The Opponent Within

The following text is the (slightly shortened) introduction from Katy Milkman’s 2021 bestseller How to Change: The Science of Getting from Where You Are to Where You Want to Be.

Her work is full of fascinating and highly relevant ideas on how to confront our toughest opponent: ourselves—and our resistance to change, even when it stands between us and the goals we long to achieve.

Milkman’s research and insights will therefore play a central role in our workshop on November 1st. I’ve highlighted a few sentences that are especially relevant for our discussion—so that you, too, can become the Andre Agassi of the German language!

How to Change

“It was early 1994 and Andre Agassi’s tennis career was veering dangerously off track. All his life, Agassi had been assured he would go down in history as one of the greats of his sport. When he turned pro at age sixteen in 1986, pundits lauded him for his natural talent, impressed by his uncanny ability to take control of points and his gift for hitting seemingly impossible shots on defense. But by 1994 it wasn’t a stellar record on the court that had won Agassi fame—it was his style. In a sport known for decorum, Agassi wore ripped jeans and tie-dyed shirts to tournaments. He grew his hair long and sported an earring. He cursed like a sailor on the court. He even starred in a splashy ad campaign for Canon with the provocative slogan “Image Is Everything.”

When it came to tennis, though, Agassi was falling laughably short of expectations. He too often lost early in tournaments to players with far less skill—a first-round flameout at a small tune-up in Germany, a third-round defeat at a Grand Slam. His ranking kept slipping, from seventh in the world to twenty-second, then to thirty-first. Agassi’s coach of ten years had recently and unceremoniously dropped him; Agassi learned the news while reading USA Today. He’d taken to telling people he hated tennis.

Agassi needed a change.

Which is why he found himself eating dinner one evening at Porto Cervo, a favorite restaurant of his near Miami, across from Brad Gilbert, a fellow pro tennis player. Gilbert’s approach to tennis was the polar opposite of Agassi’s: fastidious, methodical, and inelegant. He lacked Agassi’s obvious gift for the game. And yet Gilbert, then thirty-two years old, had been ranked among the world’s top twenty players for years, even reaching number four in 1990, much to the surprise of tennis aficionados. Just a few months before the dinner with Agassi, Gilbert had detailed his unusual approach to tennis in an instant bestseller called Winning Ugly.

It was Winning Ugly that had prompted the dinner. After reading the book, Agassi’s manager had encouraged his struggling client to talk with Gilbert. Agassi needed a new coach, and his manager had a hunch that Gilbert, who was old enough to consider retiring from the pro tour, might be the person who could turn Agassi’s career around. Agassi had agreed to the meeting, but as he would later recount in his brilliant 2009 autobiography, Open, he was skeptical. Gilbert was known for his peculiarities, both on and off the court, and as the dinner unfolded, he only added to Agassi’s uncertainty. First, Gilbert refused an outdoor seat with an ocean view (citing a mosquito phobia). Then, upon discovering his favorite beer wasn’t on the menu, he dashed to a nearby market to pick up a six-pack and insisted it be stored on ice in the restaurant’s freezer.

It took a while for the group to get settled but when they finally did, Agassi’s manager opened with a question for Gilbert. What, he asked, did Gilbert think of his client’s game? Gilbert took a long swig of his drink and swallowed slowly. He didn’t mince words. If he had Agassi’s skills and talent, he replied, he’d be dominating the pro tour. As he saw it, Agassi was misusing his gifts: “You try to hit a winner on every ball,” he said. It was a serious shortcoming. No one can hit an outright winner on every shot, Gilbert pointed out, and trying to do so was eroding Agassi’s confidence bit by bit each time he fell short. Having played against (and beaten) Agassi many times, Gilbert had witnessed this pattern firsthand.

Agassi could see the wisdom in this assessment. He’d always been a perfectionist, but until Gilbert’s remarks, he’d viewed that trait as a strength rather than a weakness. Growing up, he’d learned to go for the kill from his father, an Olympic boxer who was perpetually hunting for the knockout blow—the one punch that would vanquish his opponent. During training sessions on the homemade court in their backyard, the Olympian had echoed the advice of his former boxing coach. “Hit harder!” he’d yell at his five-year-old son. “Hit earlier!” Agassi had long considered his exceptional ability to hit knockout shots an advantage. Gilbert was saying it was his Achilles’ heel.

To win, Gilbert continued, Agassi needed to shift his focus. “Stop thinking about yourself,” he admonished, “and remember that the guy on the other side of the net has weaknesses.” It was Gilbert’s uncanny ability to size up his opponents that allowed him to beat far better players. He didn’t try for a knockout to claim each point; he found a strategy that eased that burden. “Instead of you succeeding,” Gilbert said, “make him fail. Better yet, let him fail.”

