How To Be A High School Superstar Part 3

By the time Jessica returned from this first trip, she had transformed herself into a budding Silicon Valley insider. Bolstered by the confidence she'd developed, she started her entrepreneurs.h.i.+p blog. The ability to report on conversations with top business personalities, and to bounce her ideas off of these experts, gave her credibility that attracted readers and increased her influence.

"It's like an endless cycle of goodness," Jessica explained. "You meet this person from your blog and they introduce you to other friends, or get you into events, and that leads you to something else."

By the time Jessica applied to Berkeley, this "cycle of goodness" had made her into a minor celebrity within the world of high-tech entrepreneurs.h.i.+p. In March 2008, for example, the Web site Valleywag, perhaps the most influential (and most vicious) repository of tech industry gossip, posted an article about how Jessica, then seventeen years old, had managed to gain an invitation to the ultraexclusive TED Conference, while some of the biggest names in the valley were not invited. (The article, satirically t.i.tled "After 17-year-old gets into TED, Michael Arrington now on Suicide Watch," poked fun at Arrington, the founder of the popular TechCrunch Web site.) And this is only one of the eight different articles appearing on Valleywag to date that mention Jessica-a strong indicator of her surprising visibility in Silicon Valley.

Of course, being an important player in the high-tech industry gave Jessica an aura of interestingness that few of the other thirty-six thousand applicants to Berkeley that year could match. After reviewing yet another application of a student in the top 5 percent of his cla.s.s, who joined half-a-dozen clubs and took an absurd number of AP courses, the admissions officers must have sighed in hearty grat.i.tude when they flipped to the story of a student who had snuck into important conferences, enjoyed late-night chats with powerful CEOs, and knew how to write about these experiences in a compelling manner.

"Finally," they may have thought. "Someone interesting."

Her mediocre grades and open, relaxed schedule were washed away in this tide of interestingness.

Deconstructing Jessica's Story

What strikes me most about Jessica's path is how much pivots on that chance encounter on a Jamaican golf course. I asked Jessica about this. "Having luck is important," she said. "But making extensive use of your luck is even more important."

This sentiment matches the theories of Linda Caldwell. Use free time to explore, but then follow up on the most interesting experiences. This acts like a systematic search for luck. You don't know in advance which chance encounter can spark a transformation in your life, but by seeking out lots of chance encounters you're increasing the probability that you'll stumble into the right one.

Jessica's difficult experience with her freshman-year company instilled a desire to keep her schedule open and flexible. When she met that young entrepreneur on the beach in Jamaica, and found her interest piqued by his tales of high-tech success, her open schedule allowed her to follow up aggressively-transforming a moment of inspiration into a true deep interest. If she had been the typical overscheduled student with an eye toward getting into Berkeley, this transformation would have been unlikely.

4.

The Systematic Superstar

PERCHED HIGH up in the Santa Monica Mountains, near the final ascent of North Sepulveda Boulevard, is the Skirball Cultural Center. Its architecture is a mix of the modern and the ancient Semitic. Clad in horizontal strips of concrete and pink stone, it contrasts pleasingly with the rolling mountain backdrop. It was no surprise that Claremont McKenna College chose this stunning venue, in March 2008, to launch its equally stunning $600 million capital campaign-the largest such campaign ever conceived by a liberal arts inst.i.tution.

On the evening of March 16, the main theater, filled to capacity, darkened. The stage was dominated by a pair of oversized video projection screens, each twenty feet tall. The screens lit up, alternating between clips of students on one side and faculty on the other. A young man by the name of Ben Casnocha appeared on the student screen. He had a prominent, dimpled chin and the broad shoulders of a six-foot-five, 230-pound basketball player. These bold features were offset by a delicate pair of gla.s.ses that echoed the precision with which he chose his words: "I founded my first company when I was in high school and wrote my first nonfiction book before starting college. My college counselor told me Claremont McKenna would be a perfect fit. Here, I'm learning how an intellectual foundation of history and philosophy can support my real-world experiences."

