How to Fail at Almost Everything and Still Win Big

RATING: 10/10

The best self helpy type book I’ve read. Unconventional strategies from the creator of Dilbert for success in life from career, relationships, diet, fitness, and more. The big idea, ditch goals, embrace systems. Highly recommended.

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Notes:

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 we try. I was passionate about tennis the first day I picked up a racket, and I’ve played all my life. But I also knew in an instant that it was the type of thing I could be good at, unlike basketball or football. So sometimes passion is simply a by-product of knowing you will be good at something.

This was about the time I started to understand that 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.

He said that every time he got a new job, he immediately started looking for a better one. For him, job seeking was not something one did when necessary. It was an ongoing process. This makes perfect sense if you do the math. Chances are the best job for you won’t become available at precisely the time you declare yourself ready. Your best bet, he explained, was to always be looking for the better deal.

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. The systems people are feeling good every time they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction.

For our purposes, let’s say a goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

Systems have no deadlines, and on any given day you probably can’t tell if they’re moving you in the right direction.

I figured my competitive edge was creativity. I would try one thing after another until something creative struck a chord with the public. Then I would reproduce it like crazy. In the near term it would mean one failure after another. In the long term I was creating a situation that would allow luck to find me.

One of the best pieces of advice I’ve ever heard goes something like this: If you want success, figure out the price, then pay it.

Successful people don’t wish for success; they decide to pursue it. And to pursue it effectively, they need a system. Success always has a price, but the reality is that the price is negotiable. If you pick the right system, the price will be a lot nearer what you’re willing to pay.

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.

It’s useful to think of your priorities in terms of concentric circles, like an archery target. In the center is your highest priority: you. 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. The next ring—and your second-biggest priority—is economics. That includes your job, your investments, and even your house. You might wince at the fact that I put economics ahead of your family, your friends, and the rest of the world, but there’s a reason. If you don’t get your personal financial engine working right, you place a burden on everyone from your family to the country. Once you are both healthy and financially sound, it’s time for the third ring: family, friends, and lovers. Good health and sufficient money are necessary for a base level of happiness, but you need to be right with your family, friends, and romantic partners to truly enjoy life. 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.

Priorities are the things you need to get right so the things you love can thrive.

The easiest way to manage your attitude is to consume as much feel-good entertainment as you can.

My imagined future acts as a cue to keep my mood elevated today.

But remember, goals are for losers anyway. It’s smarter to see your big-idea projects as part of a system to improve your energy, contacts, and skills. From that viewpoint, if you have a big, interesting project in the works, you’re a winner every time you wake up.

The smiling-makes-you-happy phenomenon is part of the larger and highly useful phenomenon of faking it until you make it. You’ll see this two-way causation in a wide variety of human activities. Later I’ll tell you that putting on exercise clothes will make you feel like working out. I’ve also discovered that acting confident makes you feel more confident. Feeling energetic makes you want to play a sport, but playing a sport will also make you feel energetic. Loving someone makes you want to have sex, but having sex also releases the bonding chemicals that make you feel love. High testosterone can help you win a competition, but winning a competition can also sometimes raise your testosterone.2 Being tired makes you want to lie down, but lying down when you are rested can put you in the mood for a nap. Feeling hungry can make you want to eat simple carbs, but eating simple carbs can make you feel hungry.

It’s irrelevant that lucky socks aren’t a real thing. The socks can still improve an athlete’s performance, even if the wearer has a flawed idea of why.

When you hear stories about famous actors as kids, one of the patterns you notice is that before they were stars they were staging plays in their living rooms and backyards. That’s gutsy for a kid. A child who eagerly accepts the risk of embarrassment in front of a crowd—even a friendly crowd—probably has some talent for entertaining.

Where there is a tolerance for risk, there is often talent.

The pattern I noticed was this: 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 into a stellar success. Small successes can grow into big ones, but failures rarely grow into successes.

The predictor is that customers were clamoring for the bad versions of the product before the good versions were even invented. It’s as if a future success left bread crumbs that were visible in the present.

The first filter in deciding where to spend your time is an honest assessment of your ability to practice. If you’re not a natural “practicer,” don’t waste time pursuing a strategy that requires it. You know you won’t be a concert pianist or a point guard in the NBA. That’s not necessarily a bad thing. You’re not doomed to mediocrity. You simply need to pick a life strategy that rewards novelty seeking more than mindless repetition. For example, you might want to be an architect, designer, home builder, computer programmer, entrepreneur, Web site designer, or even doctor.

The Success Formula: Every Skill You Acquire Doubles Your Odds of Success.

In California, for example, having one common occupational skill plus fluency in Spanish puts you at the head of the line for many types of jobs. If you’re also a skilled public speaker (good but not great) and you know your way around a PowerPoint presentation, you have a good chance of running your organization. To put the success formula into its simplest form: Good + Good > Excellent

Recapping my skill set: I have poor art skills, mediocre business skills, good but not great writing talent, and an early knowledge of the Internet. And I have a good but not great sense of humor. I’m like one big mediocre soup. None of my skills are world-class, but when my mediocre skills are combined, they become a powerful market force.