Because Agassi was looking to hit a perfect shot every time, Gilbert explained, he was “stacking the odds against” himself and “assuming too much risk.”

Gilbert’s message was simple: the self-focused approach to tennis on which Agassi had built his career was not the best approach—not if he wanted to win. There was a better way—one that required sizing up the competition and tailoring his game to capitalize on his opponents’ weaknesses. It might be a less dazzling style of tennis than Agassi was used to playing, but it would be more effective.

Fifteen minutes into the conversation, Gilbert got up to use the restroom. Agassi immediately turned to his manager. “That’s our guy,” he said.

A few months later, Agassi entered the U.S. Open unseeded—he wasn’t even expected to crack the top sixteen. But with Gilbert’s coaching, his style had changed. He faced an old rival early on—the tournament’s sixth seed, Michael Chang—and remained unshaken in a nail-biter, holding on to the win by the thinnest of margins. He took out the ninth seed with ease, recognizing his opponent’s “tell”—a tendency to look at the spot where he planned to hit his serves—and exploiting that weakness.

And, suddenly, Agassi had reached the finals. There was 550,000 dollars in prize money on the line, but far more in pride. It was Agassi’s chance to prove himself—to show everyone that he could live up to the hype after all.

His opponent was Michael Stich, a German champion and the tournament’s number four seed. Agassi came out strong, hitting crisp, clean balls on point after point. He won the first set handily, then eked out the second set in a tiebreaker. But Stich wasn’t ready to fold. In the third set he hung with Agassi on long rallies and made him work for every point; eventually, the set was tied at five games apiece. The most direct path to victory would require Agassi to break serve, which meant besting Stich when he had the advantage of beginning each point.

Agassi’s confidence began to waver. Stich wasn’t giving up—he kept blasting powerful serves, one after another. But then Agassi noticed Stich gripping his side, the telltale sign of a cramp, and saw his opening. He broke Stich’s serve. He was four points away from winning his first U.S. Open Championship—the sweetest of possible victories for a struggling onetime phenom whom the oddsmakers had counted out.

Before hiring Gilbert, Agassi was notorious for falling apart in high-pressure matches. He went for too many knockouts, took too many risks, and blew it when he should have held steady. But now Agassi stayed focused. Instead of going for winners, he concentrated on keeping the ball in play. He could hear Gilbert’s voice in his head: “Go for his forehand. When in doubt, forehand, forehand, forehand.” And he stayed on task. He hit the ball over and over again to Stich’s forehand, his feeblest shot. And on match point, Stich missed.

The tournament was over. Agassi fell to his knees with tears in his eyes. He was the first unseeded player to take home a U.S. Open trophy in twenty-eight years. He’d made history.

• • •

If you’ve ever tried to make a big change to your life—to accomplish more at work or in school, to get in shape for a marathon, to build a nest egg for retirement—then you know there’s a lot of advice out there about how to succeed. In fact, you’ve probably tried acting on some of it. Maybe you’ve tracked your steps with a Fitbit or set calendar reminders on your phone to practice deep-breathing exercises on your lunch break. Perhaps you’ve cut out your afternoon coffee habit, putting the money you would have spent at the café into a savings account. You know your goals should be specific and measurable. You know the power of positive thinking and incremental progress. You know it’s helpful to have a support group.

Thanks to a booming popular interest in behavioral science, the last two decades have seen an explosion of new research and information—TED talks, books, workshops, apps—about practical tools that can help you change your behavior and encourage others to do the same.

But, as you’ve likely noticed, widely touted techniques don’t always help you, or others, change. You forget to take your medication again, in spite of downloading that goal-setting app to help. You procrastinate on that big quarterly report for your boss in spite of setting daily reminders to work on it. Your employees don’t take advantage of company-sponsored educational programs or retirement benefits even when they’re offered rewards for signing up.

Why is it that these tools and techniques designed to spur change so often fail? One answer is that change is hard. But a more useful answer is that you haven’t found the right strategy. Just as Andre Agassi spent years falling short of his potential by playing tennis with the wrong approach, we often fail by applying the wrong tactics in our attempts at change. Like Agassi, we search for solutions that will deliver the quick knockout victory and tend to ignore the specific nature of our adversary.

But to give yourself the best chance at success, it’s critical to size up your opponent and develop a strategy tailored to overcome the particular challenges you face. The surest path to success is not one-size-fits-all. Instead, you must match your approach to your opponent.

In tennis, there’s a generic playbook that works reasonably well: hit hard serves; run your opponent side to side; get to the net whenever you can. It’s not a bad strategy. But if you’re a really good tactician, like Gilbert, you’ll take advantage of the fact that specific opponents have specific weaknesses. Maybe the player you’re facing can’t handle a low slice to the backhand side. You can torture them with that shot again and again and winning will be far easier.

