When Dillon Hill was in the fifth grade, his friend Chris was diagnosed with cancer and had to spend months in the hospital. Dillon would visit every day, bringing their favorite video games, because Dillon knew they would make his friend smile. Chris’ story ends well: He eventually recovered.

Fast forward to Dillon’s senior year in high school. Dillon was volunteering at a food shelter and feeling dissatisfied with the experience. He wanted to see the people whose lives he was impacting, but spent all his time packing bags in the back. “Obviously all these things, they help,” Dillon said, “but it just wasn’t rewarding.” Dillon’s mind went back to the video games he had brought to his friend Chris’ hospital bed, and that led him to start the charity that eventually came to be called Gamers Gift, bringing virtual reality headsets to children’s hospitals, assisted living facilities, and people with disabilities.

Now, setting up a 501(c) nonprofit isn’t simple, and until recently the only way to get it done was to work with a high-priced attorney. But Dillon filed all the paperwork himself. In his words: “I think we probably Googled every single line on the tax paperwork because we had no idea what a lot of it meant. But I mean, we have the Internet, you know? We can figure out anything.”¹³⁹

As inspiring as the actual work and impact of Gamers Gift is, let’s focus on the process by which Dillon created it. For a teenager to figure out the legalities of setting up a not-for-profit entity by applying sheer tenacity and a little help from Google is impressive. At the same time, for those who work in specialized fields where much of the work depends on knowledge that most people don’t have, it is deeply concerning. The rigorous education required to gain entry to the field of law was once a golden ticket to a secure and prosperous life, and the same is true for other white-collar professions like accounting, banking, engineering, and more. Just completing this challenging and expensive training (and passing the associated professional requirements, like lawyers taking the bar exam) was enough to guarantee a job for those who could make the cut. As the old joke goes, “What do you call the person who graduates at the bottom of his class at medical school? Doctor!”

But Dillon Hill’s experience is just one of many points of proof for George Couros’ pointed statement in his book The Innovator’s Mindset: “Information is abundant; it’s common.”¹⁴⁰ And as anyone with any economics training can tell you (or you can Google for yourself!), the laws of supply and demand dictate that there is a direct trade-off between abundance and value. This is a big problem for many industries, and the most vulnerable sectors may not be the ones you’d expect.

There was a time when the jobs that were most vulnerable to automation and outsourcing were menial and repetitive. In the early days of technological automation (and indeed, the Industrial Revolution!), there was a lot of low-hanging fruit in the form of jobs that relatively simple technology could automate or accelerate (like bank tellers replaced by ATM machines, receptionists replaced by phone tree systems, and electronic buttons replacing Aldous Huxley’s elevator operator), or allow us to ship offshore (like the shipping and communications that make it feasible for so much of what we buy to be manufactured in China).

These days, most of that low-hanging fruit has already been picked, and the fruit on the higher branches is much harder to reach. Further automation of physical work often will take robotics that are much more sophisticated and expensive¹⁴¹—so much so that in many cases, it makes sense for businesses to stick with flesh-and-blood employees.

But there’s a different kind of low-hanging fruit to be had: the jobs that are less about doing and more about knowing and relatively rudimentary thinking (both tasks that computers are already much better, faster, and more reliable at than we are). The knowing jobs are being eliminated by disintermediation (like real estate or travel agents who are slowly becoming an endangered species now that we can look up listings and itineraries on our own), and the simple thinking jobs are being eliminated by automation through artificial intelligence (like bookkeepers being replaced by QuickBooks and Bench, accountants by TurboTax, and legal researchers by document-reading artificial intelligence).¹⁴² As economist Paul Krugman writes:

…The idea that modern technology eliminates only menial jobs, that well-educated workers are clear winners, may dominate popular discussion, but it’s actually decades out of date. The fact is that since 1990 or so the U.S. job market has been characterized not by a general rise in the demand for skill, but by ‘hollowing out’: both high-wage and low-wage employment have grown rapidly, but medium-wage jobs—the kinds of jobs we count on to support a strong middle class—have lagged behind.¹⁴³

