It was the spring of 2007, and Austin McChord was running out of options. A student at Rochester Institute of Technology, he sported a 2.2 GPA and had failed to graduate on time. Austin’s peers were, in the go-go days before the Great Recession, accepting jobs at Apple, Google, Wall Street banks, and hot new startups flush with Silicon Valley cash. Austin, on the other hand, had no job, no degree, and a pile of Legos in his father’s basement office.
But he had a vision. As a geek who’d spent his high school and college years messing around with computers, Austin understood the importance of protecting data in the digitized economy. While big companies could afford to hire professionals to deal with storing and protecting sensitive data, smaller businesses needed cheaper and faster ways to make sure their files were always accessible. With zero startup capital, Austin used the Legos, hot glue, parts from a Linksys router, and a soldering iron to create a series of barely functional prototypes of a product that could replicate data to servers in the cloud. Before long, he had racked up $80,000 in credit card debt and his closest friends and advisers were urging him to cut his losses before he went bankrupt.
But Austin pushed on. Later that year he founded his company, Datto, and eventually managed to secure patents. But he still wasn’t making any money, and he was constantly making mistakes. When his friends talked about their civilized jobs, Austin talked about his mission, sounding, they often told him with an awkward smile, like some crazy, obsessed person. It was hard not to wonder whether he had done the right thing by staying at home in small town Connecticut while his friends left and made real money.
Yet after hustling for several years and crisscrossing the country to build his customer base, Austin had a devoted following of IT professionals who trusted and relied on Datto’s products. His hardware had allowed businesses in New York City to retrieve their data and get back on their feet after Hurricane Sandy destroyed billions of dollars’ worth of infrastructure. Impressed, a large company offered Austin $100 million for Datto. Not bad for a C student who took six years to graduate from college. Austin called his lawyer and asked if he should take the deal.
“Absolutely accept this offer,” the lawyer urged him. “You can then spend the rest of your life regretting it from your own private island in the South Pacific.”
But Austin wasn’t so sure. He had a hunch that his company could do even more, that cashing out now would be wrong, that his employees deserved a cut of the action, that the best was yet to come. He turned down the money. Austin continued to grow his company, and five years later another offer for north of $1.5 billion came along from Vista Equity Partners, one of the largest private equity firms in the country. This time Austin accepted, and the erstwhile Rochester Institute of Technology slacker became one of the nation’s wealthiest people.
If you ask me what made Austin succeed—and many have—I can give you a simple answer: Austin succeeded because he is a primitive. More specifically, Austin is a relentless primitive who is able to distinguish the signal from the noise and maintain his focus. He knew when to charge full steam ahead and when to slow down. He knew when to cut corners and when to be a perfectionist. He knew when to say “Yes” and he knew when to say “No.”
In the traditional sense, relentless means being oppressively constant. Context matters, naturally: an advancing band of bloodthirsty orcs is relentless, just as Amazon.com’s march toward retail hegemony is relentless. While Jeff Bezos may not have conquered middle-earth (yet), the meaning of the word relentless is essentially the same.
When it comes to building a career, a civilized person may cruise relentlessly onward like a marathon runner, but not necessarily smartly or successfully. Take me, for example. The fall of 1991 was one of the most hopeful periods in my life. I had earned my master’s degree in international affairs from Columbia University a few years earlier, and I was fortunate enough to have secured a string of promising entry-level jobs, including as an aide to then–California congressional representative Mel Levine and as an intern on the foreign desk of CBS News. With a little bit of experience and a few impressive lines on my résumé, I eagerly jumped into what I imagined would be the rest of my life. I dreamed of a challenging and meaningful career in diplomacy, public policy, or media. I thought I had everything it took to get me where I wanted to go. I applied to every job I could find and prepared a portfolio of enthusiastic recommendation letters. I was sure it wouldn’t be long before I was invited to join the educated and the skilled in some dynamic office. Like every American success story, all I had to do was hustle and play by the rules to get that dream job—or so I believed.
And yet, time after time, I was turned down.
Rationally, I knew I shouldn’t take the rejections personally. The notes I received were form rejection letters, probably sent to dozens if not hundreds of other job seekers. But in reality, I thought that I wasn’t just any other job seeker. I was special. Yet, with each “We regret to inform you…,” I began to wonder if there was, in fact, something wrong with me. I had relentlessly sent out résumé after résumé, but that strategy clearly hadn’t worked. To make matters worse, I was running out of cash; I had already quit my PhD program after falling behind on tuition payments. As my father, who was also nearly broke at the time, told me: “Don’t be overeducated and underemployed.”
One day, a friend casually mentioned a name that piqued my interest: Elias “Buck” Buchwald, who helped start Burson-Marsteller, which was then the world’s largest PR firm. A World War II veteran, Buchwald had counseled the leaders of industry giants including IBM, General Motors, DuPont, and General Electric—iconic brands that owed their success in no small part to Buck’s ability to help tell their stories in a clear and truthful way. He even trained the senior diplomats of the Israeli foreign ministry. Having worked for the Israeli diplomatic mission to the United Nations, I thought maybe I had a personal connection. I had to meet this guy. But how?
