How to Fail at Almost Everything and Still Win Big

I have always been a Dilbert ™ fan. Maybe it’s because professionally I consort with HR professionals, being one myself. That evil HR Director makes me laugh out loud every time. So, when I had the chance to read Scott Adams latest book offering, How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life, I grabbed it and didn’t look back.

Similar to his comic strip, Mr. Adams has written this book in a no-nonsense, straight to the point style, sprinkled with some Dilbertisms along the way. He finds the nugget of truth from his experiences of failure and shares them with us in a way we can relate to.

We get a hint from the book’s title as to what awaits us on the pages ahead—that the reality of failure is an intrinsic part of a successful life. Mr. Adams is as fluid with his words as he is with the pencil. In fact, he often uses street vernacular with utmost prowess, hitting the target every time. He gets our attention with his stories of being a miserable office drone turned syndicated comic strip author. You keep reading because you want to know how this is possible.

The Big Idea

The Big Idea: The biggest takeaway from the book

See failure as a friend, not foe

"Failure is where success likes to hide in plain sight. Everything you want out of life is in that huge, bubbling vat of failure."
- How to Fail at Almost Everything, page 16

Through various topics including find a system, pare away all else except what energizes you, and strategically improve your odds against the elusive lady of luck, Scott Adams sets out a template for success that is only accessible if one cultivates a relationship with failure. He is quick to point out that while his book is not an advice book, he has gathered some experiential wisdom over the years as a ‘wanna be’ restaurateur, closet inventor, and a programmer geek of computer games.  In fact, Mr. Adams encourages us to “invite failure, survive it, and even appreciate it, because failure always brings something of value with it.”

Insight #1

An actionable way to implement the Big Idea into your life

You need a system

"Goals are for losers. Systems are for winners."
- How to Fail at Almost Everything, page 32

At first read you may react personally and wonder if the goal you are currently working towards means you are a loser! But if you stick with Scott Adam’s train of thought, you may come out feelings intact and with a new system.

The author suggests that there is a hidden gem of wisdom in thinking about goals and systems as very different concepts. A goal, as he defines it, is a specific objective that you either achieve or don’t sometime in the future. A system, in contrast, is something you do on regular basis that increases your odds of happiness in the long run and has no deadlines. He goes on to share that because goals are a reach-it-and-be-done situation, they are often associated with frustration and a sense of failure if goals are not met. Or that once you meet your goal you stop moving. He proposes that the most successful people have a system that is always in motion. There may be hiccups along the way, but the system keeps on chugging along. There is no complacency in a system. You are always striving for something beyond where you find yourself today. Something better.

Insight #2

An actionable way to implement the Big Idea into your life

Passion is overrated

"Energy is good. Passion is bull."
- How to Fail at Almost Everything, page 13

When you are in the middle of that bubbling vat of failure it is hard to have passion about what you are doing. No kidding. Scott Adams suggests that it isn’t passion that is going to rescue you, but rather the choices you make that maximize your personal energy. His thinking here is that if you learn how to make the right choices (eating right, exercising, avoiding unnecessary stress, getting enough sleep etc.) to get  your personal energy right then the quality of your work will be better, more creative, more efficient. Energy like this has longevity whereas passion can be fleeting.

Mr. Adams says that we need to find something that completes this sentence: “The main reason I (insert your job/hobby) is because it energizes me.” If nothing comes to mind quickly, think about what gets you going in the morning. That thing that you do that you don’t need another reason to do it.  Until you can answer this question you are not doing what you will be most successful at.  In his words, “Let your ideas for the future fuel your energy today.”


More than once the Dilbert creator warns us not to take advice from a cartoonist.  But I would suggest that this cartoonist has some real truths for those looking to turn failure into success.

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Barb Brittain-Marshall

ABOUT Barb Brittain-Marshall

Barb Brittain-Marshall is addicted to reading. Seriously, it has become a bit of a problem. Stacks of books clutter her home. She fears an intervention is close at hand...
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