Along with Henry Ford, Alfred P. Sloan is one of the founding titans of the American automotive industry. He led General Motors through the Great Depression, German rearmament, fascism, appeasement, and World War II, eventually growing GM into the world’s largest corporation. His 1950s memoir, My Years with General Motors, is a seminal text in the field of modern management education, and business leaders continue to study the lessons that he taught and the anecdotes that give a glimpse into his management philosophies and ways of thinking. One such anecdote is recounted by brothers Chip and Dan Heath in their book Decisive:

Alfred Sloan, the longtime CEO and chairman of General Motors, once interrupted a committee meeting with a question: ‘Gentlemen I take it we are all in complete agreement on this decision here?” All the committee members nodded. “Then,” Sloan said, “I propose we postpone further discussion of this matter until our next meeting to give ourselves time to develop disagreement and perhaps gain some understanding of what this decision is about.”¹⁴⁹

Wise leaders through the years have echoed Sloan in their insistence that they prefer employees with the backbone to challenge them and disagree. William Wrigley Jr., who built the chewing gum company that bears his name, famously said, “When two men always agree, one of them is unnecessary.”¹⁵⁰ This idea needs constant reinforcement because of the multitude of reasons why voicing disagreement is difficult, especially to people in positions of authority. Challenges range from the fear of real or imagined repercussions, to the simple awkwardness of conflict, and everything in between.

There’s a simple prerequisite to voicing disagreement that doesn’t get nearly as much attention: In order to disagree, you need an insight that hasn’t already been voiced. That insight is a key ingredient to meaningful impact and success, which is the thinking behind investor Peter Thiel’s now-famous challenge to entrepreneurs: “Tell me something that’s true that nobody agrees with.”¹⁵¹ This is true beyond the realm of Silicon Valley entrepreneurs; across the board, the most successful participants in the modern table stakes for success, as neuropsychologist Elkhonon Goldberg argues in his book Creativity:

In our time, much of the knowledge acquired in graduate school ten years ago is obsolete today. Most of us don’t share an intrinsic interest in science or technology, but even as consumers of technology, we will inhabit a world where tomorrow will be unrecognizably different from today, and our brains will be increasingly challenged by novelty whether we like it or not.¹⁵²

Novelty is the watchword here. Insight necessarily means coming up with something that hasn’t already existed: an idea, a connection, or a perspective. Coming up with that sort of novelty, and navigating it effectively, is what it takes to thrive in such a rapidly changing world. But how do we develop insights that are unique, novel, and valuable? Insight isn’t just a higher level of knowledge or skill. There’s a massive difference between knowing a fact, a procedure, or even a complex process, and being able to provide insight into a challenging, ill-defined problem.

So where do we develop this sort of insight? How do we find what’s true that nobody else agrees with? A glaring flaw of most current approaches to education is that they focus entirely on imparting knowledge or fostering proficiency in certain skills. The ability to develop insight is left unexamined. It’s often treated as a mysterious, almost magical trait. Sure, we can see and celebrate the outcomes—the insights that lead to new products, solutions, or ways of thinking—but the capacity for insight is imagined to be something you either have or lack.

Except that the research and data show that this simply isn’t true. Insight lives at the intersection of two rarefied abilities: critical thinking and creativity. Although the current education system does a horrendous job of teaching these things—in fact, strong arguments can be made that conventional education makes you worse at these rather than better—the fact is that we do know what it takes to develop them.

Getting stopped at airports is usually a bad thing, but there are exceptions, as American rapper Armando Christian Pérez discovered in 2010. Walking through airports on his way to catch a flight, he would be stopped repeatedly by passers-by wearing T-shirts that said “Zumba.” Calling him by his stage name Pitbull, they wanted to tell him that his song Calle Ocho (“I Know You Want Me”) was one of their favorites. After this happened a few times, Pitbull picked up the phone and called the owners of Zumba Fitness. “You guys are like a radio station,” he said, “with DJs in gyms around the world.”

