Try Try Again

Rethinking the game plan made all the difference for these 3 career changers

Photograph by Getty Images/Imagezoo

The Misstep: "I didn't specialize until late in the game."

The Fix: Finding his niche.

Barry Densa always wanted to be a writer. Over the years he penned a novel, a stage play and a screenplay, while moonlighting as a bartender, polo teacher, and real estate agent. His longest stint was as a stockbroker. "I wasn't getting anywhere because my heart wasn't in it," he says. "I was doing odd jobs to support myself so I could write, but I was too tired to write."

One day he came upon an article about copywriting and learned you could make six figures. "At the time I thought of copywriting as low class and selling out, but that article made me reassess." He reached out to the author, Bob Bly, learned everything he could, and at 51 became a copywriter.

Problem was, he was a jack of all trades. "For about 10 years I wrote for anyone and everyone who would pay me, from plumbers to business owners. I worked on direct mail, brochures, fliers—anything to earn money." But he still wasn't making a great living. "It was hills and valleys, feast or famine," remembers Densa. He'd always heard that the key to success was specializing, but the idea didn't appeal. "I was stubborn, and so I struggled."

One day a client asked him to write a financial newsletter. Densa was not enthusiastic but he took the gig—and did a great job. "My background in finance enabled me to write persuasively about investment topics," he says. "Before I knew it, I was a hot commodity."

That was two years ago. Today he exclusively writes subscriber acquisition sales letters for investment newsletters. "Once I realized a good sales letter is actually a good story, I was able to enjoy the art of it," he says. "I can satisfy my creativity as well as my financial obligations." Densa, who lives outside L.A., has so many clients he isn't accepting new ones. "I work seven days a week to make up for all of the lost time and lost income," he says. "But it feels good to have found my niche."

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The Misstep: "Lack of funding almost kept me from my passion."

The Fix: Asking family and friends to become investors.

Judy Devincentis had been running her family's gravel company for nearly 10 years when her mother-in-law became ill. She and her husband hired an in-home caregiver who turned out to be young and inexperienced. After accidentally setting off the smoke alarm, the caregiver ran out the back door, leaving Devincentis's ailing mother-in-law to be rescued by first responders.

"I remember thinking there had to be a better way," says Devincentis, who's 56. "People deserve to maintain their dignity." But she couldn't imagine starting a new career—until the economy tanked and Devincentis' company fell on hard times. "That's ultimately what encouraged me to take a hard look at what I was doing."

When Devincentis found a buyer for her struggling company, it was just the push she needed to seriously research home-care franchises. Then the deal fell through — a big setback. Devincentis believed she had to sell the business to make her dream come true. "But my mind had already shifted toward helping people," so she continued to explore buying a franchise. Things looked up when she found a willing investor. Then the investor dropped out. Once more, she wondered if she would be able to pursue her vision.

"My business partner and I had finally gotten the letter from FirstLight HomeCareoffering us the ownership opportunity," she says. "And suddenly we didn't have funding. But once I felt compelled to do this, there was no turning back," she says.

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Devincentis and her business partner appealed to friends and family, who loaned them the money to purchase the franchise in Grand Junction, Colorado. A year later they won their company's Rookie of the Year award; today, the franchise has more than 50 caregivers and is operating in the black. "I love knowing we make a difference in someone's life every single day," Devincentis says.

The Misstep: "I didn't spend enough time researching a career I would enjoy."

The Fix: Starting his own venture.

David Bakke worked in restaurant management for nearly 15 years. But once he got married and had a baby, the long hours and weekend shifts were unsustainable. Changing careers was tougher than he'd reckoned. "I really struggled with convincing employers in other fields that my management skills were transferable," he says.

After about a year of searching, he landed a position at a financial services company. He thought the job would be a good fit given his management experience and personal interest in finance, but there was another reason he took it: "I was desperate to escape the restaurant business."

The new job left him unmotivated and dispirited. Bakke now realizes he should have spent more time finding a career he truly enjoys. "The company had little room for advancement," says Bakke. "I was afraid I'd be doing the same boring work for the rest of my career." After four years, he wanted out.

Unfortunately, time wasn't on his side. "I was in my mid-forties and didn't have the luxury of going back to school," he remembers. Deciding to start his own venture, he self-published a book on personal finance based on his experiences, and created a blog to market it.

A much bigger financial website, Money Crashers, took note. "The owner complimented me on my work," he says. "I picked his brain about online publishing and we developed a relationship." Eventually Bakke, who lives in Atlanta, was offered a position contributing for the website.

"Now that I'm an editor, I have a vastly improved work/life balance," Bakke says. "I'm happier and healthier, and my relationship with my son is deep and strong. While Bakke hasn't yet equaled his old salary, he says, "It's been a blessing in disguise. It has forced me to look for new and creative ways to save money."