Smartcuts: The Breakthrough Power of Lateral Thinking

by Shane Snow

The difference between Franklin’s unconventional work and Abagnale’s was that the former managed to create value for others while the latter cheated others. Franklin’s approach was a lateral solution to the unfairness of present convention. Abagnale’s, however entertaining, was a con, and he paid for it. And that’s the difference between rapid, but short-term gains, which I call shortcuts, and sustainable success achieved quickly through smart work, or smartcuts. Whereas by dictionary definition shortcuts can be amoral, you can think of smartcuts as shortcuts with integrity. Working smarter and achieving more—without creating negative externalities. Abagnale took shortcuts and regretted it. Franklin used smartcuts and got his face on a $100 bill. After being released from prison, Abagnale spent three decades repaying his debt to society, working for the FBI, without pay. Eventually, he started a security business, met his future wife while on undercover assignment, and had three kids. “True success is not defined by how much money do I make, how well do I speak, how well do I deal with the subjects I deal with,” he says. “But how great of a father I am.” As we explore the unconventional behavior of history’s overachievers in Smartcuts, I hope we’ll keep Abagnale’s lesson in mind. To some people, success means wealth. To others it means recognition, popularity, or promotions; it means free time, inventing products, growing businesses, making breakthroughs at work. Those can...

I see this book as a simultaneous hat tip and counterpoint to some of the great success and innovation literature out there (check out shanesnow.com/booklist for my recommendations). It’s a re-analysis and first codification of the ways rapid success has happened throughout history. The step-by-step advice that made an ancient Greek hero rapidly prosperous will be entirely different from what makes a 21st-century businesswoman successful, just as the exact methods an Internet startup uses to grow today will be irrelevant in five years. But the patterns of lateral thinking (smartcuts) behind each of their success stories can be harnessed by anyone who seeks an edge—at work, at the gym, in the arts or education, from social enterprise to personal development, from big companies to small startups.

Increasingly in today’s culture, “hacking” is something done not just by criminals and computer scientists, but by anyone who has the capability to approach a problem laterally. (This is the original usage of the term, in fact.) Can’t get that horrible plastic “blister pak” for those headphones open? Use a can opener. (It works!) Not enough seats for the four of you? Give yours up and weather the storm with the person of your dreams. The first section of this book discusses how some people use such “hacker” thinking to shorten paths to success. It’s how some people take a few years to become president while others spend 30. It’s how unknown comedians get on Saturday Night Live and Internet companies get to millions of users in months. Lateral thinking doesn’t replace hard work; it eliminates unnecessary cycles. Once they’ve shortened their path, overachievers tend to look for ways to do more with their effort,

Leverage is the overachiever’s approach to getting more bang for her proverbial buck. It’s how brand-new startups scale and young sci-fi geeks become movie directors. It’s how below-average school systems turn around and revolutions are won. It’s how surfers take championships and artists go from homeless to the Grammys.

Too many of us place our hopes and dreams in the unreliable hands of luck, but the world’s most rapidly successful people take luck into their own hands (even though many are too humble to say so). Too many of us accept the plateaus our lives have offered us and succumb to passivity, to the well-meaning delusion of “If I work hard enough, something good will hopefully happen to me.” By the end of this book, I’d like to convince you that serendipity can be engineered, that luck can be manufactured, convention can be defied, and that the best paths to success—no matter how you define it—are different today from what they were yesterday.

FOR HUNDREDS OF YEARS, people from every corner of the planet have flocked to New York City for the reason Frank Sinatra immortalized: to prove they could “make it.” The allure, the prestige, the struggle to survive, breeds a brand, an image of the city that ripples out to the rest of the world. Sinatra sang about proving himself to himself. “If I can make it there, I’ll make it anywhere.” New York was the yardstick. New York has indeed become a global yardstick—for artists, businesspeople, and dreamers of all stripes. He was a lawyer in New York? He must be good. Doesn’t matter if he was the worst lawyer in the city. If you can make it in New York, people assume that you can make it anywhere. The yardstick the public uses when judging a presidential candidate, it turns out, is not how much time the candidate has in politics. “It’s leadership qualities,” explains the presidential historian Doug Wead, a former adviser to George H. W. Bush and the author of 30 books on the presidents. Indeed, polls indicate that being “a strong and decisive leader” is the number one characteristic a presidential candidate can have. The fastest-climbing presidents, it turns out, used the Sinatra Principle to convey their leadership cred. What shows leadership like commanding an army (Washington), running a university (Wilson), governing a state for a few years—even if you started out as an actor (Reagan)—or building a new political party and having the humility to put aside your own interests...