Ben's image froze on the screen while a clip featuring a professor began to play on its twin. The professor launched into a spiel about how the college supported and nurtured young talents like the impressive young man captured in a moment of still-frame contemplation on the screen beside him.

Ben's a superstar. There's no question about that. By the time he appeared on that screen he had written a book, made regular appearances on NPR, and given speeches across the country. When Ben's clip played that March evening, he was one of just a handful of students chosen to represent the best of Claremont McKenna at the gala. Even more amazing, Ben was only a freshman and had completed just a single semester of college. The day he arrived on campus, he had already been identified by the inst.i.tution as one of its best.

There are two things about Ben that should interest you. First, fifteen months earlier, when he graduated from high school and set off on a precollege gap year, he was not a superstar-he had not written a book or become a radio personality or a popular speaker. If he had gone straight from high school to Claremont, the college probably would not have selected him to help kick off its record-breaking capital campaign. Second, during the year that launched him into stardom, Ben lived according to a simple experiment designed to answer this question: What would happen if you built your entire life around the law of underscheduling? The answer turned out to be a lot.

This story is important, as it previews your own trajectory if you decide to apply the systematic advice in the upcoming playbook. Whereas Olivia and Jessica naturally gravitated toward the underscheduled lifestyle, the strategies that follow teach you how to artificially inject this philosophy into your daily routine. Ben's story will prove that this proactive approach can provide fantastic results much faster than you may believe possible.

The Experiment

When Ben graduated from high school, in the spring of 2006, he had inconsistent grades and a busy extracurricular schedule dominated by an unusual pursuit: he had founded a technology business, Comcate, Inc. The concept started as a cla.s.s project for a junior high school technology elective. Ben and his fellow students were challenged by their teacher to come up with a useful Web site. They soon settled on a problem of great importance to teenage baseball fans from the San Francisco area: the rundown condition of the stadium seats at Candlestick Park. Ben recalls thinking, "These seats are just plain dirty; there should be a way for citizens to efficiently complain about such civic travesties." Because he knew something about building Web sites, he kept working on the idea after the cla.s.s concluded. "I learned that local government is no good at handling complaints," Ben recalls. "So I thought, Why not start a company to help them deal with these issues?" Comcate, Inc. was born.

The company grew into a solid small business. It acquired clients and employees, and it still exists today, though Ben has given up his role in its day-to-day operations. The business, combined with traditional activities like editing the school newspaper and playing on the varsity basketball team, no doubt helped Ben get into Claremont, but it was not enough to transform him into a superstar. Due in large part to the demands of his business, Ben earned only a 2.67 GPA and SAT scores that were "good, not great." His college counselor once told him: "I'm going to be blunt, your numbers will hurt the averages of [the top] schools.... You're facing an uphill battle."

Ben was burned-out and disappointed by an admissions process that placed many of the nation's top schools out of reach for him, even though he was an obviously talented student. Around this time he wrote on his blog, "Let's face it: I got my a.s.s kicked," adding, "but I'm still happy, and I'm still dreaming." He decided to take a gap year before matriculating at Claremont-a school with a fiercely independent ethos that Ben's counselor thought would be a good fit.

This is where Ben's story becomes relevant to our quest to understand underscheduling. He wrote on his blog that one of his life principles is "to expose myself to bulk positive randomness." He made few plans for his gap year beyond booking plane tickets to various international destinations. His goal was to keep his itinerary open, encounter as many interesting things as possible, and then follow up on whatever caught his attention. In other words, he was going to travel the world living the underscheduled life.

He tempered his expectations for the trip, casting it more as a time of relaxation and contemplation, but underneath those careful words was the thought that perhaps something big might come out of his underscheduled walkabout. As he wrote right before leaving, "Who knows ... maybe I'll move a mountain."

If you had asked him then to predict the events that would unfold during the year to follow, he would never have guessed just how effective his strategy would prove.

