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

Practical wisdom in an easy-to-read book. You'll breeze right through and learn a lot in the process.

14 min read


  • Learn from your failures.
  • Success causes passion, not the other way around.
  • Execution > Ideas. Ideas are dime a dozen. Execution is what matters.
  • Systems are for winners. Goals are for losers. Processes over outcomes.
  • Learn multiple skills. Each skill increases your odds of success drastically. You don't have to be world-class at them. Just 'good enough'.
    • "The Success Formula: Every Skill You Acquire Doubles Your Odds of Success"
    • Quantity often beats quality.
    • "The Knowledge Formula: The More You Know, the More You Can Know"
  • Get yourself right first. Then you can focus on the external.
  • Step one in your search for happiness is working towards having control of your schedule.
  • Fix your health. Get more resources and new skills through hard work. Look for opportunities that give you freedom (a flexible schedule).
  • Maximizing personal energy makes everything else easier. Maximize it for the long term and for the big picture.
  • When choosing between different actions to take, pick the one that gives you the greatest personal energy (or the one that takes the least). This is not law, but it's a good guideline.
  • Stop wishing. Take action. Figure out the price of success and then pay it.
    • "Successful people don't wish for success; they decide to pursue it."
  • The price of success is usually negotiable — picking the right system will put it a lot closer to what you are willing to pay.
  • We pick up the habits and energy from those who surround us. So surround yourself with the right people to make their good habits and energy rub off on you.
  • Figure out when you do your best work and do it then.

Important skills to learn*

  • Public speaking
  • Business writing
  • Psychology
  • (acquire a) working understanding of the psychology of persuasion
  • Understand basic technology concepts
  • Social skills
  • Proper voice technique
  • Good grammar
  • Basic accounting
  • Conversation — Making small talk with strangers.
  • Not being an asshole.
  • (developing a habit of) simplifying.
  • Design
  • Golf
  • A second language
  • Overcoming shyness

Good Conversation Technique

  • Ask questions
  • Don't complain (much)
  • Don't talk about boring experiences )TV shows, meal, dream, etc.)
  • Don't dominate the conversation. Let others talk.
  • Don't get stuck on a topic. Keep moving.
  • Planning is useful but isn't conversation.
  • Keep the sad stories short, especially medical stories.

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

Highlights & Comments

Failure always brings something valuable with it. I don’t let it leave until I extract that value.

Success caused passion more than passion caused success.

This is basically the premise of So Good They Can't Ignore You (with a different definition of success).

So forget about passion when you’re planning your path to success. In the coming chapters I’ll describe some methods for boosting personal energy that have worked for me. 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.

Good ideas have no value because the world already has too many of them. The market rewards execution, not ideas. From that point on, I concentrated on ideas I could execute. I was already failing toward success, but I didn’t yet know it.

As a side note: In Anything You Want, Derek Sivers states that execution simply is a multiplier of ideas. Goes well with the above.

To put it bluntly, goals are for losers. That’s literally true most of the time. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal—if you reach it at all—feeling as if you were short of your 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. In time, it becomes heavy and uncomfortable. It might even drive you out of the game.

Then he offered me some career advice. 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. The better deal has its own schedule. I believe the way he explained it is that your job is not your job; your job is to find a better job.

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.

James Clear once said something that, to me, sums up the systems-mindset:

if you optimize for the outcome, you win one time.

If you optimize for a process that leads to great outcomes, you can win again and again.

Goals are optimizing for outcomes. Systems are optimizing for processes.

An example of systems versus goals:

The system-versus-goals model can be applied to most human endeavors. In the world of dieting, losing twenty pounds is a goal, but eating right is a system. In the exercise realm, running a marathon in under four hours is a goal, but exercising daily is a system. In business, making a million dollars is a goal, but being a serial entrepreneur is a system.

Practical example of systems versus goals

On the system side, consider Mark Zuckerberg, founder of Facebook. It’s apparent that his system for success involved studying hard, getting extraordinary grades, going to a top college—in his case Harvard—and developing a skill set with technology that virtually guaranteed riches in today’s world. As it turns out, his riches came quickly through the explosive growth of Facebook. But had that not worked out, he would likely be a millionaire through some other start-up or just by being a highly paid technical genius for an existing corporation. Zuckerberg’s system (or what I infer was his system) was almost guaranteed to work, but no one could have imagined at the time how well.

