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

“The best way to increase your odds of success—in a way that might look like luck to others—is to systematically become good, but not amazing, at the types of skills that work well together and are highly useful for just about any job.” – Scott Adams

3 Universal Systems/Skills that increase your odds of professional success

Clear Writing

The goal of all business writing is to write clearly. That means removing unnecessary words and passive language.

“As it turns out, business writing is all about getting to the point and leaving out all of the noise. You think you already do that in your writing, but you probably don’t.

Consider the previous sentence. I intentionally embedded some noise. Did you catch it? The sentence that starts with “You think you already do that” includes the unnecessary word “already.” Remove it and you get exactly the same meaning: “You think you do that.” The “already” part is assumed and unnecessary. That sort of realization is the foundation of business writing.” – Scott Adams

Your sentences should follow the structure of ‘Actor-Action-Object’.

“Your brain processes “The boy hit the ball” more easily than “The ball was hit by the boy.” In editors’ jargon, the first sentence is direct writing and the second is passive. It’s a tiny difference, but over the course of an entire document, passive writing adds up and causes reader fatigue.” – Scott Adams

Book Summary: How to Fail at Almost Everything and Still Win Big - Kind of the Story of My Life

Making Conversation

The goal of conversation is to get people to like you. A proven conversation technique is smiling, using open body language, introducing yourself, and searching for a common interest by asking questions.

“The technique is laughably simple and 100 percent effective. It’s all you need to be in the top 10 percent of all conversationalists.” – Scott Adams

Here are five go-to questions:

  • Where do you live?
  • Do you have a family?
  • What do you do for a living?
  • Do you have any hobbies/sports?
  • Do you have any travel plans?

“The secret to making the list of questions work without seeming awkward is in understanding that the person you meet will feel every bit as awkward as you. That person wants to talk about something interesting and to sound knowledgeable. Your job is to make that easy. Nothing is easier than talking about one’s self.” – Scott Adams


“No matter your calling in life, you’ll spend a great deal of time trying to persuade people to do one thing or another.” – Scott Adams

Scott is a trained hypnotist, and he knows a thing or two about persuasion. Here are two of his favorite persuasive words/phrases:

“…Because”: People are more cooperative when you ask for a favor using a sentence that includes the word because, even if the reason you offer makes little or no sense. – Scott Adams

“Would You Mind…?”: It’s hard to be a jerk and say no to any request that starts with “Would you mind.” The question comes across as honest, while also showing concern for the other person. It’s a powerful combination. – Scott Adams



“How to Fail at Almost Everything and Still Win Big” by Scott Adams is a hilarious and thought-provoking book that offers a unique perspective on failure and success. I was intrigued by the title and eager to dive into the book to see if it lives up to its promise. In this review, I will provide a detailed analysis of the book’s strengths, weaknesses, and key takeaways, as well as its relevance to readers.

The book is divided into three parts:

  • Part 1: The Failures – In this part, Adams talks about all the things he has failed at in his life, including his corporate career, his inventions, and his investments. He also talks about how he learned from his failures and how they ultimately led to his success.
  • Part 2: The System – In this part, Adams talks about his “secret system” for success. He argues that success is not about setting goals or working hard, but about creating a system that allows you to succeed.
  • Part 3: The Advice – In this part, Adams offers advice on how to apply his system to your own life. He talks about the importance of personal energy, the power of positive thinking, and the importance of failing forward.


  • Humor: Scott Adams’ writing style is engaging and humorous, making the book an enjoyable read from start to finish. His use of witty anecdotes, puns, and satire keeps the reader entertained while also conveying valuable lessons.
  • Relatability: The book is filled with relatable stories and examples from Adams’ own life, making it easy for readers to connect with the author and his experiences. This personal touch adds depth and authenticity to the book, making it more impactful.
  • Practical advice: While the title suggests a focus on failure, the book actually offers practical advice on how to succeed in various areas of life. Adams provides actionable tips and strategies for improving one’s mindset, decision-making, and problem-solving skills.
  • Realistic perspective: Adams’ candid and unapologetic approach to failure and success is refreshing and realistic. He acknowledges that failure is an inevitable part of life and that it can often lead to greater success. This perspective is inspiring and can help readers overcome their fear of failure.


