How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life
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If we can’t count on schools to teach kids the systems of success, how will people learn those important skills? The children of successful people probably learn by observation and parental coaching. But most people are not born to highly successful parents. The average kid spends almost no time around highly successful people, and certainly not during the workday, when those successful people are applying their methods. The young are intentionally insulated from the adult world of work. At best, kids see the television and movie versions of how to succeed, and that isn’t much help.
Books about success can be somewhat useful. But for marketing reasons, a typical book is focused on a single topic to make it easier to sell and packed with filler to get the page count up. No one has time to sort through that much filler.
When I speak to young people on the topic of success, as I often do, I tell them there’s a formula for it. You can manipulate your odds of success by how you choose to fill out the variables in the formula. The formula, roughly speaking, is that every skill you acquire doubles your odds of success.
The Success Formula: Every Skill You Acquire Doubles Your Odds of Success
Notice I didn’t say anything about the level of proficiency you need to achieve for each skill. I didn’t mention anything about excellence or being world-class. The idea is that you can raise your market value by being merely good—not extraordinary—at more than one skill.
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
Successwise, you’re better off being good at two complementary skills than being excellent at one. I’m ignoring the outlier possibility that you might be one of the best performers in the world at some skill or another. That can obviously be valuable too. But realistically, you wouldn’t be reading this book if you could throw a baseball a hundred miles per hour or compose hit songs in your head.
When I say each skill you acquire will double your odds of success, that’s a useful simplification. Obviously some skills are more valuable than others, and the twelfth skill you acquire might have less value than each of the first eleven. But if you think of each skill in terms of doubling your chances of success, it will steer your actions more effectively than if you assume the benefit of learning a new skill will get lost in the rounding. Logically, you might think it would make more sense to have either an accurate formula for success or none at all. But that’s not how our brains are wired. Sometimes an entirely inaccurate formula is a handy way to move you in the right direction if it offers the benefit of simplicity. I realize that’s not an obvious point, so allow me to give you an example.
When writing a résumé, a handy trick you’ll learn from experts is to ask yourself if there are any words in your first draft that you would be willing to remove for one hundred dollars each. Here’s the simple formula:
Each Unnecessary Word = $100
When you apply the formula to your résumé, you surprise yourself by how well the formula helps you prune your writing to its most essential form. It doesn’t matter that the hundred-dollar figure is arbitrary and that some words you remove are more valuable than others. What matters is that the formula steers your behavior in the right direction. As is often the case, simplicity trumps accuracy. The hundred dollars in this case is not only inaccurate; it’s entirely imaginary. And it still works.
Likewise, I think it’s important to think of each new skill you acquire as a doubling of your odds of success. In a literal sense, it’s no more accurate than the imaginary hundred dollars per deleted word on your résumé, but it still helps guide your behavior in a productive direction. If I told you that taking a class in Web site design during your evenings might double your odds of career success, the thought would increase the odds that you would act. If instead I only offered you a vague opinion that acquiring new skills is beneficial, you wouldn’t feel particularly motivated. When you accept without necessarily believing that each new skill doubles your odds of success, you effectively hack (trick) your brain to be more proactive in your pursuit of success. Looking at the familiar in new ways can change your behavior even when the new point of view focuses on the imaginary.
I’m a perfect example of the power of leveraging multiple mediocre skills. I’m a rich and famous cartoonist who doesn’t draw well. At social gatherings I’m usually not the funniest person in the room. My writing skills are good, not great. But what I have that most artists and cartoonists do not have is years of corporate business experience plus an MBA from Berkeley’s Haas School of Business. In the early years of Dilbert my business experience served as the fodder for the comic. Eventually I discovered that my business skills were essential in navigating Dilbert from a cult hit to a household name. 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.
This would be a good time to tell you what kind of student I was in Berkeley’s MBA program. In my first semester I often had the lowest grades in the class. I worked hard and rose to scholastic mediocrity through brute force. In the end, all that mattered is that I learned skills that complemented my other meager talents.
When I combined my meager business skills with my bad art skills and my fairly ordinary writing talent, the mixture was powerful. With each new skill, my odds of success increased substantially. But there was still one more skill I acquired in my day job at Pacific Bell that ended up mattering a lot: I knew about the Internet before most people had even heard of it.