At first I considered trying the same thing I’d done earlier: submitting an application to Burson-Marsteller’s human resources department. But that approach had already failed me. What’s more, Buck was surrounded by an impenetrable wall of assistants; my résumé would be buried among hundreds of others. It was time to try something radically different. Instead of hoping to outlast my competition, I had to make a primitive move and sprint to the front of the pack.
The next day I was at Columbia University’s business school library, twisting the knobs of the old microfilm and microfiche machines and scouring archived publications for intel about Buck and his firm. What today takes a few seconds with a smartphone took, back in the prehistoric days of the early 1990s, an entire afternoon. But climbing up the stairs to my fourth-floor walk-up that evening, I knew everything I needed to know about the man I was trying to impress. This time I’d write a letter that would get noticed.
“Dear Mr. Buchwald,” I began. “I’ve been practicing public relations without a license.…”
I went on to talk about my experience, but not as dull bullet points on a curriculum vitae. I had some fun, giving obvious but playful hints to get Buck interested in me. I sent the letter. A few days later, I picked up the phone and called Burson-Marsteller’s offices. Buck’s secretary picked up. My voice quivering, I explained to her that I’d written Mr. Buchwald and wanted to speak with him briefly. Shockingly, she put me through.
“I got your letter, Mr. Greenberg, but we’re not hiring anyone right now,” Buck told me gruffly.
“I understand, sir,” I replied. “All I want is just a few minutes of your time.”
Finally, he relented. “Be here Friday, 9:00 a.m.,” he said, then hung up the phone.
I showed up in his office at the appointed hour. Like a drill sergeant, he asked me a series of rapid-fire questions: Could I write well and fast? Could I work with the media? Was I able to handle myself well in crisis situations? I gave my best answers, and Buck summoned the company’s head of HR. The following Monday, I took a writing test. On Tuesday, I received a job offer.
Why did I succeed? I hadn’t followed the rules. I didn’t wait in line like everyone else. I wasn’t particularly qualified. Instead, I acted like a primitive. I was still relentless with respect to my goal—getting a job—but I bent the rules. I took a shortcut.
Contrast my experience with the prescriptions contained in Battle Hymn of the Tiger Mother. In that international bestseller, the author, Amy Chua, a professor at Yale Law School and the daughter of Chinese immigrants, advocates for strict, no-nonsense parenting that stresses self-motivation, sweat, and a perpetually positive attitude that never wavers even when hard work yields little or no results. Former British prime minister David Cameron, a big fan of the book, explained that Chua’s message was especially important for children: “Work, try hard, believe you can succeed, get up and try again,” he said. Or, as another famous British prime minister once said at the dawn of World War II: “I have nothing to offer but blood, toil, tears, and sweat!”
When I was applying to job after job and being rejected from all of them, Chua might have told me to keep at it. I needed to stay positive and keep relentlessly sending out résumés—eventually, one of them would find its way to the right person. Chua’s and Cameron’s idea of being relentless might have its merits when it comes to conquering algebra, practicing piano, and maybe fending off a Nazi invasion, but it’s not necessarily helpful in the modern economy.
By the time I was joining a much more rapidly growing workforce, amid economic changes accelerated by the advent of the internet, the traditional “apply and wait” approach was already feeling antiquated. Today, it’s positively ancient. While LinkedIn and Indeed have replaced snail mail, the same idea applies for the civilized: you drop your line in the water, sit back, and wait for a bite. As I learned all those years ago, the relentless primitive doesn’t have the patience for any of this; she grabs her spear and goes hunting. She understands that being relentless doesn’t just mean trying hard—it means leapfrogging ahead. As we’ll see in this chapter, a primitive isn’t afraid to reach her goals by telling white lies, being selfish, and flashing that chip on her shoulder. Most important, when she’s headed in the wrong direction, she isn’t afraid to stop moving, turn around, and find a new road.
A decade ago I was hired by a nonprofit, Iran180, to help publicize human rights abuses by the Iranian regime. Human rights, I thought, was a topic everyone understood instinctively; you didn’t need a master’s degree in international relations to grasp that executing people because they were gay was a horrendous crime, or that a state that supported terrorism shouldn’t be allowed to develop nuclear weapons. Our task was to find simple ways to explain the horrors of the Iranian regime to the general public. Sitting on the roof deck of our office, we threw around ideas about how to get the attention of people with only a passive interest in foreign affairs. My buddy David Galper, just riffing, began talking about the furry mascots that dance in between innings at baseball games. These mascots are crowd favorites, David said, because they are garish and over the top. You can’t help but watch.
So instead of taking our campaign to Washington, DC, think tanks, we took it to the streets with a ten-foot-high puppet of Iran’s leader at the time, Mahmoud Ahmadinejad, holding a giant atomic rocket. Then we sent the puppet, accompanied by street theater performers and cheerleaders blasting loud music, to cavort outside the United Nations. We staged a mock trial and then had the puppet “arrested.” Everyone from passersby to diplomats knew exactly what our message was.
