It’s time to define the new era. Our faith has been shaken. We’ve lost confidence in our leaders and in our institutions. Our beliefs have been tested. We’ve discredited the notion that the Internet would change everything (and the stock market would buy us an exit strategy from the grind). Our expectations have been dashed. We’ve abandoned the idea that work should be a 24-hour-a-day rush and that careers should be a wild adventure. Yet we’re still holding on.
We’re seduced by the idea that picking up the pieces and simply tweaking the formula will get the party started again. In spite of our best thinking and most searing experience, our ideas about growth and success are mired in a boom-bust mentality. Just as LBOs gave way to IPOs, the market is primed for the next engine of wealth creation. Just as we traded in the pinstripes and monster bonuses of the Wall Street era for T-shirts and a piece of the action during the startup revolution, we’re waiting to latch on to the new trappings of success. (I understand the inclination. I’ve surfed from one boom to the next for most of my working life — from my early days as a bond trader to my most recent career as a writer tracking the migration of my generation from Wall Street to Silicon Valley.)
There’s a way out. Instead of focusing on what’s next , let’s get back to what’s first . The previous era of business was defined by the question, Where’s the opportunity? I’m convinced that business success in the future starts with the question, What should I do with my life? Yes, that’s right. The most obvious and universal question on our plates as human beings is the most urgent and pragmatic approach to sustainable success in our organizations. People don’t succeed by migrating to a “hot” industry (one word: dotcom) or by adopting a particular career-guiding mantra (remember “horizontal careers”?). They thrive by focusing on the question of who they really are — and connecting that to work that they truly love (and, in so doing, unleashing a productive and creative power that they never imagined). Companies don’t grow because they represent a particular sector or adopt the latest management approach. They win because they engage the hearts and minds of individuals who are dedicated to answering that life question.
This is not a new idea. But it may be the most powerfully pressing one ever to be disrespected by the corporate world. There are far too many smart, educated, talented people operating at quarter speed, unsure of their place in the world, contributing far too little to the productive engine of modern civilization. There are far too many people who look like they have their act together but have yet to make an impact. You know who you are. It comes down to a simple gut check: You either love what you do or you don’t. Period.
Those who are lit by that passion are the object of envy among their peers and the subject of intense curiosity. They are the source of good ideas. They make the extra effort. They demonstrate the commitment. They are the ones who, day by day, will rescue this drifting ship. And they will be rewarded. With money, sure, and responsibility, undoubtedly. But with something even better too: the kind of satisfaction that comes with knowing your place in the world. We are sitting on a huge potential boom in productivity — if we could just get the square pegs out of the round holes.
Of course, addressing the question, What should I do with my life? isn’t just a productivity issue: It’s a moral imperative. It’s how we hold ourselves accountable to the opportunity we’re given. Most of us are blessed with the ultimate privilege: We get to be true to our individual nature. Our economy is so vast that we don’t have to grind it out forever at jobs we hate. For the most part, we get to choose. That choice isn’t about a career search so much as an identity quest. Asking The Question aspires to end the conflict between who you are and what you do. There is nothing more brave than filtering out the chatter that tells you to be someone you’re not. There is nothing more genuine than breaking away from the chorus to learn the sound of your own voice. Asking The Question is nothing short of an act of courage: It requires a level of commitment and clarity that is almost foreign to our working lives.
During the past two years, I have listened to the life stories of more than 900 people who have dared to be honest with themselves. Of those, I chose 70 to spend considerable time with in order to learn how they did it. Complete strangers opened their lives and their homes to me. I slept on their couches. We went running together. They cried in my arms. We traded secrets. I met their families. I went to one’s wedding. I witnessed many critical turning points.
These are ordinary people. People of all ages, classes, and professions — from a catfish farmer in Mississippi to a toxic-waste inspector in the oil fields of Texas, from a police officer in East Los Angeles to a long-haul trucker in Pennsylvania, from a financier in Hong Kong to a minister at a church on the Oregon coast. These people don’t have any resources or character traits that give them an edge in pursuing their dream. Some have succeeded; many have not. Only two have what accountants call “financial independence.” Only two are so smart that they would succeed at anything they chose (though having more choices makes answering The Question that much harder). Only one, to me, is saintly. They’re just people who faced up to it, armed with only their weaknesses, equipped with only their fears.
