How to Fail at Almost Everything and Still Win Big

Recommended by Alexey Guzey, the book that changed his life during a depressive period. It does not have stellar reviews, but I am curious, and I like Dilbert’s humor. Note: the author has recently made racially charged remarks, which I do not appreciate. That said, he writes very well and simplifies extraordinarily, offering a kind of encyclopedia on how to live life, from what to eat, how to think, how to work, plus some basic, cynical philosophy. It could be life-changing, especially with a couple of insights like “Thing people vs People people.”

A master at simplifying difficult concepts, a strong writer, a bit of a show-off.

Notes

• Never take advice from a cartoonist, especially on health. He speaks from personal experience.
• A long, tear-jerker story about losing his voice and battling illness.
• See failure as an opportunity to learn. If you find manure in your yard, do not despair. Use it as fertilizer and hope the cow returns every week. He failed many times (e.g., the Dilberito).
• He also explains how he rose through corporate ranks by being good at speaking and not afraid to jump in. Note: he says he hit a ceiling because they could not promote another white male; this comes across as a questionable take.
• Job seeking: every time he found a job, he looked for a better one. It was a continuous process. There is little chance you will find the perfect job by waiting until you feel ready, so always be looking. It is the best way to grow. Loyalty rarely pays.
• Systems are better than goals; they are for the long term. The more complex a system, the more likely it is to fail, so favor simple ones. Who better than a cartoonist to simplify?
• Do not work where you relax: your brain adapts to what it is used to, so separate rest space from focus space. Even the chair. Do not work in an armchair.
• Do not be intimidated by new topics. Once you ask around and start learning, you know 90% of the basics. There will always be websites and professionals to help. Do not be afraid to ask about things you do not know.
• Smile. Even if they cannot see you (on the phone), smiling will automatically put the other person in a better mood, given how our brains are wired.
• If you are already reading this book, you are already in a privileged group that wants to improve; you are one of the people who can make it (a bit flattering).
• The formula for success is to become competent in as many skills as possible to a decent level you can live on. The more of these disciplines you know, the better your odds. Luck is crucial.
• I do not read the news to find the truth; that would be a silly waste of time. I read to get quick summaries to form a rough idea and learn a little, then dig deeper if needed.
• Luck can find you more easily if you have some skills in these areas; the more, the better:
• Public speaking -> absorb the audience’s energy and use it to be upbeat, knowing most will leave with a good memory of the experience
• Psychology
• Business writing
• Accounting
• Design -> L layout; leave a corner empty to unclutter the space
• Conversation -> the trick is to introduce yourself and ask questions until you find common ground. People love to talk about themselves, even shy ones. Ask simple things like where they are from, name, family, hobbies, travel, what they do, etc. Learn to structure everything as a short story with a twist at the end. Keep a small collection.
• Beating shyness -> act. He pretended to be someone who is not afraid to fail or speak and jumped in, knowing he was performing. Push back against the feeling that you do not deserve to be in the conversation.
• Thing people vs People people: some love to talk about things and systems, others about people and feelings. Shape your stories accordingly.
• A second language
• Golf (for networking)
• Grammar (get it wrong and you look bad)
• Persuasion -> steal the tricks and approaches of the bold. You can say “I am not interested” to quickly decline requests and proposals without arguing, or “I have a rule.”
• Tech (as a hobby)
• Voice -> correlated with success; the greats tend to have a commanding voice. Aim for a lower, deeper tone. Humming “Happy Birthday” can give you a sense. Replace “uh” and “um” with silence; you do not have to speak.
• Traits of successful people: do not fear embarrassment (proactivity), be polite, and exercise.
• Being funny can help; it balances other flaws. It improves mood and motivation.
• Do not always trust experts: they will be right in 98% of simple things, but they are fallible on complex, unfamiliar cases like Scott’s condition.
• Your only purpose in life is to maximize your happiness. Which means, if you are not a sociopath, also treating others well to be happy.
• To be happy you need schedule flexibility. Prioritize the freedom to organize your activities above everything. If you are in a bad mood, it is usually a lack of flexibility, diet, exercise, sleep, or imagination.
• Minor tips on diet and exercise; his good method: test. Eat and note what happens. For exercise, start by putting on your shoes and unrolling the mat; inertia will carry you forward.