Articles: Real Stories About Living the Dream

Ann Rea worked at a variety of jobs in software, investment and fundraising until an encounter with a breast cancer patient made her realize that life is too short to spend it doing things she didn't like.

"I realized, 'I hate my life, I'm completely miserable, I want to paint,' " said Rea, 41, a graduate of the Cleveland Institute of Art who lives in San Francisco.

Drawing on skills she'd learned in business, Rea drafted a 30-page plan outlining how to make a living from her art. Rea loved painting landscapes. And she realized that she lived within driving distance of some very marketable landscapes -- California vineyards.

So she came up with a strategy of contracting with wineries to do oil paintings of their vineyards, sell them prints and postcards of her work, and then sell the originals to wine lovers through shows and receptions at tasting rooms.

"My assumption was that the wine lover is a collecting personality, and likely to collect art," Rea said. "And I don't really care if I'm painting vineyards or some other scene. I'm painting the ambient light and color."

Rea started painting full time two years ago. She sought free consulting from the San Francisco Small Business Development Center to learn bookkeeping and sales negotiation, and to help set long-term financial goals.

She now has seven winery clients, including Gloria Ferrer Champagne Caves and E. & J. Gallo Winery. She is negotiating to publish a book of her vineyard paintings, and she expects to reach 150 percent of her sales goal of $100,000 for the year.

Iain Douglas, vice president of marketing for Gallo, said his company was impressed with both Rea's painting style and her business savvy.

"Wine is a live product, and her style of plein-air painting captures it live," Douglas said. "And her business approach was the best I've seen from the art world. Her flexibility in offering her paintings in so many different forms allows us to share it with our customers in many different ways, from thank-yous for key customers to postcards in our tasting rooms."

Rea's first year as a full-time painter was marked by constant anxiety, but she has moved past that.

"It was very scary," she said. "But it's the best. I finally get to do what I love. I had chosen to abandon art, chosen to believe it was unpractical and I couldn't do it. Now I would rather stick a dull needle in my eye than go back to a cubicle."

You can! If you feel stuck or afraid, hunker down in a comfy chair or cafe with one of these books. They've helped millions get over their shoulds / coulds and are very easy reads:

I Could Do Anything If I Only Knew What It Was by Barbara Sher

Wishcraft by Barbara Sher (This is also available online.)

Life Strategies: Doing What Works, Doing What Matters by Dr. Phil