Ryan Irelan

is building Mijingo and doing limited consulting.

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

The subtitle of this book is “Kind of the Story of My Life” and that summarizes the content. Scott Adams takes his life experience, specifically how he was able to overcome failure in life and career, and weaves it into a narrative that gives you steps and practical advice for improving your own life.

If you’ve read any of Scott’s blog posts over the years you will recognize the style. The book reads like a collection of his blog posts (but I don’t think it is). Scott is introspective and analytical about his experience in the world; he seeks how his actions affect him (and others) and how he can change things for maximum happiness.

The only reasonable goal in life is maximizing your total lifetime experience of something called happiness.

This isn’t a typical “life hack” book but it does have a lot of that same type of instruction: here’s my one-time or limited experience and how it helped me achieve X. You should now do this, too.

Except that Adams regularly tells you that he can’t claim that any of this will work for you, or even that his experience (and the scientific studies and literature he cites) proves anything.

Scott Adams gets a lot of flack online for his blog posts, many of which are grand thought experiments on controversial topics. Many readers of his blog react in a predictable way by chiding him for his lack of grip on reality. If your mind is of such width that you aren’t able to follow along with Scott as he journeys through another thought experiment on everything from psychology to employment to finances, then you shouldn’t read this book. It will drive you mad.

How to Fail at Almost Everything and Still Win Big regularly touches on psychology as a map to navigate life. He writes:

Knowledge of psychology is the purest form of power.

Adams claims that you can always benefit from understanding how the mind interprets the world. There is no objective reality and if we approach the world and life like there is then we’ll be disappointed by the results. You have to know how others see the world, not just how you perceive it.

One of my favorite things about the book is that he advocates for broad, ongoing learning:

Everything you learn becomes a shortcut for understanding something else.

The simple example Adams gives is if you wanted to understand what a zebra is. It’s easier to describe and explain what a zebra is if you already know a horse. Oh, it’s a horse but with stripes. Easy enough.

By having knowledge of one thing you create hooks, as he calls them, for understanding other things.

The biggest takeaway from this book–and it could’ve been a book of its own–is the idea that we should be using systems not goals to be sucessful (as we define it for ourselves) and happy in life.

A goal is to lose 15 lbs by April 1st. You do whatever you can to meet it but you’re probably racing toward that goal with blinders on.

A system is a regular, maintinable routine of activities that make that happen not just once but ongoing. You are not “losing 15 lbs,” you are living a healthy life that keep you at a healthy weight. Instead of starving yourself for a month, which isn’t maintinable at all over an extended period, you set up a system of meals that are good for you. You build exercise into your day (like changing to a bike commute instead of loafing in your car the 4 miles).

Most of the chapters are short and fast to read. You could read them out of order but he does reference previous material as the books moves on toward the end.

I read the 200 or so pages very quickly. The prose are simple and approachable. Scott cites research papers and other sources of the information he uses to make his arguments. Even if you find the book a lighter read, you can very easily trawl the footnotes for deeper learning.

More on books I’ve read.

Want to share your thoughts? @Reply to me on Twitter.

There’s more to read in the archive.