How to Fail at Almost Everything and Still Win Big Summary
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How to Fail at Almost Everything and Still Win Big Summary and Review | Scott Adams

Kind of the Story of My Life

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Scott Adams’ Perspective

Scott Adams is the artist and creator of the Dilbert comic strip and the author of several nonfiction works of satire, commentary, and business. His Dilbert series came to national prominence through the downsizing period in the 1990s America and was then distributed worldwide. Adams worked in various roles at big businesses before becoming a full-time cartoonist in 1995. By 2000, the comic had been published in 2,000 newspapers in 57 countries and translated into 19 languages.


How to Fail at Almost Everything and Still Win Big is a guide to succeed despite your failures. Adams admits he has failed at more things than anyone he has ever met. But, he managed to transition from working in an office to being the creator of a world-famous comic strip within a few years. The key to this success were fundamental principles that he picked up along the way. This book outlines these principles and how they will benefit you more than what society suggests is best for you and your future.

StoryShot #1: Goals Have Two Major Problems

Self-help gurus have a knack for encouraging people to create and stick to goals. But Adam believes goals are for losers. According to him, the reality is that even the clearest goals have two problems that will always persist:

  1. Goals are future-oriented
  2. Goals can become overly-specific

Firstly, there is the issue that goals are placed in the future, but we have to work in the present to achieve them. This means you are unlikely to see any results from your actions until much further down the line. Most people would find this reality frustrating and discouraging. The specific nature of goals can also lead to similar frustrations. For example, people often feel like failures if they don’t accomplish exactly what they set out to do. They may still be highly successful, but not meeting their goals leaves them feeling they haven’t accomplished anything. An example of this would be losing weight by a specific date. This goal prevents you from feeling successful during the journey of losing weight and will leave you feeling like a failure if you fall even one pound short by that date.

StoryShot #2: The Effectiveness of Systems

Adams believes that systems are more effective than goals. Systems are firmly grounded in the present. This means they can be grounded in your life right now, and you will get daily pleasure from successfully operating them. Adams describes the time he first learned of the power of systems. He sat on a flight next to a man who explained to Adams how systems had transformed him from an employee to a CEO. The CEO said he became successful by always looking for a better job. You see, most people wait until they need a job to start looking for one. When they reach their goal of finding a job, they stop. The CEO followed a system by constantly looking for the next promotion, even when he didn’t need it. In the long run, this was a much more effective strategy.

StoryShot #3: Examples of Systems

An exercise system would focus less on an end goal and more on day-by-day improvement. For example, committing to daily exercise. This shows one of the greatest strengths of systems, which is that it helps establish habits.

Adams used systems as a young man to help him achieve the success he now has. He created a system around writing and drawing things people were receptive to rather than having a clear end goal. This meant he did not feel like a failure if it was not successful, which helped him keep going. This continual motivation meant he could create the hit comic strip Dilbert.

StoryShot #4: The Benefits of Being a Generalist

We must understand our talents, but we must also be willing to favor new skills over our talents to become a generalist. The business world was previously obsessed with specialization. Adams points out that general knowledge about several fields is more useful in the modern world. This does not make you mediocre or your average Joe. 

Adams explains that he has always been a generalist. When he started Dilbert, he was not a talented writer, artist or businessman. He was just relatively proficient at each skill. This general competence is what allowed Dilbert to become a success. A wide range of skills like this will help you adapt to the constant changes of the world. That said, Adams notes that not all skills are created equal. There will be some skills that are more relevant within a specific field. So, consider your passion and identify all the relevant skills. Also, think about skills that will be useful in every field, like grammar, vocal techniques and the ability to hold engaging conversations.

StoryShot #5: Specialize in the Areas You Enjoy

As well as developing general skills, you must use introspection to identify your unique skills. Parents and teachers often pressure people to pursue specific careers. You are in the best position to notice your special skills and think about which career would suit those skills. If you are struggling to notice these skills, Adams recommends thinking about what you like to do. It is generally the case that the activities we enjoy the most are the things we are good at. Suppose this doesn’t help you recognize your unique skills. In that case, you should consider the areas in your life where you have always been comfortable taking risks. Adams uses an example from his own life to reinforce this point. As a child, he would draw humorous comics in class. Adams knew he could get in trouble if the teacher found out what he was drawing, but Adam was willing to take this risk as he enjoyed it so much.

