The Book I Keep Coming Back To

I recently revisited one of my favorite books: How to Fail at Almost Everything and Still Win Big that profoundly shaped my worldview back in 2016. Reading it again with a few more years of experience under my belt, I found myself coming across insights I had completely missed the first time around. I strongly recommend reading it. But if you’re short on time, I’ve shared my notes below, written as lifelong advice to myself, and hopefully valuable to you too.

1. Consistency is the best marker of truth that we have, imperfect though it may be.
2. You can debate the morality of viewing profits as the top priority in business, but you can’t argue that it doesn’t work.
3. You’re the best judge of what works for you, as long as you acquire that wisdom through pattern recognition, trial, and observation.
4. Sometimes the only real difference between crazy people and artists is that artists write down what they imagine seeing.
5. You can cure your loneliness only by doing the talking yourself and—most important—being heard. For the next three and a half years I experienced a total disconnect from normal life and a profound sense of aloneness, despite the love and support of family and friends.
6. When you stand in front of an audience, your sensation of time is distorted.
7. That’s why inexperienced presenters speak too rapidly. I mentally adjusted my internal clock to match the audience’s sense of timing. I also wanted them to wait in silence for a beat or two, to engage their curiosity.
8. Is passion a useful tool for success, or is it just something that makes you irrational?Passionate people who fail don’t get a chance to offer their advice to the rest of us. But successful passionate people are writing books and answering interview questions about their secrets for success every day. Naturally those successful people want you to believe that success is a product of their awesomeness, but they also want to retain some humility.Passion can also be a simple marker for talent. We humans tend to enjoy doing things we are good at, while not enjoying things we suck at. We’re also fairly good at predicting what we might be good at before
9. You already know that when your energy is right you perform better at everything you do, including school, work, sports, and even your personal life. Energy is good. Passion is bullshit.
10. Everything you want out of life is in that huge, bubbling vat of failure. The trick is to get the good stuff out.I’ve long seen failure as a tool, not an outcome. I believe that viewing the world in that way can be useful for you too.Success is entirely accessible, even if you happen to be a huge screwup 95 percent of the time.My failure taught me to seek opportunities in which I had an advantage.
11. Timing is often the biggest component of success. And since timing is often hard to get right unless you are psychic, it makes sense to try different things until you get the timing right by luck.
12. I believe the way he explained it is that your job is not your job; your job is to find a better job.
13. This was my first exposure to the idea that one should have a system instead of a goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. That feeling wears on you. Goal-oriented people exist in a state of continuous presuccess failure at best, and permanent failure at worst if things never work out. Systems people succeed every time they apply their systems, in the sense that they did what they intended to do. The goals people are fighting the feeling of discouragement at each turn.
14. At various times I was a branch banking trainee, project manager, computer programmer, product manager, lending officer, budget supervisor, and a few other jobs I’ve forgotten.I had officially failed at my banking career and, against all odds, my incompetence wasn’t the cause. Little did they realize that looking good on paper was my best skill.
15. This was one of many examples in which the universe makes sure there isn’t much of a link between job performance in the corporate world and outcomes.
16. Wishing starts in the mind and generally stays there. If you want success, figure out the price, then pay it.
17. Successful people don’t wish for success; they decide to pursue it.
18. 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.
19. At every turn, we cheat our own future to appear generous today.
20. We humans are wired to be easily influenced by the people who are in relationships with us, no matter what those relationships are.Influence works best when the person being influenced has no objection to the suggested change. Often all one needs is some form of permission to initiate a change, and it doesn’t always matter what form the permission is in, or if it even makes sense. I’m sure you already want to be fit and successful and happy.
21. Apparently humans are wired to take care of their own needs first, then family, tribe,country, and the world, roughly in that order.The healthiest way to look at selfishness is that it’s a necessary strategy when you’re struggling.
22. The problem with all of this wanting is that the time you spend chasing one of those desires is time you can’t spend chasing any of the others. So how do you organize your limited supply of time to get the best result? I make choices that maximize my personal energy because that makes it easier to manage all of the other priorities.
23. For years, the prospect of starting “my own thing” and leaving my cubicle behind gave me an enormous amount of energy. “Energy” is a simple word that captures a mind-boggling array of complicated happenings. For our purposes I’ll define your personal energy as anything that gives you a positive lift, either mentally or physically. Like art, you know it when you see.
24. Simple systems are probably the best way to achieve success. Once you have success, optimizing begins to have more value.
25. To change how you feel, and how you think, you can simply change where you are sitting.
26. Most of my problems were caused by my own bad decisions, lack of skill, and bad luck.
27. I would define an asshole as anyone who chooses to make the lives of others less pleasant for reasons that don’t appear productive or necessary. I assume asshole behavior exists because it feels good when you do it.
28. 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.
29. The next rings are your local community, your country, and the world, in that order. Don’t bother trying to fix the world until you get the inner circles of your priorities under control.
30. It’s not a foolproof gauge, but if you know a particular path will make you feel more stressed, unhealthy, and drained, it’s probably the wrong choice.
