Getting Unstuck

Not long ago, I saw an old friend who recently realized she was—at last—totally happy at work, much to her surprise. "I have finally figured out what I want to be when I grow up," she told me. Ten years earlier, she had moved from Boston to the Midwest because of her husband's job. She didn't exactly kick and scream, but her jaw was surely clenched and she was trying to hold back tears. She had left behind everything and everyone familiar to her, including a rewarding if not perfect part-time position as a hospice worker. Her two sons, then ages 8 and 10, were similarly glum about the move. But move they had to, and move they did.

At first, as the family settled in, my friend stayed home, convinced that her dream of a fulfilling career was stalled, possibly over. But slowly, due to a mixture of financial necessity and boredom, she began to inch back into the workplace. A hospice offer fell through, so she worked as a medical center administrator for a few years and then as a community college admissions officer. She liked aspects of both jobs, but neither felt like a calling. Eventually, with a sigh of resignation, she took a job as a religion teacher at a parochial high school. I was a philosophy major in college, so this will do for now, she told herself.

Then a funny thing happened. My friend noticed that the career she'd backed into and settled for filled her with joy. She found teaching teenagers exhilarating—and sometimes downright hilarious. As we spoke, she was moved to tears recounting how she helped the son of a poor Iraqi family, a recent immigrant to the United States, get into a well-known university. She described reading each student's graduation essay, titled "How I Want to Live My Life."

"You should hear these kids," she said with pride. "They've got goals as big as the sky. They all seem to know what they want to be when they grow up. I've only just discovered that myself!"

She is 51 years old.

And that is exactly how it usually goes. You can figure out what you want to be when you grow up. You just have to be very grown up to do it.

Sure, there are women among us who decide they want to be federal judges at age 12 and get appointed by age 32. But they are more annoying than average. Most women discover their "exactly right" job through a messy, iterative process that involves years of experimentation and reinvention. They grab opportunities when they zip by; they make wrong turns and run twice as fast to correct them; they juggle the husbands and kids who show up along the way; and, very often, they sacrifice a piece of their own dreams on their families' behalf. Most women search, adjust, and search some more for the right career...until one day, it finally appears out of the fog of life's experiences.

In other words, there are no shortcuts to discovering the perfect job. There is just a journey.

Now, can you hurry that process along and make it less bumpy? Can you actually speed up finding the answer to the "What should I be when I grow up" question?

I think you can, but you need to embrace a practice that requires discipline, candor, and a bit of courage. Simply put: You need to relentlessly ask yourself five questions.

 Question 1
Does this job allow me to work with "my people"—individuals who share my sensibilities about life—or do I have to put on a persona to get through the day?

Question 2
Does this job challenge, stretch, change, and otherwise make me smarter—or does it leave my brain in neutral?

Question 3
Does this job, because of the company's "brand" or my level of responsibility, open the door to future jobs?

Question 4
Does this job represent a considerable compromise for the sake of my family and if so, do I sincerely accept that deal with all of its consequences?

Question 5
Does this job—the stuff I actually do day-to-day—touch my heart and feed my soul in meaningful ways?
These questions won't tell you if you should become a veterinarian, work in high tech, write a novel, manage a restaurant, or open your own advertising agency. The questions will, however, guide you once your journey has begun, their answers suggesting whether you should stay in a job and give it your all or get up the gumption to move on to something else. Eventually, the questions, which you can ask about either the job you currently hold or a position you are considering, will steer you toward the career that, like my friend's in the Midwest, turns work into joy.

These five questions came to me not as I was searching for my own perfect job (although I think I have finally found it after 20 years!) but as my husband, Jack, and I conducted research for our book, Winning. For three years, we traveled around the world talking with people in every line of work about their biggest challenges. In all, we spoke to nearly 250,000 people in hundreds of wide-ranging Q&A sessions. When we set out on our travels, we expected most of these conversations to be about the usual business topics, like customer satisfaction and foreign competition. These subjects certainly did come up, along with plenty of questions on strategy and leadership. Much to our surprise, however, the people we interviewed wanted passionately to know whether or not they were in the right job in the first place. They yearned for a way to understand who and what they were meant to be in life.

The question of who and what to be is profound, huge in its impact, and by no means limited to the young. Yes, plenty of recent college grads and MBAs we encountered wanted to know how to find the perfect job. But we also heard the "when I grow up" question from executives with jobs that looked, from the outside, to be ideal in every way. We heard it from people who had been running their own companies for decades.

