Summary/Key Takeaways

I really like this book. Adams covers almost all aspects of buiding a successful life, but without any “froo froo” stuff. Instead, it’s grounded in his understanding of current science, psychology, and his work experience.

Favorite Quotes from the Book

Following are quotes from “How to Fail at Almost Everything and Still Win Big”, sorted by category of advice.

Don’t Trust Experts (Including Me)

Most people think they have perfectly good bullshit detectors. But if that were the case, trial juries would always be unanimous, and we’d all have the same religious beliefs.

When it comes to any big or complicated question, humility is the only sensible point of view.

my best guess is that experts are right about 98 percent of the time on the easy stuff but only right 50 percent of the time on anything that is unusually complicated, mysterious, or even new.

Try Lots of Things

I wanted to create, invent, write, or otherwise concoct something widely desired that would be easy to reproduce.

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.

You can’t directly control luck, but you can move from a game with low odds of success to a game with better odds… The hard part is figuring out the odds of any given game, and that’s harder than it looks.

generate lots of opportunities for luck to find you and take the sort of risks that will allow you to come out ahead even if the project fails.

Be Constructively Selfish

During your journey to success you will find yourself continually trying to balance your own needs with the needs of others. You will always wonder if you are being too selfish or not selfish enough.

By becoming a person with good energy, you lift the people around you. That positive change will improve your social life, your love life, your family life, and your career.

Capitalism channels selfishness in a direction that benefits civilization

Simplify Plans, Communication, and Systems

If you can’t tell whether a simple plan or a complicated one will be the best, choose the simple one.

If the situation involves communication with others, simplification is almost always the right answer.

Human nature is such that we’re good at following simple systems and not so good at following complicated systems… Simple systems are probably the best way to achieve success. Once you have success, optimizing begins to have more value.

Systems are Better than Goals

Systems people [feel] good every time they apply their system.

Goal-oriented people exist in a state of continuous presuccess failure… enjoying the spoils of success until they bore [of them]… or set new goals and reenter the cycle of permanent presuccess failure.

Build a Skill Set

You might think a topic is too complicated to master for your use, but you might learn otherwise in less than a minute if you bother to check… So it has been with about 90 percent of the topics that have intimidated me throughout my career. When you start asking questions, you often discover that there’s a simple solution

When it comes to skills, quantity often beats quality… Every skill you acquire doubles your odds of success… You’re better off being good at two complementary skills than being excellent at one.

Acquire as many key skills as possible: public speaking, business writing, the psychology of persuasion, basic technology concepts, social skills, proper voice technique, good grammar, and basic accounting.

Avoid career traps such as pursuing jobs that require you to sell your limited supply of time while preparing you for nothing better.

Learn to Socialize and Tell Stories

The point of conversation is to make the other person feel good.

Faking social confidence leads to the real thing over time… Observe outgoing people and steal their little tricks if you can. I’ve been doing that for years. It works great.

Smile, ask questions, avoid complaining and sad topics, and have some entertaining stories ready to go. It’s all you need to be in the top 10 percent of all conversationalists.

imagine telling the story to someone in particular–a spouse, friend, or relative… storytelling is a learnable skill and not a genetic gift… If something story-worthy happens to you, spend some time developing the story structure in your head.

Develop a Good Attitude

You do better work, and you more enjoy life, when your attitude is good… Understand your basic nature as a moist robot that can be programmed for happiness if you understand the user interface.

Smiling makes you feel better even if your smile is fake. This is the clearest example of how your brain has a user interface.

You shouldn’t hesitate to modify your perceptions to whatever makes you happy, because you’re probably wrong about the underlying nature of reality anyway… hope has a lot of practical utility.

If you have a big, interesting project in the works, you’re a winner every time you wake up.

Happiness tends to happen naturally whenever you have good health, resources, and a flexible schedule… [it] has more to do with where you’re heading than where you are.

The formula for happiness is as simple as daydreaming, controlling your schedule, napping, eating right, and being active every day.


I have condensed the entire field of fitness advice into one sentence: Be Active Every Day

The right amount of exercise today is whatever amount makes me look forward to being active tomorrow.

Most normal adults, including me, find running to be little more than the most cost-effective way to be bored and uncomfortable.

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