FOUR QUESTIONS

I had gone from a washed-out baseball player to a struggling rower to an elite Vesper assassin to nearly qualifying for the Olympics. But now, the time had come to test my mettle against my most serious challenge yet: the art of the perfect latte.

As it turns out, regatta trophies don’t take you quite as far in the job market as I’d hoped. Most respectable companies choose instead to focus on stupid things like “skills” or “experience.” That’s companies for you.

After Vesper, the only job I could get in a hurry was at a Peet’s Coffee near where I grew up. Every morning, faithful patrons would stream into Peet’s to grab a morning jolt and see what happens when you cram a six foot four rower into a small kitchen surrounded by hot liquids.

Skidding so suddenly from the highest levels of athleticism to the lowest levels of hot bean water preparation gave me a nasty case of professional whiplash. I had decided to forgo another four years of Olympic training, but I never thought I would be this far removed from the forces of competition that fuel my psyche.

I tried my best to bring some elite thinking to the good people of Peet’s, but my coworkers quickly tired of me shouting out my victory every time I completed a drink in half the time allotted by the manual. This wasn’t working out.

I won’t bore you with every step on my Holden Caulfield journey for purpose as a young, Vesper-less adult. But after being cast out of the barista life, I managed to bluff my way into a few higher-profile jobs and eventually landed at a professional development firm.

This company dispatched me all over the country to help struggling CEOs get better results out of their struggling teams. That job sowed the seeds for what would eventually become a company of my own, but all the time it was significant for two reasons.

When we look back on our lives, we tend to boil entire years down to one or two major outcomes. We reduce our entire childhoods to the same five or six anecdotes. You might say that high school was amazing because you met your wife. Your first job mattered because it led to that better one.

That sounds depressing, but it should actually excite you. Every phase of your life will have a least one major impact on the next step in your journey. Nothing is ever wasted. For me, this phase of life would be defined by one decision I made and one person I met. Let’s start with the decision.

THE GOAL

The Talisker Whiskey Atlantic Challenge. The idea for an Atlantic rowing race was conceived in 1997 by Sir Chay Blyth. Since then, the race has bounced around between a few different owners and changed names a few times. In 2012 the race was purchased by Atlantic Campaigns SL, which found a sponsor in the Scottish spirits company Talisker. The race’s official name is The Talisker Whiskey Atlantic Challenge—the World’s Toughest Row.

In my circles it’s called something else: The World’s Most Impossible Race.

Once a year, teams from around the world compete to cross more than 3,000 miles of open ocean in single-, two-, four-, and eight-person boats. More people have been in space than have completed the Talisker. But finishing is one thing. Winning is another.

To win this race you have to keep your boat moving at all times. That doesn’t sound too hard until you remember what’s powering it: you. This is a rowing race, so no sails, no motor, nothing but you, your teammates, and the ocean.

To keep pace, most crews embrace the two-hours-on-two-hours-off system. That means you’re sleeping for two hours, rowing for two hours, and repeating that pattern until the race is over. That adds up to 12 hours of the toughest rowing possible every single day until the race is finished, which can take well over a month. And that’s when everything’s going your way.

If the wind stops blowing, if there’s a storm, if one of your teammates gets hurt, your task gets even more insane. Then you need to row 18 hours a day with only four hours of intermittent sleep sprinkled sparingly throughout. For Talisker rowers, hallucinations, disembodied voices, and detailed conversations with the cast of Frasier are par for the course.

Each member of the team is allotted a carefully controlled five liters of water a day. Not exactly a doctor-recommended hydration plan. And this water isn’t just for drinking. It’s also for your food.

Race rules state that each boat must carry 5,000 calories worth of food per person per day for at least 60 days. In a competition where every ounce counts, that’s a lot of weight. Welcome to the wonderful world of freeze-dried food. You haven’t lived until you’ve torn open a pouch of desiccated beef stroganoff, mixed it with two ounces of the only thing keeping you alive, stirred it half-heartedly, and felt that telltale crunch as you chomped down on each partially rehydrated morsel. Just like mama used to make.

Competitors in the Talisker lose an average of 20 percent of their body weight. Since most of the male competitors weigh in at over 200 pounds at the starting line, that’s 30 to 50 pounds shed by your body in a month. Take notes, Atkins.

And, don’t forget, all these amazing experiences take place on a boat not that much larger than your average living room sectional. Four-person ocean rowing boats are roughly 30 feet long and six feet wide. They’re made of fiberglass, which is light and sturdy enough to withstand the journey ahead. These boats are self-righting, meaning that if a wave flips them, they’re designed to roll themselves back into a safe position. File that one under Cool Features You Never Want to Use.