And we heard it—especially—from women in their 30s and 40s who had been working feverishly for years, both at the office and at home, only to find themselves not exactly where they had hoped to be when they set out, all those years ago, to conquer the world.

Their stories were often told with poignant acceptance, but sometimes with deep sadness and confusion. How could they have run so hard and so fast for so long and ended up nowhere near where they wanted to go?

This phenomenon was so common that Jack and I gave it a name: the Everyone's Happy But Me Syndrome.

Women in this situation had arranged their days to be "good enough" at work and "there enough" at home but found they were living in a kind of purgatory, waiting for a time when their own dreams and needs could be met. They didn't dare ask any of the five questions above—the answers would have revealed a big, aching emptiness in the center of their lives.

Some of the women we met during our travels broke out of the Everyone's Happy But Me Syndrome and found fulfilling careers after a major personal crisis. There was a neurosurgeon in Virginia who admitted to herself, at age 40, that she had gone into medicine only to please her parents. That was the easy part. To realize her authentic life dream—she had always wanted to be a portrait photographer—she had to ask her husband to change his job to make up for the substantial loss of income. He made the sacrifice willingly, the woman told us, "but to be honest, I know he misses his old company and his friends there, and that has left a little hole in our relationship." Gone, too, are the vacations the family used to love. Yet, she said, "everyone in the family is happy that I am finally happy. They wouldn't go back, and neither would I."

In Detroit we met a woman who'd spent 14 years at a prestigious international accounting firm but at age 45 found she just couldn't bring herself to go to the office another day. "For one week, I stayed in bed and cried," she said. "I realized I was working to pay the mortgage on a beautiful house. The job bored me, and my life was passing by. That Friday I sent my resignation by e-mail." She sold her house, ended a long-term relationship with a coworker who opposed her decision, and took a job teaching in an inner-city elementary school. "The first year was hell," she told us. "Teaching was not the fantasy I had imagined. The kids were hard on me; I was raw and inexperienced. I missed my boyfriend a lot. I even missed my house. A day didn't go by when I didn't wonder if I'd lost my mind." She stuck it out and today runs a charter school for immigrant children in another city. "My work finally feels important," she said. "It took a while, but I have no regrets."

These women turned their lives upside down to be what they wanted to be; their journeys weren't just bumpy, they were tumultuous and painful for themselves and their families.

That kind of pain, we came to see during our research, was avoided by a small number of women who, along the long road of their careers, never stopped asking themselves the five questions. And once they uncovered the answers, they had the courage to adjust accordingly, moving to another job or field. Some changes were small, others large—but they all moved the women toward the job they were meant to have. And that is how the journey goes.

Let's look at the questions in a bit more detail.

Does this job allow me to be with "my people"? I will never forget a happy firecracker of a woman we met in Florida who told us, "When I graduated from college, all I knew was I wanted a job—any job—where I could wear high heels and carry a briefcase! For a country girl like me, that meant you'd made something of yourself." She threw herself into nabbing a position as a junior analyst with a buttoned-down New York consulting firm. The "marriage" lasted exactly two years. "It was torture," she recalled. "No one laughed at what I laughed at. No one thought it was okay to argue now and then if you needed to get some issues on the table. No one even enjoyed the same kind of music or TV shows I did. I'm not saying it was a bad place; it just wasn't my kind of place."

This woman zigged and zagged through three more careers before she ultimately found success and fulfillment in the world of (believe it or not) aquarium administration. She wears a T-shirt, shorts, and flip-flops to work and hasn't owned a briefcase for 20 years. Most important, she says, "I love the folks I work with. We agree about what matters—I mean, we just see the world in the same way."

The facts are: No job or profession will ultimately be right if it requires you to work with people who don't share your sensibilities. If you are a brainy introvert, you should work with brainy introverts. If you are a boisterous extrovert, find a profession where that's embraced as the norm. You spend most of your life with your colleagues. You have to like them—and feel and act real around them—if you are going to be what you want when you grow up.

Does this job make me smarter? Some people gravitate toward certain professions simply because they are good at them. Women who excel in English in college become editors. Women who love children become teachers. Women who can crunch numbers with the best of them go to Wall Street. This feels very natural, and, to be blunt about it, companies love the deal, too. After all, they want nothing more than to hire a candidate who comes fully equipped for the job.

Now, doing what you're good at is not a bad thing, except that it can eventually lead you down a garden path to...utter boredom.