The presidents, for the most part, got to high office by not playing the game everyone else plays. They acquire leadership experience in disparate fields, then use Frank Sinatra–style credibility to switch ladders to politics. There’s one remaining question, however. We’ve seen how dues and experience are bad proxies for ability or merit. But does bypassing dues and experience leave us without the necessary skill to do the job? The Sinatra Principle helps presidents get the job, but does it qualify them for it? Why don’t we ask the ten top-rated presidents in history:*

All ten of the top ten presidents in C-SPAN’s survey were hackers. Only one, JFK, climbed a semblance of a traditional ladder; he served in both houses of Congress, but was a war hero and author of a Pulitzer Prize–winning book—clearly not the average ladder climber. Each of the men on this list worked hard in his career, learned and proved leadership through diverse experiences, and switched ladders multiple times. They continuously parlayed their current success for something more, and they didn’t give up when they lost elections (which most of them did). The ladder switching made them better at getting elected and better at the job. To be a good president, Wead says, “You’ve got to be able to think on your feet.” Stubbornness and tradition make for poor performance—as we see with Andrew Johnson and other presidents at the bottom of history’s rankings. The fact that our best presidents—and history’s other greatest overachievers—circumvented the system to get to the top speaks to what’s wrong with our conventional wisdom of paying dues and climbing the ladder. Hard work and luck are certainly ingredients of success, but they’re not the entire recipe. Senators and representatives, by contrast, generally play the dues-and-ladder game of hierarchy and formality. And they get stuck in the congressional spiderweb. “The people that go into Congress go step by step by step,” Wead explains. But presidents don’t. It begs the question: should we?

WE LIVE IN AN age of nontraditional ladder climbing. Not just in politics, but in business and personal development and education and entertainment and innovation. Traditional paths are not just slow; they’re no longer viable if we want to compete and innovate. That’s great news, because throwing out the dues paradigm leads us toward meritocracy. But to be successful, we need to start thinking more like hackers, acting more like entrepreneurs. We have to work smarter, not just harder. We’ll see throughout the following chapters how Sinatra-style credibility and ladder switching—always parlaying for something more—are the foundation for how the most interesting people and companies in the world succeed. It’s not just how presidents get to the top. It’s how CEOs and comedians and racecar drivers hone their skills and make it in the big leagues. It’s how new businesses grow fast, and old businesses grow faster. It’s how entrepreneurs create life-changing products in record time and inventors parlay dreams for bigger dreams. Hacking the ladder is the mind-set they use to get places. The rest of this book is about becoming good enough to deserve it.

Jimmy’s goal since childhood, he explained to Siegel, had been to join the cast of Saturday Night Live. He was endearing. After a two-hour call, Siegel offered to represent him. She had one question, however. “Why don’t you stay and graduate?” Jimmy was a semester shy of a degree. Siegel suggested that they get started in the summer, so he’d have a bachelor’s degree to fall back on, just in case. “No, no,” Jimmy insisted. “I need to get on Saturday Night Live, and you’re going to make it happen, because you know Adam Sandler! I don’t want to do anything else.” Siegel knew this was a long shot—and a long-term endeavor—especially for an out-of-town kid with zero acting credits. But for some reason, she couldn’t turn him down; she had never met someone as focused and passionate about a single dream as this grinning bumpkin from the tiny town of Saugerties, New York. And though his skills were rough, given some time in the industry, she thought he might just make it. “OK, let’s do this,” she said. So, in January 1996 Jimmy quit college and moved to Los Angeles. For six months, Siegel booked him gigs on small, local stand-up comedy stages. Then, without warning, SNL put a call out for auditions; three cast members would be leaving the show. Having worked with one of the departing actors, David Spade, Siegel pulled a few strings and arranged a Hail Mary for the young Jimmy Fallon: an audition at The Comic Strip. SO HERE HE WAS. Fresh-faced, sweating in his light shirt, holding h...

