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Book Notes: “How to Fail at Everything and Still Win Big” by Scott Adams


How to Fail at Everything and Still Win Big by Scott Adams (2013) is part autobiography, part self-help book and, most importantly, an overview of Adams’ philosophy of success.

The best parts of the book are Adams’ ideas about systems. Systems, not goals, are emphasized as the key tool in the pursuit of success. Adams juxtaposes the idea of systems vs. goals in the following way: “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. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.” A system, as Adams sees it, will always outperform a goal. Or as he puts it more bluntly: “Goals are for losers and systems are for winners.”

One system Adams describes in great detail is his method of combining mediocre skills to create a compelling sum greater than its parts. Adams suggests that you can be good in several skills and that the intersection of those skills can result in something amazing. His equation for this idea is: Good + Good > Excellent. For instance, it might be very difficult to be the absolute best in a single activity like the 50-meter dash. But, as Adams own life demonstrates, it is possible for a so-so artist, with a decent sense of humor, some business experience and a nerdier bent along with some technological know-how to create one of the most beloved comic strips of all time, Dilbert.

This notion of effective skill collection is attractive not only because it is so practical and attainable by anyone willing to put in the effort.

Adams’ writing always yields keen observations and cogent insights. Although I prefer his newer book Loserthink to this one, it’s clear that this book represents an important step in the evolution of his ideas on systems, successful habits and optimal decision-making. For the reader seeking a practical success-oriented framework, this is a worthwhile starting point.

Pros: The golden nuggets of information (systems vs. goals and skills acquisition strategies) in this book far outweighs any issues I have with the structure or meandering nature of the book.

Cons: Structurally this book is a bit of a mess.

Verdict: 7/10

Notes & Highlights

Chapter 2

  • Embrace the lessons and opportunities of failure: “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.”

Chapter 3

  • Survivor bias clouds our judgment about success: “Passionate people are more likely to take big risks in the pursuit of unlikely goals, and so you would expect to see more failures and more huge successes among the passionate. Passionate people who fail don’t get a chance to offer their advice to the rest of us. ”
  • “My passion level moved with my success. Success caused passion more than passion caused success.”
  • Success is a combination of desire, luck, hard work, determination, brains, and appetite for risk.

Chapter 4

  • Success requires effort. This is a good thing and “works to your advantage because it keeps lazy people out of the game.”
  • “I’ve long seen failure as a tool, not an outcome.”
  • Look for opportunities in which you have a natural advantage.

Chapter 6

  • A system is better than a goal.
  • “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. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.”
  • “Goal-oriented people exist in a state of continuous pre-success 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.”
  • Systems help you maintain your personal energy in the right direction through small, daily victories.
  • Examples of systems vs. goals:
In the world of dieting, losing twenty pounds is a goal, but eating right is a system.
In the exercise realm, running a marathon in under four hours is a goal, but exercising daily is a system.
In business, making a million dollars is a goal, but being a serial entrepreneur is a system.
  • Systems have no deadlines.
  • “The minimum requirement of a system is that a reasonable person expects it to work more often than not. Buying lottery tickets is not a system no matter how regularly you do it.”

Chapter 9

  • “If you want success, figure out the price, then pay it.”
  • Wishing vs. deciding: The former is daydreaming, the latter is taking action.

Chapter 11

  • Personal energy definition: Anything that gives you a positive lift mentally or physically.
  • “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”
  • “Maximizing my personal energy means eating right, exercising, avoiding unnecessary stress, getting enough sleep, and all of the obvious steps. But it also means having something in my life that makes me excited to wake up.”
  • Good personal energy will also influence people around you positively.
  • Match your activity to your mental state and time of day. For instance, if you have low-energy in the afternoon, perform tasks that aren’t as mentally demanding.
  • Simplifiers vs. optimizers:
  • Simplifiers prefer the easy way to accomplish tasks.
  • Optimizers look for the very best solution to a problem.
  • Default to the simple solution when you don’t know which will be better.
  • “Simple systems are probably the best way to achieve success.”

