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One Retiree's Second Act: From the Corporate World to Coaching Tennis

Former Boeing executive left the 9-to-5 routine for a whole new racket.

A high school tennis player early this year looked at me during practice and asked, “What’s your day job, Coach?”

“Oh, you mean this,” I said, holding up the security badge hanging from my neck. “This gets me into the school. I don’t have a day job anymore.”

I had just retired from my job at aerospace giant Boeing and started a new chapter as a tennis coach at a large Catholic high school in downtown Chicago. Now, instead of advising corporate leaders on how to talk about layoffs or new product launches, I was demonstrating how to hit proper ground strokes.

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For years, I played a lot of tennis to stay fit and unwind, frequently packing my gear to squeeze in a set whenever I could as I traveled the world for my job in public relations. With a millennial son out of the house and my financial adviser smiling at my 401(k) balance, the time was right to try making this lifelong sport more than a pastime. And after I turned 60 three years ago, I made a plan to say goodbye to the corporate world and become a tennis pro.

Plotting my strategy. In early 2017, I talked to my club’s tennis director, who suggested enrolling in one of the top programs for teaching pros, which cost about $400. Over the next few months, I plowed through six online classes, attended a weekend on-court seminar and crammed for a 100-question exam. By the summer of that year, I had my instructor certification.

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By then, Boeing had started making changes I didn’t really love, and I moved my retirement date up by six months, to November 2017. That could have left me fidgeting through the long, cold Chicago winter. But because I started planning early, I was ready.

After becoming certified, I got some on-court experience by serving up a Friday-night mixer and running a doubles tournament at my tennis club. As soon as I retired, I started networking with tennis pros over coffee—gallons of coffee—and learned that teaching part-time at a private club was the domain of former NCAA Division I and II college players, not recreational players like me. But they (and some family members) suggested volunteering to coach high school tennis.

Volunteering was an option because I didn’t have to earn a lot of money teaching tennis, thanks to my wife’s job and her employer-provided health insurance, some rental-property income, our savings and my soon-to-be-tapped company pensions.

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Coaches, it seemed, were in high demand. I quickly landed interviews with three high school athletic directors—each pleased with my cert­ification, enthusiasm for the game and (most important) my idle afternoons. Each offered a stipend of several thousand dollars for the upcoming boys’ tennis season.

I accepted a position as an assistant coach at Saint Ignatius College Prep, where 20 boys made up the Wolfpack varsity and junior varsity teams. Emphasizing teamwork and physical fitness, we ran two hours of practice each weekday to prepare for a heavy, 30-match season from mid March to mid May. Guided by two former college players among our coaches, I learned how to evaluate players, run skill-developing drills, boost the players’ fitness level and give positive feedback to help them do their best in match play.

As the boys’ season finished up, the head coach asked me to stay on to coach the girls’ team beginning in early August. Heading into summer, I landed a gig to teach a 90-minute beginner adult class at public tennis courts twice a week. But after the first four-week session, the owner said two college-level players on his coaching roster were back, and I was benched.

But I’m not worried. There are lots of ways to be professionally involved in tennis—on and off the courts. And I’m doing everything I can to make my encore career a smashing success.

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