A Fateful Decision

Two days after receiving his high school diploma, Ben left for the first leg of his gap-year travels: a seven-week tour of Europe. He eventually wandered into a quiet suburb of Zurich, Switzerland, where he visited the family he had stayed with during a summer spent as a high school exchange student.

"I was doing so much reading while traveling," Ben recalls. "I was reading, and writing blog posts, and sending these long e-mails describing my trip, and it got me thinking a lot about writing." This saturation in writing sparked an interest in Ben, which motivated him to dig deeper. (As the law of underscheduling states that when something catches your attention, you should always follow up and see where it leads.) "I started e-mailing publis.h.i.+ng contacts," Ben recalls. Most of his e-mails were a dead end-he received rejection notices from more than a dozen publishers and agents-but one resulted in a promising lead. "Earlier, this reporter wrote an article about me and my company. I had kept in touch with him, and now, when I wrote him, I asked if he knew anyone in publis.h.i.+ng. He gave me a name. I followed up. That person pa.s.sed me on to someone else at Wiley. I tracked the second person down, and he said, 'You can send me something.'"

Fortunately, Ben had something to send. Over the past several years he had kept a journal about his dual life as a teenager and an entrepreneur. He recorded his thoughts because he thought "it might be cool to look back on this time later in my life." But now these private thoughts had a public role to play. Ben put the file on disk. It was, as he describes it, "a big-a.s.s Word doc.u.ment" of seventy thousand to eighty thousand words. He was leaving the following day for the next leg of his trip, so he asked his host family if they would print the file and mail it to his contact.

This is a cla.s.sic example of underscheduling at work. When an interesting idea occurs, you should immediately follow up. Ben had a sudden interest in writing, so he took action by contacting the appropriate people in his network. Many might get this far, but then abandon the cause when the next steps become murky and difficult. Not Ben. His first round of e-mails generated a lot of dead ends, but eventually his persistence turned up a single new lead. Undeterred, he followed up on this lead, and the leads it generated, pa.s.sing from one person to another until he landed at someone willing to look at some writing. As he was about to discover, his persistence would pay off.

When Ben returned to California, he had a message waiting from the editor at Wiley. The editor wanted Ben to sign a contract and transform the thoughts into a book right away-before his gap year ended. Ben had just enough time to sign the contract before leaving for the next leg of his gap-year travels, a month in j.a.pan. He soon found himself in a position he could have never imagined on his graduation day four months earlier. He was holed up in a cramped hotel room in Kyoto, frantically editing the ma.n.u.script for his first book.

"I had eighty thousand words and I had to cut it down significantly. I was Skyping with my editor every night."

Two weeks later, he moved on to Hiros.h.i.+ma, where he finished his first draft. He e-mailed a copy to his dad and asked him to print it and send copies to Ben's mentors for feedback.

Indispensable to this step in Ben's rise to superstar status is the flexibility afforded by underscheduling. If Ben had filled his gap year with an ambitious schedule of activities and obligations, he wouldn't have been able to make such a radical s.h.i.+ft and devote so much time to an unantic.i.p.ated project. But with an open schedule, he was able to say, without reservation: "Let's go for it."

The effort paid off. After some more back-and-forth with his editor, and advice from his mentors, the ma.n.u.script was ma.s.saged into the final form that would become the memoir My Start-up Life.

Reflecting on the experience, Ben can't help but be amazed. "I knew nothing about the publis.h.i.+ng process," he told me. "It all happened because I kept in touch with some reporter in case one day I needed some advice about his world. I definitely didn't set aside six months of my life to write a book."

From Print to Radio and Beyond

Ben wasn't done. In six short months he had gone from a standard student vagabond on a European tour to an absurdly young author. In true underscheduling fas.h.i.+on, however, he refused to stop there. He leveraged his newfound credibility to expose himself to new, even more interesting sources of positive randomness.

