5 Women Break Their Own Rules

"I will never take financial risks."

Throughout her 20s and 30s, Therese Shechter was all about financial security. She had a good job as a graphic designer at a big Chicago newspaper, a cozy condo, and a membership at an upscale gym. "I used to hire freelancers, and I would always think, How can they live not knowing where their next paycheck is coming from?" recalls Therese, now 44. When a friend invited her to teach journalism in Eastern Europe, she declined. "I had always dreamed of living abroad, but now I owned a condo for crying out loud! I couldn't just pick up and leave!"

Fast-forward a few years, when a breakup with a longtime boyfriend and a rapidly approaching 40th birthday caused Therese to reassess her focus on material comfort. "I didn't want to be on my deathbed regretting things I hadn't done just so I would have enough money to redo my kitchen," she says. A self-proclaimed film geek, Therese decided to attend film school at night. "When I finished, I realized that if I didn't quit and pursue filmmaking, I would be stuck in a job that was 'just okay' for the rest of my life." So she did what she swore she'd never do: She gave up the steady paycheck and began freelancing in design to support herself while she completed her first documentary.

Coming to terms with her new cash-poor lifestyle was one thing -- convincing her friends and family that she hadn't lost her marbles was another matter. "For the first year, I think they were all waiting for me to come to my senses," Therese admits. But trading the fancy gym for workouts at the Y and gourmet dinners for take-out Chinese has paid off in personal satisfaction. "I am infinitely happier now," says Therese. "Who knows? Maybe I'll wind up in Europe after all."

Lesson Learned: Sometimes you have to sacrifice security to achieve happiness. Though you may think that you are mentally prepared to live with diminished resources, you may find it difficult, initially, to get by on less. To cushion the blow, make sure that you have all the details covered, including a workable strategy for paying your rent, a nest egg of savings to cover your living expenses for the first few months, and a fallback plan in case things don't go as expected.

You may also find that you have to constantly reassure skeptical friends and worried relatives that you're making a sound decision. As annoying as this may be, it can actually help, says Dan Neuharth, PhD, a San Francisco-based therapist and author of Secrets You Keep from Yourself (St. Martin's Griffin, 2005). "Not only will it prove you're passionate about your new life plan, but each time you make your case, the dream will become more real for you."