Famous Retirees
Retirement Reality
Hobbies and Interests
Pop Culture retirement reference
Back in the day
100

In 2023, this legendary NFL quarterback posted a short video saying he was “retiring, for good” after 23 seasons.

Who is Tom Brady?

100

The most common day of the week people dream of making their last workday.

What is Friday?

100

Some like to catch up on this game including drivers, putters, and greens. 

What is golf?

100

Many people like to throw these for people when they retire.

What is a retirement party?

100

The thing retirees never have to hear again: “Can you jump on a quick ____?”

What is a call?

200

This tennis icon said she was “evolving away from tennis” in a Vogue essay about stepping away from the sport.

Who is Serena Williams?

200

For people born in 1960 or later, this is the U.S. “Full Retirement Age” for Social Security.

What is 67?
200

This hobby is known to improve memory and focus—and can be free with a library card.

What is reading?

200

The 1985 sitcom about four older women living together in Miami.

What is Golden Girls?

200

The notification retirees no longer need to fear: “You have 73 unread ____.”

What are emails?

300

This late-night host said goodbye to NBC’s “The Tonight Show” in 2014 after a long run as host.
Answer: Who is Jay Leno?

Who is Jay Leno?

300

The three letter after tax retirement account.

What is an IRA?

300

The hobby that turns “I’m just looking” into “I built this from scratch.”

What is DIY or Woodworking?

300

This phrase is often used to describe someone enjoying retirement: “living the ____ life.”

What is good?

300

The phrase that becomes a daily reality in retirement: “I can do that ____.”

What is tomorrow?

400

This music legend wrapped up the “Farewell Yellow Brick Road” tour in 2023, billed as his final tour.

Who is John Lennon?

400

This health program is generally associated with age 65 in the U.S.

What is Medicare?

400

This hobby is both creative and practical—retirees use it to preserve family stories.

What is scrapbooking?

400

This country is commonly cited in retirement trivia as a top expat destination for Americans.

What is Mexico?

400

This is the first thing many retirees may choose to do when they wake up—because they can.

What is nothing (or “whatever they want”)?

500

This talk show powerhouse aired her final episode in 2011 after a 25-year run.

Who is Oprah Winfrey?

500

 The retirement rule of thumb that suggests withdrawing about this percent annually (often debated, but widely referenced).

What is 4%?

500

The hobby that can become a “second career” without being a job: sharing expertise part-time.

What is consulting or mentoring? 

500

The song title that’s become a “freedom anthem” and shows up in retirement playlists

What is Free Bird?

500

Clue: The hardest thing to retire from isn’t work—it’s this habit.

What is a routine (or “checking the time/phone”)?

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