Chapter Excerpt

It started out as a pipe dream. Pure fantasy. It was a notion that popped into my head while I was breathing exhaust on the Kennedy Expressway in Chicago, halfway through my daily twenty-two-mile, one-and-a-half-hour, one-way commute. I didn’t think of it as a job or a business; it was simply a wish list—a list of all the jobs I wished I could do instead of the one I was actually doing. It was 1999 and I was thirty-three years old; I was feeling and looking older than my years, gaining weight and losing my hair. With a hard-earned master’s degree in international relations, I was spending most of my waking hours plugging numbers into sales and marketing projection spreadsheets for Ameritech, the Midwest’s major phone company. The phone company! I was a living, breathing Dilbert! It wasn’t that I hated my job; I didn’t. I had a great boss. I was making great money. In the last decade I had learned a ton about management and business. But in the end, making the world better through broadband technology just didn’t set me on fire. Many Friday nights my partner, Doug, and I would get together with friends—two were architects, one was a TV station’s programming director, and another was starting his own technology-marketing business. They’d talk about their jobs and their faces would light up. They loved what they were doing. Then I’d say something about the latest data network initiative we had launched and in seconds their eyes would glaze over and their heads would hit their spaghetti plates. My job was boring. They were bored listening to it; I was bored doing it!

So every day I spent my commute fantasizing about all the things I’d rather do. Some days I imagined being a dog trainer, walking through the park, a dutiful chocolate Labrador at my side, head cocked to my every command. Other days I saw myself taste-testing wine in a cool, dark cellar in Sonoma County. Still others I saw myself leading groups of tourists through the cobbled streets of Budapest or Buenos Aires interpreting the local culture. With all that fantasy you’d think the commute would have passed quickly—but it didn’t. Ninety minutes in Chicago traffic is ninety minutes, no matter where your head is.

One evening I was staring out at the chain of rain-glazed brake lights in front of me, having just called home to tell Doug that, once again, I’d be late for dinner. (As had become my custom, I’d also used a few choice words to describe my commute and my state of mind at that particular moment. To his growing impatience, he was becoming the misplaced recipient of my disillusionment and lack of career fulfillment.) As I clicked off the phone I thought, why am I just fantasizing about these jobs? There must be a company that arranges short-term internships so people like me can try out their dream jobs. That night I went online, but to my surprise I couldn’t find one. Nothing on the Web offered the kind of experience I was seeking. Guess I wasn’t going to be able to do it after all, I thought. But then a second later I had a brainstorm: if no one else has done it, maybe I could do it! I even knew what I would call such a company: VocationVacations, because the company would offer vacations that let you test-drive your dream vocation. And before “reason” could stop me, I registered the domain name: www.vocationvacations.com.

And that was the last serious thought I gave to VocationVacations for almost two years. I was too devoted to making money to think seriously about starting a business—especially one for which there was no precedent. I liked my benefits, I liked my lifestyle, and I liked the nest egg I was building. I liked the security of the life I had created. Sure, my job was boring and I envied friends who loved their work. But it wasn’t that boring and I didn’t envy them so much that I was willing to risk my security for a “great idea.” I just wanted to do my own little “vocation vacation.” I didn’t want to create the whole company.

That was over eight years ago. It took me two years, a corporate merger and acquisition, a layoff, September 11, and a stock market “correction” before I realized that working for a corporation was not as secure as I had imagined and I began to take the idea of starting a business seriously. But finally, after I’d left my phone company job, and the “make a million” job I’d taken at a dot-com start-up had imploded, and my hard-earned savings had nose-dived with the stock market, something clicked and I realized there was no point in waiting. Doug and I pulled up stakes and drove cross-country looking for the perfect place to live. Along the way I asked everybody who was standing still if they would want to test their dream job if they had a chance. The answer was a resounding yes!

So I figured I was onto something.

But it still took me a long time to get around to acting on it. We had settled in Portland, Oregon (indifferent to the fact that it was suffering its worst recession in decades), and I wanted to get to know the terrain. My head argued that I better get a job—a real job—and make as much money as I could, but my heart kept me ambling around the city, checking out neighborhoods and coffee-houses, driving down the Oregon coast, touring the pinot noir vineyards of the Willamette Valley, meeting people, and talking about my idea. When reality hit and I realized I needed to make money, instead of looking for another corporate job I went for a dream job of my own—working at a small family wine distributor for a fraction of what I’d been making in Chicago, selling wine out of a white Chevy Tahoe and loving it.