Both C.K. and Bieber are extremely gifted performers. Both climbed to the top of their industry, and in fact, both ultimately used the Internet to get big. But somehow Bieber “made it” in one-fifteenth of the time. How did he climb so much faster than the guy Rolling Stone calls the funniest man in America—and what does this have to do with Jimmy Fallon? The answer begins with a story from Homer’s Odyssey. When the Greek adventurer Odysseus embarked for war with Troy, he entrusted his son, Telemachus, to the care of a wise old friend named Mentor. Mentor raised and coached Telemachus in his father’s absence. But it was really the goddess Athena disguised as Mentor who counseled the young man through various important situations. Through Athena’s training and wisdom, Telemachus soon became a great hero. “Mentor” helped Telemachus shorten his ladder of success. The simple answer to the Bieber question is that the young singer shot to the top of pop with the help of two music industry mentors. And not just any run-of-the-mill coach, but R&B giant Usher Raymond and rising-star manager Scooter Braun. They reached from the top of the ladder where they were and pulled Bieber up, where his talent could be recognized by a wide audience. They helped him polish his performing skills, and in four years Bieber had sold 15 million records and been named by Forbes as the third most powerful celebrity in the world. Without Raymond’s and Braun’s mentorship, Biebs would probably still be pl...

Research from Brunel University shows that chess students who trained with coaches increased on average 168 points in their national ratings versus those who didn’t. Though long hours of deliberate practice are unavoidable in the cognitively complex arena of chess, the presence of a coach for mentorship gives players a clear advantage. Chess prodigy Joshua Waitzkin (the subject of the film Searching for Bobby Fischer) for example, accelerated his career when national chess master Bruce Pandolfini discovered him playing chess in Washington Square Park in New York as a boy. Pandolfini coached young Waitzkin one on one, and the boy won a slew of chess championships, setting a world record at an implausibly young age. Business research backs this up, too. Analysis shows that entrepreneurs who have mentors end up raising seven times as much capital for their businesses, and experience 3.5 times faster growth than those without mentors. And in fact, of the companies surveyed, few managed to scale a profitable business model without a mentor’s aid. Even Steve Jobs, the famously visionary and dictatorial founder of Apple, relied on mentors, such as former football coach and Intuit CEO Bill Campbell, to keep himself sharp. SO, DATA INDICATES THAT those who train with successful people who’ve “been there” tend to achieve success faster. The winning formula, it seems, is to seek out the world’s best and convince them to coach us. Except there’s one small wrinkle. That’s not quite tru...

Indeed, equal amounts of research support both assertions: that mentorship works and that it doesn’t. Mentoring programs break down in the workplace so often that scholarly research contradicts itself about the value of mentoring at all, and prompts Harvard Business Review articles with titles such as “Why Mentoring Doesn’t Work.” The mentorship slip is illustrated well by family businesses: 70 percent of them fail when passed to the second generation. A business-owner parent is in a perfect spot to mentor his or her child to run a company. And yet, sometime between mentorship and the business handoff, something critical doesn’t stick. One of the most tantalizing ideas about training with a master is that the master can help her protégé skip several steps up the ladder. Sometimes this ends up producing Aristotle. But sometimes it produces Icarus, to whom his father and master craftsman Daedalus of Greek mythology gave wings; Icarus then flew too high too fast and died. Jimmy Fallon’s mentor, one of the best-connected managers Jimmy could have for his SNL dream, served him up on a platter ...