Once you have found your skills, you have to find a career that matches this skill. This process requires sampling, which means trying many jobs until you find one that is both enjoyable and uses your particular skills.

StoryShot #6: Allocate the Right Tasks to the Right Time of Day

You have likely experienced occasions where you have gone on a run when you have felt drained and unmotivated. These circumstances occur when you adhere to a schedule rather than listening to your bodily rhythms. Adams believes this is an inferior approach and recommends using your energy levels as a metric for allocating tasks. You will feel far more energized and become more efficient if you allocate the right tasks to the right time of day.

StoryShot #7: Allocate the Right Tasks to the Right Location

As well as timings, you should also consider how a location makes you feel and the order of activities. For example, you should avoid working in spaces where you feel relaxed. You can also couple activities which help each other. By identifying the tasks that drain you, you can pair this task with a primary task you find energizing. Adams’ energizing task is blogging, while his draining task is shopping. So, he tries to blog as much as possible and shop as infrequently as possible. If he must shop, he will pair it with a blogging session.

StoryShot #8: Prioritize Personal Energy

Instead of worrying about which task to prioritize first, you should always make personal energy your priority. This is because personal energy allows you to achieve all your other priorities. Exercise, food and sleep are all essential for looking after your energy levels. So, these should be the first buttons to push to elevate your attitude and raise your energy. Adams recommends experimenting with food to learn which food groups and diets will improve our personal energy levels. This means he also advises against just taking health experts’ knowledge as gospel. There will always be certain foods that work for you while others don’t. Adams calls this the food-is-mood hypothesis. For example, white carbs make him sleepy and lethargic, but this is not the case with pasta. Adams often eats pasta as a source of carbohydrates. 

StoryShot #9: How to Maintain Healthy Eating and an Exercise Routine

Adams also recommends spicing up foods that you know are healthy but find bland. For example, vegetables and grains are clearly healthy. That said, he doesn’t find them tasty when they are by themselves. He uses nutritious additions to make them tempting, e.g., by adding honey, lemon, soy sauce or pepper. 

Adams offers similar advice for those struggling to establish an exercise routine. Spice up your exercise by joining a group that meets consistently weekly. This will keep you accountable but will also add an enjoyable social side to your exercise. Adams uses an example from his own life to push this point. His wife plays tennis every Thursday, and because there are only four people in their group, she must turn up; otherwise, they can’t play.

A final tip for maintaining an exercise routine is to use food or drink as a motivator. We are like dogs. We strive for rewards and try to avoid punishment. So, Adams recommends giving yourself a healthy snack or tiny indulgence as a reward once you have completed a workout. Adams uses an indulgent cup of coffee as his motivator.

StoryShot #10: Use Association Programming

Moods are infectious, so the moods of those around us heavily influence us. This is called associate energy and means we should always strive to associate ourselves with people we want to be like and people who give us energy. This idea was brought to Adams’ attention when one of his friends decided to live in an affluent neighborhood, as he felt this would push him to become affluent himself. Adams was initially skeptical, but then read a scientific article explaining how spending time with overweight friends can lead to weight gain. Adams started implementing the law of associate energy into his life. He worked with three aspiring writers before writing Dilbert. He believes these writers’ energy helped inspire him to write his most famous comic.

Adams still doubts whether associate energy is a physical concept. That said, he does not get why that matters. Many successful people have delusions in their routines that they believe have a positive impact on their performance. For example, athletes may have pregame superstitions. These delusions can still have a positive psychological impact that keeps you focused on your priorities. This is why Adams used and still uses positive affirmations like “I, Scott Adams, will be a famous cartoonist.”

StoryShot #11: Selfishness is an illusion

Society tells us that selfishness is something we should avoid at all costs, and you should make other people’s desires your priority. Adams challenges this view and points out that there are three kinds of people in this world: stupid, a burden on others, and selfish. 

