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Adventures in Self Publishing

Book Review: How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life

April 6, 2022 by John Champaign Leave a Comment

The Amazon links in this post are affiliate links, meaning I get money if anyone clicks on them then makes a purchase.

Scott Adams is most famous as the cartoonist behind Dilbert.  Leading up to his success with his comic strip, and since achieving his success with his comic strip he has attempted all sorts of ventures, such as starting a restaurant (which I’ve eaten at during a trip to the SF Bay area), creating his own burrito to sell in supermarkets (which I’ve bought and eaten), software programs, online companies, stock investing, creating a TV series (which I’ve watched) and writing novels (which I’ve read).

More recently he’s written and been promoting How to Fail at Almost Everything and Still Win Big, a retrospective of these failures and how they’ve led to his eventual success.  He discusses his overarching strategy through these ventures and why he remained confident in his eventual success – and how to apply similar strategies within your own life.

As an aside, the introduction makes clear that I’m definitely a Scott Adams fan.  I’m a very friendly audience for his material, regularly read his blog, and like what he produces.  That being said, if what he produced was no good, I’d have no problem saying so.  Few critics are as vicious as a disappointed fan – fortunately, this book was not a disappointment.

The early part of his book was a similar idea to that of Cal Newport’s “So Good They Can’t Ignore You“, which Mr. Adams expresses with the chapter 3 title “Passion Is Bullshit”.  He discusses that the idea of “follow your passion and the money will follow” is popular because it SOUNDS good, not that it’s actually worthwhile advice to follow.  He talks about when he was a commercial lender and he was told never to lend to someone who was “following their dream”.  The ideal borrower was someone with a spreadsheet who wanted to open a dry cleaner and work hard.  His theory for the popularity of the passion hypothesis is that passionate people are more likely to take big risks, so we hear about this from the successful ones, but not the failures – it’s a survivorship bias.  He also feels that it sounds more humble than successful people saying “I succeeded because I’m better than other people”.

Rather than goals, he advocates systems.  A goal would be to lose 10 pounds.  A system would be to go to the gym Mondays, Wednesdays, and Fridays.  He feels that goals bring you down because you’re constantly failing except for the brief period you accomplish your goals – then it’s finished.  In contrast, you can constantly be following your system and working toward the long-term benefit and feel good about it the entire time.

He strongly advocates the benefit of exercise and controlling your eating, with the objective of maximizing your energy and helping you focus on the other tasks you want to accomplish.

His view of failure is that instead of being sad that the thing you tried to do didn’t work out, view it as having had the opportunity to learn a new skill or make some new business contacts.  He iterates through his failures, what he learned from each one, and how that helped him eventually be successful with Dilbert.  He believes that combinations of skills are what lead to success, rather than being the best in the world at one thing.  The formula he recommends using is the idea that every new skill you learn roughly doubles your chance of succeeding.

Throughout the book, he explores many of the issues he’s discussing in the context of dealing with a serious, chronic medical condition, spasmodic diphtheria, and how he eventually used the techniques from this book to overcome it.

I’ve found this book to have a large number of very meaty, interesting concepts, and have already read through it twice.  It obviously has a massive “self-help” vibe to it, but for people who can view it as a meta-analysis of techniques for being successful with a variety of ventures in your life, I think it’s well worth the read and very interesting.

Time has hosted 6 articles from Mr. Adams writing about some of these ideas.  If you’re on the fence about the book, you can read them here:  1, 2, 3, 4, 5, and 6.

You can buy How to Fail at Almost Everything and Still Win Big at Amazon.com or at book sellers everywhere.

Have you read this book?  What did you think?

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