QUIT LIKE A WINNER

I am an adventurer.

This means I make a living by doing things that have never been done before. Whether it’s rowing 3,000 miles across the ocean or hiking through a desert that no human has ever crossed, before I do the things I do people call them “impossible.” After I’m done, they call them “crazy.” I call them “world records.”

I love what I do. Those words don’t bother me at all. But there are five words that do: “I could never do that.”

In addition to being an adventurer, I’m also a teacher. I travel the world teaching business leaders, academics, and others how dangerous those five words can be. I teach them that you don’t need to be a six foot five genetic freak like myself to do something amazing. I teach them that even simple goals can, and should, be tackled with the adventurer’s spirit. I teach them that they should stop saying, “I could never do that” and start saying, “I could never do that alone.”

The real secret to doing impossible things—whether it’s something life-threatening or just something career-threatening—isn’t learning to be tough, or strong, or magical. It’s learning to build, lead, and sustain high-performance teams.

This book is the story of how I built an exceptional team, the process I learned along the way, and how you can use that process to tackle any goal you may be facing. Because no matter how impossible something seems, the right team can make it possible.

This process isn’t simple, and it isn’t easy, but it is worth it. So let’s begin by talking about the darkest day of my life.

AUGUST 2004

Northern California

My left arm is wrapped tight in a sling, but I can still feel it throb every time my heart beats. And it’s beating an awful lot.

I have no problem with doctors, but they do seem to make you wait longer when you’re panicking. I’m trying my best to stay positive, but every second that ticks by is another jolt in my elbow and another whisper in my ear that the news might be terrible.

Around 400 jolts later, the door finally opens, and my doctor walks in carrying an unnervingly thick chart. He wastes little time before delivering my diagnosis. Suddenly, I wish he’d let me wait a little longer. I can see his mouth moving, but I’ve stopped listening. He’s just confirming what I already feared, what I knew the moment I heard that “pop” on the mound and felt that electric sting spread slowly through my arm, devouring my future as it went.

The medical term for my condition is a tear in the ulnar collateral ligament. Think of a rubber band connecting your elbow to your forearm. Now imagine blasting that rubber band with a cannon ball.

According to the doc, the only fix is a highly invasive reconstructive surgery with a name too complicated to remember. Baseball players have a shorter name for it, a name that strikes fear in the hearts of aspiring professionals around the world: Tommy John surgery. In that moment, I feel that it might as well be called your-life-is-over-now-Jason surgery.

I leave the office with a prescription for painkillers and an ultimatum: have the surgery, fight through the months of physical therapy, risk permanent injury, and maybe live to throw another day, or . . . don’t.

I’ve worked my whole life to get to where I am, but I also really want to keep having a life in the future. I don’t know exactly what that means, but I am willing to bet it will require at least two functioning arms.

For the rest of the day, I’m a zombie. My feet carry me around the campus of Sonoma State University unseeing, oblivious to my surroundings. I crisscross the property for hours, lost in a world of what-ifs and shit-this-sucks. The only place I don’t go is the baseball field.

I’ve been trying to ignore the weight in my pocket all day, but as the sun begins to set I know I can’t stall any longer. I reach in and pull out my cell phone. The number I need to dial is already on the screen. I finally find the guts to hit Send.

My dad answers on the second ring. I’ve made my decision. I just hope we both can live with what happens next.

AN INTRODUCTION TO HIGH PERFORMANCE

I never went back to baseball. I’m an athlete. I need to be physical in my life. I have to compete against something or someone in order to function. I decided my health was too important to risk on a single sport. You don’t hear this a lot from athletes, but quitting is allowed. In fact, it changed my life.

Fourteen years after I walked away from baseball, I walked out of a boat onto a sunny dock in Antigua, an island in the West Indies. Together with a team of three other men, I had rowed more than 3,000 miles to cross the Atlantic Ocean in 35 days, 14 hours, and 3 minutes. Together, we won the Talisker Whiskey Atlantic Challenge, which I call “The World’s Most Impossible Race,” shattering a world record that had stood for more than a decade. It did take me two tries, but that’s not bad for a guy with a busted elbow.