This is why Sheryl Sandberg, the COO of Facebook and the author of Lean In, dedicates a chapter in her book to this concept, arguing that asking someone to formally mentor you is like asking a celebrity for an autograph; it’s stiff, inorganic, and often doesn’t work out. “Searching for a mentor has become the professional equivalent of waiting for Prince Charming,” she writes. “Young women are told that if they can just find the right mentor, they will be pushed up the ladder and whisked away to the corner office to live happily ever after. Once again, we are teaching women to be too dependent on others.” This waiting for luck to strike is the antithesis of lateral thinking. And the research shows she’s right. All those expensive mentorship programs that corporations put on to smash strangers together in the hopes of increased success are basically just rolling dice. But in light of Underhill’s research, the GOSH doctors did something very right: They managed to build an organic bond with the Formula 1 pit crews. By the time the handover problems had been fixed, the relationship between the doctors and racers had developed beyond what Elliott and Goldman originally envisioned. They had gone to Formula 1 seeking technical help, and ended up becoming friends.

There’s a big difference, in other words, between having a mentor guide our practice and having a mentor guide our journey. OUR TYPICAL PARADIGM FOR mentorship is that of a young, enterprising worker sitting across from an elderly executive at an oak desk, engaging in Q&A about how to succeed at specific challenges. On the other hand, a smartcut-savvy mentee approaches things a bit differently. She develops personal relationships with her mentors, asks their advice on other aspects of life, not just the formal challenge at hand. And she cares about her mentors’ lives too. Business owner Charlie Kim, founder of Next Jump and one of my own mentors, calls this vulnerability. It’s the key, he says, to developing a deep and organic relationship that leads to journey-focused mentorship and not just a focus on practice. Both the teacher and the student must be able to open up about their fears, and that builds trust, which in turn accelerates learning. That trust opens us up to actually heeding the difficult advice we might otherwise ignore. “It drives you to do more,” Kim says. The best mentors help students to realize that the things that really matter are not the big and obvious. The more vulnerability is shown in the relationship, the more critical details become available for a student to pick up on, and assimilate. And, crucially, a mentor with whom we have that kind of relationship will be more likely to tell us “no” when we need it—and we’ll be more likely to listen.

Aristotle was privileged to study at Plato’s Academy, but some kid on the other side of the world was probably just as promising as young Aristotle and never got the mentorship. How can building deep relationships with master mentors be a smartcut if it hinges on our being lucky enough to know the master? Hip-hop icon Jay-Z gives us a clue in one of his lyrics, “We were kids without fathers . . . so we found our fathers on wax and on the streets and in history. We got to pick and choose the ancestors who would inspire the world we were going to make for ourselves.” In ancient Greece, few people had access to the best mentors. Jay-Z didn’t either, but he had books from which he could get an inkling about what those kinds of mentors were like. With every increase in communication, with every autobiography published, and every YouTube video of a superstar created, we increase our access to the great models in every category. This allows us to at least study the moves that make masters great—which is a start.

Oscar Wilde once said, “Experience is the name everyone gives to their mistakes.” The mourners at Startup Funeral are among the many people in the American technology culture who regularly celebrate said experience. Since the rise of the Web, the Silicon Valley crowd has decided that failure in the quest to build a business is not only OK, but cool. “Fail often” is a guiding aphorism.

They called the results a “paradox of failure.” It turns out that the surgeons who botched the new procedure tended to do worse in subsequent surgeries. Rather than learning from their mistakes, their success rates continuously declined. On the other hand, when surgeons did well on the new surgery, more successes tended to follow. Just like the startups in the Compass and Harvard studies. But what’s really interesting is what happened to the surgeons who saw their colleagues fail at the new CABG procedure. These showed significant increases in their own success rates with every failure that they saw another doctor experience. Further perplexing, however: seeing a colleague perform a successful surgery didn’t seem to translate to one’s own future success. It was indeed a paradox. Screwups got worse. When colleagues screwed up, observers got better. When a doctor succeeded, she did better on her subsequent surgeries. When her colleagues did well, it didn’t affect her. There’s no fun in the funeral of a heart patient whose surgery you failed. But every doctor fails sometimes. Seasoned physicians learn to become mentally and emotionally immune to it. They learn to live with the reality that some patients don’t survive. Staats concluded that this coping mechanism was itself responsible for the paradox. He and his colleagues called this attribution theory. The theory says that people explain their successes and failures “by attributing them to factors that will allow them to fee...