But all the while, VocationVacations was brewing. I asked all the people I met what their dream jobs were, how far they would travel and how much they would pay to try one, and what they would expect in a “dream job vacation.” By six months into my wine job I was calling businesses in popular industries, looking for people who were passionate about their jobs and would be genuinely interested in sharing them with others. Four months later, I had ten mentors lined up—in everything from inn keeping and beer brewing to horse training and auto raceway management—who had agreed to take in “vocationers” for one to three days for total-immersion, hands-on learning. Now all I needed was customers. Build it, I told myself, and they will come.

I asked my friend Berit McClure to help me write a press release describing the company and we sent it out to fifteen West Coast newspapers. Nothing happened. Not a single one picked it up. The wine job was starting to look more like a career. And then two months after I sent out the release, Outside Magazine saw it and did a story—and everything exploded. The Associated Press picked it up and the next thing I knew VocationVacations was in 250 papers. My home phone (the official VocationVacations telephone) began ringing off the hook, and in March 2004, Gail Haskett bought the very first VocationVacations package—a brewmaster experience at Full Sail Brewing in Hood River, Oregon—as a birthday present for her husband, Steve.

That same month I realized two things: first, if I didn’t hustle my buns off and get more than ten mentors I would never be able to meet the demand; and, second, if I didn’t grab the momentum while I had it, I might as well kiss the opportunity good-bye. So on March 15, I handed in my resignation at the wine distributor; on April 1, I became the first employee of VocationVacations. I took it as a good sign that it was April Fools’ Day.

Three more April Fools’ Days have passed since then—giving me plenty of time to make mistakes, learn on the job, build a fabulous team, feel the fear of being far from shore without a life raft and also the incredible pride and exhilaration that come from knowing you dreamed something and made it happen. In those three years I’ve watched hundreds of other people take their own first steps toward their dream careers. I’ve watched an IT programmer test-drive a career in voice-overs and a lawyer roll up her sleeves as a cheese maker. I’ve cheered as an airline pilot got behind the mic as a sports announcer and a Web designer sat behind the desk in an architect’s office. I’ve watched software engineers put down roots as vintners and a veterinary technician don toque and apron as a pastry chef. People of both genders and all ages, heads of households and single moms, postretirement planners and people just starting out, have all gone starry-eyed into vocationing and come out with something closer to 20/20 vision. And almost every one of them has come away buoyed, invigorated, and more determined than ever to make his or her dream job happen. When I call vocationers six months later, many have actually gone ahead and written business plans, relocated, started school, or in other ways moved their dream job forward. After years of fantasy, something about living the job for just a few days empowered them to take action. Partly it was the learning—the concrete knowledge they gained about the desired business. Partly it was the mentor, who held their hand, boosted their confidence, and offered ongoing help. Partly it was the contacts they made, which made taking the next steps easier. But above and beyond those practical things, there was something else: the vocationing awakened and energized something deep inside them. It connected them with the truest part of themselves, a part that had previously felt dormant and that, once awakened, refused to be ignored.

You know—if you’re considering a dream job—that the push toward a dream career is not just about how you spend your working hours. It’s about meshing your work life with your deepest sense of self. It’s about having work that matches your values, that feeds instead of exhausts you, that doesn’t require you to leave your priorities at home and check your heart at the door. When we imagine a dream job, we imagine a job in which we are fully ourselves, in which our hearts and minds are equally engaged.

This engagement is what people feel while vocationing. And once they reconnect with that deepest sense of self, few are willing to return to their status quo.

Which of course brings up the next question: what happens after vocationing? You go; you fall in love with a career; you leave, fired up to work in your chosen field . . . and then what? Sure, you had a great couple of days; sure, you know what you want to do—but there’s a gaping chasm between wanting and making it happen. And when you look down into that chasm it’s brimming with house payments, car payments, college educations, health care, food bills, utility bills . . . How exactly do you take the next step?

The question is its own answer. You take the next step. The next small step. The biggest surprise for people who find or create their dream job is that it doesn’t have to happen all at once. It doesn’t have to be an all-or-nothing, hold-your-nose leap from security into the unknown. Instead, it can be a series of small steps that you take only as you feel ready. Sure, there are the few really bold (or independently wealthy) vocationers who cut the ties to their previous careers and hurl themselves full-time into new ones. But most people take it more slowly. They continue at their current jobs while transitioning gradually into the dream. They do research, they write a business plan, they figure out how to begin the new career without taking on more risk than they can handle. Some go to school to get more training. Some dedicate a period of time to paying off debt and building savings so they’ll have funds for their new careers. Some find work in the new field while they put together a business of their own. The path and the timeline vary from vocationer to vocationer; what they all have in common, though, is the passion and the vision to move ahead.

