What Should I Do With My Life?

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.