These four-person boats typically have two cabins—a larger one in the stern and a smaller one in the bow. By “cabin” I mean tiny metal caves that can sleep one rower very uncomfortably or two if they agree to get married first.

The first thing most people ask after finding out all this is “why?” Why would any rational adult leave friends, family, and career for an entire month (or much more if you take into account training time), to do something so incredibly dangerous, inhumanly uncomfortable, and obviously unnecessary?

Is there a huge cash prize for winning? No. Does a victory automatically get you a spot on an Olympic team? No. Is there some sort of sea monster you’ve all been hired by the government to try and kill? We’re not supposed to talk about that.

Why? is the question of the hour. Why did Alex Honnold climb 3,000 feet up the face of El Capitan without a rope to catch him if he fell? Why did James Tabor descend 7,000 feet into the earth exploring the Krubera Cave in the Republic of Georgia? Why did three wonderful men with children strap themselves into a rocket that launched them to the moon? Why do adventurers go on adventures?

The answer is more practical than you might think, and it has nothing to do with poorly developed brains or daddy issues. The reason adventurers are able to identify these apparently insane directives and motivate themselves to finish is because adventurers have a system for choosing the right goals.

I’m about to teach it to you.

LEADERSHIP LESSON:
FOUR QUESTIONS TO ASK YOUR GOALS

I discovered the Talisker in the most boring way possible. I didn’t hear the legend from some old sea dog at the bar or discover a map to the finish line in a clamshell on the beach. I googled it.

One day I was in my apartment after a long stint of traveling for my company. I enjoyed my job. I was starting to hit respectable levels of real, adult success. But something was missing.

You might call this “the call of the wild.” A millennial would call it “chasing my bliss.” But I call it “disappointment.” Not in myself, but in the challenges I was tackling. None of them felt right for my skills, my opportunities, and my ambitions. So I decided to ask four questions that would hopefully help me identify one that was.

Question One:
Is this goal worthy of me?

This is the first and most important thing anyone can and should demand of their goals. It also happens to be the question most people never even think of. We ask ourselves so many questions about a goal before we ever even consider this one.

How much money will I make? Where do I have to live to pull this off? How much money will I make? What will my office look like? How much money will I make? These aren’t bad questions. They just shouldn’t be your first questions.

The concept of worthiness has gone out of fashion. The idea is basically this: some goals are simply not big enough for the effort you’re going to give to them. When you’re triaging potential goals, you need to start here. But what does assessing a goal’s “worth” even look like? There’s a useful subprocess that you can use to answer this larger question.

Check Your Glory

Every goal has its own glory, and it’s important to be picky about the ones you want. You wouldn’t hire someone at work who didn’t match a job description. So create a job description for your goal.

How many years do you want it to take? What sort of experiences would you like it to offer? What skills would you like to use in achieving it? Once you build out this job posting for the goal, you can start auditioning goals to see which one fits.

The first thing you should check on each goal’s CV is this: what glory is it offering? Say you’re an executive manager now, but do you even like your company? You got into a top med school, but are you sure that a doctor’s life is what’s driving you? You’re dating a guy who would probably marry you, but he eats his peas one at a time.

Knowing which glory a goal offers is a matter of looking past its appearance to see where it ends. If you can put your eyes on that, and if you’ve taken the time to formulate a job description that any goal has to meet, then finding a goal worthy of you stops being ambiguous and starts being practical.

Question Two:
What are the limits?

Growing up, most of us had parents who said things like “You can be anything when you grow up!”

That’s an example of terrible motivation. Sorry, Mom. In a world where every decision is equally viable, nothing can reasonably be chosen. That’s why constraint is a decision maker’s best friend. What you won’t do will point you more clearly to what you should do.

All of us have lines we simply refuse to cross. Some people will tell you that those lines are holding you back, but I think they are essential tools for crafting good decisions.

One of my lines was a beautiful California ballerina named Amelia. The two of us were speeding happily toward marriage during the time I was researching new goals, and I was completely unwilling to choose one that would take me farther from her than was absolutely necessary. Many of the goals I considered during this period would have required me to move to different countries. They went straight into the No column.

It’s much easier to farm the 100 acres you’ve put a fence around than it is to plant corn across the entire planet. Put up boundaries early in the goal-setting process, and what follows will proceed with far more clarity, efficiency, and sanity.

Question Three:
Is this goal realistic?

It may seem odd to start talking about realism in a book about rowing across the ocean, but this question is another key safeguard that prevents you from choosing the wrong goal.