Of course, after vocationing, some people find that the job they tried was not the job they thought they wanted. A woman who vocationed with the general manager of a hotel came away exhausted, shocked at the amount of physical energy the job required. Her mentor helpfully brainstormed other hotel-related jobs with her that would involve her financial services background but better suit her “laid-back” manner. A woman who dreamed of being a veterinarian learned while vocationing that while she loved the animals she hated dealing with their owners—and that a better job for her would be working as a veterinary surgeon where she would have minimal owner contact. Finding that you don’t love your dream job as much as you’d hoped can be disappointing; the dream is dashed, the “what next?” question is alarmingly reopened. But even people who have that experience usually consider their test-drive a success; they’re thankful that it showed them what they didn’t want before they ventured further.

For most people—whether or not they find their dream job—vocationing is like opening the door to a long-closed room. Sunlight and fresh air touch something that has long been in the dark, and the result is a renewed sense of self and a new sense of possibility.

So perhaps I should offer a word of caution. Vocationing will be fun (it is a vacation, after all); it may be exhausting (people tend to work hard at the jobs they love); it will be exhilarating to spend time with someone who works at his or her passion. And it will probably leave you changed. Sandy Huddle put away her dream of doing video production right after college, then years later vocationed in TV production just to “finally close that door.” Instead, she came away with her passion so rekindled that within months she had changed locations within her company so she could attend a top-notch school for TV and film production. Robin Simons, who cowrote this book with me, vocationed as a horse trainer “just for fun,” not to change vocations; and two days on the ranch so rekindled her childhood love of horses that she’s since made time to ride at a nearby stable every day. So don’t vocation if you’re afraid of sparking something passionate inside you. Do it only if you’re ready to be renewed.

This book will tell you how to test-drive your dream job by creating a VocationVacation of your own. It will tell you how to find a mentor, how to prepare for the vocation, and, most important, what to do once the vocationing is over. It will map out the small steps you can take to move from where you are now to where you really want to be. Along the way you’ll meet lots of people who have done it—the former teacher who became a country music songwriter, the therapist-turned-airline pilot, the architect and air traffic controller who together opened an artisan bread bakery. You’ll hear from them and many others about the fears and challenges, the mistakes and lucky breaks, the surprises and accomplishments they experienced as they moved into their dream careers.

You’ll see that few of these people consider themselves risk takers. They describe themselves as “ordinary,” “security-oriented,” “401(k)-type” folks. Most are still shocked to find they’ve taken so bold an action. But after years of working in jobs that didn’t feed their passions they reached a point when they felt they had no choice: they had to push past their fears and make the switch. “I got to the point where I couldn’t live with myself if I didn’t try,” they say. “If I tried and failed, well, at least I’d know I’d tried. Not trying at all would have been failure.”

What helped many of these vocationers was realizing that the risks they needed to take were not as overwhelming as the ones they had imagined. The scariest moments—quitting their jobs, purchasing property, signing a bank loan, moving cross-country—didn’t occur until they were already far along in their planning, or even until after their new career was already up and running. It was still scary; it was still a risk; but it was a calculated risk. By the time they took it, they felt they were likely to succeed.

What if you don’t know what your dream job is? What if you’re itchy and unsatisfied in your current job but when you think about what’s next you draw a total blank? Well, you’re not alone. There’s very little in our society that encourages us to know what we really want to do. When we’re children people ask us what we want to be when we grow up, but once we’re teenagers we’re taught what we should be; we’re channeled into a narrow range of careers based on security and stability rather than on passion. The notion that we could follow our hearts when it comes to work is pretty much trained out of us by the time we graduate from high school. So who can blame us if, by the time we realize that our “practical” jobs don’t fulfill us, we’ve already forgotten how to find our own passions inside? That may be another reason to consider vocationing. It enables you to experiment, to test out all sorts of jobs that might be appealing. As Jimmy Jones, a renowned horse trainer, once said, “A man’s gotta make at least one bet a day, else he could be walking around lucky and never know it.” It’s the same thing with dream jobs: you could have a dream job and not even know it if you don’t give one or two a try.

Knowing the ins and outs of your dream job—and coming to believe that you really can do it—makes transitioning into it easier. So does knowing other people who have done it. So let me introduce you to three people who left their old jobs to pursue their dreams.

• Sue Burton Kirdahy left her corporate job with no clear idea of where she was headed, then used a series of “experiments” to figure it out.

• Tim Healea thought he knew what his dream job was, only to discover through an internship that it was something different.

• Toni Cory had a solid handle on her passion—but no experience to guide her. So she went vocationing to get the knowledge and confidence she needed.

Sue was thirty-seven and, after fifteen years in financial services marketing, was feeling increasingly dissatisfied and unfulfilled in her career. But as the major breadwinner for her family of four, she was not in a position to leave. Nor did she know what other path she wanted to pursue. Then a series of volunteer “experiments” helped her figure that out and opened the pathway to the career of her dreams.