Let’s pause the story for a moment. What do you imagine the next words out of Pitbull’s mouth would be? Certainly, given the modern climate of legitimate concerns of artists and record labels about piracy and copyright infringement, you might expect something along the lines of “You’re playing my songs without permission, and you have to pay me.” But Pitbull deserves far more credit. When he learned about Zumba playing his song, his mind went to a different problem facing artists: breaking new music to the public.

In the music business, “breaking a new record” refers to the up-front investment that must be made in getting new music enough play time and exposure for audiences to start asking for it. This is critical to the promotion of new music, particularly from lesser-known artists, because research by American psychologist Robert Zajonc has shown that familiarity breeds fondness rather than contempt. Sometimes referred to as the “familiarity principle” or the “mere exposure effect,” the basic idea is that the more times we’re exposed to a person, idea, or song, the more we tend to like it.¹⁵³ That’s why a rule of thumb in the music industry is to budget $50,000 for the first three months of marketing a new song.¹⁵⁴

Unpausing the story, Pitbull continues, “I think you can break records. I’ll give you my songs as soon as they launch, and you put them in your Zumba classes.” This strategy apparently worked well for Pitbull, whose next album included his first number-one single in the United States. Other musicians took note, and now major artists like Wyclef, Daddy Yankee, Shaggy, and Timbaland work with Zumba to get their songs into one of the thirteen coveted monthly spots that will be played repeatedly to more than fifteen million people each week.¹⁵⁵

Pitbull’s insight illustrates an important realization: We like to believe that we make the best decisions we can with the information that we have, but that isn’t true. In fact, we make the best decisions we can with the inferences that we draw from the information that we have. The ability to solve complex problems by drawing better inferences and thinking critically is exactly what a 2013 study showed that 93 percent of employers value over an undergraduate degree.¹⁵⁶

How to Develop Critical Thinking

Let’s explore what it takes to develop critical thinking. For that matter, what is critical thinking anyway? The term has become so widely used that it is arguably a bit clichéd. Looking deeper, though, we discover a powerful and nuanced concept. According to the Foundation for Critical Thinking (emphasis added):

Critical thinking is that mode of thinking—about any subject, content, or problem—in which the thinker improves the quality of his or her thinking by skillfully analyzing, assessing, and reconstructing it… thinking that explicitly aims at well-founded judgment and hence utilizes appropriate evaluative standards in the attempt to determine the true worth, merit, or value of something… The critical thinking tradition seeks ways of understanding the mind and then training the intellect so that such ‘errors’, ‘blunders’, and ‘distortions’ of thought are minimized. It assumes that the capacity of humans for good reasoning can be nurtured and developed by an educational process aimed directly at that end.¹⁵⁷

Critical thinking is traditionally taught through repetition and osmosis; if you practice enough and spend enough time in the right environment, those vaunted critical thinking skills will eventually and magically appear. This argument is found most often in the context of the liberal arts—just learn enough different things, and critical thinking skills will automagically appear. But the data show that it doesn’t work that way. As Joseph Aoun writes:

In their 2011 study, Academically Adrift: Limited Learning on College Campuses, professors Richard Arum and Josipa Roksa found that at least 45 percent of the undergraduates they surveyed showed “exceedingly small or empirically nonexistent” gains in critical thinking, complex reasoning, and written communication during their first two years in college. After four years, 36 percent of their sample still showed no improvement at all: “They might graduate, but they are failing to develop the higher-order cognitive skills that is widely assume college students should master.”¹⁵⁸

Another, ostensibly more directive example is the case method which many business schools have adopted from Harvard Business School. Students review hundreds of case studies of different business scenarios over the course of their degree program. It’s an incredibly time-consuming method even when it does work. Unfortunately, for many students, it leads to a kind of brainwashing rather than the restless, independent, critical thinking necessary for deeper insight. Investigative journalist Duff McDonald argues that “[Harvard Business] School is telling [MBA students reviewing cases] what to think, whether they realize that they’re doing it or not.”¹⁵⁹ He explains:

Most business schools are adept at the teaching of so-called respondent behavior—solving problems that have already been identified and using facts gathered by someone else. But the sniffing out and exploiting of opportunity is another thing entirely—“operant behavior”—and that’s something that can really only be learned by doing.¹⁶⁰

Clearly we need a better approach to help people develop these skills.

