Our culture specializes in specialization. But despite popular messaging and our obsession with efficiency, the modern world is not safe for specialists. It is the generalist who will thrive in a world that is unpredictable.

How beneficial is experience? It depends on the domain. In activities like chess or golf, events occur within a predictable framework. In chess, bishops only move diagonally, rooks only move vertically or horizontally, and all pieces move on an eight-by-eight grid. Chess Grandmaster Gary Kasparov says he can see a pattern with every move that his opponent makes. He’s seen comparable combinations thousands of times before. In golf, you always hit a small ball with metallic rods of varying weight and girth, and the golfer always hits the ball short, wide, far, or on the mark.

But what would happen if golfers were suddenly expected to hit bowling balls or pawns could slide around the board as effortlessly as the queen?  Everything that these experts had learned, the skills they’d spent their lives honing and agonizing over, would be useless.

Unfortunately, the messaging in the media does not take this into account. The moral of stories like Tiger Woods and chess grandmasters is that, “If you work hard enough, you can do it, too! And whatever you may love, even if it isn’t chess or golf, you can accomplish comparable feats if you are precocious and tenacious enough!”

But there’s an important distinction to be made between different kinds of activities: there are “kind games” and then there are “wicked games.” In kind games, the rules and expectations remain relatively constant. Variation is great only within a very narrow range of acceptable actions. Chess and golf are kind games. Firefighters and accountants also play kind games, and this shows when something suddenly falls outside the scope of the experience. What happens when a fire chief who can competently give orders for two-story houses gets a call about a skyscraper on fire? Seasoned accountants who are given new tax laws to integrate into their process tend to do worse than amateur accountants.

There are kind games, and then there are wicked games. In wicked games, the rules are incomplete, imprecise, or subject to change. The feedback is not statistically predictable. Experience can end up reinforcing the wrong lessons. A status quo altered just slightly can topple the specialist’s “expertise.” Rice University professor Erik Dane refers to this as “cognitive entrenchment.” Using golf and chess as analogs for life more generally is a comforting thought because it contains the neatness and simplicity of a kind-game learning environment—but that’s not the world we live in. Real life is much more of a “wicked game.”

Psychologist Robin Hogarth developed the distinction of “kind” and “wicked” learning environments. Kind environments, like golf and chess, operate with tremendous statistical regularity. Each game is different, but the games are conducted within predictable, well-defined parameters. Wicked learning environments lack the predictability, because the rules can be unclear, incomplete, and mutable. The world we live in has, in this sense, become increasingly wicked. But how did the world become so?

In 1981, a New Zealander named James Flynn discovered a remarkable phenomenon that changed psychology forever. The Flynn Effect, as it came to be known, is the well-documented phenomenon of IQ rising by about three points every decade of the twentieth century. This occurrence is not unique to a particular country or continent. The results have been consistent in the 30 countries where it’s been tested: particularly the ability to abstract has improved dramatically. Someone today with an average IQ would be in the 98th percentile 100 years ago.

The Ebbinghaus Illusion suffuses another example of the change that modernity has brought to society’s thinking. This illusion consists of two congruent circles, each surrounded by circles arranged in a circular pattern. The circle on the left is surrounded by a ring of circles larger than itself. A ring of circles also surrounds the second circle, to the right, but the surrounding circles are smaller and closer to the circle at the center. When asked which of the two center circles was bigger, subjects from a modern industrialized background almost always think the circle on the right, surrounded by smaller circles is bigger. What’s remarkable is that when the same pictures are shown to people in remote villages, they are able to tell that the two center circles are exactly the same size.

It seems that people who are touched by modernity are more apt to consider holistic contexts and develop abstract categories. Premoderns see the trees. Moderns see a forest. Even in remote regions of the world, researchers found that people who had some kind of exposure to modern institutions were able to conceive of the world in more abstract terms. They weren’t entirely tied to the concrete for knowledge of the world.

We have failed to realize just how comfortable we’ve become with abstraction or what a gift it is. For instance, take the word “percent.” The word was used in almost zero percent of the  literature we have from the year 1900. But a century later, every 5,000th word was “percent,” and it’s a concept that most people comfortably grasp. We think in terms of such concepts, and can even hold multiple layers of concepts together. It helps us handle complexity more competently and has made us more flexible—if only we would make the most of it!

There’s no need to make a judgment as to whether the premodern or modern skill set is better. As one Arab sociologist observed, a city dweller attempting to traverse a desert would be utterly dependent upon a nomad. In such a setting, it is the nomad who is the genius. But in the modern world, a different skill set is required. Villagers learn from experience, but they cannot learn without experience at the base. We don’t have that luxury in a wicked world that is in constant flux. We have to learn without experience. Kind learning environments like the chessboard or a golf green simply aren’t representative of what we encounter in our lives.

Can we connect new ideas and maneuver comfortably between different contexts? The more statistically predictable and repetitive a task, the more likely it is to become automated. This is true of not just blue collar work, as theorists used to predict. Plenty of white collar jobs are also vulnerable to a machine’s breathtaking efficiency. It is people capable of exercising the kind of creativity and insight that machines can’t replicate who will thrive in a wicked world.

The world of specialization assumes that it’s vital to get a head start and specify early. But there are plenty of people who take circuitous paths to the vocation where they find greatest success and fulfillment.