We hit the kind of home run that PR people can only dream about. Early the next morning I drowsily opened the New York Times to discover that our puppet had made the front page. A few weeks later, I donned the puppet suit on The Daily Show with Jon Stewart, where I talked to Samantha Bee about nontraditional protests. Sure, we could have fired off a strongly worded position paper and influenced a few dozen people. Instead, we approached the problem like a five-year-old would: we threw a big party with puppets and dancers and music.
Austin McChord certainly understands the power of the childlike mind. The man who built his first server using Lego bricks was often called a “man-child” by older executives at Datto. Austin encouraged his employees to paint their offices crazy colors and play with toys at the office. He left the key to his Tesla on his desk and let his employees take it for a spin anytime they wanted. Datto workers even created T-shirts with their fearless leader’s silhouette and the caption: “Keep Austin Weird.”
Here’s another childlike quality that’s surprisingly useful as an adult: telling white lies. Even the most devoted parent would agree that children often lie. When my wife and I asked our son, Noah, one of the purest primitives I know, if he had done his math homework, he’d reply, “Yup.” When we’d ask if he’d read his book for English class, he’d reply, “Yup,” and give us a brief synopsis. Noah, it turns out, never did his homework or read his books, but he was such a confident character that he could fool his teachers (and his parents) into believing he had. I remember thinking at the time: Noah may struggle a bit in school, but he’s going to make a ton of money one day in business. As it turns out, while he wasn’t doing his homework, thirteen-year-old Noah was buying Tesla stock long before most of Wall Street caught on.
When Austin was still running his company out of his father’s basement, he knew he would have a hard time being taken seriously. To make the company seem larger and more important, he would answer his phone with a British accent, pretending to be a nonexistent colleague.
Whether it’s imitating a secretary, embellishing non-critical details on a résumé, claiming the messenger failed to deliver documents you actually forgot to send, or purporting to be further along on a project than you actually are, to the relentless primitive, white lies are part of doing business. Naturally, it’s up to you to measure and limit the seriousness of your lies, and prevent yourself from crossing any lines. For example, with Elizabeth Holmes, the once-celebrated founder of blood-testing firm Theranos, a few early lies quickly became the very backbone of an enterprise that eventually crumbled under its own fraud.
In some other cases, however, a single white lie has sometimes saved a company. One of my favorite examples involves Rent the Runway, the online business that allows users to rent high-end designer clothing. Today, Rent the Runway is hugely successful, but in 2008 it was merely an idea in the minds of two Jennifers—Jennifer Hyman and Jennifer Fleiss—who were section mates at Harvard Business School. They had secured a meeting with legendary designer Diane von Furstenberg, hoping she could help them break into the notoriously cliquish fashion industry. As they were en route to their dream meeting, Hyman’s cell phone rang. It was von Furstenberg’s assistant: she was canceling the meeting, and it wouldn’t be rescheduled. Fleiss began sobbing, but Hyman, every bit the relentless primitive, knew instinctively what to do: she pretended she had poor cell phone reception and couldn’t hear von Furstenberg’s assistant. Hyman and Fleiss arrived as planned at the famous designer’s office, pled ignorance, and insisted they keep the meeting. The assistant relented. The two Jennifers met with von Furstenberg and emerged with a powerful ally and a couple of priceless introductions.
Another crucial childlike quality? Having playdates.
Grown-ups have meetings. They’re endless, frequently leave you drained, and rarely seem to accomplish anything. Kids have playdates, which leave them charged up, excited, and ready to take on the world. Instead of boring meetings, why not have playdates? Relentless primitives constantly crave inspiration to fuel their journey—inspiration that often does not come in the workplace. Austin, for example, competed in BattleBot competitions with his friends and colleagues, crashed drones, and infected his own computers with ransomware to figure out how to beat it. A little creative problem-solving outside of the office helped him approach problems at work with a fresh mindset.
Practice the five-to-one rule: for every five unavoidable meetings in conference rooms with agendas and PowerPoint presentations, have one work playdate. I don’t necessarily mean drunken karaoke or catching a dumb movie with a colleague (although these are great ways to get to know your coworkers). Rather, I mean getting together with someone you genuinely, truly like—a friend, a vendor, a partner, a boss, an employee—and bouncing ideas around in an environment that isn’t the office and doesn’t feel restrictive. Billionaire Yvon Chouinard, the founder and CEO of Patagonia, for example, formed a group called Do Boys with his fellow entrepreneurs and executives to embark on a major outdoor adventure at least once a year.