Another Practical example of systems versus goals

Warren Buffett’s system for investing involves buying undervalued companies and holding them forever, or at least until something major changes. That system (which I have grossly oversimplified) has been a winner for decades. Compare that with individual investors who buy a stock because they expect it to go up 20 percent in the coming year; that’s a goal, not a system. And not surprisingly, individual investors generally experience worse returns than the market average.

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. It sounds trivial and obvious, but if you unpack the idea it has extraordinary power.

I know a lot of people who wish they were rich or famous or otherwise fabulous. They wish they had yachts and servants and castles and they wish they could travel the world in their own private jets. But these are mere wishes. Few of these wishful people have decided to have any of the things they wish for. It’s a key difference, for once you decide, you take action. Wishing starts in the mind and generally stays there.

So many people say "I wish that..."

Well, what's stopping you from doing it right now?

Figure out what that is and start climbing obstacles.

When you decide to be successful in a big way, it means you acknowledge the price and you’re willing to pay it. That price might be sacrificing your personal life to get good grades in school, pursuing a college major that is deadly boring but lucrative, putting off having kids, missing time with your family, or taking business risks that put you in jeopardy for embarrassment, divorce, or bankruptcy. 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. If you neglect your health or your career, you slip into the second category—stupid—which is a short slide to becoming a burden on society.

The first step to taking care of others is to take care of yourself.

If you pursue your selfish objectives, and you do it well, someday your focus will turn outward. It’s an extraordinary feeling. I hope you can experience it.

I’m suggesting that 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.
When I talk about increasing your personal energy, I don’t mean the frenetic, caffeine-fueled, bounce-off-the-walls type of energy. I’m talking about a calm, focused energy. To others it will simply appear that you are in a good mood. And you will be.

Asshole behaviors:
Changing the subject to him/herself
Dominating conversation
Cheating, lying
Disagreeing with any suggestion, no matter how trivial
Using honesty as a justification for cruelty
Withholding simple favors out of some warped sense of social justice
Abandoning the rules of civil behavior, such as saying hello or making eye contact

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.

The way I approach the problem of multiple priorities is by focusing on just one main metric: my energy. I make choices that maximize my personal energy because that makes it easier to manage all of the other priorities.

Maximizing my personal energy means eating right, exercising, avoiding unnecessary stress, getting enough sleep, and all of the obvious steps. But it also means having something in my life that makes me excited to wake up. When I get my personal energy right, the quality of my work is better, and I can complete it faster. That keeps my career on track. And when all of that is working, and I feel relaxed and energetic, my personal life is better too.

Similarly, when you manage your personal energy, it’s not enough to maximize it in the short run or in one defined area. Ideally, you want to manage your personal energy for the long term and the big picture. Having one more cocktail at midnight might be an energy boost at the time, but you pay for it double the next day.

One of the most important tricks for maximizing your productivity involves matching your mental state to the task. For example, when I first wake up, my brain is relaxed and creative. The thought of writing a comic is fun, and it’s relatively easy because my brain is in exactly the right mode for that task. I know from experience that trying to be creative in the midafternoon is a waste of time. By 2:00 P.M. all I can do is regurgitate the ideas I’ve seen elsewhere. At 6:00 A.M. I’m a creator, and by 2:00 P.M. I’m a copier.

It's about knowing yourself.

I prefer simplicity whenever I’m choosing a system to use. People can follow simple systems better than complicated ones. I’ll give you some examples of that in later chapters about fitness and diet. The most optimized diet plan or fitness plan will also be the most complicated. But few people have enough willpower in reserve to follow complicated plans.

Simple systems are probably the best way to achieve success. Once you have success, optimizing begins to have more value. Successful people and successful businesses have the luxury of being able to optimize toward perfection over time. Start-ups often do better by slapping together something that is 80 percent good and seeing how the public responds. There’s time to improve things later if the market cares about the product.

Don’t Be an Asshole

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.

All of your priorities overlap and conflict. What you need is a simple rule for keeping your priorities on track while handling all of the inevitable exceptions. One simple way to keep your priorities straight is by judging how each of your options will influence your personal energy. 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. Right choices can be challenging, but they usually charge you up. When you’re on the right path, it feels right, literally.

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.

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.

If the first commercial version of your work excites no one to action, it’s time to move on to something different. Don’t be fooled by the opinions of friends and family. They’re all liars.
If your work inspires some excitement and some action from customers, get ready to chew through some walls. You might have something worth fighting for.