  • Lack of depth: While the book covers a lot of ground, it doesn’t delve into any one topic in-depth. As a result, some readers may find the information superficial or lacking in substance.
  • Disorganization: The book’s structure is somewhat disorganized, with some chapters feeling disconnected from the others. This can make it challenging for readers to follow along or find the information they’re looking for.
  • Limited scope: While the book covers various aspects of life, it primarily focuses on personal and professional success. Readers may find the book less helpful in other areas of life, such as relationships or personal growth.

Key Takeaways:

  • Embracing Failure: Adams challenges the conventional notion of failure and argues that it is an essential part of the path to success. He shares numerous stories from his own life, highlighting how failures and setbacks ultimately led to his greatest achievements.
  • Systems over Goals: The book emphasizes the importance of focusing on systems rather than relying solely on goals. Adams suggests that building strong habits and systems increases the likelihood of success, even if individual goals are not always achieved.
  • Personal Energy Management: Adams delves into the concept of personal energy management and the impact it has on performance and well-being. He provides practical tips on managing energy levels, including sleep, exercise, and nutrition, to optimize productivity and overall quality of life.
  • Skill Stacking: The author encourages readers to develop a diverse set of skills that can complement each other and create unique opportunities. Adams shares how his own skill stacking, combining his background in art, writing, and business, contributed to his success as the creator of the Dilbert comic strip.
  • Embracing the Unknown: How to Fail at Almost Everything and Still Win Big encourages readers to embrace uncertainty and take calculated risks. Adams emphasizes that success often lies outside of one’s comfort zone and that being open to new experiences and opportunities can lead to unexpected breakthroughs.
  • Personal Responsibility and Mindset: The book emphasizes the importance of taking personal responsibility for one’s own success and adopting a growth mindset. Adams discusses the power of positive thinking, resilience, and adapting to change as key factors in overcoming challenges and achieving long-term success.
  • The Power of Persuasion: Adams explores the art of persuasion and effective communication techniques. He shares insights from his career in the corporate world and offers practical advice on influencing others and building strong relationships.
  • Humor and Optimism: Throughout the book, Adams infuses his unique brand of humor and optimism. He shares entertaining anecdotes and witty observations, creating an engaging and enjoyable reading experience.

Critique and Recommendation:

While I found “How to Fail at Almost Everything and Still Win Big” to be an excellent read, there are a few areas where the book could be improved. Some readers may find the book’s structure, which jumps back and forth between Adams’ life story and his advice, to be a bit disjointed. Additionally, some of the book’s themes and ideas may feel repetitive or overly simplistic.

Despite these minor criticisms, I highly recommend “How to Fail at Almost Everything and Still Win Big” to anyone looking for a motivational and thought-provoking read. The book’s message of perseverance, creativity, and the power of “optional thinking” is both inspiring and empowering. Whether you’re looking to overcome failure, achieve success, or simply improve your outlook on life, this book is an excellent choice.


“How to Fail at Almost Everything and Still Win Big” is a humorous and insightful book that challenges readers to rethink their approach to failure and success. While it has some weaknesses, the book’s strengths make it a valuable read for anyone looking to improve their mindset, decision-making, and problem-solving skills. By embracing failure and focusing on the process, readers can learn to succeed in various areas of life.

Alex Lim is a certified book reviewer and editor with over 10 years of experience in the publishing industry. He has reviewed hundreds of books for reputable magazines and websites, such as The New York Times, The Guardian, and Goodreads. Alex has a master’s degree in comparative literature from Harvard University and a PhD in literary criticism from Oxford University. He is also the author of several acclaimed books on literary theory and analysis, such as The Art of Reading and How to Write a Book Review. Alex lives in London, England with his wife and two children. You can contact him at [email protected] or follow him on Website | Twitter | Facebook

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