Right out of college, Sue fell into financial services marketing and, from the get-go, she loved it. She loved the intellectual demands, the brokering of big deals, the extensive travel, and the chesslike challenge of climbing the corporate ladder. But she also craved creative pursuits—writing, theater, humor—that had less of an outlet at work, so at night she took classes in those areas. One class was a course in stand-up comedy. For the class final, she had to prepare a five-minute stand-up routine and perform it in a comedy club. To her surprise, “the exhilaration and endorphins I felt coming off that stage were like nothing I had ever experienced.” She had always been “the kid who cracked up all the others at the bus stop,” but she had never imagined that doing comedy intentionally as an adult would provide so much pleasure.

Over the next thirteen years Sue thought about that experience repeatedly, but she never took it any further. “I can’t be performing at midnight at some Chinese restaurant and then go into a big meeting the next morning,” she said. But nonetheless, she put “stand-up comedy” on every résumé. It seemed like an important part of her identity, and often a hiring manager’s reaction was a good barometer of whether or not she’d fit into that company’s environment.

By the time she was in her thirties, Sue’s enthusiasm for her career had begun to wane. She’d gotten married and had children and was cultivating other interests, and while her yearning for creativity was growing, it still had no outlet in the corporate world. Although she was busier than ever—traveling, working sixty hours a week, leading a staff of twenty-five—she began taking more and more classes, even retaking the comedy class she had taken thirteen years before. The mismatch between her “real” self and her work self was becoming starker. In late 2003, in an effort to build its female leadership, Sue’s company had her work with a career coach. “As part of the coaching I went through a process to uncover my core values and look at how my life was in or out of line with them. Well, the values I uncovered were creativity, acceptance, and humor, and when I matched that to my day-to-day existence at the company, I was pretty far out of alignment.” The misalignment was further highlighted when, as part of a course she was teaching, she wrote a “personal mission statement.” Her mission, she wrote, was to “ignite creative transformation in people through the use of humor and play.” Not exactly her job description in the corporation. “And once I knew that,” she said, “I felt compelled to do something about it.” She realized she had to leave.

But how could she leave? Her salary provided 85 percent of the family income as well as the medical benefits. She couldn’t just go off and start a business or find a low-paying job in the arts or social services. Hoping for a compromise, she proposed that the company create a new role of “innovation catalyst,” which would allow her more creative freedom and positive impact. But, ultimately, the company wasn’t able to meet her request. Instead, it asked her to lead an employee engagement campaign that consisted of trying to boost employee morale while strategizing downsizing alternatives and reviewing lists of people who were about to be laid off. It was the antithesis of what she wanted to be doing. So in March 2005 she handed in her resignation. She had managed to negotiate a severance package that would pay her salary and benefits for six more months. That gave her a six-month runway to get a new career—whatever it was—off the ground.

What could that career be? For a businesswoman with an interest in creativity, what kind of jobs were even available? Perhaps TV production? TV producers brought together resources to bring creative ideas to fruition. That might use her expertise and business skills in a new context—but she didn’t know the first thing about it. So she reached out to friends, family, and colleagues, asking if anyone knew any producers. Remarkably, several did and she was able to set up informational interviews in order to learn about the field. A friend of a friend was even able to get her an interview with a high-level ABC executive producer who met with her in his New York office. “If you were twenty-two,” he said, “I could hire you as my assistant, but you’ve already had a very successful career and we’ll both feel extraordinarily awkward if you’re making coffee and dubbing videos.” She left discouraged—too old and needing too much money to start over in the world of TV.

Then she learned that she could vocation at Brave Street Productions, a TV production company in New York. Thrilled that she could experience a TV career firsthand, she signed up, and for two days worked with producers Russell Best and Tammy Leech, developing pitch treatments, preparing interviews, editing videotape, reviewing concepts, and setting up location shoots. It was exhilarating and it was exhausting, and by the end of the second day she knew it wasn’t the job for her. She had loved the front office work—writing pitches and packaging shows—but she had no interest in the mechanics of production or in being on a shoot. Helpfully, Russ brainstormed other paths she might pursue that would use her business experience and creative talent: perhaps she could be a development executive; perhaps she could package shows and take them to Wall Street to find investors. She was grateful for his suggestions; those were ideas she never would have thought of.