31. On the other hand, if your boss routinely asks you to work overtime for no good reason other than to claw through piles of brain-deadening administrative work, you probably need to look for a new job.
32. Priorities are the things you need to get right so the things you love can thrive.
33. Your brain is wired to continuously analyze your environment, your thoughts, and your health and to use that information to generate a sensation you call your attitude. You can control your attitude by manipulating your thoughts, your body, and your environment. A positive attitude is an important tool. It’s important to get it right. The best way to manage your attitude is by understanding your basic nature as a moist robot that can be programmed for happiness if you understand the user interface. Exercise, food, and sleep should be your first buttons to push if you’re trying to elevate your attitude.
34. For the truly bad moods, exercise, nutrition, sleep, and time are the smart buttons to push.
35. Let your ideas for the future fuel your energy today. No matter what you want to do in life, higher energy will help you get there.
36. Walk away from the soul suckers. You have a right to pursue happiness and an equal right to run as fast as you can from the people who would deny it.
37. 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.
38. The way I motivate myself to take on a task this large is by imagining that I have fascinating and useful things to say that will help people.
39. If you manage your illusions wisely, you might get what you want, but you won’t necessarily understand why it worked.
40. Never assume you understand the odds of things. My optimism is like an old cat that likes to disappear for days, but I always expect it to return.
41. Thanks to my odd life experiences, and odder genes, I’m wired to think things will work out well for me no matter how unlikely it might seem.
42. A child who eagerly accepts the risk of embarrassment in front of a crowd—even a friendly crowd—probably has some talent for entertaining. The smartest system for discerning your best path to success involves trying lots of different things—sampling, if you will.
43. Things that will someday work out well start out well. Things that will never work start out bad and stay that way. What you rarely see is a stillborn failure that transmogrifies
44. The predictor is that customers were clamoring for the bad versions of the product before the good versions were even invented.
45. My observation is that some people are born with a natural impulse to practice things and some people find mindless repetition without immediate reward to be a form of torture.It’s naive to expect the average person to embrace endless practice in pursuit of long-term success.
46. Success isn’t magic; it’s generally the product of picking a good system and following it until luck finds you.
47. The formula, roughly speaking, is that every skill you acquire doubles your odds of success.
48. My combined mediocre skills are worth far more than the sum of the parts. If you think extraordinary talent and a maniacal pursuit of excellence are necessary for success, I say that’s just one approach, and probably the hardest. When it comes to skills, quantity often beats quality.
49. The More You Know, the More You Can Know
50. The more time you spend exposing yourself to bad news, the more it will weigh on you and sap your energy.
51. Don’t think of the news as information. Think of it as a source of energy.
52. That seems like an obvious strategy and you probably think you already do it. The hard part is figuring out the odds of any given game, and that’s harder than it looks. Several years ago I gave a talk to a fifth-grade class.
53. Don’t assume you know how much potential you have. Sometimes the only way to know what you can do is to test yourself.
54. When I look at the list of my personal failures and successes, one of the things that stand out is psychology.
55. Quality is not an independent force in the universe; it depends on what you choose as your frame of reference.
56. When politicians tell lies, they know the press will call them out. They also know it doesn’t matter.
57. A lie that makes a voter feel good is more effective than a hundred rational arguments. That’s even true when the voter knows the lie is a lie. If you’re perplexed at how society can tolerate politicians who lie so blatantly, you’re thinking of people as rational beings.
58. If your view of the world is that people use reason for their important decisions, you are setting yourself up for a life of frustration and confusion. You’ll find yourself continually debating people and never winning except in your own mind. Few things are as destructive and limiting as a worldview that assumes people are mostly rational.
59. Steve Jobs’s understanding that the way a product makes users feel trumps most other considerations, including price. If Steve Jobs had seen people as rational beings, he might have followed a path similar to Dell, selling highly capable machines at the lowest possible price.
60. Rational behavior is especially useless in any situation that is too complex for a human to grasp. Cell-phone companies exploit that fact by offering pricing plans that are too complicated to compare with the competition. (I coined the word “confusopoly” to describe that strategy.)
61. Instead, consumers make largely uninformed decisions and convince themselves they did well.
62. “The boy hit the ball” more easily than “The ball was hit by the boy.” Unnecessary words and passive writing kill the timing of humor the same way they kill the persuasiveness of your point. If you want people to see you as smart, persuasive, and funny, consider taking a two-day class in business writing. There aren’t many skills you can learn in two days that will serve you this well.
63. In my entire life I have never met a stranger who didn’t have some fascinating life experiences that spilled out if I asked the right questions.
64. The point of conversation is to make the other person feel good. If you do that one simple thing correctly, the other benefits come along with the deal.