This is what my team, Latitude 35, does: We race and adventure around the world. Together, we currently hold eight Guinness World Records that span three oceans and four continents. Our job is to do things that haven’t been done before. I guess you could say we’re in the impossible business. It pays the bills. But the insurance is a nightmare.

Speaking of bills, it turns out that rowing across an ocean isn’t just dangerous, difficult, and dangerous (did I say that already?), it’s also expensive. Napoleon said that an army marches on its stomach. Well, an adventurer marches, climbs, rows, or runs on his sponsors.

When I set out to get funding for my Atlantic crossings, people told me to call on Under Armour, Red Bull, and all the usual players. I did, but they weren’t interested. As it turns out, ocean rowing isn’t quite as popular as professional basketball or the X Games.

My sponsor ended up being Carlisle Companies. Carlisle manufactures things that make other things work: wiring harnesses, building materials, machinery—that’s all Carlisle. What they do they do well, but they aren’t exactly known for their connection to the athletic world. General Mills won’t put a high-performance fiber-optic cable on a box of Wheaties no matter how innovative it is. But when I pitched them on my idea, they became the best partner I could have ever asked for.

One of my current sponsors is Booking.com. Its parent company, Booking Holdings, owns most of the online travel solutions you’ve heard of—Kayak, OpenTable, Priceline, and so forth. The company generated over $12 billion in revenue last year.

Last year, Booking flew me to their corporate headquarters in Amsterdam to speak at their annual meeting. The schedule had me giving my presentation at the same time as people with more business experience and corporate accolades than Gordon Gekko, Don Draper, and Scrooge McDuck combined. I didn’t think anyone would choose to hear my boat stories when they could be learning how to shift paradigms and create synergies. I was wrong.

More than 4,000 people crowded Booking’s main stage to hear my story. It was standing-room only. I felt like I should be wearing a pinstripe suit and telling them all how “greed is good.” For the record, I didn’t. Pinstripes don’t really work for tall guys.

Joining forces with Carlisle Companies and Booking has reinforced a lesson I’ve been learning since the early days of my career as a professional adventurer: the corporate world really wants to buy what the competitive world is selling.

Productivity, leadership, efficiency, endurance, discipline, success—these are the traits of elite athletes. They are also the traits that a sales manager in Phoenix or Seattle really wishes he could bottle and slip into his team’s morning pot of coffee.

I don’t condone spiking company beverages, but I do agree that people who do what I do have learned at least a few lessons that could benefit the world of business. The issue, however, is that we suck at sharing them.

There’s a reason that Mount Everest summiteers telling ballrooms full of hungover salespeople to “never give up on their dreams” has become cliché. Empty platitudes and hollow “motivations” seem to abound whenever athletes try to apply their experiences to anyone outside of our little world. If I had a dime for every time I squirmed in my seat as an athlete or adventurer told an audience that the secret to success is simply to put in more effort and never give up, I’d be rich enough to name all my kids Jason regardless of gender. That’s called “Foreman money.”

I’m a confident guy, but I’m not confident enough to say that I hold the secret to a perfect life. What I do have is experience with extreme success and extreme failure. I’ve learned from the latter in order to achieve the former. I can tell you from experience that success isn’t about refusing to quit. It’s about the teams you build and how you chose to lead them.

This book is for people who have a destination in mind and know there are miles to go before they sleep—miles that will be filled with absolutely brutal terrain. It is designed as a guide to teach leaders how to build, sustain, and guide high-performance teams through the challenges they will face in order to capture the glory waiting on the other side. If your only focus right now is collecting a paycheck, then this book is not for you.

But if you’re ready to show the world, and yourself, what you’re capable of as a leader, stay with me. In the lessons that follow you will learn what I know about creating teams that can, and will, do the impossible. It all starts with a single question: why?

ANSWERING THE QUESTION WHY?

I have done incredible things, but I have never achieved anything great on my own. Every record I’ve set, every stroke I’ve taken, and every mile I’ve hiked is made possible by my teams. Not every member of the team may have been with me at the finish line, but they were the ones who ultimately made it possible for me to be able to cross it at all.

Every team I build is meant to do something impossible. Doing the impossible in this case means accomplishing a goal that subverts the expectations of rational people.