Meanwhile, Sue had begun actively pursuing comedy again. Shortly after she quit her job she had worked up her courage and gone to an “open mike” at a local comedy club. It was terrifying to get up onstage, but, once again, coming off, she felt that endorphin high. In the weeks after that, she had gone to other clubs, met local comics, and begun doing semi-regular stage time. As a result, when Russ suggested that she go to a “boot camp” held by the National Association of TV Program Executives (NATPE) where she would be able to pitch an idea for a program, she knew exactly what she wanted to pitch. Working with the comics she had met, she wrote a pitch for a TV sitcom called Open Mike, about the trials and tribulations of a band of small-town comedians. To her surprise, when she presented it at the boot camp, executives from two cable networks asked her to create a demonstration pilot. With further advice from Russ and help from a local cable access director, she and her comedian colleagues taped a ten-minute pilot demonstration. Ultimately the pilot wasn’t picked up, but she was thrilled to have experienced the development process first-hand. She’d been out of work for eighteen weeks, she wasn’t close to finding a job—but for the first time in a decade she felt she was following her heart and moving ahead under her own creative power.

When there were two months to go before her salary and benefits ran out, she got a surprising phone call. She had made a point of staying in touch with people from her former career, letting them know what she was doing, and now the marketing director at another financial services company called to ask her to help produce TV commercials on a freelance basis; the pay would be close to what she had been previously making. Sue leaped. It wasn’t her dream career—the work was about financial services rather than her own creative product—but it was a perfect opportunity to combine her former experience with all that she had learned and it was less than full-time, which would leave her time to continue to explore options. She had started her quest thinking she wanted to be a producer—because that was a title she knew—but her explorations in the world of entertainment were showing her that other possibilities existed. Now she saw that it was only through further “experiments” that she would ultimately find the place that was right for her.

Intrigued by Russ’s idea of packaging TV content for Wall Street, she volunteered for a company that found financing for independent films. What she learned was that she absolutely hated asking people for money! She volunteered as an event planner for a children’s charity and found that while it was personally fulfilling, it also lacked the creative and intellectual challenge she had been craving. Eventually, her research led her to a motivational humorist named Loretta LaRoche. Loretta’s business—using humor to help people manage stress and build resilience—was almost exactly what Sue had outlined for herself when she had written her personal mission statement twenty months before. She had seen Loretta perform and thought her show excellent, so when she learned that Loretta lived in a nearby town, she worked up her courage to call. Her “pitch” was straightforward: “I’m in marketing; I love what you do; maybe there’s a way I can use my marketing skills to help you.” Over lunch, the two women brainstormed ideas for expanding and marketing Loretta’s business; the next week Sue began volunteering, implementing the ideas they had come up with. It was a win-win situation: Loretta profited from Sue’s marketing know-how; Sue learned firsthand about life as a motivational humorist.

When they had been working together for several months, Loretta asked Sue to open for her onstage. Sue was terrified. It was one thing to write a few jokes and tell them in a club or bar; it was altogether different to write twenty minutes of inspirational humor and deliver it to an audience of a thousand! It would mean doing what she’d said she wanted to do! She wrote a draft skit, tore it up, wrote it again, and then wrote it a third time. She thought it was good—but was it good enough? She performed it for Loretta, who gave her the thumbs-up. Finally it was time to go out onstage. To her amazement, the audience responded. Laughter and applause filled the theater and that endorphin high came back again, even bigger and brighter than it had the first time. When the set was over, Sue knew that she had found not just a career, but a calling.

Today Sue has a “portfolio career,” a cluster of part-time jobs all related in some way to her dream career. She works part-time as Loretta’s creative director; she opens frequently for Loretta onstage; she also books her own humorous and inspirational speaking engagements. Recently she vocationed a second time with a professional comedian in New York who mentored her on how she could make presenting to corporate audiences a lucrative, full-time career. She still produces TV commercials for the financial services firm to pay the bills, but the old feelings of dissatisfaction and misalignment are gone. “Now I am actually doing what I said I wanted to do two years ago,” she says. “I still don’t feel as though I’ve arrived at a final destination, but as time goes on, my transition to my dream career comes more and more into focus. With each experiment I learn more about what I like and what I don’t, I make new contacts and learn about new possibilities, and I uncover back-door paths for getting into this career. Maybe most important, with each experiment I live less exclusively in my head and more and more in my heart. I am really enjoying the journey.”

Tim was twenty-three and two years into an editorial job at a New York magazine when he realized that journalism was not the dream career he’d once imagined. But what was? Three internships let him test a hunch and then refine it, and ultimately led him to the job he still adores ten years later.

“I’ve always been really curious,” says Tim. “I love asking questions and exploring new things, so I always thought journalism would be the perfect job.” And perhaps it would have been if he had landed a job at a consumer magazine, but right out of journalism school he got a job at a magazine for discount retail chain executives and instead of doing probing interviews he found himself red-penning copy about executive compensation and retail security. Two years in, when he’d been unable to land a more interesting job, he decided that his career in journalism was a failure.

Now what?