What I learned from them was far more powerful than what I had expected or assumed. The first assumption to get busted was the notion that certain jobs are inherently cool and that others are uncool. That was a big shift for me. Throughout the 1990s, my basic philosophy was this: Work=Boring, but Work+Speed+Risk=Cool. Speed and risk transformed the experience into something so stimulating, so exciting, so intense, that we began to believe that those qualities defined “good work.” Now, betrayed by the reality of economic uncertainty and global instability, we’re casting about for what really matters when it comes to work.
On my journey, I met people in bureaucratic organizations and bland industries who were absolutely committed to their work. That commitment sustained them through slow stretches and setbacks. They never watched the clock, never dreaded Mondays, never worried about the years passing by. They didn’t wonder where they belonged in life. They were phenomenally productive and confident in their value. In places unusual and unexpected, they had found their calling, and those callings were as idiosyncratic as each individual.
And this is where the second big insight came in: Your calling isn’t something you inherently “know,” some kind of destiny. Far from it. Almost all of the people I interviewed found their calling after great difficulty. They had made mistakes before getting it right. For instance, the catfish farmer used to be an investment banker, the truck driver had been an entertainment lawyer, a chef had been an academic, and the police officer was a Harvard MBA. Everyone discovered latent talents that weren’t in their skill sets at age 25.
Most of us don’t get epiphanies. We only get a whisper — a faint urge. That’s it. That’s the call. It’s up to you to do the work of discovery, to connect it to an answer. Of course, there’s never a single right answer. At some point, it feels right enough that you choose, and the energy formerly spent casting about is now devoted to making your choice fruitful.
This lesson in late, hard-fought discovery is good news. What it means is that today’s confused can be tomorrow’s dedicated. The current difficult climate serves as a form of reckoning. The tougher the times, the more clarity you gain about the difference between what really matters and what you only pretend to care about. The funny thing is that most people have good instincts about where they belong but make poor choices and waste productive years on the wrong work. Why we do this cuts to the heart of the question, What should I do with my life? These wrong turns hinge on a small number of basic assumptions that have ruled our working lives, career choices, and ambitions for the better part of two decades. I found hardly any consistencies in how the people I interviewed discovered what they love to do — the human soul resists taxonomy — except when it came to four misconceptions (about money, smarts, place, and attitude) that have calcified into hobbling fears. These are stumbling blocks that we need to uproot before we can find our way to where we really belong.
MONEY Doesn’t Fund Dreams
Shouldn’t I make money first — to fund my dream? The notion that there’s an order to your working life is an almost classic assumption: Pay your dues, and then tend to your dream. I expected to find numerous examples of the truth of this path. But I didn’t find any.
Sure, I found tons of rich guys who were now giving a lot away to charity or who had bought an island. I found plenty of people who had found something meaningful and original to do after making their money. But that’s not what I’m talking about. I’m talking about the garden-variety fantasy: Put your calling in a lockbox, go out and make a ton of money, and then come back to the lockbox to pick up your calling where you left it.
It turns out that having the financial independence to walk away rarely triggers people to do just that. The reality is, making money is such hard work that it changes you. It takes twice as long as anyone plans for. It requires more sacrifices than anyone expects. You become so emotionally invested in that world — and psychologically adapted to it — that you don’t really want to ditch it.
I met many people who had left the money behind. But having “enough” didn’t trigger the change. It had to get personal: Something had to happen such as divorce, the death of a parent, or the recognition that the long hours were hurting one’s children. (One man, Don Linn, left investment banking after he came home from a business trip and his two-year-old son didn’t recognize him.)
The ruling assumption is that money is the shortest route to freedom. Absurdly, that strategy is cast as the “practical approach.” But in truth, the opposite is true. The shortest route to the good life involves building the confidence that you can live happily within your means (whatever the means provided by the choices that are truly acceptable to you turn out to be). It’s scary to imagine living on less. But embracing your dreams is surprisingly liberating. Instilled with a sense of purpose, your spending habits naturally reorganize, because you discover that you need less.
This is an extremely threatening conclusion. It suggests that the vast majority of us aren’t just putting our dreams on ice — we’re killing them. Joe Olchefske almost lost his forever. Joe started out in life with an interest in government. In the early 1980s, he made what seemed like a minor compromise: When he graduated from Harvard’s Kennedy School of Government, he went into public finance. He wouldn’t work in government, he’d work with government.