Back when I was taking 7:00 a.m. CrossFit classes, I became friendly with a group of successful guys who loved having playdates. There was Anthony, who worked as publisher of a music magazine; Brian, an FBI agent who holstered his Glock in the locker room; Kirk, who ran security operations at the United Nations and made a habit of flaunting his stab wounds from his peacekeeping days in the former Yugoslavia; Scott, a successful hotelier; and Tim, a computer engineer. At first I was a bit weirded out by the “Morning Posse,” as they called themselves, but we became fast friends. We took vacations together, and I even forged professional connections with each member of the Morning Posse. Years later, when Kirk was dying of colon cancer, the rest of the group dropped everything and flew to his home in Nova Scotia to say goodbye. The once 190-pound chiseled rock had wasted away, but he still found the energy to give me words of encouragement on his deathbed, just as he had for years at the gym. In fact, without Kirk MacLeod, this book wouldn’t have happened.
Make a habit of scheduling regular meetups with friends and colleagues—whether it’s coffee, lunch, after-work drinks, or ski trips. You might think that sounds trivial, but old-fashioned social interaction can be as important to your overall health as hitting the gym. And no, that group text thread or the occasional FaceTime on your smartphone isn’t good enough. Press some flesh and play in real life. You will be surprised how much it helps; playing around with people you enjoy connecting with is an excellent way to work that childlike muscle and escape whatever professional rut you may be stuck in.
Anyone who spends time with children knows another truth about them: they aren’t afraid to throw a tantrum to get what they want. When Indra Nooyi became CEO of PepsiCo in 2006, she sought advice from none other than Apple CEO (and über-primitive) Steve Jobs. “He said, if you really feel strongly about something—if you don’t like something people are doing—throw a temper tantrum,” Nooyi recalled. “Throw things around, because people have got to know that you feel strongly about it.” While Nooyi may not have quite gone to Jobsian lengths to get what she wanted, she is not afraid to channel her inner toddler.
Finally, just like our ancestors, relentless primitives do not shy away from self-preservation. To be relentless is to be focused on yourself and your goals; everything else is secondary. My friend John, who works for Fidelity Investments, is a generous person, but he isn’t selflessly so. People frequently ask him for help getting a job, so John came up with a selfish-ish rule: he will help out if he can, but he’ll never meet for coffee or a beer. Instead, John takes phone calls and limits them to ten minutes. He’ll make an introduction for you, but never more than one. And perhaps most important, he is not afraid to ask for a favor in return when he sees an opportunity. John protects his most prized possession: his time. He is generous with his ideas, but selfish with his hours. Does he occasionally rub people the wrong way? Of course. But by being up-front with his rules and expectations, he ensures his relentless energy is focused on his career and his family.
One of the most successful financial services firms in the country is one you may not have heard of. You won’t find its office on Wall Street, and its employees aren’t would-be masters of the universe who orchestrate multibillion-dollar mergers and acquisitions. Rather, you’ll find its storefronts in small towns and suburban strip malls across America.
Meet Edward Jones. The nearly century-old firm has some forty-seven thousand employees and more than $8 billion in revenues, but its sales associates don’t spend their days screaming into telephones and pounding away at Bloomberg terminals. Instead, they knock on the doors of ordinary people and conduct business in living rooms and kitchens. They try to form genuine, personal bonds with their clients, and it all begins with a handshake. You might see your Edward Jones broker at the grocery store or the bowling alley; he might even be your neighbor. The company has more retail offices than any other brokerage firm for the purpose of forging personal relationships between financial advisers and clients. It also routinely outranks other national full-service brokerage firms in workplace satisfaction, and has a permanent spot near the top of Fortune and J.D. Power’s lists of the best places to work. One of the primary reasons is because the company nurtures independent thinking, with executives encouraging frontline sales associates to pitch new ideas and rethink sales techniques.
Edward Jones is a throwback organization in a time when most business is conducted over email, texts, and Slack messages. Meetings that once required a dozen people to congregate in the same conference room can now be easily arranged by looping in everyone on the same conference call. While efficiencies like these have certainly made us more productive, this convenience has its downsides. Chief among them is that we’re losing our ability to simply connect, in person, shaking hands and looking each other in the eye.
It’s a skill that Austin understood well. He struggled to find customers after he launched Datto, so he turned to small IT shops who could sell his backup hardware directly to end users. Austin would drive bleary-eyed to visit the many loyal clients who took a chance on his product, even ones in tiny towns. They were fellow entrepreneurs and so rabidly loyal to Austin that, during the company’s annual convention in 2018, he attracted a far larger band of autograph seekers than the keynote speaker, Sir Richard Branson.
And so, here’s a simple rule to follow: take a page out of the Edward Jones playbook and think like a door-to-door salesperson, not a Wall Street banker. How do you earn a great reputation? It’s not just the quality of the returns, but rather the quality and variety of the conversation that keeps customers coming back. Take your work personally. There are many ways to do this, starting with the line of work you choose to get into.