Critical Thinking in 7 Easy Steps

We can start by decomposing the broad concept of critical thinking into specific techniques and developing ways to introduce those techniques. For example, the Minerva Schools have developed a new college-level curriculum with a strong focus on seven steps in the process of critical thinking:

1. Evaluating claims: One must evaluate the background assumptions as well as the logic that underlies the claim.
2. Analyzing inferences: Even if a claim is correct, the inferences one is invited to make from it may not be. Formal logic provides a method for determining which inferences are valid and which are not.
3. Weighing decisions: Evaluating claims and analyzing inferences are important in part because they help us decide how to act. To make decisions rationally, one must analyze the various choices and identify their respective trade-offs.
4. Analyzing problems: Being able to characterize the nature of the problem.
5. Facilitating discovery: There are no recipes or rules for how to make discoveries; however, certain heuristics can set the stage, facilitating discovery. These practices include the ability to create well-formed hypotheses, predictions and interpretations of data.
6. Solving problems: One must use creative thinking to solve a problem.
7. Creating products, processes, and services: Techniques including iterative design thinking, reverse engineering, and application of the principles of perception and cognition can help to create new products, processes, and services.¹⁶¹

Learners who are specifically challenged to evaluate claims, analyze inferences, weigh decisions, and so on, will develop far greater capacity for critical thinking. This, in turn, will make it possible for them to begin developing unique insights in specific situations. Conversely, failure to do so will do nothing more than continue to churn out what former Yale professor William Deresiewicz calls “excellent sheep,” which is antithetical to both critical thinking and its sister skill of creativity.

In his 2005 Stanford University commencement speech, Apple co-founder Steve Jobs famously told the graduating class and the world about how dropping in on monk Robert Palladino’s calligraphy class at Reed College in Oregon was the creative spark that led to beautiful typography on Mac computers.¹⁶² It’s a captivating bit of history, with inspiring lessons about following your interests wherever they take you, because you never know when something you learn might end up being useful in the last place you expect.

It isn’t a lesson in creativity or how to develop it; if it were that easy, we’d all enroll in calligraphy courses and go on to launch blockbuster electronics products. Alas, creativity isn’t so easily developed or even understood. Like critical thinking, the notion of creativity often is seen as mysterious and ineffable. What is the invisible spark that allows artists to create beauty from raw materials, or scientists to discover deep patterns in the structure of the universe, or industrial designers to create products that operate in delightful harmony with our hands?

Creativity is neither just about art, nor limited to geniuses with ground-breaking ideas. Creativity is for everyone, and its applications can be as diverse as making things, finding unique solutions, hacking systems, exploiting patterns, curating information, designing systems, leading movements, and creating changes.¹⁶³

Components of Creativity

How do we do it? What are the components of that ever-so-elusive skill of creativity? A great many ingredients collaborate in the creative process, as described by Elkhonon Goldberg in Creativity:

• Salience: The ability to pose central problems and to ask important questions.
• Novelty: An interest in and ability to find solutions for problems not tackled before. It is intellectual nonconformity, the ability to distance oneself from the established scientific theories and concepts, or artistic forms.
• Ability to relate old knowledge to new problems: The opposite of novelty, this is the ability to recognize familiar patterns in seemingly new and unique problems.
• Generativity and mental flexibility: The ability to generate multiple and diverse approaches to a problem is essential to the creative process in science. A scientist would be exceptionally lucky to hit upon the solution of a daunting problem from the first go.
• Drive and doggedness: In a sense, the opposite of the previous, an ability to deploy sustained effort toward tackling a problem. This is about the relationship between inspiration and perspiration.
• Mental wandering: The mysterious capacity for the productive and seemingly effortless pursuit of ideas wherever they take you.
• Mental focus: The opposite of mental wandering, this is an ability to systemically pursue a logical train of thought.
• Iconoclastic frame of mind: In order to forge ahead of society, a creative individual must be driven by a sense of dissatisfaction with the intellectual, scientific, or artistic status quo.
• Resonance with central societal and cultural themes: A creative individual, and certainly a genius, is ahead of society, but his/her work must be recognized by society as important and valid in order to survive.
• Social grace: Certain supremely creative individuals were known to history for their social suaveness and adaptability, and others for a notorious lack thereof.
• A favorable cultural milieu: Historically, certain societies and epochs were richer in discovery and innovation than others. The relationship between a creative individual and his/her social and cultural milieu deserves a closer examination.¹⁶⁴

Teaching this skill can be a challenge, though, because there’s a world of difference between teaching about these ideas, and teaching how to do actually do it!

