A 10-year-old boy sits quietly on the sofa in my office, his legs not quite touching the floor. I ask whether he’s ever thought about what he’d like to do when he grows up. With no hesitation, he perks up and exclaims, “I want to run a start-up.” He doesn’t even know what a start-up is, but he does know, in exacting detail, the trajectory he will need to take to become wildly successful in running one. Not yet finished with middle school, he has charted the next 15 years of his life: He plans on applying to the most competitive high school in town, hoping that this will increase his odds of going to Stanford. He knows he will have to serve time as an intern, preferably at Google. He is intent on being a “winner.”
My young patient’s parents, teachers, and community are all likely to encourage this way of thinking, but they are only making his future chances of being successful less likely. In the enclaves of privilege in this country, part of the culture is more and more centered on a narrow notion of what success looks like and how to attain it. Money is overvalued, and character undervalued. The 10-year-old sitting before me is the logical outcome of this culture. He wants to be a winner, but knows nothing about the kind of work he’s signing on for.
Too many of us are worried about how our kids will compete globally and are baffled by the desirability of jobs whose titles mystify us: digital overlord, director of insights, growth hacker, innovation Sherpa. We fervently believe that staying “on track” beats wandering around. However, reality suggests otherwise. And instilling this concept of success as a straight line can set kids up for unrealistic expectations and disappointment.
I’ve spent more than 15 years traveling the country talking to large audiences about the intersection of child development, psychology, and education. At the start of my presentation, I pull up two PowerPoint slides: One is simply a straight line on a 45-degree angle. The other is a squiggly line with multiple ups and downs that trends in an upward direction. With the image on-screen, I ask the audience to raise their hands in response to one of these two questions: “How many of you who consider yourself successful have followed the straight path? How many have followed the squiggly path?” I have asked more than 100,000 people these questions. Whatever the composition of my audience—techies from Silicon Valley, cops and teachers from middle-class neighborhoods, the highest levels of management from some of America’s biggest companies—the proportion of “straight arrows” and “curious wanderers” is always the same. Straight arrows make up, at most, 10 percent of the people who consider themselves successful. The remaining 90 percent are folks who have taken risks, failed, changed course, recovered, often failed again, but ultimately found their stride.
Even if parents ascended a relatively smooth track from school to career success, it’s misguided to assume that what worked for them will be right for their kids, too. (See: the parents who push their kids to apply to their alma mater, for instance.) Encouraging children to follow a linear path makes them cautious and competitive, when what they are most likely to need are curiosity, a willingness to take risks, and a talent for collaboration.
I’ve talked with people from all walks of life whose stories seem to show that it is rare to go from point A to point B without multiple detours. One of these people is Steven Kryger, who has lived a life full of sudden reversals. The first in his family to attend college, he started out at the University of Pennsylvania as a computer-engineering major before transferring to the Wharton School of Business. “I don’t think I even knew what ‘business’ meant,” he told me. “I never had any firsthand experience, because I didn’t know people in the business world.” After graduation, Kryger moved to the San Francisco Bay Area, where he got a position in Macy’s executive-training program. He initially enjoyed the position, but soon started to find the job unfulfilling.
“I started thinking, What would I really love to do? I figured being a fireman or law-enforcement officer would be a lot of fun,” Kryger said. So in 1988, he became an officer on the Oakland police force.
On January 20, 1993, while searching a house with his team, Kryger was shot in the thigh by a suspect. The bullet severed his femoral artery, vein, and nerve. Surgery and months of rehabilitation saved his leg, but he needed to wear a brace for physical activity. “The police department wouldn’t let me go out on the streets in that condition. They offered me a whole bunch of other positions, but I knew I wouldn’t be satisfied if I had to stay inside a building all day.” At 32, he switched careers again.
Thinking of the “amazing high-school coaches” who inspired him, Kryger met with the assistant superintendent of his school district, who advised him about the courses he’d need to complete in order to coach and teach math in the public-school system. It took three more years of college, plus another year when he was teaching high school during the day and completing his own studies at night. But he kept at it. Two decades later, Kryger is the athletic director at Menlo-Atherton High School, where he also teaches four math classes and coaches the boys’ varsity lacrosse team.
When I observed that some people might have reacted far less optimistically to events like getting shot and having to abandon a career they loved, Kryger said, “Initially your reaction is frustration, and you wish these bad things didn’t happen. But very quickly, you’ve got to move on with life. As we talk about in sports and I tell my kids, the most important play is always the next one.”
Kryger’s story is similar to that of Nate McKinley, who overcame a set of internal challenges before settling on the job that would become his career. McKinley started out following the path that had been set for him by his father, an international businessman. He majored in global studies, with a concentration in business, choosing his classes at his father’s suggestion. After graduation, he worked at a financial institution before switching to a securities-lending start-up. At first he found the job exciting, but his enthusiasm waned after a year or so, and the three-hour round-trip commute seemed longer and longer. Eventually, McKinley told me, he decided he wanted to try something more challenging: “A friend brought me an old apple press, and I made my first batch of hard cider. It was revolting! So during my commute on the train, I would read about yeast, fermentation, and the hundreds of varieties of apples. My next batch of cider wasn’t gross; it was actually drinkable.”
McKinley persisted, and soon he had batches of five-gallon jugs of fermenting cider in his basement. A year or so later, he was ready to let others try his brew: “At our annual Halloween party, we had a tasting and encouraged the neighbors to bring apples to press and to have a taste. People liked it!”
McKinley was still working in Boston from 7 a.m. to 7 p.m., but he often stayed up past midnight making cider. Soon he was making his first sales, to a local farm stand and a brewery. A year after McKinley went retail, he was laid off from his day job. “Although it was scary, it was a blessing in disguise. I could finally dedicate myself to my passion.”
In another year, McKinley’s cider was on the menu at seven local restaurants, and his retail sales had expanded beyond nearby liquor stores and specialty shops to stores on Cape Cod. He was producing 5,000 gallons of cider annually, with plans to double production the following year. His wife, Tessa, told me, “He’s happier than he’s ever been, and as our kids make their way through school, I can’t think of a better role model.”
What exactly constitutes success is, of course, open to a world of meaning. Financial independence is one way to measure success, a sense of doing meaningful and fulfilling work is another, and raising a healthy family and contributing to one’s community yet another. Sometimes these varying definitions converge; sometimes they don’t. One of the patterns that I see regularly among people who consider themselves successful is real passion about the work they do: the kind of passion that makes them work harder than others, welcome mistakes and even failures as learning opportunities, and feel that what they do has impact. While money may be inherited, real success always has to be earned.
If a linear progression tightly tied to grades, SAT scores, admittance to selective colleges, and high-powered internships for well-known companies were in fact the path taken by most successful people, we still would have to weigh its value against healthy child development, but at least we would have some evidence that our kids would one day benefit from all of the aggressive preparation, coaching, and tutoring. However, reality—that is, real people following real trajectories—suggests that this particular template is only modestly accurate. More often, a meandering and unexpected path is what leads to success.
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