I read the news to broaden my exposure to new topics and patterns that make my brain more efficient in general and to enjoy myself, because learning interesting things increases my energy and makes me feel optimistic. Don’t think of the news as information. Think of it as a source of energy.

Quality is not an independent force in the universe; it depends on what you choose as your frame of reference.

The reality is that reason is just one of the drivers of our decisions, and often the smallest one.

Politicians understand that reason will never have much of a role in voting decisions. 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.

Here’s a summary of good conversation technique. Ask questions. Don’t complain (much). Don’t talk about boring experiences (TV show, meal, dream, etc.). Don’t dominate the conversation. Let others talk. Don’t get stuck on a topic. Keep moving. Planning is useful but it isn’t conversation. Keep the sad stories short, especially medical stories.

If you’re physically attractive, it probably isn’t a good idea to talk too much. 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 into. The less you say, the better, at least in the early stages of getting to know someone.

If you’re unattractive—and this is my area of expertise—your conversation skills will be especially important. It might be all you have to sell yourself unless you’re accomplished in some world-class way. You’ll need to take your conversation skills up a notch. And that means becoming the master of short but interesting stories.

Try to get in the habit of asking yourself how you can turn your interesting experiences into story form.

I don’t think people realize that storytelling is a learnable skill and not a genetic gift. Once you know the parts that compose any good story, you have all you need to sculpt your own out of your everyday experiences.

All good stories are about personalities.

Your story isn’t a story unless something unexpected or unusual happens. That’s the plot twist. If you don’t have a twist, it’s not a story.

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.

It turns out that a shy person can act like someone else more easily than he can act like himself. That makes some sense because shyness is caused by an internal feeling that you are not worthy to be in the conversation. Acting like someone else gets you out of that way of thinking.

The 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.

You should also try to figure out which people are thing people and which ones are people people. Thing people enjoy hearing about new technology and other clever tools and possessions. They also enjoy discussions of processes and systems, including politics. People people enjoy only conversations that involve humans doing interesting things. They get bored in a second when the conversation turns to things.

People who appear outgoing are usually employing a learned social skill that you think is somehow natural. It probably isn’t, at least not entirely. Outgoing people usually come from families with at least one outgoing parent. They observe and imitate. Being outgoing is partly genetic, but you still need to know what to say when. That part is learned. And the good news is that you can learn it too. Observe outgoing people and steal their little tricks if you can. I’ve been doing that for years. It works great. I also find it helpful to remind myself that every human is a mess on the inside. It’s easy to assume the good-looking and well-spoken person in front of you has it all together and is therefore your superior. The reality is that everyone is a basket case on the inside. Some people just hide it better. Find me a normal person and I’ll show you someone you don’t know that well. It helps to remind yourself that your own flaws aren’t that bad compared with everyone else’s.

The correct term for an unproven and untested explanation is “hypothesis.”

If someone asks you to attend the annual asparagus festival, don’t say it doesn’t sound fun; that’s just begging the asparagus lovers in your group to endlessly describe just how joyous it could be if only you would try it. Instead, say something like “I don’t do food festivals.” And if anyone asks why, say, “I’m just not interested.” Some of these persuasive sentences work well in tandem.

Crazy people also take more risks and act more confidently than the facts would warrant. That’s a potent combination. Crazy + confident probably kills more people than any other combination of personality traits, but when it works just right, it’s a recipe for extraordinary persuasion. Cults are a good example of insanity being viewed as leadership.

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.

Humor makes average-looking people look cute and uninteresting people seem entertaining.

For in-person humor, quality isn’t as important as you might think. Your attitude and effort count for a lot.

So-called dry humor is the best strategy if you plan to go for quantity.

say quality is overrated when it comes to humor, but you do need to achieve a minimum threshold. And that usually means avoiding a handful of traps. If you avoid the traps, you’re golden. Allow me to map the traps for you. I’ll start with a summary then explain. Overcomplaining is never funny. Don’t overdo the self-deprecation. Don’t mock people. Avoid puns and wordplay.

The pattern I noticed is that the affirmations only worked when I had a 100 percent unambiguous desire for success.

When you choose a career, consider whether it will lead to a lifetime of ever-improved performance, a plateau, or a steady decline in your skills.

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.

Unhappiness that is caused by too much success is a high-class problem. That’s the sort of unhappiness people work all of their lives to get. If you find yourself there, and I hope you do, you’ll find your attention naturally turning outward. You’ll seek happiness through service to others. I promise it will feel wonderful.

Recapping the happiness formula: Eat right. Exercise. Get enough sleep. Imagine an incredible future (even if you don’t believe it). Work toward a flexible schedule. Do things you can steadily improve at. Help others (if you’ve already helped yourself). Reduce daily decisions to routine.

Another possible reason that affirmations appear to work is that optimists tend to notice opportunities that pessimists miss.

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