Chapter 12

  • A positive attitude will help you do better work and enjoy life more.
  • Avoid things that will bring you down or depress you. Examples: news and negative people.

Chapter 18

  • “Where there is a tolerance for risk, there is often talent.”
  • Try and sample many different things. Quit and move on to something else if things don’t come together.
  • “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.”
  • “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.”
  • Look for small clusters of enthusiastic fans: “The best predictor is not the average response. Averages don’t mean much for entertainment products. What you’re looking for is an unusually strong reaction from a subset of the public, even if the majority hates it.”
  • If NO ONE is excited about your art/product/idea in the beginning, they never will be.

Chapter 19

  • Practice is important but figuring out WHAT to practice is tough to figure out.
  • “Your skills will increase with experience, which is the more fun cousin of practice.”

Chapter 20

  • “Success isn’t magic; it’s generally the product of picking a good system and following it until luck finds you.”
  • Interesting critique of self-help books: “Books about success can be somewhat useful. But for marketing reasons, a typical book is focused on a single topic to make it easier to sell and packed with filler to get the page count up. No one has the time to sort through that much fuller.”
  • The success formula: Every skill you acquire doubles your odds of success. Or put another way:
Good + Good > Excellent
  • “When it comes to skills, quantity often beats quality.”

Chapter 21

  • “Systematically become good, but not amazing, at the types of skills that work well together and are highly useful for just about any job.”
  • Adams list of essential skills:
    - Public speaking
    - Psychology
    - Business writing
    - Accounting
    - Design (the basics)
    - Conversation
    - Overcoming shyness
    - Second language
    - Golf
    - Proper grammar
    - Persuasion
    - Technology (hobby level)
    - Proper voice technique

Chapter 22

  • Important patterns for success:
    - Lack of fear or embarrassment
    - Education (the right kind)
    - Exercise
  • Successful people treat success as a learnable skill. “They figure out what they need and they go and get it.”

Chapter 24

  • “Affirmations are simply the practice of repeating to yourself what you want to achieve while imagining the outcome you want.”
  • “You don’t need to know why something works to take advantage of it.”

Chapter 28

  • “Experts are right about 98 percent of the time on the easy stuff but only right 50 percent of the time on anything that is unusually complicated, mysterious, or even new.”
  • “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.”

Chapter 29

  • You become like the people around you. Associate with people who have the habits and energy you desire.

Chapter 30

  • Freedom and agency as biggest component to happiness: “The single biggest trick for manipulating your happiness chemistry is being able to do what you want, when you want.”
  • “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.”
  • “Pessimism is often a failure of imagination…if you can’t even imagine an improved future, you won’t be happy no matter how well your life is going right now.”
  • Adams’ “Happiness Formula”:
    - Eat right.
    - Exercise.
    - Get enough sleep.
    - Imagine an incredible future.
    - Work toward a flexible schedule.
    - Do things you can steadily improve at.
    - Help others (if you’ve already helped yourself).
    - Reduce daily decisions to routine.

Chapter 32

  • “Simplification is often the difference between doing something you know you should do and putting it off.”
  • Routines are systems and ensure that activities, like exercise, get accomplished. If you leave an activity up to change or “spare time”, it will not happen. Nobody has “spare time.”

Chapter 37

  • Optimists notice the opportunities that pessimists miss.

Chapter 38

  • A summary of Adams’ system:
    - Focus and optimize your personal energy: diet, exercise, sleep.
    - Optimize your luck by employing strategies with better success probabilities. Example: learning multiple skills, overcoming embarrassment, embracing failure, persistence (time).
    - Embrace systems
  • Learn to simplify.
  • “Goals are for losers and systems are for winners.”

Notes: You might notice that the above outline skips chapters from Adams’ book. This is on purpose. Many chapters in this book yielded no resulting annotations (most often the highly biographical accounts).

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