How To Fail At Almost Everything And Still Win Big

Mike Gorlon
5 min readJul 15, 2018

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I decided to read Scott Adam’s book since I agreed with the initial assessment I read of his view on succeeding in life, business, and the corporate world. His model of the world has a lot to do with not relying on luck, but putting yourself in the best position for luck to find you. This means increasing your skill sets and marketing them in a way that will put your chances at a higher probability to succeed.

“Was my eventual success primarily a result of talent, luck, hard work, or an accidental just-right balance of each? All I know for sure is that I pursued a conscious strategy of managing my opportunities in a way that would make it easier for luck to find me.” — Scott Adams

Another thing I really enjoyed was his view of failure. His view is that even when he fails, he still wins because he understands that inside every failure is a lesson to be learned that can be used in another aspect of his life.

“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. Failure always brings something valuable with it. I don’t let it leave until I extract that value. I have a long history of profiting from failure. My cartooning career, for example, is a direct result of failing to succeed in the corporate environment.” — Scott Adams

Scott also delves into different parts of his life that consist of his college years, his early years in his 9 to 5 corporate job, his years when he became successful as a cartoonist, and his years beyond. He talks about his experiences, his emotions, and more importantly, the lessons he learned.

One form of adversity that Scott endured during his life was he had difficulty drawing at one point because of an issue related to the neurons in his brain. This is a pretty serious issue for Scott since he was a cartoonist and that relies a lot on being able to draw. He was able to get around it though and he later finds outs that this issue was related to a voice dysphonia that he got later on in his life. He discussed the luck involved, how he didn’t quit, and his devotion to solve this issue of not being able to draw.

In this book, you will also find a lot of examples of Scott refusing to quit. He tried his best to understand a problem as best as possible, analyze that problem, and put into action a strategy to solve it.

Scott’s solution to not being able to draw with his hand was to buy a drawing pad that was electronic. This allowed him to continue his lucrative career as a cartoonist, but Scott isn’t blind to the luck involved in his life. He understood that he got lucky that there was an invention of an electronic drawing pad that allowed him to continue his career. Had he been born in an earlier period before this electronic drawing pad was invented instead, then he would not have been able to become the successful cartoonist that he is today.

“The biggest component of luck is timing. When the universe and I have been on a compatible schedule — entirely by chance — things have worked out swimmingly. When my timing has been off, no amount of hard work or talent has mattered.” — Scott Adams

I found his chapter titled The Math of Success to be the most helpful because of the wisdom he discusses from his life as an entrepreneur, a cubicle worker, and a cartoonist. It is also very helpful because it discusses the skills that have helped Scott in his career and which he recommends everyone learn. Some of the skills he recommended everyone learn were:

  1. A basic understanding of accounting and psychology
  2. Conversation

“Six simple questions to start a conversation: 1. What is your name? 2. Where do you live? 3. Do you have a family? 4. What do you do for a living? 5. Do you have any hobbies/sports? 6. Do you have any travel plans?” — Scott Adams

3. Business writing

4. Public speaking

5. Overcoming shyness

One more thing he recommends is to never have goals. Instead, he recommends having systems.

To conclude, I posted 8 important parts from the book below that I found meaningful to myself. I hope you enjoy reading them as well.

“If your view of the world is that people use reason for their important decisions, you are setting yourself up for a life of frustration and confusion. You’ll find yourself continually debating people and never winning except in your own mind. Few things are as destructive and limiting as a worldview that assumes people are mostly rational.”

“Good ideas have no value because the world already has too many of them. The market rewards execution, not ideas. From that point on, I concentrated on ideas I could execute.”

“Timing is often the biggest component of success. And since timing is often hard to get right unless you are psychic, it makes sense to try different things until you get the timing right by luck.”

“Overcoming obstacles is normally an unavoidable part of the process. But you also need to know when to quit. Persistence is useful, but there’s no point in being an idiot about it. My guideline for deciding when to quit is informed by a lifetime of trying dozens of business ideas, most of them failures. I’ve also carefully observed others struggling with the stay-or-quit decision. There have been times I stuck with bad ideas for far too long out of a misguided sense that persistence is a virtue. The pattern I noticed was this: Things that will someday work out well start out well. Things that will never work start out bad and stay that way.

“We all think we know the odds in life, there’s a good chance you have some blind spots. Finding those blind spots is a big deal.”

“I find it helpful to see the world as a slot machine that doesn’t ask you to put money in. All it asks is your time, focus, and energy to pull the handle over and over. A normal slot machine that requires money will bankrupt any player in the long run. But the machine that has rare yet certain payoffs, and asks for no money up front, is a guaranteed winner if you have what it takes to keep yanking until you get lucky.”

“Happiness has more to do with where you’re heading than where you are. A person who is worth two billion dollars will feel sad if he suddenly loses one billion because he’s moving in the wrong direction, even if the change has no impact on his ability to buy what he wants. But a street person will celebrate discovering a new dumpster behind an upscale restaurant because it means good eating ahead. We tend to feel happy when things are moving in the right direction and unhappy when things are trending bad.”

“Happiness isn’t a mystery of the mind and it’s not magic. Happiness is the natural state for most people whenever they feel healthy, have flexible schedules, and expect the future to be good.”

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Mike Gorlon
Mike Gorlon

Written by Mike Gorlon

Accountant, part-time investor, reader, blogger. I use this platform to improve my thinking and writing. www.mikegorlon.com

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