Another guy who takes his work personally is Dan Mullen. On a cold Thanksgiving evening in 1989, Dan was sitting alone on the sidelines of Gill Stadium in Manchester, New Hampshire. His team had recently been eliminated from the state playoffs and Dan, the senior quarterback, would never again play high school football. His coach found him quietly sobbing. “If someone asked me to describe Dan as an athlete and a person, I would say he was relentless,” he later said. “You always got his best effort.” Fast-forward thirty years, and Dan is now head football coach at the University of Florida, where he is still taking football every bit as personally as he did as a teenager. He blurs the line between family and football; his wife, Megan, is heavily involved with team events and recruiting, and the two “treat every player on the team like they’re our own kids,” Dan explained in an interview. In return for his devotion, he insists that his players work just as hard as he does. “You will see a team that plays with relentless effort,” Dan promised before the 2018 season. He was right: When he arrived in Gainesville, the Gators were coming off a 4–7 campaign. In his first season, the team went 10–3 and the Associated Press ranked it seventh in the nation. The following year Mullen’s Gators jumped to No. 6 with an 11–2 record.
The old cliché goes that you should do what you love. “Follow your bliss and the universe will open doors for you where there were only walls,” as Joseph Campbell once said. It’s hard making a career out of what you love to do, but some people hit the jackpot: Dan Mullen may love coaching football more than anything else on the planet, and it turns out he’s pretty good at it. Stephen King adores writing so much that he aims to churn out a minimum of two thousand words per day; it happens that most of those words end up in bestselling novels. But the painful truth is that a lot of us aren’t very good at doing the things we love. For example, I love to sing. But as my family not-so-gently reminds me, I’m terrible at it. It pains me to admit it, but as much as I enjoy crooning, I will probably not be the next Frank Sinatra.
One of my favorite movies is Thank You for Smoking, a satirical comedy about Big Tobacco. Aaron Eckhart plays Nick Naylor, a smooth-talking spokesperson who lobbies on behalf of a product that kills people while also trying to be a role model for his twelve-year-old son. After Naylor sagely talks down his bosses as they careen from one scandal to another, he remarks to the audience: “Michael Jordan plays ball. Charles Manson kills people. I talk. Everyone has a talent.”
The film hopefully did not spawn a new generation of tobacco lobbyists, but it makes a broader point about choosing a career path: find something you are a natural at and then milk it as much as humanly possible. Relentless primitives often do not have the patience to learn a new skill from scratch; they find something they are good at and then search for a way to monetize it. When I was eight years old, I certainly didn’t dream of becoming a PR executive. But it turns out I’m very good at talking, and I’m even better at helping people and businesses talk about themselves.
When I was a kid growing up in Venice, California, my dad had a weekly touch football game on the beach with his friends. They’d drink beer, smoke dope, watch the sunset. One of the regulars was a guy named Jeff Smith. For the first twenty years of his work life, Jeff had a series of odd jobs and hustled to make a living, but nothing stuck. At one point he discovered his passion: writing. He wrote a number of screenplays, but, apparently, he simply wasn’t good enough at writing movies. But it turned out he was good at editing other people’s movies, and he built himself a wildly successful career in the movie trailer industry. He became extremely valued for his skill in producing previews, trailers, and TV spots for blockbusters. Once he made his fortune, Jeff sold his company, Open Road Entertainment, and is once again trying to make a go of it as a writer.
When you focus on what you are good at, work inherently becomes more personal. You are valued for a skill that you possess, and you make money doing that. You might find that you grow to love that skill—or, at the very least, you’ll love being valued for it. Or, like Jeff, you’ll make a boatload of money doing something else, shift gears, then re-devote yourself to your true passion.
Of course, finding something you’re a natural at doesn’t mean there won’t be obstacles standing in your way. Sometimes these obstacles are money, education, or loved ones. When someone is affected by these obstacles, we often say he has “a chip on his shoulder.” This phrase has a negative connotation, suggesting that this person is bitter and unable to set aside past grievances. A relentless primitive is always looking forward, but that does not mean he doesn’t occasionally glance backward at the zigzagging road he has traveled. And he never forgets just how difficult it may have been—or who may have stood in his way. That’s because refusing to let go can be a powerful motivator, as in the case of former NFL defensive tackle John Randle. He grew up during the 1970s in a shack in rural East Texas, sleeping in a bed with his three brothers after his father abandoned the family. Randle and his family didn’t have indoor plumbing or even a toilet. They could barely get by on his mother’s $23-per-week salary as a maid.
Randle was very, very good at playing football. His position was defensive lineman, and no opposing line could contain his unique combination of strength, speed, and ferocity. But he was considered too small to play at the highest levels. Randle didn’t brush this criticism aside—it pissed him off. He ground his way onto his high school team, then the local community college team, and then Texas A&M University–Kingsville. Just like he had in high school, Randle continued to terrorize his opponents, relying on brute force over form. Yet scouts still thought he was undersized, and no team took him in the 1990 NFL draft. He managed to secure a tryout with the Tampa Bay Buccaneers, but the team wanted to switch him to linebacker, a position more suited to his size. Randle refused. Finally, he landed with the Minnesota Vikings, where he won a spot on the practice squad, then special teams, then, finally, the starting lineup. Before every game, he’d smear his face with war paint and memorize obscure facts about the other teams’ players to throw his rivals off their game. Randle finished his career with more sacks than any interior lineman in the history of the league.
