Skip to content

Weekly dose of self-improvement

Sign up
book quotes and summaries

Big ideas from How to Fail at Almost Everything and Still Win Big

In “How to Fail at Almost Everything and Still Win Big: Kind of the story of my life,” Scott Adams shows how to overcome failure and set back.

Ed Latimore
Ed Latimore
Writer, retired boxer, self-improvement enthusiast

I’ve seen this book mentioned a few times, but I only became seriously interested in it when I started reading Scott Adams’ blog. While you may not know Scott Adams the blogger, you likely know Scott Adams, the famous cartoonist, from his famous comic strip, Dilbert.

In his bestseller How to Fail at Almost Everything and Still Win Big: Kind of the story of my life, the creator of Dilbert delivers exactly what he promises in the title of the book: a series of strategies from his personal experience that helped him win big despite encountering numerous failures, setbacks, and obstacles.

This is truly a great book that is simultaneously inspirational, practical, and contains a lot of common sense The writing style is a mix between casual narrative and memoir. He does a good job of getting you to look at things through his worldview that you put the book down, fired up to act on your plan, and better able to plan so that you’re fired up.

Adams gives detailed accounts of things he tried and failed at, what he learned from failing, and how he applied what he learned to his next endeavor.

In chapter 4, “Some of My Many Failures in Summary Form” (one of the longest chapters in the book), and chapter 5, “My Absolute Favorite Spectacular Failure,” Adams discusses his biggest failures, the lessons he learned, and how these failures taught him something useful for next time.

These chapters are early on in the book, and for a good reason. Once he has established that he’s a big failure who’s managed to become famous and rich, you start to believe that you can do it too.

To guide you in your pursuit of an ideal life, Adams discusses how to manage your personal energy. Adams believes that your personal energy is the most important metric to track, and he discusses how to do this in several chapters. He also discusses his strategy for setting goals.

Check out my other book quotes and summaries

Scott Adams’ criticism of goal-oriented people

In short, he thinks setting goals is for losers. Instead, he recommends that you have a system instead. Many of the stories he shares and the lessons he learned from them detail how to build these systems. A natural part of the construction process is acquiring new skills. Adams explains in detail how each added skill increases your chance of succeeding.

He doesn’t simply tell you that adding skills is important; the man devotes an entire chapter, 43 pages, to listing the specific skills you should learn and how those skills will bring you closer to the life of your dreams.

One of the most interesting things I took from the book is that a collection of mediocre skills, when combined, can give you an incredible advantage and unique positioning. Adams hammers home the lesson that it’s better to be a C+/B- in many things than an A+ at only one. This type of thinking is counterintuitive, but it’s hard to argue with someone who has had such success.

Want even more book quotes and summaries?

My collection is small because I only read what I care about, but if you want to explore a MUCH larger collection, check out Blinkist.

It’s perfect for curious people who love to learn, who don’t have time to read and even those who aren’t into reading. That’s because you can listen to the summaries as well.

For learning while driving, taking a walk, or just lounging around the house. There are over 4,000 titles on Blinkist so there is something for everyone. 

Check them out!

Learn more about Blinkist

Scott Adams on increasing your odds of success

He also speaks, at length, on the proper mindsets to have.

These are designed to serve as a foundation to aid you in getting more out of this world. Adams gives detailed treatments on

  • How people should look at and manage luck,
  • How to decide whether you should optimize or simplify a task
  • Using affirmations
  • Priming your mind to see failure
  • How to invite failure to succeed
  • Dealing with human nature
  • Getting enough sleep
  • Maintaining good health

Some ideas I immediately put into play in my own life were from his sections on pattern recognition, managing your odds of success, and practice. Adams shares examples from his life where, at first, he was doing poorly. He then shares how he improved to demonstrate the importance of these three ideas. And he, of course, tells you how you can do the same.

I’ll summarize Adams’s summary in the final chapter to summarize this review.

Reading this book, you will learn how to manage your personal energy levels. With these energy levels optimized, you’ll then need to manage your luck. A lot of that work will come down to recognizing and optimizing patterns. You’ll be in a much better position to exploit patterns as you learn different skills. To facilitate all of this, you’ll need to learn how to use affirmations. When it’s all said and done, you will have set aside your goals in favor of employing a system that will run on autopilot and carry you closer to the life you desire to live.

And remember this: “Failure is your friend. It is the raw material of success.”

Get the book audiobook, paperback, or kindle here on Amazon—>How to fail at almost everything and still win big

Check out my other book quotes and summaries

Ed Latimore
About the author

Ed Latimore

I’m a writer, competitive chess player, Army veteran, physicist, and former professional heavyweight boxer. My work focuses on self-development, realizing your potential, and sobriety—speaking from personal experience, having overcome both poverty and addiction.

Follow me on Twitter.