Joe went on to run Piper Jaffray in Seattle. By the mid-1990s, he realized that one little compromise had defined his life. “I didn’t want to be a high-priced midwife,” he said. “I wanted to be a mother. It was never my deal. It was my clients’ deal. They were taking the risk. They were building hospitals and bridges and freeways, not me. I envied them for that.”
One night, riding up the elevator of his apartment building, Joe met newly hired Seattle schools superintendent John Stanford. Soon after, Stanford offered Olchefske a job as his CFO — and partner in turning the troubled school system around. Olchefske accepted. Stanford rallied the city around school reform and earned the nickname Prophet of Hope. Meanwhile, Olchefske slashed millions from the budget and bloodlessly fired principals, never allowing his passions to interfere with his decisions. People called him Prophet of Doom.
Then Stanford died suddenly of leukemia. It was one of the great crises in the city’s history. Who could fill this void? Certainly not the green-eyeshade CFO. But Stanford’s death transformed Olchefske. It broke him open, and he discovered in himself a new ability to connect with people emotionally, not just rationally. As the new superintendent, he draws on that gift more than on his private-sector skills. He puts up with a lot of bureaucrap, but he says that avoiding crap shouldn’t be the objective in finding the right work. The right question is, How can I find something that moves my heart, so that the inevitable crap storm is bearable?
SMARTS Can’t Answer The Question
If the lockbox fantasy is a universal and eternal stumbling block when it comes to answering The Question, the idea that smarts and intensity are the essential building blocks of success and satisfaction is a product of the past decade. A set of twin misconceptions took root during the celebration of risk and speed that was the 90s startup revolution. The first is the idea that a smart, motivated individual with a great idea can accomplish anything . The corollary is that work should be fun, a thrill ride full of constant challenge and change.
Those assumptions are getting people into trouble. So what if your destiny doesn’t stalk you like a lion? Can you think your way to the answer? That’s what Lori Gottlieb thought. She considered her years as a rising television executive in Hollywood to be a big mistake. She became successful but felt like a fraud. So she quit and gave herself three years to analyze which profession would engage her brain the most. She literally attacked the question. She dug out her diaries from childhood. She took classes in photography and figure drawing. She interviewed others who had left Hollywood. She broke down every job by skill set and laid that over a grid of her innate talents. She filled out every exercise in What Color Is Your Parachute?
Eventually, she arrived at the following logic: Her big brain loved puzzles. Who solves puzzles? Doctors solve health puzzles. Therefore, become a doctor. She enrolled in premed classes at Pepperdine. Her med-school applications were so persuasive that every school wanted her. And then — can you see where this is headed? — Lori dropped out of Stanford Medical School after only two and a half months. Why? She realized that she didn’t like hanging around sick people all day.
The point is, being smarter doesn’t make answering The Question easier. Using the brain to solve this problem usually only leads to answers that make the brain happy and jobs that provide what I call “brain candy.” Intense mental stimulation. But it’s just that: candy . A synthetic substitute for other types of gratification that can be ultimately more rewarding and enduring. As the cop in East L.A. said of his years in management at Rockwell, “It was like cheap wood that burns too fast.”
I struggled with this myself, but not until I had listened to hundreds of others did the pattern make itself shockingly clear. What am I good at? is the wrong starting point. People who attempt to deduce an answer usually end up mistaking intensity for passion. To the heart, they are vastly different. Intensity comes across as a pale busyness , while passion is meaningful and fulfilling. A simple test: Is your choice something that will stimulate you for a year or something that you can be passionate about for 10 years?
This test is tougher than it seems on paper. In the past decade, the work world has become a battleground for the struggle between the boring and the stimulating. The emphasis on intensity has seeped into our value system. We still cling to the idea that work should not only be challenging and meaningful — but also invigorating and entertaining. But really, work should be like life: sometimes fun, sometimes moving, often frustrating, and defined by meaningful events. Those who have found their place don’t talk about how exciting and challenging and stimulating their work is. Their language invokes a different troika: meaningful, significant, fulfilling. And they rarely ever talk about work without weaving in their personal history.