THE SECOND CITY MANAGES to accomplish three things to accelerate its performers’ growth: (1) it gives them rapid feedback; (2) it depersonalizes the feedback; and (3) it lowers the stakes and pressure, so students take risks that force them to improve. For the first year, Leonard explains, The Second City’s goal is to get students used to anticipating negative feedback and to get them out of their own heads. This is about building confidence and creating a “safe” environment in which it’s OK to screw up. Then, second-year classes ratchet up the feedback, putting actors in a succession of situations where they will fail small in front of live crowds. It’s one thing for your coactor or director to tell you a joke is funny, but it’s entirely another to hear the pins drop when a live audience disagrees. Or conversely to hear wild cackling from the crowd at something that may have seemed like a bad idea on paper. Every laugh or lack thereof becomes a data point that the actors can use to better themselves. By embracing all these tiny failures, there is no actual failure.* In contrast, a typical acting class might spend an entire semester building up to a single performance. Students practice together in class, but they don’t know if the audience will like their show until the final day. And if the audience hates it, there’s nothing students can do.

A filmmaker made a short documentary about this happy-go-lucky teenager on death row, called My Last Days. It showed Zach living happily, hanging out with his family, and playing music. Everybody loved Zach. When you see the footage, you can’t help but like him. As you watch him laugh and love and sing, you catch yourself forgetting: this kid is about to die. Zach’s family tells the camera how knowing he would die has helped them realize what matters in life and to find true meaning. “It’s really simple, actually,” Zach says. “Just try and make people happy.” As the 22-minute film closes, Zach looks into the camera, smiling, and says, “I want to be remembered as the kid who went down fighting, and didn’t really lose.” Not long after he said those words, Zach passed away. When Eli Pariser and Peter Koechley of Upworthy saw the film, they thought, This is a story that needs to be heard. Now just over a year old, Upworthy has become quite popular. In fact, it recently hit 30 million monthly visitors, making it, according to the Business Insider, the fastest-growing media company in history.* (Seven-year-old BuzzFeed was serving 50 million monthly visitors at the time.) The Zach Sobiech story illustrates how Upworthy used rapid feedback to do it: According to Upworthy’s calculations, My Last Days had the potential to reach a lot of people. But so far, few had seen it. The filmmaker had posted the documentary under the headline, “My Last Days: Meet Zach Sobiech.” Though descrip...

“The Happiest Story about a Kid Dying of Cancer I’ve Ever Seen.” Upworthy watched the “feedback” pour in, monitoring both the percentage of people who clicked each headline and the number who shared it with their friends. It was a perfect, dispassionate science experiment, where the feedback could show Upworthy editors exactly which packaging would have the biggest impact—before they released it to the rest of the world. In moments, the results became clear: people clicked on the third headline 20 percent more often than the original. But that wasn’t the end of the test. Upworthy wrote alternate versions of the winning headline and sent it out to several other groups. It repeated the process a ruthless 18 times, for a total of 75 variations in all. Here are a few of the contenders: Headline % Lift We Lost This Kid 80 Years Too Early. I’m Glad He Went Out with a Bang 0% I Cried Through This Entire Video. That’s OK Though, Because This Kid’s Life Was Wonderful +9% The Happiest Story about a Kid Dying of Cancer I’ve Ever Seen +28% RIP Amazing Rock Star Teenager Who Punched Cancer in the Face with Love on the Way Out +65% Cancer Wasn’t a Death Sentence for This Kid. It Was a Wake Up Call. -22% Her Parents Asked, “Would You Date Him If He Didn’t Have Cancer?” So There Ya Go. +75% This Kid Just Died. What He Left Behind Is Wonderful. +96% In the end, Upworthy tweaked the winning headline one more time: Headline % Lift This Kid Just Died. What He Left ...