How did he do it? How did he distill his complex emotions into a potent brew that made him better? Not by obsessing about his disadvantages or allowing himself to fester with resentment—that’s never helpful—but by reframing the experience and learning to see each rejection as nothing but an invitation to work harder, do better, and find another way to channel that relentless energy that’s so personal and pure.
Many of the most successful people I’ve met never stop trying to prove themselves to haters—real or imagined—standing in their way. They don’t forget slights, and they aren’t quick to forgive. But while some people are consumed by their resentments, relentless primitives are fueled by them. For example, Austin’s academic adviser at the Rochester Institute of Technology called his data backup idea “terrible” and insisted he focus on graduating. Austin used that C average and his skeptical adviser to drive him, proving he could succeed against the odds. Yet, after he sold his company at age thirty-two, he immediately donated $50 million to RIT—the single largest donation in the school’s history.
There are many ways to make use of those chips on your shoulder without letting them overly burden you. I still keep a folder of my rejection letters from my first job search and I look through it from time to time for motivation. Brad, one of my favorite former clients, is a very successful tech CEO who keeps an old wooden shoeshine box in his closet. Many years ago, he shined shoes in South Boston to make ends meet. He keeps the box to remind himself of where he came from and of all the obstacles he had to overcome.
Rather than being quick to forgive and forget—a very civilized attitude—find some physical object of your own that reminds you of a past setback and look at it at least once a week. Reflect on your hardships. Remember your difficult beginnings and use them to fuel your progression.
Each year, the tiny Welsh town of Llanwrtyd Wells holds a curious ritual called the Man Versus Horse Marathon. The twenty-two-mile course is a mixture of roads, farm pasture, forest trails, and rocky streams, and it is open to two- and four-legged competitors with the simple rule that the human or animal who finishes the course fastest wins. You might think horses, which can reach a top speed of 30 mph, always win. They usually do, but humans occasionally prevail despite their obvious physical shortcomings. Humans may not be built to compete at the Kentucky Derby, but we are built to run at a moderate pace for very long stretches. Our approximately three million sweat glands keep us cool, and our springy tendons act like pogo sticks to convert elastic potential energy into kinetic energy.
Anthropologists believe that our great endurance abilities were crucial two to three million years ago, when early humans first began hunting. We may not have been able to run down a gazelle like a cheetah, but we could jog for hours at a time, wearing down our prey until they keeled over from heat exhaustion. This practice, known as persistence hunting, is still practiced by indigenous tribes in Africa’s Kalahari Desert and elsewhere in the world.
Fortunately, we now have Trader Joe’s, so we can choose our meat in the safety of a climate-controlled building. But many of us can still endure. Generations of sitting at desks and standing on assembly lines has not entirely undone our abilities to keep going through physical challenges. The key is that some evolved primitives know when to stop jogging and start sprinting.
Studies show that endurance athletes who implement high-intensity interval training like sprinting into their routine can actually improve their overall endurance levels. That’s great, you’re probably thinking, but what does that have to do with my own goals? For civilized people, work is always about the long run. They are structured folks, wedded to their respective routines, and they like to feel like everything they do is part of an ongoing and orderly track that leads them very clearly from point A to point B. When they’re relentless, it’s about carrying on in their path, like marathon runners slogging through the pain at a steady pace to reach the finish line. Relentless primitives are different. They’re just as mindful of that ribbon, but they have a very different idea about running races. Like endurance runners who have also trained as sprinters, they feel more comfortable with a series of mad dashes than with one long slog.
The relentless primitive knows that to summon the energy necessary to bust through the tedium, you often need to act like the house is on fire and drop everything and run. Not long ago I was scheduled to fly and meet an important client. It was a stormy afternoon, and, to my great annoyance, my flight was canceled. A civilized person, even the most relentless one, would likely have called the client, apologized, and offered to fly in the next day or set up a videoconference. But my gut convinced me to make a primitive move: this client was just too important to reschedule, and he expected me to be there for him. I told my colleagues I wouldn’t be available for the next day or two, kissed my slightly confused wife goodbye at 8:00 p.m., and drove four hundred miles across four states. I slept in a roadside motel and made my morning meeting on time. I made sure that the message to my clients was clear: I will literally go the extra mile for them. My colleagues back home thought I was a little nuts, but they had to grudgingly give me credit for my devotion.
Moves like these are instinctual for primitives. One of the most important skills of the modern workplace is prioritizing. For instance, deciding which emails must be replied to now and which can wait an extra day, or which meetings need to happen and which are less important. Relentless primitives can immediately recognize what requires their attention, and they have no problem dropping everything else on a moment’s notice. Like an ER doctor conducting triage, you have to look at your to-do list and determine what is urgent and what can wait.