Realistic here does not mean simple. It does not mean risk-free. It does not mean predictable. It doesn’t even mean possible. Realistic in this context means that this goal can be completed, by you, in this lifetime. It has nothing to do with asking whether or not it will be easy. It means asking yourself if you were built to make this thing happen.

Barack Obama was built to become president. So was Donald Trump. Now that I’ve offended everyone, let me explain. Both of those men had exactly the right tools in their kits to successfully carve a tunnel through the morass that is a presidential election.

Obama and Trump were built for different times and would be embraced by those with different sentiments, but both of them could look at a goal like becoming president and say with confidence, “That is realistic for me personally.”

Pursuing a goal that’s realistic means doing an audit of yourself and then doing a stress test of the goal. What qualities does this goal demand? Do you have those qualities? If not, move on. As someone who should never ski black diamonds but does, I can guarantee that only disaster awaits when you pick the wrong path.

Question Four:
Will my passion carry me through?

You may find that even the most worthy goal is hard to care about when you’re halfway through it. You must choose a goal that you can see yourself pursuing day in and day out for as long as it takes.

For example, as soon as they find out I’m a professional adventurer, everyone always asks me if I’m going to climb Mount Everest. I have some major problems with the entire Mount Everest industrial complex, but, aside from that, it still wouldn’t be a good goal for me.

I’m tall, broad, and built for difficult, repetitive actions over a long period. Rowing, hiking, cross-country skiing, binging The Office—these are my things. To climb Everest I’d have to restructure my entire mind and rebuild my entire body. The diet and training it would take to accomplish it doesn’t sound impossible to me, but they do sound like hell.

I’m okay with pain. I’ve built a career out of enduring pain, but it’s my pain. When we talk about passion, what we’re really talking about are things we’re willing to do even when they cost us something. Even when it hurts.

Can you stay up until 4 a.m. building PowerPoints? Can you speak in front of 4,000 people without throwing up beforehand? Do you live for helping people with their personal problems even when the problems are extremely difficult?

Everyone has a pain they can take. Find yours, and you’ll find your passion, and that will lead you to your goal.

THE PROCESS IN ACTION

I knew I was going to race the Talisker. I had sent the coal of possibility through the fiery furnace of the process above. Then I held in my hand an indestructible diamond of purpose. But the man across from me was the one who had to buy it.

By the time I got to Chris Coke, I had been rejected by Nike, Under Armour, all the major athletic players. None of them wanted to shell out more than $150,000 to sponsor an athlete they’d never heard of in a sport very few 18- to 35-year-olds care about. But where these companies saw an uncompelling request on a very large stack, Chris saw a perfect fit.

Chris is the CEO of Carlisle Companies, and in this case I was the goal he had to evaluate. Was I worthy? Was I realistic? Was I in line with his passion? Executing my dream meant that I would be his dream.

The Carlisle sponsorship is an example of goal setting done right. It didn’t make as much direct business sense for him to sponsor my boat as it did for Nike or Adidas, but Chris was interested in something more than the obvious.

Chris is a leader through and through. He has more than 15,000 employees, and most of them work hard days in busy factories. That’s a lot of people looking to you to make sure that their tables are full and their 401(k) contributions are matched. Chris feels that pressure and uses it to select better goals.

After our contract was signed, Chris looked at me and said point-blank that he wasn’t doing this to sell more products. He was doing it to reach his people: To show them that their company believes in something beyond the machinery they create. To inspire them to set big goals. To prove that he would support them if they did that.

He was fulfilling a piece of advice that my friend John Cady, head of business education for the Kelley School of Business at Indiana University, told me when I started to hit brick walls in my search for funds.

He told me to pursue people who shared my values, not my industry. And that’s my advice to you as you go out and start setting goals. Once you pick a goal, share it with the people who will push for it just as hard as you will, if not harder.

That’s exactly what I was going to do next. I had a goal. I had a sponsor. Now all I needed was a team.

GATHERING POINT:
INTERROGATE YOUR GOALS

High-performance goals: When setting a goal, ask yourself a set of questions. These questions are designed to build the focus and confidence you will need when the suffering and sacrifice starts to kick in. They are also designed to ensure that you are being efficient with your time.

Question One: Is this goal worthy of me?

Question Two: What are the limits? How far am I willing to go, and what am I willing to do?

Question Three: Is this goal realistic? Knowing myself and my capabilities, is this goal realistic for me to achieve?

Question Four: Will my passion carry me through? Said another way, is this something I really want?