F50 Issue #24: Three Lessons from Unretiring Athletes


F50 Issue #24: June 11, 2024


Be Your Own Biggest Fan: Lessons from Unretiring Athletes

Imagine you’re competing for the championship trophy in a popular sport. As the clock ticks down, you’re poised to score the winning goal. During the last few seconds, you look up at the stands for support.

Scanning the crowd, you see a row of people cheering you on — friends, family, whoever is nearest and dearest to you.

And … wait a minute. Who’s that? Are your eyes deceiving you?

You see YOURSELF sitting up there, cheering louder than anyone else. Astonished, you blink your eyes, refocus on the goal, and wind up to take a shot.

The crowd roars. You’ve done it! Looking back up at the stands, you see your row of supporters smiling and clapping. And once again, you see yourself alongside them, giving you a thumbs-up.

It’s easy to forget to be your own biggest fan, in sports and business. When you become a freelancer, you need to hear your own voice cheering alongside business coaches, mentors, and mastermind groups.

See yourself as your favorite player on your favorite team. Be a loyal fan in good times and bad. Review your stats, do a post-game analysis, and whatever happens, look forward to next season.

Cheering for yourself will give you the stamina needed to continue your work or start a new second-act career. You’ll thrive with a positive mindset, like a skilled athlete who refuses to hang up the skates yet.

Speaking of athletes, here’s some inspiration from three superstars with unretirement mindsets.

1. “I’m Jaromir Jagr … and my favorite player growing up was Jaromir Jagr.”

In 2013, the Boston Bruins were competing for the Stanley Cup in the National Hockey League’s (NHL’s) annual championship series. On a Hockey Night in Canada TV broadcast, members of the team told viewers who their favorite player was when they were growing up.

David Krejci from Sternberk, Czechia, said his favorite player was his Bruins teammate, Jaromir Jagr. How exciting that he got to play alongside his childhood hero!

Then, Jaromir Jagr appeared on the screen. With a serious expression, he said, “Hi, I’m Jaromir Jagr from Kladno, Czech Republic, and my favorite player growing up was … Jaromir Jagr.”

We heard laughter offscreen, and then Jagr burst out laughing too. But it was no joke. He has staying power and continues his career to this day as a right winger with his club, Kladno, in Czechia. In fact, on April 18, 2024, at age 52 and 63 days, he became the oldest professional hockey player, according to a Sportsnet article.

He’s still going strong, and he’s an inspiration to fellow hockey players and fans around the world!

2. “My place is still on the field and not in the stands.” — Tom Brady

In 2022, football quarterback Tom Brady announced his retirement after 22 seasons. But that retirement didn’t last. In an article titled “Tom Brady, Retirement Remorse & The Retirement Planning Questions You Should Be Asking,” Joseph Coughlin describes the turnaround this way:

“It’s official, after 20 seasons of cold in New England and heat in Tampa, Tom Brady finally retired. No wait, he’s back!
“After only 41 days, football’s GOAT has retirement remorse and is making a U-turn back to the field.”

On social media, Brady explained,

“These past two months I’ve realized my place is still on the field and not in the stands. That time will come. But it’s not now. I love my teammates, and I love my supportive family. They make it all possible. I’m coming back for my 23rd season in Tampa. Unfinished business LFG”

If you follow football, you probably know that Brady finally retired from playing in 2023. But he isn’t done with sports! He’s set to come back as a Fox Sports broadcaster in September 2024.

And as he moves forward with his second-act career, he can be proud of his longevity and accomplishments. At age 43, he became the oldest quarterback to ever win a Super Bowl!

3. “I have never liked the word retirement.” — Serena Williams

Tennis player Serena Williams announced her retirement from tennis in 2022, but she didn’t want to call it retirement. In an article titled “Serena Williams Serves Up A New Vision Of Life And Retirement,” Joseph Coughlin explains,

“In her interview with Vogue Magazine, Williams commented, ‘I have never liked the word retirement. It doesn’t feel like a modern word to me....Maybe the best word to describe what I’m up to is evolution. I’m here to tell you that I’m evolving away from tennis, toward other things that are important to me.’”

Now, through her venture capital fund, Serena Ventures, she continues to invest in companies that benefit women and people of color. She’s also developing her own jewelry collection, makeup, and clothing lines.

As an entrepreneur, she benefits from the determination and winning spirit that brought her success on the tennis court!

Lessons from Unretiring Athletes

So, what can we learn from these athletes? If you decide to become a freelancer after 50, hold on to these three nuggets of wisdom.

1. Be your own biggest fan.

You don’t have to go on national television like Jagr did and announce your fandom (unless you want to!). But find other ways to cheer yourself on:

  • Post encouraging quotes around your desk.
  • Celebrate milestones by rewarding yourself with a special treat or activity.
  • Use positive self-talk during successes and challenges.
  • Build healthy habits that make you feel like a superstar!

2. It’s okay to change your mind.

Like Tom Brady, you can change your mind about retirement. If you enjoy the job you’re currently doing, don’t feel pressured to give it up. And if you can continue your current work as a freelancer, go for it! Don’t let anyone tell you that you’re too old and it’s time to retire.

And consider this advice from Joseph Coughlin in his article,“Tom Brady’s Decisions Tell Us A Lot About Retirement Planning”:

“Whether your ‘next’ life chapter is enjoying well-earned time off, being with family, volunteering, working part time, full time, starting a business, going back to school, or even starting a new career, mapping out the possibilities long before Friday’s retirement bell rings requires real preparation. You might just find you are more like Tom Brady than you ever imagined. Not at football, but at retirement. Your retirement might be on, off, and on again, too.”

3. Leave your options open.

If you’ve already retired or are planning to retire from your current job, don’t view it as an ending. Remember how Serena Williams said she’s “evolving away from tennis, toward other things that are important to [her].”

Those other important things can be the inspiration for a fulfilling second-act career that may be entirely unrelated to your first career. The sky’s the limit, especially when you become a freelancer!


Did You Know?

According to a CBC News report, 60% of Koreans are over 40, and South Korea is seeing a surge in interest in preparing for a second career after retirement. By next year, 20% of its 50 million people will be over 65, making it a “super-aged society.”

To address this issue, centers have been established where older workers can train to transition to new careers. As the report says, “South Korea's rapidly aging society presents economic and productivity challenges, but experts there believe keeping older people working is critical to maintaining public services and productivity.”


Handy Tools

StretchClock is an online tool that reminds you when it’s time to stretch and guides you through “easy exercises you can do at the desk in office attire.” You can choose from over 100 exercises and create a favorites list with the ones that help you the most.

It’s available for free as an ad-supported trial, with paid memberships starting at $3/month (when you purchase a one-year subscription). Access the tool online through the StretchClock website or as a Windows app.


Now you’re ready for the big game, and maybe even a new freelancing career. We’re always here for you as you explore the exciting options available to you in unretirement!

Until next time,

Craig & Kelly

PS: Be sure to join our NEW Freelance After 50 Facebook Group and get a copy of the guide: "Top 24 Careers for Freelancers After 50."

Co-founders of Freelance University

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