A few years after Chris Evert's 1989 retirement from tennis, her brother John urged her to open a tennis academy in Boca Raton. After quite a bit of convincing she agreed to invest, but with the condition that she wouldn't be obligated to show up every day and punch a clock.
Before long though, she was at the newly-christened Chris Evert Tennis Academy nearly every day, hitting with the 14-18-year-old students and sharing her perspective from a professional career that included 157 tournament victories and 18 grand slam championships.
"They want to know about the pressure of being on the court at Wimbledon," she says.
Some kids are aiming to get on the pro tour, others are chasing a college scholarship, but Evert says all of them impress her with their discipline and commitment, which is what draws her to spend more time at the academy than she expected to.
"I never wanted to have a full-time job again," says Evert, "and I don't. I could go to the Caribbean tomorrow if I wanted to, but I also want to have a reason to get out in the morning."
Professional athletes like Evert, who retired at the age of 34, are faced with the challenges of preserving and growing their wealth long after the peak earning phase of their playing career. Luckily she had an ace in the hole, her father, who majored in economics at Notre Dame and was always on top of her finances.
"My dad really took care of my money," she says. "In the 70s, when a lot of athletes were losing money on things like oil, there was no way he was going to let me lose money."
Evert's father, now 90, served that role until just a few years ago and always had a conservative investment philosophy borne of growing up during the Great Depression. That served her well during the 2008 financial crisis.
"I did OK when a lot of people were hit hard," Evert says, though she moved quite a bit of her fixed-income portfolio into equities as the stock market rebounded.
"I'm conservative, but I also want to be diversified," she says.
That doesn't apply solely to her investments, it also extends to her numerous business ventures beyond the tennis academy. Evert writes a monthly column for Tennis magazine, which she owns a stake in, and is designing a line of tennis clothes for apparel company Tail.
She has also returned to the broadcast booth for
In fact, it was launching her own academy that helped Evert get a better perspective on the game by learning more about training techniques and the nuances of different players' skills.
For someone who didn't want a demanding profession in her retirement, Evert certainly has a lot going on, and that's before getting to her annual Pro-Celebrity Tennis Classic, which has raising money to combat drug abuse and child neglect in Florida since 1989.
With her three sons almost on their own – two are in college and one is a high school senior – Evert is glad to have plenty on her plate.
"My kids are gonna be like 'Adios Mom,' so I better have a life," she says. "I don't want to just be a lady having lunch, getting manicures and pedicures every day and that's it. I want to have a passion for what I'm doing."