With book promotion on his mind, Ben called the public relations department at Claremont. He wanted to see if they had any contacts that might prove useful. (Sense a pattern? Part of Ben's approach to exposing himself to positive randomness is the relentless contacting of people who might lead somewhere interesting.) Ben chatted with a publicist, who was impressed with both the book and Ben's boldness in calling. The publicist made some calls on Ben's behalf. One of the calls went to a friend who happened to be an editor for Marketplace, an NPR program produced in Los Angeles and syndicated to 490 stations nationwide.

"The timing was perfect," Ben recalls. "It was back-to-school week on the show, so they commissioned a commentary from me on how college students could think like an entrepreneur"-one of the main ideas in Ben's upcoming book. This was serendipity, for sure, but it never would have happened without Ben's active efforts to make potentially serendipitous contacts.

As usual, Ben jumped at the opportunity. He wrote his essay, got feedback from people he trusted, and in general took the time required to make it as good as possible. The producers accepted the clip. Once this entree was established, Ben began pitching new pieces, following the underscheduling dictum that once something proves interesting you should follow up aggressively. Some of his pitches were rejected, but a few were accepted. The program's editors eventually made him a regular commentator, allowing him to speak on a variety of topics.

Ben had no master plan for becoming an NPR commentator. He was just performing the standard underscheduling shuffle: expose and follow up, expose and follow up. Or, as Ben modestly puts it: "One thing led to another."

Once Ben had the book and the NPR slot, his exploration began to yield new opportunities at a furious rate. He contacted anyone he had ever met who was affiliated with a university and tried to arrange a time to come speak about his book. This coalesced into a speaking tour that dominated the final months of his gap year. The meager speaking fees added up to enough to cover travel expenses, and he was soon crisscrossing the country, forming relations.h.i.+ps with influential academics and business personalities. The tour even allowed him to fulfill a "long-dreamed-about goal": after a speech at the University of Arizona, he spent a night in the Grand Canyon. During this period, Ben spent a few months helping out a prominent venture capitalist in Boulder, Colorado, which, in turn, ratcheted up his connections in the world of entrepreneurs.h.i.+p.

By the time Ben arrived at Claremont, in the fall of 2008, his story was radically different from that of the young student who had graduated from high school fifteen months earlier. At that point he had been a bright kid with mixed grades who once ran a Web company. He was now an author, radio personality, popular speaker, and well-known business pundit. The Politics Online portal named him one of the twenty-five most influential people in the world of Internet and politics, and the Silicon Valley / San Jose Business Journal named his blog one of the top twenty-five in Silicon Valley. When the organizers of the Claremont gala needed to select a handful of students to represent the school, choosing Ben was a no-brainer.

Looking back on this frenzied period, Ben concludes: "This all happened because I had these months free of commitments." His experiment with underscheduling proved an unequivocal success. No amount of careful planning or ambitious scheduling could have matched the levels of interestingness generated by the simple strategy of keeping an open schedule, exploring things that seem interesting, and persistently following up on every cool opportunity.

For Ben, underscheduling worked phenomenally well and phenomenally fast. This gives hope that if you use the advice in the upcoming playbook to systematically expose yourself to the world, your transformation may follow a similarly speedy trajectory.

5.

The Underscheduled Student

IN 2007, a college counselor named Pam Proctor published a guide t.i.tled The College Hook. The book promised to help students develop a "hook" to differentiate themselves from the great ma.s.ses of overachievers applying to the same schools. Proctor uses a cooking metaphor to describe this strategy-hooks are something you "cook up" according to a "recipe." Her approach asks the student to list the "ingredients" he or she has on hand-that is, the student's interests and accomplishments. The student then uses the list to choose the best match from one of the ten "hook" recipes described in the book, including the "International Hook," the "Technology Hook," and the "Music Hook." Next, the student plans a bold action to strengthen his or her connection to the hook. For example, if you like computers, and therefore decide that you fall into the Technology bin, Proctor suggests "creating a computer service organization to help senior citizens."

Pick up almost any guide on the admissions shelf and you'll read some variation on this strategy, which I summarize as: Identify something that interests you.

Devise an impressive activity that proves your commitment to the interest.