65. People are predisposed to liking attractive people. Talking can only make things worse. If you’re attractive, be sure you’ve created a solid connection before discussing your hobby of collecting baby animal skulls or whatever the hell you’re
66. Try to get in the habit of asking yourself how you can turn your interesting experiences into story form.
67. People drift off when you stop talking about stuff that isn’t, well, them.
68. remember that most people feel awkward in social situations at least some of the time. Chances are that the person you are talking to is feeling just as shy. e single best tip for avoiding shyness involves harnessing the power of acting interested in other people. You don’t want to cross into nosiness, but everyone appreciates it when you show interest.
69. The more you put yourself in potentially embarrassing situations, the easier they all become.
70. Success builds confidence and confidence suppresses shyness.
71. It’s surprising how uncommon common sense is.
72. “Hopefully” should be an adverb. Say instead, “We waited hopefully for dessert.” In the latter case, “hopefully” is correctly modifying the verb “waited.” In the first example, hopefully just sits there like the wrong word choice.
73. A good starting point in learning the art of persuasion is to go to your preferred online bookstore and search for “persuasion.” You’ll see a number of books on the topic. Keep reading those books until they seem to be repeating the same tricks.
74. Apparently the word “because” signals reasonableness, and reasonableness allows people to let down their defenses and drop their objections.
75. If you show enthusiasm, others will want to experience the same rush.
76. Cults are a good example of insanity being viewed as leadership.
77. In any kind of negotiation, the worst thing you can do is act reasonable. Reasonable people generally cave in to irrational people because it seems like the path of least resistance.
78. It’s important to keep a lot of distance between your fun voice and your persuasive voice. For people who know you, the serious voice will send an unambiguous signal that the topic is important and you might not be open to negotiating. But research shows that voice quality is far more important to your overall health and happiness than you might imagine.
79. I was literally acting, but it didn’t feel disingenuous because the business world is a lot like theater. Everyone tries to get into character for the job they have.
80. Despite my obvious lack of ability, nearly every boss I had—and there were many—identified me as a future corporate executive. I doubt that was the case. I think my fake professional voice and body language were at least half of the reason I was seen as having management potential. Unfortunately the flirting stopped as soon as anyone saw me in person. That’s why I assume my fake voice was the secret sauce.
81. I see in successful people: They treat success as a learnable skill.
82. People who enjoy humor are simply more attractive than people who don’t. It’s human nature to want to spend time with people who can appreciate a good laugh or, better yet, cause one.
83. “I, Scott, will become rich.” The long version of the story involves two ridiculously lucky stock picks that came to me out of nowhere in separate flashes of something that felt like intuition.
84. I’m just a good stock picker and far more handsome than my lying mirror is willing to admit. Whatever the real reason for my success, I got enough of a payoff to encourage me to keep trying affirmations just in case there was something to them.
85. I tried a lot of different ventures, stayed optimistic, put in the energy, prepared myself by learning as much as I could, and stayed in the game long enough for luck to find me. I hoped a buck would eventually walk by, and with Dilbert it did.
86. Luck won’t give you a strategy or a system—you have to do that part yourself. I find it helpful to see the world as a slot machine that doesn’t ask you to put money in.
87. The pattern I noticed is that the affirmations only worked when I had a 100 percent unambiguous desire for success.
88. My attitude was always the same: Escape from my cell, free the other inmates, shoot the warden, and burn down the prison.
89. My observation and 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. If your gut feeling (intuition) disagrees with the experts, take that seriously. You might be experiencing some pattern recognition that you can’t yet verbalize.
90. There are probably dozens of ways we absorb energy, inspiration, skills, and character traits from those around us. Sometimes we learn by example. Sometimes success appears more approachable and ordinary because we see normal people achieve it, and perhaps that encourages us to pursue schemes with higher
91. We can’t always know the mechanism by which others change our future actions, but it’s pretty clear it happens, and it’s important.
92. The programming interface is your location. To change yourself, part of the solution might involve spending more time with the people who represent the change you seek.
93. For starters, the single biggest trick for manipulating your happiness chemistry is being able to do what you want, when you want.
94. A person with a flexible schedule and average resources will be happier than a rich person who has everything except a flexible schedule. Step one in your search for happiness is to continually work toward having control of your schedule.
95. In your personal life and your career, consider schedule flexibility when making any big decision.
96. Don’t let reality control your imagination. Let your imagination be the user interface to steer your reality.
97. Happiness is the natural state for most people whenever they feel healthy, have flexible schedules, and expect the future to be good.
98. I’m here to tell you that the primary culprit in your bad moods is a deficit in one of the big five: flexible schedule, imagination, sleep, diet, and exercise. The usual reaction is a blank expression followed by a change of topic. No one wants to believe that the formula for happiness is as simple as daydreaming, controlling your schedule, napping, eating right, and being active every day. You’d feel like an idiot for suffering so many unhappy days while not knowing the cure was so accessible. I know from experience that you might
99. My best estimate is that 80 percent of your mood is based on how your body feels and only 20 percent is based on your genes and your circumstances,
100. That’s why I include diet and fitness in a book about success. If you get your health in order, success will come more easily.
101. And always remember that failure is your friend. It is the raw material of success. Invite it in. Learn from it.