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Who among us has not experienced that "woulda coulda shoulda" feeling? If only you had stuck with those piano lessons. If only you had signed up for Creative Writing 101 instead of Advanced Trigonometry. If only you had applied for that leadership management course.

Of course, the feeling usually passes, often with the help of some vague adage about accepting one's lot in life or it being too late to change. "Everything happens for a reason," or "Que sera, sera."

As it turns out, you may not have to give up your dream without a fight. VocationVacations.com founder Brian Kurth has thrown away all the adages and done something about that "woulda coulda shoulda" feeling. Based on his own dissatisfaction with a job, he created a company that allows people to try out a new career for a few days, pairing wanna-be park rangers and private investigators with mentors who can help them test-drive their pipe dream.

Internships on Steroids
In fact, the Portland, Ore. matchmaker has more than 75 options, including baseball team manager, music producer, chocolatier, wine sommelier, bison rancher and restaurant critic. The vacations themselves usually last between two and five days, and can run from $399 per person (that's for the beer brewer vacation in Portland, Me.) up to $1299 per person (for the sled dog kennel owner vacation in Gakona, Ala.).

"Basically, we specialize in internships on steroids," said president and founder Brian Kurth. "Our customers are seasoned professionals, for the most part, and they're looking to make a change in the career. We're the first step, the baby step, in that process."

Kurth came up with the idea back in 1999, while sitting in traffic on the Kennedy Expressway in Chicago, on his way to work at telecommunications company Ameritech. As the cars around him inched forward, he started feeling an emptiness about his overall lifestyle, which led to fantasizing about a place that matched you with a dream job mentor.

After being laid off from Ameritech in late 2001, he tried out the idea by asking to work with a dog trainer friend for a few days.

"Before the company even existed, I was playing around with the concept," Kurth said. "As my ex and I traveled the country – we were looking to get out of Chicago – I started asking folks if they had a dream job. The solid majority said they did, and it wasn't what they were actually doing."

After working in the wine industry for a year (another dream job), Kurth launched VocationsVacations.com from his new west coast home in 2004. Only 10 jobs were available at the time but thanks to word-of-mouth, the company has a stable of about 250 mentors, a number which could be a lot bigger, Kurth said, if his company was less strict about who they do and do not accept as mentors.

It's All About the Passion
"First of all, they have to exude a passion for what they do and be able to communicate that passion," he said. "If a candidate's first question to us is ‘How much does it pay?' then we know they're no mentor."

It appears passion is contagious: Kurth says around 70 percent of those who take a VocationVacation wind up pursuing that career in some form, either through enrollment in training classes, internships or full-fledge career switches. He plans on taking advantage of that encouraging statistic to create a Web community, a place online where people can go to discuss the ups and downs of pursuing a dream job.

"It took about a year and a half to get it off the ground," said Kurth, "but I think we've got a really good brand, here. We're a career change company."

Related Links

• Want to make an escape? Try our Travel section.
• Want to make a plan? Try our Finance section.
• Explore VocationVacations.com.