He thought about cooking. His mother and grandmother were great cooks and had inspired a similar passion in him. What would a career in cooking look like? Wary after his journalism foray, he decided to do some exploring. School was out of the question—he couldn’t quit work to go to school, nor could he do both things simultaneously—so he “apprenticed” himself at a small culinary program in Manhattan. In exchange for helping out in the kitchen, he was permitted to sit in on classes and could do it on weekends and evenings alongside the magazine job.

He loved it. The duties were basic—setting the table, washing pots and pans—but he loved working around food and meeting people in the industry. Within weeks he knew it was what he wanted to do. Under the guidance of one of the instructors, who had become both a mentor and friend, Tim decided that instead of spending two years and a lot of money to attend a high-end culinary institute, he would do an eleven-month work-study program at Peter Kump’s New York Cooking School. There he could spend two days working at the school for every day in the classroom, and his tuition would be free. The only hitch would be living money. To attend school, he would have to quit his journalism job; how would he eat and pay his rent? His friend and mentor helped him there as well. Stephen Schmidt was the lead consultant for the new edition of the Joy of Cooking and got Tim a part-time job testing recipes. He also referred him as an assistant to Suzen O’Rourke, who ran a private cooking school out of her Manhattan loft. Together, the two jobs would just cover his bills for the duration of school.

Heart in mouth, he handed in his resignation. Standing in his boss’s office, for a moment he felt that it seemed crazy to give up the good salary and the stable future publishing offered, especially when he had no idea what he would do when school ended in eleven months. But the minute he left the office and closed the door behind him he knew he’d made the right decision. The cost of being in the wrong career far outweighed the security and the paycheck.

School was everything he’d hoped it would be. “I learned as much working at the school as I did in the classroom,” he said. “I dealt with all the purveyors and accepted all the deliveries; I developed a close relationship with the instructors; I got a complete behind-the-scenes look at how a professional cooking operation runs.” Through his two part-time jobs the learning continued. “Every few days I’d meet with the editor of the Joy of Cooking, who was the top cookbook editor in the country. She’d give me a pile of recipes and I’d go home and test them. And at the private cooking school, professional chefs came in to teach and I got to work with and learn from them.”

Midway through his course work, Tim bought a book on baking artisan breads. Rustic, handcrafted breads were new in the United States in 1997 and Tim became fascinated. He began experimenting with his own dough and starters and was amazed that with such basic ingredients—flour, water, yeast, and salt—he could create something so alive. When it was time to do an internship for school, he decided to try an artisan bakery and applied to the Pearl Bakery in Portland, Oregon. Unfortunately, Greg Mistell, the bakery’s owner at the time, wasn’t so sure. He had never had an intern and had to be convinced by one of the managers that taking Tim was a good idea. But within days both Greg and Tim knew they were well matched. “I didn’t know going into it that that passion would blossom in me,” Tim said. “But when I got there I fell in love with it. Even coming in at four in the morning didn’t bother me. I was just so excited to be around bread every day.” When the internship ended, the bakery hired him full-time. A year later he became head baker.

For the next four years Tim reveled in the baking. His goal was “to make the best breads and pastries and do the best production work every day”—and he did. In 2002 he was selected to be one of three people on the U.S. team in the Coupe du Monde de la Boulangerie. The world baking competition is the Olympics of the baking profession, and Tim and his team took home the silver medal.

After that, his focus began to change. As much as he loved the baking, he realized he was also interested in learning the numbers side of the business. “It seemed like the natural evolution of my passion,” he said. “I wanted to use my creativity and problem-solving ability to look at how to grow the business. I wanted to learn to read a financial statement, how to calculate the break-even point, and how to use numbers to make decisions going forward.” So Tim approached the bakery’s new owner, Eric Lester, with a proposal for changing his job in a way that would enable him to grow his skills. Eric agreed and together he and Tim developed a long-range plan that would expand Tim’s role in the operation.

Today, Tim has moved out of the head baker position into the job of “expert mentor” to the entire bakery staff. “Even a dream job can get boring,” he says. “It’s not always new and fresh. So you have to take initiative and create pathways so you get what you want out of your life and career.” One of his roles today is mentoring other people who want to learn the art and business of baking. It’s a full circle that gives him enormous pleasure.

Toni was forty-nine and facing the closing of the factory where she had worked for over two decades. She knew what she wanted to do next—and it wasn’t to take another factory job. She wanted to open her own dog kennel and day care. What she didn’t know was how to go about it—until she spent a day with Dawn and Dick Walton at The Dog Zone.

