) stupid or 3) a burden on others. One of the myths you will encounter is that you should not be selfish with your time. Scott argues that you certainly should, in fact, you are morally obliged to. The best way you can help others is to focus on your career and your health. If you don’t do those things, you are being stupid, and eventually, you will become a burden on other people.

Pick the Delusion that Works

Sometimes, deluding yourself is a good idea – if it can get you to work harder on something, Reality can be oppressive, and you don’t have to always succumb to it. Your imagination can help you manufacture useful illusions about the future that will help you improve.

Recognizing your Talents and Knowing When to Quit

Most people don’t have world-class talent, but you don’t need world class talent to succeed, you just need to be good enough at several things. Find things that you are naturally drawn to, think about what you were doing obsessively before the age of 10. It is very important to have a tolerance for risk. You must be willing to look stupid, to be laughed at, if you are going to improve at anything.

Know when to quit.

There have been times I stuck with bad ideas for far too long out of a misguided sense that persistence is a virtue. The pattern I noticed was this: Things that will someday work out well start out well. Things that will never work start out bad and stay that way. What you rarely see is a stillborn failure that transmogrifies into a stellar success. Small successes can grow into big ones, but failures rarely grow into successes.

The thing that predicted Dilbert’s success in its first year was that it gained a small but enthusiastic following.

If your work inspires some excitement and action from customers, get ready to chew through some walls. You might have something worth fighting for.

The Success Formula

Every skill you acquire doubles your chances of success. Some useful things to be good at: psychology, business writing, accounting, public speaking, design (basics), overcoming shyness, conversation, persuasion, technology (hobby level), proper voice technique.

An important lesson from psychology is that people do not behave rationally, and if you live in this world constantly feeling dumbfounded by people’s irrational decisions, such as voting for half-wit politicians, you will have a long struggle. Instead, understand that rationality is important, it is not everything. A complete idiot won’t become president, but a half-wit with a good haircut might. Hypnosis teaches us that people respond to stimuli in predictable ways. If you want to influence them, find out what stimuli is important.

A summary of good conversation technique.

      Ask questions.

  1. Don’t complain (much)
  2. Don’t talk about boring experiences (TV show, meal, dream, etc.).
  3. Don’t dominate the conversation. Let others talk.
  4. Don’t get stuck on a topic. Keep moving.
  5. Planning is useful but it isn’t conversation.
  6. Keep the sad stories short, especially medical stories.

If you want a stranger to like you, smile and maintain open body language. Ask questions and act like you care, find common interests. If you’re attractive, talk less – it is likely that you will only make things worse since people are already predisposed to liking you. If you are unattractive, become a master at telling short, interesting stories.

Overcome shyness by acting. Act like someone else and eventually you will find that it is better to do that than to be yourself and awkward. All people pretend to be socially talented; you are no different. Find out what kind of person you are dealing with. Thing-people want to talk about the latest technology, People-people want to talk about humans doing cool things.


If you are resistant to persuasion, it might be because you believe that people should be given solid, logical reasons for doing something. While you should never make someone do anything against their interest, trying to influence people with logic is impossible. Use words and phrases that are persuasive, like ‘Because’, ‘Would you mind?’, and ‘I have a rule’.

Be funny, eat healthy food, exercise regularly, and do things that make you feel good so that you are always energized for work.

Don’t hang around overweight people, lest you want to become overweight – don’t hang around bad influences.

Your best bet in life is to maximize your happiness, so get your body chemistry right through a proper lifestyle.


Recapping the happiness formula:

  1. Eat right.
  2. Exercise.
  3. Get enough sleep.
  4. Imagine an incredible future (even if you don’t believe it).
  5. Work toward a flexible schedule.
  6. Do things you can steadily improve at.
  7. Help others (if you’ve already helped yourself).
  8. Reduce daily decisions to routine.


If you have time, do these exercise ‘musts.’

Here are a few of the exercise “musts” you hear all the time.

  1. Do thirty minutes of aerobic exercise daily.
  2. Stretch.
  3. Hydrate.
  4. Eat protein within thirty minutes of strength training.
  5. Carb load the night before a big exercise day.
  6. Do resistance/weight training every other day.
  7. Do three sets of ten to fifteen reps.
  8. Get lots of rest.
  9. Vary your workout to create “muscle confusion.”
  10. Use proper form for lifting.

"Silence is the best expression of scorn" - G.B. Shaw

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