I've noticed that this approach dominates popular thinking about how to boost your admissions chances. Many high school students, for example, have sent me an e-mail that follows this basic format: Hi, Cal! I'm trying to look more interesting to colleges. I guess I've always liked [name of some activity that the student has some interest in], so would it be impressive to the admissions officers if I [vague, unoriginal plan involving the activity-usually starting a club dedicated to it]?

One young man, for example, told me that he liked Ping-Pong and wondered if starting a Ping-Pong club at his high school would increase his chances of cracking the Ivy League.

It doesn't take an admissions guru to see the problem with this approach: it produces unoriginal, contrived, and fake-sounding accomplishments. These watered-down, counselor-inspired "hooks" are so common that I've taken to calling them prefab. When students sit down with their parents or counselors and try to mastermind an extracurricular strategy, they invariably default to one of the same small number of bland formulas. The resulting prefab hooks bore admissions officers to tears. For example: You started a club around your hobby? Prefab!

You signed up for a summer program at your local university? Prefab!

You spent a month on an international mission trip that accepts anyone whose check clears? Prefab!

Here's the important point: I've never met a relaxed superstar who planned the sources of his or her interestingness in advance. (There was certainly nothing prefab or preplanned about the eventual accomplishments of Olivia, Jessica, or Ben.) This is the crucial distinction that separates the life of an underscheduled student from that of the average student looking to boost his or her admissions chances. The former lets interestingness form naturally from an interesting life, while the latter tries-and almost always fails-to force it all at once.

With this in mind, let's revisit the wording of the law that motivated Part 1: The Law of Underscheduling Pack your schedule with free time. Use this time to explore.

The lifestyle generated by this advice follows a different rhythm. Forget trying to identify your interest in advance. The underscheduled student enjoys free time-abundant free time-in her schedule. She doesn't fill every minute with the heaviest course load conceivable or the uninspired activities chosen to support a prefab hook. She instead experiences the rare pleasure of having more than enough time to handle her work exceptionally well, while still leaving many hours free to relax. She takes advantage of this freedom to explore-exposing herself to as many potentially interesting ideas and opportunities as possible, looking for that one serendipitous match that will blossom into a deep interest.

"I wasn't stressed like the other students at my school, because I wasn't interested in trying to impress colleges," Olivia told me. "I still don't understand how I got into UVA. I find myself to be the luckiest person in the world."

It's a nice life.

I hope that I've convinced you that underscheduling yields more benefits than trying to think up prefab hooks or suffering through the conventional strategy of showing commitment to as many things as possible. I must admit, however, that the details of making the underscheduled lifestyle real are nontrivial. Two practical questions plague those who follow this approach. First, how do you inject free time into your schedule without simply quitting everything and looking like a slacker? Second, how do you effectively "explore" in this free time without having it degenerate into a mora.s.s of TV watching and Web surfing? In the playbook that follows, I will walk you through specific strategies to avoid both of these pitfalls, and to successfully integrate underscheduling into your student life.

Part 1.

Playbook.

THE HIGH-LEVEL concepts behind the law of underscheduling are simple. By keeping an open schedule and using your free time to explore, you maximize your chances of developing deep interests. The powerful trait of interestingness, in turn, can be generated only by these deep interests. And interestingness will make you s.h.i.+ne in the admissions process.

As mentioned, however, putting the law into practice can prove complicated. For example, you have to decide how much free time is enough, and what it actually means to "explore interesting things." This playbook addresses these issues with specific advice. For clarity, I've divided it into two sections. The first section focuses on how to simplify your schedule. It covers topics from planning your workday to reducing the time demands of your course load. The second section tackles how to explore interesting things. The advice ranges from the power of developing a reading habit to techniques for soliciting guidance from experts in fascinating fields.

As always, my advice is meant to provide a starting point for your experiments with the underscheduled lifestyle, but it's hardly the last word on the subject. Use it to build your momentum, but then please, by all means, break away from my suggestions and begin to experiment with different strategies to see what fits your personality best.