(LifeWire) -- Jessica Caulfield decided to open a women's clothing boutique in Hoboken, New Jersey, she had no idea what she was doing.
"I knew zero about retail or owning a business," says the 29-year-old New Yorker, then a real estate agent. "I'd never even had a summer job at the Gap folding sweaters."
She went store to store, peppering owners with questions. But the experience was frustrating, and to complicate matters, she was pregnant. "The clock was literally ticking," she says with a laugh. "I needed to know if this was something I could do."
When she learned about a company VocationVacations, Caulfield knew she'd found what she needed. Soon she was shadowing fashion buyer Mercedes Gonzalez, going to trade shows, meeting with sellers and getting a taste of her dream career. Halfway through the second day, Caulfield called her husband. "Start looking for a storefront," she told him.
Caulfield -- who just opened a Manhattan outpost of her Hoboken boutique, Jessie James -- used VocationVacations to match her with an established mentor in her chosen field which enabled her to test-drive her dream job. The Portland, Oregon, company fills that need for people interested in learning about everything from winemaking to TV producing.
Brian Kurth, 41, founded VocationVacations after questioning his own career choices. "I was like Dilbert," says Kurth, describing Internet and telecommunications jobs. Then the dot-com bust hit, leaving Kurth with a pink slip and no idea what to do next.
He started asking everyone he met about their job, and a pattern emerged: "I found lots of well-off people who were embarrassed about their careers. Scratch the surface, and you'd get the real story: 'I'm a lawyer, but I've always wanted to be X' -- invariably, it was some passion left over from childhood."
Something clicked. In 2003, Kurth's VocationVacations opened with a small stable of mentors that's now 300 strong. Mentorships last a few days and cost anywhere from $600 (animal therapist, brewmaster) to $2,000 (music producer, race car pit crew member).
The most popular? Brewmaster, cheesemaker, sports announcer and comedian. Mentors pocket a small fee -- and may even meet their next hire: A few adult interns have left the stint with a job offer.
"To answer that nagging 'What if?' without losing the time and cash that switching careers usually takes is huge," says Kurth, whose book, "Test-Drive Your Dream Job," encourages readers to answer that question. For a relatively small investment, he says, "people walk away with peace of mind."
Testing the waters of your next career
There are other ways to get your feet wet before taking the career-switch plunge.
• Temporary (and frequently unpaid) internships or apprenticeships provide the most hands-on experience. You may do the grunt work, but you'll get a real sense of job duties and culture -- and demonstrating your abilities to a potential employer may land you a full-time gig.
• Shadowing someone who does your dream job involves observing them at work for a set period. It's not as hands-on but gives you a day-in-the-life perspective.
• A sabbatical from your current gig puts you in a plum position to try something new -- with a safety net. Your boss may be more open to it than you think if it increases the chances you'll stay at your current job since replacing you might be harder than doing without you for a few months.
• Itching to land at a specific company? Contact human resources about an informational interview. You'll get answers to your questions (prepare a list), and you might be able to put yourself in front of someone with hiring clout.
• Mentors may be hardest to find -- they require the most commitment from the other person -- but the rewards will be greater as they share hard-won career experience (and contacts) to help you move ahead. Ask around to sniff out potential mentors, or contact associations in your chosen field; many have mentoring programs.
Not all experiences are great
Kurth says that while about a quarter of his clients switch careers post-mentorship, the experience can be just as useful for those who don't make the leap -- including those who discover their dream job is a bad fit.
Henry Yamamoto, who'd spent days at his software job daydreaming about running a canine daycare, needed that reality check. "I'd been thinking, 'I'll get to spend all day around a bunch of dogs,'" he says.
After a VocationVacations mentorship at Seattle's Dog Day Out, he realized "it's like running a preschool: 25 dogs from 7 a.m. to 7 p.m., all getting revved up and tired at different times ... and they all poop."
Yamamoto, 40, is still at his day job, but his adjusted expectations haven't killed his dream. "I was exhausted," he says, "but it wasn't stressful like my corporate job is. And you get to surround yourself with like-minded people" -- something he "didn't even realize was missing" from his 9-to-5 gig. With downsizing looming in his company's future, he's scouting for a space his new venture can call home.
Pointing to people like Yamamoto whose jobs are on shaky ground in the face of impending recession, Kurth says there couldn't be a better time to consider a fresh start: "Don't wait for the pink slip!"
"We're not anti-corporate America," he adds. "We're pro-taking your life back, and that means considering those intangible payoffs that are about lifestyle, not money. Work shouldn't be a four-letter word." E-mail to a friend
LifeWire provides original and syndicated lifestyle content to Web publishers. Elizabeth Bougerol is a writer in New York City