“Intuition is the result of nonconscious pattern recognition,” Dane tells me. However, his research shows that, while logging hours of practice helps us see patterns subconsciously, we can often do just as well by deliberately looking for them. In many fields, such pattern hunting and deliberate analysis can yield results just as in the basketball example—high accuracy on the first try. And that’s where, like the dues-paying presidents or overly patient programmers, what we take for granted often gets in the way of our own success. Deliberate pattern spotting can compensate for experience. But we often don’t even give it a shot. This explains how so many inexperienced companies and entrepreneurs beat the norm and build businesses that disrupt established players. Through deliberate analysis, the little guy can spot waves better than the big company that relies on experience and instinct once it’s at the top. And a wave can take an amateur farther faster than an expert can swim. It also explains why the world’s best surfers arrive at the beach hours before a competition and stare at the ocean. After years of practice, a surfer can “feel” the ocean, and intuitively find waves. But the best surfers, the ones who win championships, are tireless students of the sea. O’Connell says, “One of the main things that you do when you learn to compete is learn how to pick out conditions. Know that the tide is getting higher. Counting waves, how many waves come into a particular area tha...

Google was in the water when the waves of Internet traffic came because it was tinkering with new ideas under the umbrella of Google’s famous “20% Time.” “20% Time” is not Google indigenous. It was borrowed from a company formerly known as Minnesota Mining and Manufacturing, aka 3M, which allowed its employees to spend 15 percent of their work hours experimenting with new ideas, no questions asked. 3M’s “15% Time” brought us, among other things, Post-it Notes. Behind this concept (which is meticulously outlined in an excellent book by Ryan Tate called The 20% Doctrine) is the idea of constantly tinkering with potential trends—having a toe in interesting waters in case waves form. This kind of budgeted experimentation helps businesses avoid being disrupted, by helping them harness waves on which younger competitors might otherwise use to ride past them. It’s helped companies like Google, 3M, Flickr, Condé Nast, and NPR remain innovative even as peer companies plateaued. In contrast, companies that are too focused on defending their current business practice and too fearful to experiment often get overtaken. For example, lack of experimentation in digital media has cost photo brand Kodak nearly $30 billion in market capitalization since the digital photography wave overwhelmed it in the late ’90s. The best way to be in the water when the wave comes is to budget time for swimming.

Dr. Adam Grant, professor of organizational psychology at the Wharton School of the University of Pennsylvania, says this is because J. J. Abrams is “a giver,” a rarity in an industry full of takers. No good TV show or film is made by one person, but whereas Hollywood bigshots are known for being credit-hogs, J. J. Abrams is a fantastic collaborator. Grant would know. He wrote the book on the subject. In his bestseller, Give and Take, he presents rigorous research showing that a disproportionate number of the most successful people in a given industry are extremely generous. From medical students to engineers to salespeople, his studies find givers at the top of the ladder. “Being a giver doesn’t require extraordinary acts of sacrifice,” Grant writes in Give and Take. “It just involves a focus on acting in the interests of others, such as by giving help, providing mentoring, sharing credit, or making connections for others.” Abrams is known, acquaintances tell me, for his kindness and lack of ego, in addition to his penchant for mystery. That’s how he attracts the best people to his staff. And that’s how he’s managed to climb so far so fast.* Staffers with whom I e-mailed and met at the “typewriter shop” were eager to keep Abrams away from me because, according to his reputation, he’d probably spend way too much time helping this shaggy-haired writer out when he ought to be, you know, filming Star Wars. Initially, Abrams helped out better-connected people than himself, and...

Some of the most influential Digg and Reddit users fell in love with the Mint blog, which gave them content that would make them look good to their own fans. Those influential users shared these stories, sending millions of visitors to Mint.com. Thus Mint built relationships with an enormous number of people—by helping them. Over the next two years, 1.5 million people who discovered Mint through its blog posts ended up actually signing up for Mint’s service. In 2009 Patzer sold the business to Intuit for $170 million. Mystic energy isn’t the secret to the success of Grant’s givers; just as we learn from Mint, when we give and teach, we build up fan bases that become more likely to support us. And that, actually, was the key component of Che and Fidel’s revolution.

