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

How to Fail at Almost Everything and Still Win Big is chock full of self deprecating humor meant to simultaneously assuage the reader's fears about this being a self help book and convince them that Mr. Adams isn't full of shit. Luckily, he mostly isn't. Most self help books unabashedly share patterns observed from successful people without acknowledging any survivorship bias. How to Fail acknowledges it. Other self help books take a topic worthy of a blog post and stretch it into 50,000 words. How to Fail tries to dump a toolbox on you.

That last bit, that it dumps a number of mental models, perspectives, and practices on you, is the source of this book's success, and its failure. Success is something we do every day, affected by our environment, our histories, our energy, and, especially, our luck. Each factor is deserving of examination. Mr. Adams does disappoint, including factors often left out of other self help books, reframing goals as something that we succeed at when we pursue them every day. But he occasionally strays into navel gazing. The book would be better without the author's diet plan, for example.

Generally, however, the author does the book a service by relating personal anecdotes and perspectives. Despite mysteriously having few relatable failures:

  • A restaurant that fails because the decor was too expensive
  • a line of veggie burritos that fails because it was big enough to draw notice from the competition
  • a TV show based on the author's successful comic that fails because it isn't the Simpsons

Are these emblematic of problems many people have? In fairness, this is the author's life and he's seemed to learn things he's willing to share from it. The humor that makes usual groan-worthy self-help ideas memorable is where the book sings.

How to Fail and Almost Everything has a place on most reader's bookshelves as a better intro to the Self Help genre than most. Just don't ignore the author when he tells you, jokingly, that he doesn't have all the answers.

Selected Ideas

Passion follows success, not the other way around. You don't give a loan to the guy who's passionate about his business, you give it to the person who is willing to grind to success

Systems > goals. If you hold stringently to goals you'll miss opportunities. And success is largely about luck. Systems are about examining the rules and playing the game. Also, goals are failure until you finish. Every time you apply your system you succeed. Systems are the work.

Choose delusions that work. You're delusional anyway, you might as well use it to your advantage.

Positivity can trick us into being better. Compliments give us the confidence to keep trying and try harder in the face of our lack of ability.