Toni had been working at the Motorola factory in Mt. Pleasant, Iowa, for twenty-seven years when the company announced it was going to close the plant. “I could have found another manufacturing job,” she said, “but I was tired of working in a factory. I thought, if it happened here where we’re a profit center, it could happen anywhere, and I didn’t want to leave one factory and go to another and have it happen again. I was forty-nine years old; I had another twenty years of work. I didn’t want anyone else controlling it. I wanted to be happy.”

So Toni and her husband, Paul, started planning. Crazy for their dogs, they’d had dozens of conversations over the years about how much they wanted a great place to leave them when they went away. The conversations had always ended with a little note of fantasy, “What if we started one ourselves . . . ?” Now, suddenly, Toni saw her chance.

As soon as word of the plant closure began to circulate, she took a How to Start Your Own Business course at the community college. By the time she finished, she and Paul had made a plan: they would sell their home and buy a larger piece of property and Paul would take a year off from his one-person construction company and build them a house and a kennel building. Of course, that would require money, which would mean getting a bank loan. So using what she’d learned in her class, Toni wrote a business plan. “I’d never done anything like that in my life,” she said, “and I didn’t think I could do it. But I’m good at asking for help and my business teacher was happy to give it, and once I got into the zone it just kind of fell out of the computer.” To gather the marketing and demographic data she needed she called the local vets. When some were unwilling to give her information, she pretended to be a student gathering data for a paper. When the plan was finished, she put it in a three-ring binder with tabs for every section and proudly gave it to the banker. Although she had been conservative in all of her projections, it showed that the business would make a small profit in the first year.

To her surprise, the banker shook his head. “Toni,” he said, “this is rural America. People here think of dogs as livestock. When they leave for the weekend they don’t need a kennel. They just throw food down and leave.”

But Toni was undaunted. “Marc,” she shot back, “whose picture do you have on your desk?”

Marc looked at his desk, where prominently displayed was a picture of his dog. He agreed to lend them the money.

But then he presented another surprise: as a condition of the loan, the bank would require that Toni and Paul put up all of their money, even their retirement account. They had expected to use some of their retirement, and had hoped to leave a cushion in the bank for first year operating costs. But the bank was intractable. So after a brief discussion, they agreed. “If we wanted to make our dream come true, this was what we had to do,” said Toni. “So we took every single penny of our retirement, plus borrowed one hundred and sixty thousand dollars. Paul even sold the 1970 pickup he’d been restoring for as long as we’d been married. He hadn’t been planning to sell it but when you do something like this your priorities change and those things don’t mean so much anymore.”

So now they had money to build their new home and the day care—but Toni had only the slimmest idea of what was involved in running a kennel and day care business. Nor did she have long to learn. Paul would be taking a year off from his own work to build the buildings, drawing a salary from the bank loan for his time, which meant that when the loan ran out, the business had to be ready to open. So right before her job ended, Toni went to The Dog Zone, a doggy day care in Cedar Rapids, for a day of on-the-job learning. There, Dawn and Dick Walton, the owners, shared everything. “Before I went I could only imagine what it would be like to own a doggy day care, but after spending a day getting body slammed by dogs, pulling rocks from a dog’s throat, cleaning the walls, and seeing everything that Dawn and Dick did, the whole thing became real. I left with the confidence that Paul and I could do it.”

As soon as her job ended, Toni used her employment benefits to go to the Tom Rose School for dog training in St. Louis to become a certified professional dog trainer. It was an intense five-month program that taught everything from obedience training to the fundamentals of running a dog-training business. Between school and the vocation experience, she was beginning to feel prepared to open the day care. Her excitement and optimism grew when she returned home and saw the progress Paul had made on their little log cabin home and the kennel building. She joined him, diving headfirst into the preparations.

“It was extremely stressful,” she said. “In addition to the construction, there were so many things to do and think about: getting signs made, getting the interior done, getting inventory bought, getting the promotional stuff in order . . . And all of it was brand new to me.” But with her willingness to ask for advice, Toni found all the help she needed. “There were so many people out there who wanted to help,” she said. “The chamber of commerce; my business school teacher; my banker; my accountant; my former neighbor, who was an interior decorator; my vet: I picked their brains for every bit of knowledge I could get and most of the time I couldn’t write fast enough to get it all down.”

At times a sense of panic would overwhelm her. What are we doing? she would think. We can’t do this! When that happened, she and Paul would take a break and drive into town, where inevitably they would meet someone on the street or in a restaurant who would say he couldn’t wait for the kennel to open. “That’s what really kept us going,” Toni said. “We’d say, okay, we’re doing the right thing.”