Daymond John, founder and CEO of apparel company FUBU and investor on the hit show Shark Tank, has a unique way of prioritizing his day. “When you wake up in the morning and look at emails, you’re going to be consumed by everyone else’s emails of people asking you what they need to be done,” he told CNBC “Make It.” “You don’t get an email in the morning that says, ‘All those problems I had last week, I solved them, and the check is on the way to you for a million dollars.’” Instead of letting emails shape his day, he arrives at the office with his own agenda in mind. Some of the tasks on his to-do list will advance that agenda and some will not, and John prioritizes them accordingly. “When I walk into the world, I’m concentrating on what I want to accomplish,” he explains.
Relentless primitives never lose sight of their mission and don’t allow less important problems to obscure it. Moves like these are selfish, as we discussed in the previous section, but they are necessary. Like John, I now begin my day by laying out precisely what I want to accomplish. Only then do I open my inbox and determine what can wait a day, a week, or a month. I focus on what can help me meet my big goals for the day. You’ll piss some people off with this strategy, but that’s the cost of doing business.
One thing to keep in mind is that while relentless primitives might find it easier to prioritize their time than civilized people, who are prone to “people please” and put the priorities of others before their own, they are just as susceptible to burning out. Henri Poincaré, the famed French theoretical physicist and philosopher, devised a math problem so complex—aptly called the Poincaré Conjecture—that it took the world’s most brilliant mathematicians nearly a hundred years to solve it. His work laid the basis for chaos theory, which has applications today in everything from cryptology to robotics to weather patterns. Poincaré also wrote extensively about his work habits—especially when he was suffering from the theoretical physicist’s version of writer’s block. Writing about one of his major mathematical breakthroughs, Poincaré described two miserable weeks of hard work and no results:
Every day I seated myself at my work table, stayed an hour or two, tried a great number of combinations and reached no results. One evening, contrary to my custom, I drank black coffee and could not sleep. Ideas rose in crowds; I felt them collide until pairs interlocked, so to speak, making a stable combination.
By the next morning, the solution appeared. What Poincaré needed to succeed wasn’t his usual routine of working hard at his desk, but just one wakeful night of letting his mind go wander wherever it needed to.
To stay nimble, the relentless primitive’s brain must be allowed to roam occasionally without purpose, to wander off without being taxed by conventional tasks, free to make all sorts of discoveries. The civilized mind, on the other hand, abhors nothing more than wasting time. In an age when entire professions are structured around billable hours, is there a more serious transgression than declaring some of those hours “me time”? Ironically, the more apps and experts emerge to provide us with new and efficient ways to manage our time, the more we treat time like a resource that must be used to the fullest, which only increases our anxiety.
So, should you disappear for vast swaths of your day to play Pokémon Go? Not exactly—the economy does have to function, after all, and I’d certainly hope the pilot of my red-eye flight or the surgeon performing my knee surgery doesn’t suddenly follow my advice. Instead, if your circumstances allow it, channel your inner Ferris Bueller and give yourself short breaks during the workday dedicated to nothing but recharging. If possible: take a thirty-minute walk, bike around the park, or, if you’re like me, take a midday yoga class or catch a matinee.
What is some regular downtime during your day that you could take advantage of? When my eldest daughter turned twelve, she insisted on getting a dog. “No way,” I said. “How could I possibly make time to walk him?” I was working long hours and often got up before sunrise to catch up on email and prepare my calendar among other busy-bee tasks that civilized relentless people insist on doing. But a child’s plea is hard to turn down, and soon a charming mutt entered our home and our hearts. It didn’t take me longer than a few weeks to understand that I could barely afford not to take the time to walk Winston. Not only was it fun, but the daily respite gave me the time to clear my head. I’d leave my phone powered off, or better yet, at home. I was still thinking about work and trying to creatively solve problems in my head—relentless primitives are almost always thinking about work—but stepping away from the office and being alone (or with Winston), helped me focus. I’ve lost count of the number of epiphanies that came to me as I scooped up poop.
Research bears this out: in his book Deep Work: Rules for Focused Success in a Distracted World, Cal Newport, a professor of computer science at Georgetown University, explains that tasks like answering email, chat messages, meetings, notifications, and social media can destroy our productivity. Instead, he explains that regularly dropping out to focus on a single goal is far more effective. As an example, he offers the tale of the renowned psychiatrist Carl Jung, who routinely escaped to his cabin in the woods for weeks at a time to read, write, and simply sit in perfect stillness. Yes, that form of primitive relentlessness allowed Jung to successfully challenge his erstwhile mentor, Sigmund Freud, whose very name at the time was synonymous with psychology. My friend Alan Lightman (whom we’ll learn more about in the Agnostic chapter) is a physicist, writer, and social entrepreneur who wrote an entire book—In Praise of Wasting Time—on the virtues of taking breaks. He even boldly proposes that “half our waking minds be designated and saved for quiet reflection.”
How often do you find yourself truly alone—not just away from people, but from your devices? It might be hard at first. If you’re like I was, you get that brief pit in your stomach when you can’t find your smartphone, or when you haven’t checked your notifications for a while. I’ve slowly trained myself to spend time away from my phone and laptop, and I crave these moments so I can think through my biggest problems at work. (Of course my inability to be reached can drive my wife crazy, so, as always, there are compromises to be made.)