PLACE Defines You
Every industry has a culture. And every culture is driven by a value system. In Hollywood, where praise is given too easily and thus has been devalued, the only honest metric is box-office receipts. So box-office receipts are all-important. In Washington, DC, some very powerful politicians are paid middling salaries, so power and money are not equal. Power is measured by the size of your staff and by how many people you can influence. In police work, you learn to be suspicious of ordinary people driving cars and walking down the street.
One of the most common mistakes is not recognizing how these value systems will shape you. People think that they can insulate themselves, that they’re different. They’re not. The relevant question in looking at a job is not What will I do? but Who will I become? What belief system will you adopt, and what will take on heightened importance in your life? Because once you’re rooted in a particular system — whether it’s medicine, New York City, Microsoft, or a startup — it’s often agonizingly difficult to unravel yourself from its values, practices, and rewards. Your money is good anywhere, but respect and status are only a local currency. They get heavily discounted when taken elsewhere. If you’re successful at the wrong thing, the mix of praise and opportunity can lock you in forever.
Don Linn, the investment banker who took over the catfish farm in Mississippi, learned this lesson the hard way. After years as a star at PaineWebber and First Boston, he dropped out when he could no longer bring himself to push deals on his clients that he knew wouldn’t work. His life change smacked of foolish originality: 5.5 million catfish on 1,500 water acres. His first day, he had to clip the wings of a flock of geese. Covered in goose shit and blood, he wondered what he had gotten himself into. But he figured it out and grew his business into a $16 million operation with five side businesses. More important, the work reset his moral compass. In farming, success doesn’t come at another farmer’s expense. You learn to cooperate, sharing processing plants, feed mills, and pesticide-flying services.
Like Don, you’ll be a lot happier if you aren’t fighting the value system around you. Find one that enforces a set of beliefs that you can really get behind. There’s a powerful transformative effect when you surround yourself with like-minded people. Peer pressure is a great thing when it helps you accomplish your goals instead of distracting you from them.
Carl Kurlander wrote the movie St. Elmo’s Fire when he was 24. For years afterward, he lived in Beverly Hills. He wanted to move back to Pittsburgh, where he grew up, to write books, but he was always stopped by the doubt, Would it really make any difference to write from Pittsburgh instead of from Beverly Hills? His books went unwritten. Last year, when a looming Hollywood writers’ strike coincided with a job opening in the creative-writing department at Pitt, he finally summoned the courage to move. He says that being in academia is like “bathing in altruism.” Under its influence, he wrote his first book, a biography of the comic Louie Anderson.
ATTITUDE Is the Biggest Obstacle
Environment matters, but in the end, when it comes to tackling the question, What should I do with my life? it really is all in your head. The first psychological stumbling block that keeps people from finding themselves is that they feel guilty for simply taking the quest seriously. They think that it’s a self-indulgent privilege of the educated upper class. Working-class people manage to be happy without trying to “find themselves,” or so the myth goes.
But I found that just about anybody can find this question important. It’s not just for free agents, knowledge workers, and serial entrepreneurs. I met many working-class people who found this question essential. They might have fewer choices, but they still care. Take Bart Handford. He went from working the graveyard shift at a Kimberley-Clark baby-wipes plant in Arkansas to running the Department of Agriculture’s rural-development program. He didn’t do this by just pulling up his bootstraps. His breakthrough came when his car was hit by a train, and he spent six months in bed exploring The Question.
Probably the most debilitating obstacle to taking on The Question is the fear that making a choice is a one-way ride, that starting down a path means closing a door forever.
“Keeping your doors open” is a trap. It’s an excuse to stay uninvolved. I call the people who have the hardest time closing doors Phi Beta Slackers. They hop between esteemed grad schools, fat corporate gigs, and prestigious fellowships, looking as if they have their act together but still feeling like observers, feeling as if they haven’t come close to living up to their potential.
Leela de Souza almost got lost in that trap. At age 15, Leela knew exactly what she wanted to be when she grew up: a dancer. She pursued that dream, supplementing her meager dancer’s pay with work as a runway model. But she soon began to feel that she had left her intellect behind. So, in her early twenties, with several good years left on her legs, she took the SATs and applied to college. She paid for a $100,000 education at the University of Chicago with the money that she had earned from modeling and during the next seven years made a series of seemingly smart decisions: a year in Spain, Harvard Business School, McKinsey & Co., a White House Fellowship, high-tech PR. But she never got any closer to making a real choice.