Your impossible could be hitting a massive sales quota, starting an innovative new company, or just making sure the people you’ve hired get to keep their jobs for another quarter. The impossible is all around us, but so is adventure, and adventure can beat the impossible if you do things in the right order. The very first step is answering the question why? Not for your team, not for your boss, but for yourself.

Why should you give all your time and effort to this particular goal? If you don’t know why you’re doing something, if you don’t have a crystal-clear image of the success you’re chasing and the reason you’re chasing it, then you will never lead a high-performance team. You might be able to scrape together a few solid returns out of a burned-out group of overstressed individuals, but it won’t last.

If I didn’t have a strong why for my team and from my team, we would not have won our world record. We would not have made it across the ocean. We probably would have never even tried.

If all this sounds emotional, that’s because it is. Leadership is way more right-brained than people give it credit for. Building strategy is important. Setting timelines is important. Project management is important. But if you don’t own the emotions of your team, then you don’t really have a team at all.

The only way to reliably build teams that succeed is to find your why and instill it into the hearts and minds of the people you’re supposed to be leading. Believe it or not, the first step in finding that why may in fact be quitting.

Quitting is not a failure. Most people have heard that “it’s not how many times you get hit that matters; it’s how many times you get back up,” and that’s what they believe.

This saying is inspirational as hell if you’re in a Rocky movie. But in real life, it’s wildly off base. I’m not here to teach you how to be good at getting up. I’m here to teach you how to learn the right lessons from your time on the ground so that when you do get back up, you’ve become such a strong leader, with such a strong team, that you cannot be knocked down again. And neither can the members of your team.

When we were rowing in the ocean, whenever one of us took a dip in the water we were tied to the boat with a rope in case the currents changed suddenly. The last thing you want is to be untethered in the middle of endless water watching hopelessly as your boat disappears over the horizon.

However, we also always kept a knife on the deck as well. This knife was meant to cut the rope in the event an unexpected wave shifted the boat into a position where it was actually injuring one of our teammates. In life, your why is just like that rope.

Some people are too afraid to bring out their knife. They cling so tightly to an opportunity that they don’t realize it’s actually strangling them to death. They prefer that choking consistency to the terrifying possibility of being set adrift in an ocean of raw possibility.

Direction is good. Goals are good. But not all goals are created equal, and you need to test and be intentional with your goals to make sure they reflect the unique abilities, emotions, and goals of you and the team you are leading. Then you need to lead the team to the success you promised. In this book you will learn a process through which you can accomplish both of these things.

It starts with finding your why, which may mean calling it quits on a goal that is wrong for your team. But how do you know when the time is right? How do you know if an opportunity is keeping you tethered securely or choking the life out of you?

LEADERSHIP LESSON:
UNDERSTAND SUFFERING AND SACRIFICE

Quitting is nothing more than weighing two variables and finding that one of them has stopped being worth it. These two variables are something that every human deals with on a daily basis: suffering and sacrifice.

Humans have a knack for understanding the amount of suffering and sacrifice that they must endure to reach their goals. The trick is that you need to start doing this consciously and channeling what you find into a decision that leads to a why, which leads to a team, which leads to an impossible victory.

As an example, let’s look at two different corporate histories.

Airbnb is a company that enables people to open their homes to paying guests. That’s a wild idea even today, when as of this writing the company is currently poised for a massive initial public offering (IPO). But it was absolute insanity back in 2008 when its founders, Brian Chesky and Joe Gebbia, started trying to raise millions for a company most people were sure would be used exclusively by serial killers.

The duo persevered, however, and held on to their idea. The hook, they believed, was the ease and intimacy of people sharing their homes with other people, giving guests the experience of really living in the city they’re visiting. That idea was too powerful to give up, and today the insane company is projected to receive a post-IPO valuation of $190 billion.

That’s one path. But let’s consider another.

Very few people have heard of Game Neverending, an innovative little internet-only video game from a company called Ludicorp. The creators of Game Neverending dreamed of creating a fully immersive digital world, complete with fluid social interactions and a real, dynamic economy. The game had trouble getting funding—and players—and soon Ludicorp was on the verge of collapse.

In the final days of the game’s life, one enterprising programmer launched some simple photo-sharing functionality into Game Neverending’s social system. Photo sharing quickly became the number one activity among the game’s band of diehard players. This put Stewart Butterfield, Ludicorp’s co-founder and chief executive, in a tough position.