Grit isn’t everything. There’s something to be said for sticking with a task, but dropping one  undertaking in pursuit of something more captivating isn’t necessarily a bad thing either. Angela Duckworth, a UPenn social psychologist and author of the bestseller Grit, found that West Point’s method of predicting who would graduate and who would quit during boot camp was ineffective. But her questionnaire about grit, a combination of passion and perseverance, anticipated who would make it more accurately.

But here’s the problem with the grit model: the underlying assumption is that the West Point students who dropped out were deficient, that the gritty cadets were the successful ones and the quitters were not—or at least less so. But this is not necessarily the case. Maybe those who quit West Point’s boot camp were not cut out for military-style discipline, but that doesn’t mean they will be less successful either. There is value to perseverance, but there’s also tremendous value to taking a more meandering road, being willing to experiment in different fields, and being ready to drop something if it doesn’t “click.”

Charles Darwin quit halfway through medical school, and was going to default to becoming a clergyman, but took a gap year of sorts when he joined the expedition aboard the Americas-bound HMS Beagle. It was a decision that led to his becoming one of the most influential scientists of all time. Michael Crichton made it through medical school at Harvard, but he decided he didn’t want to be a doctor shortly after graduating. His exposure to the medical world, however, was far from wasted: He became a writer, and his medical background inspired bestselling novels like Jurassic Park and his screenwriting for the wildly successful television drama series ER.

Flirt with your possible selves. Try them on and see how they fit. There’s no need to lock yourself into a path and see it through to the end, especially if it no longer fits you well or makes you come alive. Career choices which seem to be a perfect fit at the time may eventually seem crazy in the light of further experiences.

Neurologist Ogi Ogas at Harvard’s Mind, Brain, and Education Program says that most people commit to the “standardized covenant,” the deep-seated cultural assumption that the most rational thing to do is follow a clear career path, and the earlier the better. What she found as she researched people who were fulfilled and successful in their fields, was that not just a handful, but almost every person interviewed had taken a roundabout journey to the career where they fit best. What is more, they felt some chagrin as they detailed the frequent leaps they made over the years. They felt their path had been unconventional, that they were dark horses of sorts. But here’s the truth: that’s how it happens for the majority of the successful and fulfilled.

Studies reveal people’s tendency to believe they have changed a great deal over the past decade, but they will not likely change much more now. We’re works in progress claiming to be completed. Psychologist Dan Gilbert describes this as “the end of history illusion.” The fact is that we change plenty—and not just through our twenties, but throughout our lives, often quite suddenly.

A twenty-year study has shown that short- and long-term “expert” predictions were often horribly inaccurate. The researcher who spearheaded the project was a psychologist and political scientist named Philip Tetlock. After observing experts insisting on diametrically opposed viewpoints, he collected a variety of forecasts from almost 300 scholars—most of whom had PhDs. The predictions covered topics as diverse as economics and international relations. Telock accrued about 82,000 predictions, and the results revealed that we live in a pretty wicked world.

For all their relevant experience, degrees, accolades, and even access to pertinent classified documents, the experts were usually abysmal at predicting outcomes. This led Tetlock to test whether generalists fared better than specialists at forecasting. Borrowing the language of philosopher Isaiah Berlin, Tetlock distinguished between hedgehogs (the “experts” who bore deeply into one specific subject) and foxes (the integrators who know a lot of smaller things), pitting them against each other to see which group made more accurate predictions. In what became known as the Good Judgment Project, he recruited a team of foxes (bright volunteers with wide-ranging interests and reading preferences, but not experts in relevant fields) to see if they could forecast better than teams of hedgehogs tucked away in ivory towers.

At forecasting competitions, teams of foxes demolished their hedgehog competition. The margins of victory were embarrassingly large—about 30 percent more accurate. Smart volunteers from the general public did better than trained intelligence analysts.

Hedgehogs obsessively worked towards a solution, but their constructions of the problem were often poorly defined. Outcomes were not important for hedgehogs; whatever the results of experiments, they would downplay inaccurate forecasts and exalt when their predictions were correct. Their long-term predictions were especially wide of the mark. Their predictions actually became less accurate the more degrees and accolades they’d collected. Here again, experience appears to be overrated, as too much of it in a specific area hinders many people from honestly admitting their ideas have been proven wrong.  Hedgehogs tended not to adjust their views much in the face of compelling counterevidence. Some even tweaked their views the wrong way, doubling down on their misguided beliefs.

In contrast to the hedgehogs, the foxes were much more likely to adjust their beliefs in the face   of evidence to the contrary. The best judges and predictors were the ones who would honestly update their views. Some might refer to this process as “learning.” There are unexpected perks to being an outsider. It seems the outsider is often a better learner and more adaptable than an expert.

We live in a culture that worships efficiency. This has led us to assume that hyperspecialization is the way to go. We look for the most efficient path and try to pursue it. It’s a well-intentioned, understandable urge, but we need to cultivate inefficiency, too.

Pushing boundaries and trying new things means probing, and probing is necessarily an inefficient process. Commit to being a deliberate amateur, and your posture will become that of a learner. This will free you up to dabble and quickly pivot as you need to.

Historian Arnold Toynbee reminds us that there’s no master key that unlocks all doors. The more keys you have, the more likely you are to find hidden connections between domains that experts are missing.