Stupid people are solely interested in satisfying others before themselves. The reason Adams believes they are stupid is that it is impossible to please everyone. So, these individuals end up living an unsatisfactory life.

Those who are a burden on others are not necessarily a burden because they want to be. These individuals have often been dealt a difficult hand and left to struggle with an illness or something similar. In these situations, you might become a burden, but you should remain selfish to cure yourself. 

Finally, selfish people focus on what they want from life. This doesn’t mean they neglect others. They are simply focused on doing what they want, succeeding in life, and then helping others once the first two are accomplished.

StoryShot #12: Use Affirmations

Adams believes affirmations should be used by all individuals with aspirations for their life. An affirmation is a positive statement about what you want to achieve. You can engage with an affirmation in whatever way you want. Still, the affirmation should be imagining what you want and repeating it several times.

Adams was initially skeptical of affirmations, but he decided to test them after being recommended by a MENSA member. He still agrees affirmations lack scientific evidence, but he has several examples where affirmations have come true. Here are four examples of affirmations that came true for Adams:

  1. First, he told himself, “I, Scott, will become rich.” He received two flashes of insight, telling him to invest in two specific stocks. Both these stocks grew like crazy over the next year.
  2. His next affirmation was to date a woman he’d encountered briefly at work. She was out of his league, but they ended up briefly dating.
  3. He then made an affirmation to score 94 on the GMAT test. This was the score required to enter MBA programs. He’d only scored 77 previously, but this time he received the exact score of 94.
  4. Finally, he made an affirmation that “I, Scott Adams, will become a famous cartoonist.” This was the affirmation that changed his life. 

As well as examples of positive affirmations working, Adams also explains he has had several failures in life. These have all occurred when he hasn’t used positive affirmations—for example, his failed business ventures with restaurants.

StoryShot #13: The Six Filters for Truth

Adams credits himself with an advanced BS detector based on his experience in the business industry. He believes this detector is based around six filters for truth. The more filters something can pass through, the truer it probably is.

The Six Filters for Truth are:

  1. Personal experience: Because human perceptions are iffy.
  2. Experience of people you know: Because they are even more unreliable.
  3. Experts: Because they work for money, not truth.
  4. Scientific studies: Because correlation is not causation.
  5. Common sense: Because it’s an excellent way to be mistaken with complete confidence.
  6. Pattern recognition: Because patterns, coincidences, and personal biases lookalike

Combine these filters to refine people’s ideas and understand who is likely telling the truth and who is BSing.

Final Book Summary and Review of How to Fail at Almost Everything and Still Win Big

How to Fail at Almost Everything and Still Win Big is an insight into Scott Adam’s overarching success and how his approach prevented his failures from holding him back. The book believes goal-setting and specialization are outdated and lead to your failures becoming overwhelming. Implementing systems and becoming a generalist is better for our well-being. Adams also recommends focusing on yourself and your personal energy first. This might seem selfish to some, but it will offer you the opportunity to be happier and more efficient. In turn, you can then help others more. Finally, Adams suggests surrounding yourself with people who energize you and using affirmations to motivate you.

Here’s a recap of the key insights we covered here:

  • StoryShot #1: Goals Have Two Major Problems.
  • StoryShot #2: The Effectiveness of Systems.
  • StoryShot #3: Examples of Systems.
  • StoryShot #4: The Benefits of Being a Generalist.
  • StoryShot #5: Specialize in the Areas You Enjoy.
  • StoryShot #6: Allocate the Right Tasks to the Right Time of Day.
  • StoryShot #7: Allocate the Right Tasks to the Right Location.
  • StoryShot #8: Prioritize Personal Energy.
  • StoryShot #9: How to Maintain Healthy Eating and an Exercise Routine.
  • StoryShot #10: Use Association Programming.
  • StoryShot #11: Selfishness is an illusion.
  • StoryShot #12: Use Affirmations.
  • StoryShot #13: The Six Filters for Truth.

Which of these would you put into practice? Let us know and inspire others by sending us a tweet @storyshots or leaving us a comment.


We rate this book 4.2/5.

Our Score

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