Butterfield could ignore the success of photo-sharing and leverage the company’s remaining funds into a last-ditch effort to make the game a success—a direction that was championed by most of his employees. Or he could abandon his dream of running a gaming company and start building a photo app.

The decision was difficult, but eventually Butterfield decided to scrap the game and launch a photo company instead. He gave his new start-up an era-appropriate, vowel-discarding name: Flickr.

Flickr became, in a pre-Facebook world, the number one photo-sharing website on earth and was eventually acquired by Yahoo! in 2005 for an estimated $22 to $25 million.

As humans we have an innate desire for comparison. Are Chesky and Gebbia geniuses for holding on to their idea and building a multibillion-dollar company? Was Butterfield a master strategist for pivoting to photos and earning himself a respectable fortune of his own? The answer to both is the same: not really.

These men aren’t special or unique. For every one of them there are thousands more who refused to pivot, or did pivot and ended up with nothing. The lesson here is not that they were successful. It’s that they became successful by finding and respecting their own thresholds for suffering and sacrifice.

Every human has an undefined threshold for both suffering and sacrifice that they are unwilling to go past. We don’t talk about it. We can’t measure it on any objective standard. But it’s there, and it’s there for everyone.

A noble quitter is someone who understands where that line is and learns to respect it. Quitting has gotten a bad name from people who are unaware of or unwilling to define that threshold and therefore decide to stop before they ever hit it. There is no honor or reason in that sort of quitting.

My adventures have taught me that while we all do have a threshold for suffering and sacrifice, it is usually much higher than we think. A person who would be capable of leading a high-performance team takes the time to learn exactly where their line is. Because once you know it, you can tiptoe right up to the edge and actually go farther than all the other people who flamed out a mile back because they couldn’t imagine they could make it that far.

The path to doing difficult things is not mindless enthusiasm. It is to learn about yourself. Learning about yourself is the only way to block out negativity, endure past adversity, and meet the goal you’ve set. It means testing yourself. It means earning your own self-confidence and paying through hardship. Then you will have the right to say to your team, “This is what we have to do.”

Quitting is not failure. Quitting is realizing that this one goal isn’t right for you and your team. Failure, real failure, is never finding one that is.

My path to success started the day I quit on something I’d wanted my entire life. That was the first step in a journey that would lead me to discover the process of finding my best goals, forging strong whys, building exceptional teams, and leading them to impossible successes.

SEPTEMBER 2004

Sonoma State University

I’m finally back in the gym. I don’t have a sport to train for anymore, but I really don’t know how else to spend my time. Sonoma State University is beautiful, but it’s not exactly New York.

My elbow has healed a bit on its own. I won’t be throwing a curveball anytime soon, but at least I can curl a dumbbell without blacking out. I’m reaching the point in my routine where the world starts to slip away and all I can focus on is the work. I’ve been depending on this time lately to get me through the long depressing evenings when I know my old team is on the field practicing without me. But just as my thoughts start to scatter, I’m interrupted.

“Jason Caldwell?”

I look up expecting to see someone from one of my classes, but I don’t recognize this man at all. He’s clearly older than I am, but not by much. He has neatly parted blond hair and a smile that seems just a little too big for his face. “Yeah?” I respond. I had a real knack for conversation back then.

“My name is Mark,” he says. “Got a second?”

GATHERING POINT:
LEARN HOW TO QUIT

Answering the question why? Before attempting any goal, you must answer the question why? for yourself. Why should you give all your time and energy and talent to this particular goal or set of goals? You can’t start to build and lead great teams without answering this question for yourself.

Suffering and sacrifice: Every commitment you make requires you to weigh two concepts: suffering and sacrifice. To stay committed to a goal means that you are willing to exchange the amount of suffering and sacrifice this goal demands of you. People who say they cannot do something are actually saying they are unwilling to endure the suffering or the sacrifice, or both, that are required of them to complete the task.

Productive quitting: Quitting can be a very productive thing and is often done by those we credit the most with winning. Quitting allows you to focus on a new goal rather than paying the opportunity cost of stubbornly committing to a goal that you don’t really find worthy of your time.