My day job at Pacific Bell involved demonstrating a new thing called the World Wide Web, later known as the Internet, to potential customers. I saw the possibilities early, and when Dilbert stalled in newspaper sales, I suggested moving it to the Internet to generate more exposure, as sort of a backdoor marketing plan. I wanted people to read Dilbert online, then request it in their local newspapers. And that’s what happened. Dilbert was the first syndicated comic to run for free on the Internet, although in the beginning it ran a week behind newspapers. Today it’s hard to imagine that it ever seemed a huge risk to put Dilbert on the Internet for free. There were concerns that piracy would go through the roof (it did) and that newspapers would see the Internet as competition and cancel (none did). In the days when more exposure was a good thing, the piracy helped far more than it hurt.
My early comfort with technology helped me in another big way too. I was the first syndicated cartoonist to include my e-mail address in every strip. E-mail was still a geeky novelty in the early nineties, and some of my business associates worried that client newspapers would consider my e-mail address a form of advertisement. But my business training told me I needed to open a direct channel to my customers and modify my product based on their feedback. That’s exactly what I did,* making it a workplace-focused strip, as readers requested, and from there it took off.
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.
My sixteen years in corporate America added half a dozen other useful skills to the mix as well. I managed people, did contract negotiations, made commercial loans, wrote business plans, designed software, managed projects, developed systems to track performance, contributed to technology strategies, and more. I took company-paid classes in public speaking, time management, managing difficult people, listening, business writing
, and lots of other useful topics. During my corporate career I finished my MBA classes in the evening while working full time. I was a learning machine. If I thought something might someday be useful, I tried to grasp at least the basics. In my cartooning career I’ve used almost every skill I learned in the business world.
Another huge advantage of learning as much as you can in different fields is that the more concepts you understand, the easier it is to learn new ones. Imagine explaining to an extraterrestrial visitor the concept of a horse. It would take some time. If the next thing you tried to explain were the concept of a zebra, the conversation would be shorter. You would simply point out that a zebra is a lot like a horse but with black and white strips. Everything you learn becomes a shortcut for understanding something else.
One of my lifelong practices involves reading about world events every day, sometimes several times a day. Years ago that meant reading a newspaper before work. Now it usually involves reading news aggregator sites on my phone or tablet computer whenever I have a minute or two of downtime. The great thing about reading diverse news from the fields of business, health, science, technology, politics, and more is that you automatically see patterns in the world and develop mental hooks upon which you can hang future knowledge. The formula for knowledge looks something like this:
The Knowledge Formula: The More You Know, the More You Can Know
If your experience of reading the news is that it’s always boring, you’re doing it wrong. The simple entry point for developing a news-reading habit is that you read only the topics that interest you, no matter how trivial they might be. That effectively trains you to enjoy the time you spend reading the news, even if the only thing you look at involves celebrity scandals and sports. In time, your happy experience reading the news will make you want to enjoy it longer. You’ll start sampling topics that wouldn’t have interested you before. At first perhaps you’ll do little more than skim the headlines. But in time you’ll find yourself drawn in. It will feel easy and natural, which is the sign of a good system. If I had suggested starting every morning by reading the hard news in the Wall Street Journal, it would feel daunting for many people, and it’s unlikely you would follow through. A smarter approach is to think of learning as a system in which you continually expose yourself to new topics, primarily the ones you find interesting.
My one caution about reading the news every day is that it can be a huge downer if you pick the wrong topics. Personally, I try to avoid stories involving tragic events and concentrate on the more hopeful topics in science, technology, and business. I don’t ignore bad news, but I don’t dwell on it. The more time you spend exposing yourself to bad news, the more it will weigh on you and sap your energy. I prefer stories about breakthroughs in green technology, even knowing that 99 percent of those stories are pure bullshit. I don’t read the news to find truth, as that would be a foolish waste of time. 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.
CHAPTER TWENTY-ONE
The Math of Success
You can’t directly control luck, but you can move from a game with low odds of success to a game with better odds. 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. I started by asking them to finish my sentence. The sentence was “If you play a slot machine long enough, eventually you will …” The class yelled out in unison “WIN!” As most adults know, that is exactly the wrong answer. Slot machines are engineered to make everyone but the casino a loser in the long run. But kids don’t know that. I presume they confused the benefits of persistence, which is drilled into them as kids, with the actual odds of succeeding.
