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

As a long-time fan of Scott Adams & an aspiring cartoonist, I loved his latest book How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life. It doubles up as a sort of biography and a self-help book. The advice is unpretentious & the author makes no claims that his tips will solve your life's problems. He expounds his contrarian theory of failing forward by candidly talking about his own failures and how he has profited from them. In about 250+ pages, he details the patterns of success he has studied from his personal and entrepreneurial experiences in a light-hearted way with some great anecdotes.

A core idea of the book that Scott keeps emphasizing is that one should have a system instead of a goal - "a goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, it’s a system....if your goal is to lose ten pounds, you will spend every moment until you reach the goal—if you reach it at all—feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary...In the world of dieting, losing twenty pounds is a goal, but eating right is a system. In the exercise realm, running a marathon in under four hours is a goal, but exercising daily is a system. In business, making a million dollars is a goal, but being a serial entrepreneur is a system.... being systems oriented, I felt myself growing more capable every day, no matter the fate of the project I happened to be working on."

As a fan of lists, I liked how the author who calls himself a "professional simplifier" summarizes the key points so that you can actually put the info to use. Sample these -

Luck has a chance of finding you if you're merely good in most of these areas - 
  • Public speaking
  • Psychology
  • Business writing
  • Accounting
  • Design (the basics)
  • Conversation
  • Overcoming shyness
  • Second language
  • Golf
  • Proper grammar
  • Persuasion
  • Technology (hobby level)
  • Proper voice technique
Asshole behaviors:
  • Changing the subject to him/herself 
  • Dominating conversation 
  • Bragging 
  • Cheating, lying 
  • Disagreeing with any suggestion, no matter how trivial 
  • Using honesty as a justification for cruelty 
  • Withholding simple favors out of some warped sense of social justice 
  • Abandoning the rules of civil behavior, such as saying hello or making eye contact
His candid views & valuable tips are not only very informative but entertaining to read as well:

Scott Adams sees failure as a tool, not an outcome - My cartooning career, for example, is a direct result of failing to succeed in the corporate environment...I always had one or two side projects going on that had the potential to set me free. Cartooning was just one of a dozen entrepreneurial ideas I tried out during my corporate days.

His work prior to being a full-time cartoonist - I ..worked as a fake (literally) engineer in a technology lab, and I had a finger in strategy, marketing, research, interface design, and several other fields.

His job at Pacific Bell - “About 60 percent of my job at Pacific Bell involved trying to look busy..Most of my budget spreadsheets had formula errors, but that didn’t matter because all of the inputs from the various departments were complete lies and bullshit. If anything, my error probably smoothed out some of the bullshit and made it closer to truth.” 

Jobs - ..job seeking was not something one did when necessary. It was an ongoing process....your job is not your job; your job is to find a better job.

Experts - ..my opinion of experts, and authority figures in general, began a steady descent that continues to this day.

Investing - The experts at Wells Fargo helpfully invested my money in Enron, WorldCom, and some other names that have become synonymous with losing money...I have...done my own thing since then, mostly in broad-market, unmanaged funds. (That has worked out better.)

Priorities - The most important form of selfishness involves spending time on your fitness, eating right, pursuing your career, and still spending quality time with your family and friends. It’s useful to think of your priorities in terms of concentric circles, like an archery target. In the center is your highest priority: you. If you ruin yourself, you won’t be able to work on any other priorities. So taking care of your own health is job one. The next ring—and your second-biggest priority—is economics. That includes your job, your investments, and even your house. You might wince at the fact that I put economics ahead of your family, your friends, and the rest of the world, but there’s a reason.  Once you are both healthy and financially sound, it’s time for the third ring: family, friends, and lovers. Good health and sufficient money are necessary for a base level of happiness, but you need to be right with your family, friends, and romantic partners to truly enjoy life. The next rings are your local community, your country, and the world, in that order. 

Simplifiers vs Optimizers - A simplifier will prefer the easy way to accomplish a task, while knowing that some amount of extra effort might have produced a better outcome. An optimizer looks for the very best solution even if the extra complexity increases the odds of unexpected problems. I prefer simple, foolproof plans that allow my heart to beat normally and my mind to wander toward blissful thoughts of puppies and rose petals.

Success - A great strategy for success in life is to become good at something, anything, and let that feeling propel you to new and better victories. Success can be habit-forming....The smartest system for discerning your best path to success involves trying lots of different things—sampling, if you will.

On outsourcing to India - I decided to hire some inexpensive programmers in India to build a Web-based gift registry (essentially) for kids...managing programmers in India turned out to be impractical for me because of time differences, language issues, and my own time limitations

Other interesting insights -
Every skill you acquire doubles your odds of success

Happiness is health plus freedom

Simplicity transforms ordinary into amazing

"Failure always brings something valuable with it...I have a long history of profiting from failure"

This book has great career advice especially for youngsters starting their life's journey. Buy, beg, borrow or steal this book!

Also see: 


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