Toward the end of construction, the bank money started dwindling. They realized they could no longer afford to pay Paul a salary. And since they had no money left of their own, Toni had to go back to the bank for an additional loan. “When I had to go in and borrow money to live on, I was almost in tears,” she said. “Marc said, ‘Toni, take a breath. It’ll be okay. We’ll get through this.’ He’d gone from being skeptical to totally believing we were going to make it. Once he started talking to people and saw how excited people were about it, he started saying, ‘Toni, people will pay for this! You have to charge more!’” The bank was quick to approve an additional loan.

I DON’T KNOW WHAT MY DREAM JOB IS!

It sounds silly since I’m in the dream job business, but when I was thinking of leaving my “heads in the spaghetti plates job” at Ameritech, I didn’t know what my dream job was either. That was one of the reasons it took me so long to quit. I didn’t know what I wanted to do instead. It got to the point where even I couldn’t stand my own whining. Then one day I got an idea. I bought an enormous piece of paper and $100 worth of magazines and newspapers and got on a train to Springfield, Illinois. I had no particular interest in the Land of Lincoln; it was the downtime I wanted—eight hours on the train with no phone, no TV, nothing from real life demanding my attention. I spent the time doing what I hadn’t done since kindergarten, cutting out pictures that appealed to me and pasting them onto the paper. When I was done, I had a giant collage of travel, animals, food, buildings, fitness, and the arts. I sat back and examined it almost as if another person had done it. It was a portrait of me: all the pictures were of things that gave me pleasure, things I wanted in life, things that in some ways defined me to myself. The next day the train pulled back into Chicago and I folded the collage and tucked it in my suitcase. It hadn’t told me what kind of job I wanted, but it had opened a door. It had reminded me that there were things in the world I loved and that any one of those areas would provide a job with greater meaning.

Eventually I found work that incorporated almost every one of them.

Doing a collage is just one way of getting in touch with passions deep inside you. Another way might be doing online searches based on your avocational interests, or “going back to school” by reviewing college catalogs for signs of interests that have gone dormant. Perhaps it would be helpful to talk to people who knew you as a child and might remember things that sparked your passion then. Numerous books and Web sites can help you pinpoint your interests as well as possible careers.

Finally the building was done, the signs were in place, the details were taken care of. In early October 2006 Toni sent an e-mail to her former colleagues at Motorola inviting them to her grand opening. It was almost exactly a year to the day since she had left her job.

That October Toni took in $670; in November her receipts were $2,600. People who weeks before didn’t know what doggy day care was were bringing their dogs to try it out, falling in love, and becoming regular clients. Strictly word-of-mouth marketing was attracting customers from as much as an hour away.

Today, the business is seven months old and receipts continue to grow. Toni is working harder than she expected to. “I probably put in eighty hours a week,” she says. “I’m here from six in the morning to seven-thirty or eight at night, and Paul comes in at night to help with cleaning,” but she expects in a few months to hire part-time employees. By the end of the first year, she expects the business to support her.

“This has definitely been the experience of a lifetime,” she said. “At times I wondered whether we would live through it emotionally, financially, and physically, but Paul and I have really jumped out of our boxes on this and I am really proud of us.”

>WHY SPEND TIME VOCATIONING?

1. To “test-drive” your dream job before committing

2. To find a mentor

3. To learn the “ins and outs” of the business

4. To make contacts in the industry

5. To boost your confidence

6. To explore a passion

7. To satisfy your curiosity about “the road not taken”

8. To test possible careers when you don’t know what’s next

9. To experience an unusual, invigorating vacation

10. To try something new and challenge yourself in new ways

11. To gain perspective on your current job, lifestyle, and future

12. To reconnect with a dormant part of yourself

If I had read about Sue, Tim, and Toni eight years ago when I first had the idea for VocationVacations, I would have thought, well, good for them, but I can’t do that; not now, maybe not ever. As much as I wanted to, the idea of leaping out of my “real” job and trying to start my dream job just seemed too ambitious. I was inspired—but I was also immobilized. I was impassioned by my idea—but too scared to do anything about it.

Perhaps that’s how you’re feeling now. I know that what I needed more than anything then was help getting past my fear. I needed someone to tell me that:

1. going after my dream job didn’t require the daredevil leap that I thought it did;

2. what it did require was a series of small, incremental steps; and

3. those steps could be fun rather than scary.

If someone had told me these things back then I might have been skeptical—but I also might have been willing to give it a try. Instead of hanging on to my various cubicle jobs for so long, I might have started VocationVacations six years sooner.

You are probably skeptical too. The idea of giving up the security of a “real” job—with a real paycheck and real benefits—is pretty scary no matter how you cut it, and imagining even the most exciting dream job doesn’t do much to mitigate that fear. The only way to do that is to address those fears head-on. So let’s do that right now—because the sooner you get mobilized, step by incremental step, the sooner you’ll make that dream job real.

Copyright © 2008 by Brian Kurth