Book Review: How to Fail at Almost Everything and Still Win Big by Scott Adams

I never “got” Dilbert until I started working an office job. And then it all started to make sense.

Dilbert comic strip
Copyright Scott Adams. Used without permission. If Mr. Adams wants me to take this down, I will do so without hesitation.

In just a few panels, creator Scott Adams is able to get to the heart of the workplace absurdity in corporate America. Adams brings this same clarity of thought to his political analysis, being one of the few people to accurately predict the course of the 2016 presidential election.

Whether it’s because of his persuasion and hypnosis training or just an inborn way of looking at the world, Adams provides a fresh perspective and a clarity of thought to everything he writes about.

Oh, and in 2013 he also published one of the best “self-help” books you’ll ever read.

How to Fail at Almost Everything and Still Win Big by Scott Adams

How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life is, by Adams’s own admission, “not an advice book,” cartoonists being notoriously unreliable role-models. Instead, Adams catalogs all of his life’s failures and explains the lessons he learned from them, suggesting that the reader “compare[s] my story with the stories of other people who found success and see if you notice any patterns.” (p. 1)

This sounds funny, and it is. Adams has a way with words. But aside from making you laugh, you’ll be blown away by the insights and just how practical Adams’s advice is. Here’s a big piece, for you:

Systems are where it’s at. Goals are for losers.

There. Now you don’t have to read the book. I saved you $10.00. You’re welcome.

Dilbert creator Scott Adams
Scott Adams

That was a joke. I highly recommend you give Adams your money in exchange for his book. But I’ve made my point: Although he illustrates his lessons through the use of stories, Adams doesn’t play games and he doesn’t hide the ball. His descriptions of things that have worked for him in his life are direct and incisive, and he provides practical tips on how to incorporate these lessons into your life. Even better, he uses his persuasion techniques to plant the seeds in your head in a memorable way so that, months after you finish the last page and put the book down, the lessons still percolate in your head.

What lessons? I’m not going to summarize the entire book, but I’ll hit some big themes to whet your appetite and get you interested in buying the book. Afterwards, I will discuss some of my personal favorite bits of advice that have had a disproportionate amount of utility in my own life.

So here’s what you’ll learn, among other things, from How to Fail at Almost Everything and Still Win Big:

  • How to systematize your life to put you in the best position to succeed. You largely make your own luck, and small steps now will add up to big successes later.
  • The importance of skills. Learn as many skills as possible and “stack” them to turn yourself into something unique. In Adams’ estimation, every skill learned roughly doubles your odds of success.
  • Skills over passion, because passion is bullshitGet good at something, and chances are you’ll learn to like it.
  • Human beings are “moist robots” who can reprogram themselves to cultivate good habits. We all delude ourselves, so find a delusion that works.
  • How to create your own multi-level bullshit filter. Don’t be credulous, but don’t be cynical, because there are ways to test the veracity of nearly everything.
  • Take risks and embrace failure. Failure is often where we learn the best lessons in life.

In case the tenor of this post was a little too subtle for you, I unequivocally recommend you buy this book. And in case you don’t believe me, just know that I’m not the only one who has found it useful and entertaining.

Adams’s one-of-a-kind insights will get you motivated and excited to get out there and fail big.

Now if that’s not a ringing endorsement, I don’t know what is.

Below are some of my favorite bits of advice from How to Fail at Almost Everything and Still Win Big:

  • The beginning of a healthy and happy life is diet and fitness. If you want to eat healthier, make that healthy food taste good! And if you want to ensure you go to the gym, just put on your gym clothes, or even lay them out for you to see first thing in the morning, and you’ll be surprised how much you feel like working out.
  • You need to know when to quit. “Things that will someday work out well start out well. Things that will never work start out bad and stay that way.” (p. 88)
  • Everybody should learn something about psychology, cognitive biases, and persuasion. But don’t turn into a manipulative asshole.
  • Energy is the most important thing. And in order to get more energy, do something you look forward to each day and match your mental state to your activity. For example, if you do your best creative work at night, don’t waste time trying to force it in the morning. (p. 54)
  • Posture! You probably associate slouching with relaxation, so why do you think it would be conducive to doing serious work?
  • Surround yourself with successful people. Your environment matters. This sounds dumb until you see the evidence demonstrating the power of simply being around people you want to be like.
  • The difference between simplification and optimization. That is, knowing when to do things easier versus doing them better. There is a time and a place for each.
  • How to tell jokes and stories. Nobody likes a bore, but everybody likes a good laugh.
  • The list of must-have skills on pp. 103-104. Now you’re intrigued to buy this book (see what I did there?)

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10 thoughts on “Book Review: How to Fail at Almost Everything and Still Win Big by Scott Adams

    1. The Daytime Renegade says:

      Thanks for the kind words!

      Adams is a great writer with such a refreshing perspective. It’s funny how so many of us are reading it at the same time. Emulation of successful people like Adams writes about? Could be…

      Looking forward to your thoughts on it!


  1. rawlenyanzi says:

    I’ve read the book; it has lots of great advice, and it showed me things I haven’t noticed before, such as the fact that successful first-run products or media often succeeded despite their low quality. The quality goes up in later iterations, using the profits from the first run.

    I started noticing it everywhere; from consumer products like the iPod and the Kindle, to services like dial-up internet, to big multimedia franchises like Pokemon.

    The book has nuggets of knowledge like that all over the place.

    Liked by 1 person

    1. The Daytime Renegade says:

      That sums it up nicely! Having gone to business school, I can say that Adams covers probably about 75% of what I took away from my “formal education.”

      Liked by 1 person

      1. rawlenyanzi says:

        That sums it up nicely! Having gone to business school, I can say that Adams covers probably about 75% of what I took away from my “formal education.”

        Amazing what you can learn outside of school. 🙂


  2. Great review. I love the idea of a system and is something I now have in my life (thought I still do include goals). I also agree passion is bullshit – the number of people I observe whose lives are failing because they are obsessed with doing a job they are passionate about and then surprised it fails because there is no market for it!

    Liked by 1 person

    1. The Daytime Renegade says:

      Thanks James, glad you liked it!

      Systems help with everything, I find. One of the biggest things they do is KEEP you motivated. Counterintuitive at first, but makes sense the more you think on it.

      I’m still a bit torn on the passion thing. I agree that it’s better to find some skill to get good at and then learn to enjoy it, but what draws you to something in the first place? Plumbers/carpenters/engineers, for example, probably enjoyed taking stuff apart and putting them back together as kids…couldn’t you call that a passion?

      Maybe it’s just a semantics issue.

      Liked by 1 person

      1. From that perspective – agreed, the examples you mentioned have a benefit to society and will be needed.

        I think the problem is I have seen far too many people being passionate about things that don’t pay the bills (e.g. writer, musician, stable owner…) and are obsessed that they will achieve their life long passion, but never get there, because society is cruel and has no demand for those things.

        I am passionate about my job, but I would never have chosen to do it, I just gained the passion through doing it!

        Liked by 1 person

      2. The Daytime Renegade says:

        I have first-hand experience with that! (Poke around the of to see). I love music as art. Wanted to be a music teacher, but switched majors because I read the tea leaves and didn’t see many job opportunities.

        In law school, I gave being a gigging musician a shot. It was worth the experience and the skills I learned, and it would’ve been nice if it worked out, but you’re right: society is cruel and it’s a total long shot.

        Liked by 1 person

      3. Think the best way is to do the passion as a side project, but have some realistic expectation that it doesn’t guarantee, fame, fortune and women


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