Brian KurthBrian Kurth is the founder and president of VocationVacations, a company offering clients the chance to spend a few vacation days working in the profession they’ve always wanted. He’s also the author of Test-Drive Your Dream Job, a practical guide that gives readers tools to reshape their working life. I spent time with Brian to learn how people can pursue the career of their dreams without risking their present job, next mortgage payment or retirement funds. Brian gets personal below about making money, building a business and offers a few suggestions about managing finances when you’re self-employed.

1. How do ‘œmoney fears’ hold people back from pursuing their dream jobs?
People become accustomed to what they have and often, the fear of loss is the number one reason holding them back. We’re here to help people give themselves permission to take that pay cut because in the long run it will come back if you pursue your passion. You can stay stuck and be miserable or start moving toward your dream job.

2. What is your most significant memory about money?
Financial security has always been really important to me. I was raised in the Midwest by a German father and Norwegian mother, both who survived the great depression. They always had to have money in bank to feel secure and this view filtered down to me. I had a secure job in corporate America and deemed myself a success. I was making great money, had a nice home, a couple of investment properties and yet I was miserable. Risking financial security was huge to me when I started VocationVacations but it was a risk worth taking.

3. What is your worst habit around finances?
Eating out. I justify it by saying I work hard and I’m busy. I happen to be frugal in other areas but I eat out way too much.

Test-Drive Your Dream Job4. What’s the financial benefit of trying a short-term ‘œinternship’ while on vacation?
It offers both personal and professional due diligence and one should consider it an investment in their future. Before you go to culinary school, write that business plan, or move over to work for a not-for-profit, VocationVacations allows you to try it out. This experience circles back to money by helping you determine if this pursuit is worth it to you.

5. Why are mentors important when starting a business?
It is absolutely critical. It allows you to ask questions and get answers that you wouldn’t be able to learn any other way. Regardless of age, they can provide you with the if-I-knew-then-what-I-know-now perspective.

6. Did finances put a strain on the relationship with your ex?
As I mention in the book, Doug and I split right before I launched VocationVacations. When we moved to Portland, I wanted to be more entrepreneurial and felt it was his turn to go work the corporate job like I did while we were living in Chicago. I think there was some mutual resentment that had built up. I wanted him to support my dream of building out VocationVacations and he wanted me to go get the six figure job at Nike.

7. Do entrepreneurs typically crave personal growth in addition to career success? If so, how can they strike a balance between the two?
Yes. Most entrepreneurs are looking for a different lifestyle, not necessarily a career. This falls under the umbrella of wanting to be happier and I’ve found that entrepreneurs don’t care if they work every weekend. It doesn’t bother them because they’re doing something that they love.

8. How is retirement being redefined by Baby Boomers?
Sixty is the new forty. Boomers are not going to sit around and twiddle their thumbs. They’re discovering what’s next and looking to continue to work. It goes back to lifestyle vs. a job. They want a lifestyle they couldn’t have in their forties.

9. What suggestions do you have for managing finances when you no longer have an employer automatically deducting taxes and retirement contributions?
My experience was pretty flash cut. I was laid off and then took time to travel. I did go back to work first, but I tried something that was of interest to me. During this transition, I spent a year in sales & marketing in the wine business. This income reduced my burn and my employers hired me knowing that I was building out VocationVacations on the side. Having a salary and insurance probably saved me $50,000 during this phase.

Here are my tips: You’ve got to have health insurance. Don’t go without. It’s not worth the risk in this country. Second, know that everything takes twice as long and costs twice as much when launching a business. I also had to make a shift in my consumption and travel. When I had the corporate job, I could afford to go to Europe and South Beach a couple of times a year’¦ not that I was big circuit boy, but I liked destinations and experiences and had the money then to pay for them.

10. Is there truth to the saying do what you love and the money will follow?
Absolutely. Twenty to 25% of our vocationers are now in their dream job and while many haven’t fully replaced their income, they are happier in their pursuits and the money has become less important ‘“ refer back to question 1. With that said, there are a lot of folks in entertainment, sports and business (Donald Trump for instance) that believe if you follow your passion the money will follow. I’ve seen firsthand that this path can work.

More about Brian Kurth
A native of Madison, Wisconsin, Brian Kurth graduated with degrees in Political Science, History and International Relations from the University of Wisconsin before moving to Chicago to earn his Masters Degree in Political Science from Loyola University. Before launching VocationVacations, Brian spent more than a decade in the corporate world working his way up in the telecommunications industry with AT&T and Ameritech (now AT&T). Leaving the corporate world behind, in January 2004 Kurth launched VocationVacations, the only company of it kind that offers clients a hands-on, career immersion experience to test drive their dream job under the expert tutelage of expert mentors.

A ‘œVocationer’ himself, Kurth is a sought-after expert on how to pursue and attain one’s dream-job lifestyle (what he calls the ‘œVocationing Process’), and the author of Test-Drive Your Dream Job released in January 2008. Since launching VocationVacations, he has shared his wit and wisdom in appearances on NBC’s TODAY Show, NBC Nightly News, CNN, MSNBC, CBS Marketwatch Weekend, Bloomberg Television and FOX News. Major print media including the New York Times, Wall Street Journal, LATimes, Fortune Magazine, More Magazine, BusinessWeek and many more turn to Kurth for his comments, advice and insights.

Read other Queercents interviews in the Ten Money Questions archive.