In the end, Castro’s revolutionary message reached a massive audience through a superconnector—a radio—but the rebels won the people’s hearts because they showed that they sincerely cared. The movement harnessed the power of the superconnector by giving service as a publisher and educator. J. J. Abrams built his career by collaborating with talented, fast-rising, and well-connected people and by making them look great. And Mint grew business via its own broadcast on the Web, tapping superconnected people and then helping the members of those people’s networks through meaningful content. No matter the medium or method, giving is the timeless smartcut for harnessing superconnectors and creating serendipity. What happens post-serendipity—as we’ll learn in the final part of this book—is where things start to get really interesting.

If you had an Internet connection and lived in North America at the time, you may have seen it. Vasquez is the man behind the “Double Rainbow” video, which at last check had 38 million views. In the clip, Vasquez pans his camera back and forth to show twin rainbows he’d discovered outside his house, first whispering in awe, then escalating in volume and emotion as he’s swept away in the moment. He hoots with delight, monologues about the rainbows’ beauty, sobs, and eventually waxes existential. “What does it mean?” Vasquez crows into the camera toward the end of the clip, voice filled with tears of sheer joy, marveling at rainbows like no man ever has or probably ever will again. It’s hard to watch without cracking up. That same month, the viral blog BuzzFeed boosted a different YouTuber’s visibility. Michelle Phan, a 23-year-old Vietnamese American makeup artist, posted a home video tutorial about how to apply makeup to re-create music star Lady Gaga’s look from the recently popular music video “Bad Romance.” BuzzFeed gushed, its followers shared, and Lady Gaga’s massive fanbase caught wind of the young Asian girl who taught you how to transform into Gaga. Once again, the Internet took the video and ran with it. Phan’s clip eventually clocked in at roughly the same number of views as “Double Rainbow.” These two YouTube sensations shared a spotlight in the same summer. Tens of millions of people watched them, because of a couple of superconnectors. So where are Vasquez and...

For the billionaires, champagne baths every morning and new Lamborghinis every afternoon couldn’t deplete the fathomless amount of cash on hand. “Your entire philosophy of money changes,” writes author Richard Frank in his book, Richistan. “You realize that you can’t possibly spend all of your fortune, or even part of it, in your lifetime, and that your money will probably grow over the years even if you spend lavishly.” There are dotcom entrepreneurs who could live top 1 percent American lifestyles and not run out of cash for 4,000 years. People who Bill Simmons would call “pajama rich,” so rich they can go to a five-star restaurant or sit courtside at the NBA playoffs in their pajamas. They have so much money that they have nothing to prove to anyone. And many of them are totally depressed. You’ll remember the anecdote I shared in this book’s introduction about being too short to reach between the Olympic rings at the playground jungle gym. I had to jump to grab the first ring and then swing like a pendulum in order to reach the next ring. To get to the third ring, I had to use the momentum from the previous swing to keep going. If I held on to the previous ring too long, I’d stop and wouldn’t be able to get enough speed to reach the next ring. This is Isaac Newton’s first law of motion at work: objects in motion tend to stay in motion, unless acted on by external forces. Once you start swinging, it’s easier to keep swinging than to slow down. The problem with some rapid...