If you’re reading this book you’re probably an adult, or close to it, and you understand the odds of slot machines. If you play them, you probably think of it as recreation and not investment. But are you equally clear about the odds that rule over other areas of your life?
I’ll give you another example about odds, using my favorite topic: tennis. For a period of about seven years I played tennis once a week with the same friend. He beat me 100 percent of the time. In the early years his wins made sense because his game was stronger in every way. Eventually, my shot making improved to the point where I felt I should have been winning, but I never did. I could get close, but I lost every match during those years. I didn’t feel that I was choking from the psychological pressure, because I typically perform better in stressful situations. My natural optimism always tells me I’m going to pull a rabbit out of the hat and win against all odds no matter how far behind I am. That feeling is so strong in me that the only reason it isn’t classified as mental illness is that it works more often than you’d expect.
So I wasn’t getting psyched out by my losing record, and my strokes were good enough. Why did I lose every match against this particular opponent? I would routinely win against players who seemed about the same level as him. My losing streak was a mystery that dogged me for years. Apparently I had some sort of blind spot about … what? How could I learn to see the thing I couldn’t see? And if I saw it, would it help me win?
My tennis partner and I were good friends off the court, and we chatted a lot about our matches. I was always on the lookout for him to inadvertently spill his tennis secrets. I got little hints here and there as we talked about what was working and what wasn’t on any given day. All of our tennis conversations swirled around in my brain for years until one day the pattern revealed itself.
Some of the most powerful patterns in life are subtle. This tennis pattern was extraordinarily so. The quick explanation is that while I was playing tennis, my opponent was doing math. He was a card counter with a tennis racket. Over the course of several decades of tennis he had learned the odds associated with just about everything that can happen on a tennis court.
Learning the odds in tennis is harder than it looks because so much of it is counterintuitive. For example, when your opponent hits a forehand-to-forehand shot that takes you wide, leaving half of his court unguarded, most amateurs would try for a blistering forehand winner up the line into the open court. That shot was almost always my choice, and I missed it about 80 percent of the time. It turns out that hitting down the line when you’re moving at a right angle to your target is exceptionally challenging for a weekend player. The down-the-line shot works best when you have time to set up and step toward it. Hitting down the line while on the run only feels like it would be easy. The illusion is surprisingly strong. Every time I missed a down-the-line shot I was surprised, no matter how many times in a row I missed the same way. I assumed I would be able to lock in that shot if I just tried it a few more times. I was wrong about that for years.
I could give a dozen more tennis examples where the odds are exactly the opposite of how they feel when you are on the court. And I could give you a dozen examples of how my opponent always played the high-percentage shots while cleverly goading me into one low-percentage shot after another. The point is that while we all think we know the odds in life, there’s a good chance you have some blind spots. Finding those blind spots is a big deal.
In time I learned to avoid the low-percentage tennis shots more often and I won our matches about half the time, exactly as our shot-making skills would predict. So how does any of this help you?
The idea I’m promoting here is that it helps to see the world as math and not magic. It would have been easy for me to assume my tennis losing streak was due to my lacking the will to win. Or perhaps I might have thought my losses were lessons from the Creator of the Universe, who realized I needed help maintaining a socially appropriate level of humility. But no, it was just math.
r /> If you find yourself in a state of continual failure in your personal or business life, you might be blaming it on fate or karma or animal spirits or some other form of magic when the answer is simple math. There’s usually a pattern, but it might be subtle. Don’t stop looking just because you don’t see the pattern in the first seven years.
The future is thoroughly unpredictable when it comes to your profession and your personal life ten years out. The best way to increase your odds of success—in a way that might look like luck to others—is to systematically become good, but not amazing, at the types of skills that work well together and are highly useful for just about any job. This is another example in which viewing the world as math (adding skills together) and not magic allows you to move from a strategy with low odds of success to something better.
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
Psychology
Business writing
Accounting
Design (the basics)
Conversation
Overcoming shyness
Second language
Golf
Proper grammar
Persuasion
Technology (hobby level)
Proper voice technique