Behavior change is similar. You can use an all-purpose strategy that works well on average. Set tough goals and break them down into component steps. Visualize success. Work to create habits—tiny ones, atomic ones, keystone ones—following the advice laid out in self-help bestsellers. But you’ll get further faster if you customize your strategy: isolate the weakness preventing progress, and then pounce.

As an undergraduate and later as a PhD student in engineering, I was deeply bothered by the pesky human problems my friends and I couldn’t seem to avoid. Why did I find it so hard to stop watching Lost and study for my tests? Why couldn’t I get myself to go to the gym more regularly? Why did my roommates always put off homework until the last minute and eat Lucky Charms and Frosted Flakes for every meal? As an engineer who spent much of her time solving more technical problems, I was certain there must be a way to overcome these human struggles.

Then one day, during a required graduate course on microeconomics, I was introduced to behavioral economics—an entire field devoted to understanding, with analytical rigor and empirical depth, when and why people make flawed decisions. I was particularly taken with the idea of “nudging” people toward better choices, which was gaining popularity around the time I started my PhD. The founders of the “nudge movement,” scholars Cass Sunstein and Richard Thaler, argued that because humans make predictably imperfect decisions, managers and policy makers can and should help them avoid common mistakes. The idea was that by nudging people toward objectively better choices (say, by putting healthy foods at eye level in the cafeteria or by simplifying the paperwork necessary to apply for government aid), you could improve their lives at little to no cost without restricting their freedom.

Suddenly, I realized it might be possible to develop nudges to tackle familiar problems, such as binge-watching Lost or failing to exercise. So I jumped on the nudge bandwagon, exploring how to nudge both myself and others into healthier choices and better financial decisions. Soon I was a gym regular and Lost marathons were in my rearview mirror.

But my interest in the power of nudging took on a new urgency a few years later when, as a newly minted assistant professor at Wharton, I was confronted with strong evidence that our small, daily failures to exercise or eat healthfully aren’t trifling human foibles, but rather are serious matters of life and death. During an otherwise dull academic presentation, I encountered a pie chart that’s been burned into my mind’s eye ever since. The chart broke down why most Americans die earlier than they should. It turns out that the leading cause of premature death isn’t poor health care, difficult social circumstances, bad genes, or environmental toxins. Instead, an estimated 40 percent of premature deaths are the result of personal behaviors we can change. I’m talking about daily, seemingly small decisions about eating, drinking, exercise, smoking, sex, and vehicle safety. These decisions add up, producing hundreds of thousands of fatal cancers, heart attacks, and accidents each year.

I was floored. I sat up a little straighter and thought, “Maybe I can do something about that forty percent.”

And it was more than matters of life and death that grabbed my attention. While I’ve never seen a pie chart dissecting how our daily decisions affect our prosperity and our happiness, it stands to reason that our missteps accumulate in those areas of life, too.

Eager to make a difference, I shifted my focus and devoted nearly all of my waking hours to poring over research papers—old and new—exploring the science of behavior change. I talked with dozens of scholars from diverse disciplines about their most successful ideas, as well as their failed studies. And I worked with small start-ups as well as industry giants, such as Walmart and Google, to develop tools for nudging better decisions. As I tried to make sense of what worked well and what didn’t, I began to see a consistent pattern. When policy makers, organizations, or scientists applied a one-size-fits-all strategy to change behavior, the results were mixed. But when they began by asking what stood in the way of progress—say, why their employees weren’t saving enough money or getting flu shots—and then developed targeted strategies to change behavior, the results were far better.

Of course, when it comes to changing your behavior, your opponent isn’t facing you across the net. Your opponent is inside your head. Maybe it’s forgetfulness, or a lack of confidence, or laziness, or the tendency to succumb to temptation. Whatever the challenge, the best tacticians size up their opponent and play accordingly.

This book is intended to help you do exactly that. It takes Gilbert’s winning strategy and applies it to behavior change. The chapters ahead show you how to identify your adversary, understand how that adversary tries to thwart your progress, and apply scientifically proven techniques that are tailor-made to vanquish it. Each chapter focuses on an internal obstacle that stands between you and success. By the time you’re finished reading, you’ll know how to recognize these obstacles and what can help you overcome them.

By using these tools consistently, my hope is that you’ll see small changes accumulate into big results. This is the approach that helped Andre Agassi turn his career around. He applied Brad Gilbert’s philosophy one match at a time, using specifically tailored strategies to defeat each opponent in his path. And the wins added up. Soon after Agassi’s surprise victory at the 1994 U.S. Open, he captured the number one world ranking, a title he would go on to hold for 101 weeks over the course of his now legendary career.”