One day in October 2018, I was driving along Manhattan’s West Side Highway when I received a call from Austin. About a year had passed since he had sold Datto to Vista Equity Partners. “Do you have time to speak?” he asked. We had just spoken a few hours earlier, and I sensed that something serious was on his mind.
“Sure, what’s up?”
“I’m leaving Datto,” he said flatly. There was no hesitance in his voice. He wasn’t consulting me about his decision—he was informing me.
“Wow…,” was all I could say.
And just like that, Austin walked away from the company he had built from the ground up, the company into which he had invested nearly every waking hour of his adult life. I sat in my car, stunned. Relentless primitives don’t suddenly abandon their missions. I thought of former Uber CEO Travis Kalanick, who had to be dragged kicking and screaming from the company he founded, and Steve Jobs, who was shown the door from Apple in the early 1980s and spent the next dozen years plotting his return. But Austin? He simply got bored after Datto was sold and wanted to try something new.
I realized that Datto itself was never Austin’s purpose in life. He loved his company, but he loved his employees even more. Once he received a suitable offer for his business that would reward the people who had been by his side for years, Austin was ready to refocus on what he thought was his true mission in life: helping the little guy. Having come from a small town in Connecticut and attended college in a struggling city in upstate New York, he never fit the mold of your typical tech entrepreneur. That was the chip on his shoulder that we discussed earlier in this chapter. One of his proudest achievements was building Connecticut’s first unicorn—tech industry slang for a billion-dollar company.
Austin is now working at General Catalyst, a venture capital firm that makes early-stage investments in promising companies. The bio he wrote for the firm’s website beautifully sums up his broader goal in life:
During that amazing run [at Datto], my reason for coming to work totally changed. At first it was coding, creating, pushing the technology of the time to enable new possibilities. Over time I realized that I was coming for my employees, to empower them to break through walls and do great things. Becoming a leader was an evolution, with endless ups and downs, but it made one thing clear: If you want an exceptional result, it takes extraordinary effort.
Austin’s latest primitive move encapsulates the final ingredient of being relentless: changing lanes. Austin’s mission—helping people—has not changed. At Datto he wanted to help small businesses gain access to backup solutions. Now, at General Catalyst, he wants to assist entrepreneurs with big ideas who are trying to grow them into something special, just like he did.
We’ve all been taught to plow ahead, focus, and stay the course. That is the way of relentless civilized people who craft their careers by staying in their lanes. Think of the employee who worked his way up from the mail room to become head of the company, or the engineer who worked forty years at the same place and retired with a pension and a gold watch. They are relentless, but they never left their lane. Primitives are different: sometimes they make the easy right turn, sometimes they make sharp left turns, and they go backward just as easily as forward. With the growth of the gig economy and the financial insecurity that accompanies it, it’s never been more important to change lanes comfortably and nimbly.
Author Troy Anderson understands this principle well. In his wonderful book The Way of Go, he shares insights from the traditional Chinese game Go. Here’s one I love: don’t get too attached to your first moves. If you’re up against a good opponent, she’ll snuff out your strategy and you’ll have to reassess. The same is true in virtually every career path. Novelists and screenwriters, for example, often begin their project wedded to a cherished character or plot twist only to find that it must be jettisoned. Many civilized people will climb their own career ladder, but the relentless primitive is eager to shift lanes, whether it means making a lateral move to a new company or even switching careers entirely. Even if they occasionally sidestep or zigzag, they are always looking for the opportunity to take an enormous leap forward.
As we’ll discuss in more depth in the Agnostic chapter, not only does changing lanes keep you fresh, but it’s sometimes necessary for your very survival, not to mention satisfaction, in today’s workplace. Being a typewriter repairperson may have once been a lucrative job, but the forward-thinking primitives among them also learned how to take apart a computer. For some, that might mean stumbling onto a totally different path, as it did for the two scientists who rejected the directives of their big pharmaceutical company and accidentally discovered the molecule that led to the creation of the antidepressant Zoloft. For others, it might mean making a U-turn and returning to a former employer or career; many of us would consider that a shameful defeat, but as someone who completed three separate tours of duty with the same large multinational public relations firm, I can tell you that each time was different, instructive, and fulfilling in its own way. You can still be moving forward if you take a step back.
Even if you spent twenty years mastering a particular occupation, it doesn’t mean that you can’t make a sharp turn and try another. Jeff Bezos was once an unhappy thirty-year-old who had spent years working in the financial services industry. He took a coast-to-coast drive and decided to quit his job and launch an online bookstore from his garage.
Hitting pause does not just mean taking a breather during lunch. It can also mean stopping to reassess the weeks, months, and years ahead. What are the alternate lanes you envision your career taking? Do some include possible U-turns back to past employers or occupations? Or perhaps there are on-ramps to entirely new careers. Take frequent breaks to reexamine your situation. Whether it’s leaving work in the middle of the day or leaving your job in the middle of your career, never stop reassessing, and never be afraid to sprint to someplace new.