Teaching about Vs. Teaching To

Imagine a class for college freshman titled Introduction to Bicycle Riding. For week after week, students learn the history, mechanics, and physics of bicycles and bicycle riding. The class is taught by a professor who’s never ridden a bike, and an actual bicycle is brought into the classroom only a handful of occasions for students to marvel at but never touch. Finally, graduation day arrives. Students write an exam summarizing their knowledge, and assuming a passing grade, they are taken to the city’s busiest highway, given their first bicycle, and told to make their way home.

This sounds absurd until you swap the word bicycle out for any number of subjects taught in schools. The more nuanced or situationally-driven a subject is (think entrepreneurship, for example), the more absurdly horrifying it becomes. That difference between teaching about a given topic and teaching to actually do something—and to the extent that they’re taught at all, the skills of creativity and critical thinking that combine to create insight—are at the top of that list.

This is not only regrettable, but also understandable because of how much these skills in particular require a reimagining of the way that we teach. For example, in The Innovator’s Mindset, George Couros lays out eight elements of a mindset that fits with creative problem-solving and explains how educators can help cultivate this mindset. The approach begins with treating students as partners in the learning process, empowering them to play an active role in their learning, and placing them in environments in which they can explore ideas, work on creative challenges, and learn from one another. This is anathema to the way we’ve grown up to think of education—from the power dynamics between student and teacher, to the timelines of lessons and assignments and deadlines that leave little room for creative exploration, and everything in between. Much of this is chosen by the student, for the simple reason that the sort of learning we’re talking about can be uncomfortable, as Paul Tough explains in How Children Succeed:

“It’s uncomfortable to focus so intensely on what you’re bad at,” Brooklyn chess teacher Elizabeth Spiegel told me. “So the way people usually study chess is they read a book about chess, which can be fun and often intellectually amusing, but it doesn’t actually translate into skill. If you really want to get better at chess, you have to look at your games and figure out what you’re doing wrong.”¹⁶⁵

It’s not easy… but we don’t have a choice. It’s no longer sufficient for education to impart knowledge and skills. Our rapidly evolving economy and culture demand insight in addition to knowledge. At first glance, insight can seem like genius, a nearly magical quality that some people have, and some don’t. When we probe deeper, though, we discover that insights emerge from critical thinking and creative problem-solving. These capacities can be nurtured through new approaches to learning and growth, but they require creativity and resourcefulness in thinking about what a curriculum should be meant to accomplish and impart, then shifting it dramatically toward the practice of those all-important skills.

How to Cultivate Creativity

In the past few decades, researchers have trained their lenses on creativity and discovered that the mystery isn’t quite so mysterious. Author Keith Sawyer explains in Zig Zag:

Creativity is not mysterious. Creativity is not a rare insight that comes to you suddenly, once in a lifetime, to change the world. It’s just the opposite. Creativity is a way of life. It’s a process. The process starts with an idea. But it’s not a big insight—it’s a small idea. And that small idea can’t change the world by itself. In the creative life, you have small ideas every week, every day, even every hour. The key is to learn how to bring those ideas together, over time, and that’s the essence of the creative process. The latest creativity research shows the daily practices that exceptional creators use to keep having those small ideas, and how to bring them together in a creative process that consistently leads to successful creative outcomes.¹⁶⁶

It’s not simple, but it is eminently understandable and if we can understand this creative process, then we can help people learn it! We don’t have to wait for creative insights to pop up magically out of nowhere. We can all train and develop our capacity to work through creative processes, which in turn will yield fresh insights.