In our research, we found that the women who most successfully navigated themselves toward the right job in the right profession kept looking for work that required them to learn, stretch, and grow. In fact, the women who loved their jobs the most were those who told us that their work always seemed just a little bit challenging all the time.

Does this job open the door to future jobs? Until you have found your perfect job in your perfect profession, you can't stop thinking about next steps. This question requires you to coolly assess whether your current job—or one you are considering—is a launching pad for the next, better one.

How can you keep your options open? The best way is to work for a company with a strong national "brand"—hundreds and hundreds of companies are in this category—or for an organization with a great reputation locally. One woman we met in Southern California parlayed her low-level job at a well-known regional bank into a managerial job in her state's treasury department. "I was trusted walking in the door for the interview," she said. "The bank gave me a kind of halo."

Job halos are like little angels; they help a lot when a journey is long.

Does this job represent a considerable compromise for my family's sake? This question is tough; it forces you to confront just how long it might be before you find the career you've been waiting for.

Almost ten years ago, I took a job—as an editor at the Harvard Business Review—in large part because it wouldn't require me to travel.

It was quite a change. For years I had been a management consultant, and I loved it. The work was fascinating and the people at my firm were kindred spirits, but I was often away three days a week on business, and even when I wasn't traveling, I worked long hours.

I had three children and was pregnant with my fourth when the HBR job came up. My family needed me home, especially since my husband at the time, the family's main wage earner, also traveled extensively.

I made the trade-off. I'm not saying I didn't like my job—I enjoyed many aspects of the work. But HBR was a nonprofit monthly magazine, and I never stopped missing the fast-paced excitement of the competitive business marketplace.

Still, I would make that choice again. Sometimes you have to take or keep a job because the people who love you need you to. Eventually, though, circumstances change. Your kids grow up. Your husband gets more flexibility in his job. Your older sister steps in to care for your mother. When the moment arrives and you can stop compromising your own dream, seize it.

Finally: Does the job—the stuff I do every day—touch my heart and feed my soul? This is, in the end, the most important thing you need to ask yourself. Very simply, you will never be what you were meant to be if you aren't having fun.

The perfect job is perfect because it makes you happy inside. Something about it—the thrill of making a big sale or making something work just right for your customers, the camaraderie of hitting a deadline with your colleagues, the reward of coaching new employees—turns your crank. Your work matters to you, and, on a visceral level, it just delights your soul.

The answer to this question is a feeling—a feeling of excitement and sense of meaning. When that's what's going on inside, you know you've finally reached your destination.

It's almost never where you expected it to be.

Remember my friend in the Midwest? As a girl, she dreamed, albeit briefly, of being a surgeon like her father. She also imagined writing poetry and becoming a social worker. She had no idea the best job for her was helping teenagers reach their dreams—until she was doing it.

I met a woman recently who, as the head of development for a state college with 10,000 students, raises millions of dollars a year to fund buildings and scholarships. She has her tough days, but when I asked if there was something else she would rather be doing, she gasped. "This is the perfect job," she said. "I literally couldn't do anything else. I'd miss it too much!"

Fund-raising—and loving it—is just about the last thing she imagined she'd be doing when she began her career 25 years ago. She was the only daughter in a traditional Irish family; her parents mortgaged their home to send her four brothers to college. After secretarial school, she landed a job as a bank teller. She might have stayed at the bank forever, she says, if she hadn't needed to get out of town when her husband began physically abusing her. A bitter divorce left her broke, and so she quickly became a licensed nurse practitioner. "All I knew was that I could get a job as a licensed practical nurse," she recalls.

Four years later, needing more income, she went back to school at night to become a registered nurse. It was there that she took a class in communications and loved it. When she graduated, she found an entry-level position in public relations. That job led to several more jobs and promotions in the PR field, which led to a job as a legislative aide to a congressman, which prepared her perfectly for her current job.

"Looking back now," she told me, "I think, How sad that all those early years as a bank teller and a nurse were wasted. But then I realize they really weren't. I couldn't have gotten here if I hadn't been there. I learned something about myself and about work every step of the way."

And that's the key, ultimately—learning. To find your perfect job, you have to relentlessly gather the lessons of the journey.

Just keep asking questions. Does this job allow me to be myself? Does it make me smarter? Does it open doors? Does it represent a compromise I accept? Does it touch my inner being?

If you listen closely enough, with time, patience, and the courage to act, the answers will lead you to the very place you were always meant to be—when you finally grow up.

From the September 2005 issue of O, The Oprah Magazine.