There were certainly multiple factors contributing to these men’s post-moonwalk slump, but the question What do you do after walking on the moon? became a gigantic speed bump. The trouble with moonwalkers and billionaires is when they arrive at the top, their momentum often stops. If they don’t manage to find something to parlay, they turn into the kid on the jungle gym who just hangs from the ring. Not coincidentally, this is the same reason that only one-third of Americans are happy at their jobs. When there’s no forward momentum in our careers, we get depressed, too. As Newton pointed out, an object at rest tends to stay at rest. So how does one avoid billionaire’s depression? Or regular person’s stuck-in-a-dead-end-job, lack-of-momentum-fueled depression? Harvard Business School professor Teresa Amabile took on the question in the mid-2000s in a research study of white-collar employees. She tasked 238 pencil pushers in various industries to keep daily work diaries. The workers answered open-ended questions about how they felt, what events in their days stood out. Amabile and her fellow researchers then dissected the 12,000 resulting entries, searching for patterns in what affects people’s “inner” work lives the most dramatically. The answer, it turned out, is simply progress. A sense of forward motion. Regardless how small. And that’s the interesting part. Amabile found that minor victories at work were nearly as psychologically powerful as major breakthroughs. To moti...

Not every astronaut struggled postspace like Buzz Aldrin did. Several parlayed sideways rather than stopping their momentum. Earth orbiter John Glenn went into politics. Alan Shepard, America’s first man in space and the fifth to stand on the moon, became a successful businessman. Alan Bean, who moonwalked in the Apollo 12 mission, became a painter. And Apollo 15 spaceman James Irwin found fulfillment in helping others as a minister. Each parlayed his momentum into something that kept the wheels of life turning. Happy astronauts catch waves that lead to the moon, and then use the momentum to switch ladders to fulfilling careers on earth. Depression-avoidant entrepreneurs use levers to get massively rich, then parlay the momentum to build more things. But when Bear Vasquez tried to parlay his momentum for more, he got nowhere. What did he do wrong?

@Oreo’s tweet was clever. It was the most popular tweet of the event, in fact. But for perspective, 35,000 people is only three hundredths of 1 percent of the 108.69 million people who watched the Super Bowl. “Dunk in the Dark” was dramatically outviewed by every one of the television advertisements that aired during commercial breaks. And yet. Months later that Oreo tweet, now chiseled into the stone tablets of history as the Oreo tweet, received a truckload of awards and trophies, including two Clios. Not because the ad was amazingly designed. And not because more potential Oreo buyers saw the tweet versus Oreo’s Super Bowl TV commercial. But because Oreo managed to harness momentum with it and smother the insular advertising industry with its story. The momentum started when the tech blogs caught wind of the tweet. On game day, BuzzFeed wrote about the tweet in a post that earned 400,000 views. CNET and a handful of others wrote as well. The next day, Mashable posted an article titled, “Someone Give This Oreo Employee a Raise.” That story itself was also likely viewed more times than the actual tweet. Then the Chicago Tribune and Washington Post wrote about it. Advertising Age and Adweek wrote about how everyone else was writing about it. The frenzy of media coverage resulted in what Oreo’s advertising agency, 360i, claims were 525 million earned media impressions. (“Earned media impressions” is one of those inflated figures agencies tend to use to gauge how many people...

Michelle Phan grew up in California with her Vietnamese parents. The classic American immigrant story of the impoverished but hardworking parents who toil to create a better life for the next generation was marred, in Phan’s case, by her father’s gambling addiction. The Phan clan moved from city to city, state to state, downsizing and recapitalizing and dodging creditors and downsizing some more. Eventually, Phan found herself sleeping on a hard floor, age 16, living with her mother, who earned rent money as a nail salon worker and bought groceries with food stamps. Throughout primary and secondary school, Phan escaped from her problems through art. She loved to watch PBS, where painter Bob Ross calmly drew happy little trees. “He made everything so positive,” Phan recalls. “If you wanted to learn how to paint, and you wanted to also calm down and have a therapeutic session at home, you watched Bob Ross.” She started drawing and painting herself, often using the notes pages in the back of the telephone book as her canvas. And, imitating Ross, she started making tutorials for her friends and posting them on her blog. Drawing, making Halloween costumes, applying cosmetics—the topic didn’t matter. For three years, she blogged her problems away, fancying herself an amateur teacher of her peers and gaining a modest teenage following. This and odd jobs were her life, until a kind uncle gave her mother a few thousand dollars to buy furniture, which was used instead to send Phan t...

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