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 primary purpose of schools is to prepare kids for success in adulthood. That’s why it seems odd to me that schools don’t have required courses on the systems and practices of successful people. Success isn’t magic; it’s generally the product of picking a good system and following it until luck finds you. Unfortunately, schools barely have the resources to teach basic course work. Students are on their own to figure out the best systems for success.

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

Acquire skills.

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.

The Knowledge Formula: The More You Know, the More You Can Know

I made a list of the skills in which I think every adult should gain a working knowledge. I wouldn’t expect you to become a master of any, but mastery isn’t necessary. Luck has a good chance of finding you if you become merely good in most of these areas. I’ll make a case for each one, but here’s the preview list.
Public speaking
Business writing
Design (the basics)
Overcoming shyness
Second language
Proper grammar
Technology (hobby level)
Proper voice technique

It’s hard to imagine any business or social activity that doesn’t require a basic understanding of how the human brain perceives the world. Almost any decision you make is in the context of managing what other people will think of you. We’re all in the business of selling some version of ourselves. Psychology is embedded in everything we do.

Salespeople know they can manipulate buyers by controlling what they compare.

When you see an expensive car, the additional floor mats that you'd have to buy too do not seem very expensive — so you're more likely to buy them.

My best guess is that there are a few hundred rules in psychology that you should have a passing familiarity with. I’ve been absorbing information in this field for decades, and I don’t feel that I am getting anywhere near the end of it. And just about everything I learn about human psychology ends up being helpful.

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.

I 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.

Given our human impulse to pick up the habits and energy of others, you can use that knowledge to literally program your brain the way you want. Simply find the people who most represent what you would like to become and spend as much time with them as you can without trespassing, kidnapping, or stalking. Their good habits and good energy will rub off on you.

Recapping the happiness formula:
Eat right.
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.

Step one in your search for happiness is to continually work toward having control of your schedule.

a smarter approach is to take care of yourself first and use that success as leverage to get everything else you need.

The Simple, No-Willpower Diet System
Pay attention to your energy level after eating certain foods. Find your pattern.
Remove unhealthy, energy-draining food from your home.
Stock up on convenient healthy food (e.g., apples, nuts, bananas) and let laziness be your copilot in eating right.
Stop eating foods that create feelings of addiction: white rice, white potatoes, desserts, white bread, fried foods.
Eat as much healthy food as you want, whenever you want.
Get enough sleep, because tiredness creates the illusion of hunger.
If your hunger is caused by tiredness, try healthy foods with fat, such as nuts, avocados, protein bars, and cheese, to suppress the hungry feeling.
If you’re eating for social reasons only, choose the healthiest options with low calories.
Learn how to season your healthy-yet-bland foods.

The model for success I described here looks roughly like this: Focus on your diet first and get that right so you have enough energy to want to exercise. Exercise will further improve your energy, and that in turn will make you more productive, more creative, more positive, more socially desirable, and more able to handle life’s little bumps.

Once you optimize your personal energy, all you need for success is luck. You can’t directly control luck, but you can move from strategies with bad odds to strategies with good odds. For example, learning multiple skills makes your odds of success dramatically higher than learning one skill. If you learn to control your ego, you can pick strategies that scare off the people who fear embarrassment, thus allowing you to compete against a smaller field. And if you stay in the game long enough, luck has a better chance of finding you. Avoid career traps such as pursuing jobs that require you to sell your limited supply of time while preparing you for nothing better.

Happiness is the only useful goal in life. Unless you are a sociopath, your own happiness will depend on being good to others. And happiness tends to happen naturally whenever you have good health, resources, and a flexible schedule. Get your health right first, acquire resources and new skills through hard work, and look for an opportunity that gives you a flexible schedule someday.

Look for patterns in every part of life, from diet to exercise to any component of success. Try to find scientific backing for your observed patterns, and use yourself as a laboratory to see if the patterns hold for you.

Experiment with things. Have hypotheses and test them out. Find what works.

Most important, understand that goals are for losers and systems are for winners. People who seem to have good luck are often the people who have a system that allows luck to find them. I’ve laid out some systems in this book that seem to work for me. Your experience will differ, but it always helps to be thinking in terms of systems and not goals.

And always remember that failure is your friend. It is the raw material of success. Invite it in. Learn from it. And don’t let it leave until you pick its pocket. That’s a system.

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