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


I love Dilbert the comics. In a short sequence of drawings, Dilbert manages to make us laugh and still bring out the ironies of working life.

When I came across this book by Scott Adams, I was instantly intrigued. According to its back cover, the book was a cross between a story of his life, and some life advice that he is giving out. I also assumed that since he is so famous as a cartoonist, there should be a good dash of humour in the book, which should make the book an entertaining read.

I was not disappointed.

The book was definitely not the same as other “self-help” books that I have read before. Scott Adams has a very unique way of looking at life.

Some of them are not new to us. For example, he is an ardent believer in embracing failures. As he himself says: “… over the years, I have cultivated a unique relationship with failure. I invite it. I survive it. I appreciate it. And then I mug the shit out of it.”

However, he also has a whole new way of looking at achieving what you want. To him, goals are for losers. You need to have a “system” instead.

I really love the part about systems and goals that I will summarize it for you here. 



Basically, he says that goal-oriented people exist in a state of continuous presuccess failure at best, and permanent failure 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. And a system is something that you do on a regular basis that increases your odds of happiness in the long run.

For example, embracing challenges is a “system”. Because each time you embrace a challenge and fail, you are a step closer to achieving success. You are not failing, because you are just applying your “system”.

What he is proposing here is to focus very much on the actions that you take on a regular basis to achieve what you want, rather than what you want. He assumes that human beings are generally the same, and want the same thing from life, i.e. health, happiness, wealth, etc. So you do not really need to focus so much on where you want to go, but just on how to get there.

Err…. It kinda makes sense, right? Yet it completely overturns what popular literature say about achieving stuff in life.

However, I would caution that we take what he says with a pinch of salt. He contradicts himself all over the book by describing some of the goals that he chased after all his life. This includes his dream of becoming a cartoonist (which clearly is a goal), and his entrepreneurial dream of creating something of value and reproducing it in unlimited quantities. Nevertheless, I loved the way that he thinks of it this way, as it provokes us to think in another way.

So what exactly is his “system” for achieving happiness and success?

It is surprisingly simple. Maximize your energy metric.

Maximizing his personal energy means eating right, exercising, and having something in his life that makes him excited to wake up.

He also teaches us one important life hack. He said that if you are stuck in a corporate life that you dislike, have side projects that energizes you. He pursued half a dozen side projects while doing corporate jobs. One of them, as we know, got him to where he was. But he also made it clear that you need to put in efforts in those side projects as well. For him, he woke up at 4:30 am every morning to draw.

This book is a really a gem. Sometimes, Scott Adams says things that others have said a thousand times before, yet make them sound different. Sometimes, he says quite a lot of downright confounding things. As he himself warned at the start of the book, don’t take what a cartoonist say in its entirety. Filter it through your “crap-buster”. Still, it has quite a lot of good stuff to provoke you to think about life in a different way.

1 comment:

Hi, I would be very happy if you could leave some comments or words of encouragement!