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Sandy St. John, 54

Sandy St. John, 54

Old career: Microwave path engineer
New venture: Commercial pilot

Not many people decide to become a commercial pilot later in life, but St. John says flying is in her blood. Her father was a pilot in World War II, and, even while she was working in the telecommunications industry, St. John always thought about getting her pilot's license. Unlike flying for the major airlines, commercial pilots aren't beholden to age restrictions. And her new job could include offering scenic tours or flying freight. But becoming a pilot requires time and money—it cost St. John $5,000 to get licenses along with the expense of owning and maintaining a plane. "Financing comes from good financial planning and not mindless spending," she says.