Like most Phi Beta Slackers, she was cursed with tremendous ability and infinite choices. Figuring out what to do with her life was constantly on her mind. But then she figured something else out: Her need to look brilliant was what was keeping her from truly answering The Question. When she let go of that, she was able to shift gears from asking “What do I do next?” to making strides toward answering “To what can I devote my life?”
Asking “What Should I Do With My Life?” is the modern, secular version of the great timeless questions about our identity. Asking The Question aspires to end the conflict between who you are and what you do. Answering The Question is the way to protect yourself from being lathed into someone you’re not. What is freedom for if not the chance to define for yourself who you are?
I have spent the better part of the past two years in the company of people who have dared to confront where they belong. They didn’t always find an ultimate answer, but taking the question seriously helped get them closer. We are all writing the story of our own life. It’s not a story of conquest. It’s a story of discovery. Through trial and error, we learn what gifts we have to offer the world and are pushed to greater recognition about what we really need. The Big Bold Leap turns out to be only the first step.
Two different answers to one ultimate question – Organization Man
Of the 900 people who I talked to, only one has had the same employer for his entire adult life. His name is Russell Carpenter, he’s 35, and he’s an aerospace engineer at NASA Goddard. We can all learn from him. Russell began working at NASA during college. In exchange for his summers, they paid for his tuition and, later, financed his PhD. Russell is a GS-14, stuck to government pay scales. The money is okay, but it’s never the reason to stay. He’s building a guidance system for the newest type of satellite.
The halls and offices at NASA are quiet. These engineers are content with slowly pushing toward a solution. Which I took as Extractable Lesson number one: time frame. At NASA, Russell has found an intermediate time frame where he can accomplish the high-minded objectives that his division is charged with, but he’s not under absurd pressure to do it all in 90 days.
Aerospace engineers are obsessed with redundancy and backup systems. Russell knows that metals give, that gears slip, and that motors overheat, and he plans for that in his designs. Not everything has to go right in order for it to work. And that way of thinking shows up in every aspect of his life, including how he achieves his ambitions. Which I took as Extractable Lesson number two: His backup plans do not lead to different destinations, such as “If I don’t get into business school, I’ll be a schoolteacher.” His backup plans lead to the same destination, and if he has to arrive late by a back road, that’s fine.
Later, Russell and I went to a baseball game, which clued me in to Extractable Lesson number three: Russell doesn’t let himself get burned out. He doesn’t think it’s a big deal that he’s only had one employer. His method is his secret, but it’s no secret.
“So what do you do?” For five years, Marcela Widrig had a dream job that compensated her well, let her live in Barcelona, and paid for her frequent travel throughout Southern Europe. She sold modems for a big modem manufacturer. Modems were her means to her ends: money, travel, human connection.
When her company moved her to San Francisco, she suffered culture shock. The Internet was destroying everything that she loved about sales. The new ethos was speed. Get the deal done in a day! Don’t even fly — email makes it so easy! The human contact was gone.
The worst part was constantly being asked The Inevitable Cocktail-Party Question: “What do you do?” Marcela had been away long enough to have forgotten about this disgusting American custom. She found it degrading and reductive and mercenary. I too used to think that The Inevitable Cocktail-Party Question was a scourge on our society. But I’m starting to see that it is really about freedom to choose. A status system has evolved that values being unique and true even more than it values being financially successful.
In other words, if you don’t like The Inevitable Cocktail-Party Question, maybe it’s partly because you don’t like your answer.
Marcela no longer liked her answer. She endured migraines and insomnia. After flying all the way to Hong Kong for a meeting that didn’t even last one hour, she vowed, “I cannot sell one more modem.” But she didn’t quit for two more years. On her vacations, she flew to Switzerland to train in a school for deep-tissue massage. It was her way to move toward genuine human contact. The day she returned from one of her Switzerland trips, the modem company went under, and she was forced into her new life.
It took her about a year to drop the business-suit persona and truly embrace her new profession. The Inevitable Cocktail-Party Question no longer bothers her. “I do body work,” she says. “I love what I do, and I think that comes across.”
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