The process itself is fairly straightforward. Sawyer outlines eight stages:

1. Ask: How to ask the right question.
2. Learn: Prepare your mind.
3. Look: Spot the answers around you.
4. Play: Imagine possible worlds.
5. Think: How to have great ideas.
6. Fuse: How to combine ideas.
7. Choose: Make good ideas even better.
8. Make: Make your ideas visible.¹⁶⁷

Clearly we need to do better if we want to foster creative problem solving and help people develop deep insights, starting by incorporating these powerful aspects of creative thinking into different educational experiences. Recent advances in creative education and design thinking make this more feasible than ever before. The most exciting part is that none of the steps in the process is particularly hard. The biggest challenge isn’t to follow the steps, but rather to create the time and space for the steps to be followed.

Even if you mix all the right ingredients in just the right order, you won’t have a cake unless you have an oven to put the mixture into, and the time to let it cook. Similarly, all the tools, steps, and frameworks that we’ve shared in this chapter only work if we bake time into the equation as well. Even the smartest and most creative people can’t generate great ideas on command. The “aha!” moment requires that the right stage be set, and that enough time be dedicated to the incubation of the eventual insight.

This isn’t a new idea. Way back in 1926, psychologist Graham Wallas conducted a wide-ranging analysis on what poets, scientists, and history’s creative thinkers had written about how their insights came to be. Based on that research, he developed a series of mental steps that thinkers take to reach an insight:

• Preparation. The initial time spent wrestling with the logical or creative problem in question. This includes not only understanding the specific problem that needs solving and clues or instructions at hand, but also working to the point where all obvious ideas have been exhausted.
• Incubation. The stage that begins when you put aside the problem (for example, by abandoning your work and going for a walk in the woods). There are mental processes occurring during this “downtime,” and they are crucially important. The mind works on these problems “offline,” moving the pieces it has and adding ideas that were held in reserve but not initially considered.
• Illumination. The “aha!” moment, when the solution appears seemingly out of nowhere.
• Verification. Checking to make sure the resulting insight actually works and holds water.¹⁶⁸

All four of these steps are crucial, but incubation in particular is likely to be discounted as a frivolous waste of time. It is critical that as both learners and educators, we have the discipline to protect incubation time as the important part of the process that it is. That time creates the shell and context in which creativity can be cultivated, critical thinking can be explored, and insight can finally emerge.

There’s just one challenge we haven’t tackled yet. Learning and applying these capacities for critical thinking and creativity isn’t easy. It takes considerable fortitude to work through the mindset shifts, skill development, and attitude changes necessary to make real progress. In the next chapter, we’ll examine this challenge of fortitude and how to address it.

Want to test your understanding of the ideas that we just covered? Or start conversations with interested friends and colleagues? Here are a few questions to guide you:

1. What is disintermediation?

2. Give examples of jobs that may soon be eliminated by disintermediation?

3. Menial jobs aren’t the only ones getting wiped out. Instead, the U.S. job market has been characterized by a “hollowing out.” What does this mean?

4. Top professionals in their fields are doing fine and will continue to do so because they bring something different than just knowing something. What do they bring?

5. Why do wise leaders value and prefer employees who challenge and disagree with them?

6. Insight lives at the intersection of two rarefied talents. What are those talents?

7. What is the “mere exposure effect”?

8. According to a 2013 study, 93 percent of employers value this ability over an undergraduate degree. What is this ability?

9. What is the critical thinking?

10. Critical thinking is traditionally taught through osmosis, repetition, or—as in business schools—the case method. Minerva instead focuses on the seven steps of critical thinking. What are those steps?

11. What are the eight stages of creativity, according to Keith Sawyer?

12. In The Innovator’s Mindset, George Couros explains an approach for educators to help cultivate a mindset for creative problem solving. What are the three elements of this approach?

Like What You Read, and Want to Go Deeper?

Here are a few good books to take a look at if you’d like to go deeper on some of the ideas presented in this chapter.

• George Couros’ The Innovator’s Mindset
• Mihaly Csikszentmihalyi’s Creativity
• Elkhonon Goldberg’s Creativity
• Keith Sawyer’s Zig Zag