This audio recording marks Episode 100 of Don’t Be Caged By Your Age. As I thought about that milestone, I realized something. After one hundred conversations with remarkable people over 65, I’ve heard countless stories of reinvention, resilience, creativity, and purpose. Not one of those stories began because someone decided they were too old to try.
I first discovered Ray Toole on TikTok, where he regularly shares outstanding live performances from The Yellow Room with musicians spanning multiple generations and fave rock songs from the 60s/70/80s. (Led Zeppelin Friday is my fave!) After following him for several months, I reached out on Instagram to ask if he’d share how he’s thriving after 65 with the Don’t Be Caged By Your Age audience.
During our conversation, I learned the story behind The Yellow Room. When Ray and his wife bought their home decades ago, he immediately recognized one room’s incredible acoustics and imagined musicians gathering there someday. Today, that vision comes to life week after week, and I love watching every single reel.
Ray spent more than thirty years working as a train conductor before picking up his guitar again during COVID. What surprised me most wasn’t that he started playing again. It was hearing him say that he believes he’s ten times the guitar player today at 65 than he was at 25.
How wonderfully hopeful is that?
Throughout our conversation, one phrase kept coming up: “Life’s too short.” Ray even hosted annual “Life’s Too Short” parties! It wasn’t a throwaway expression for him. It’s a philosophy that reminds him not to put off the things that bring him joy.
And maybe that’s the real gift of Ray’s story.
It’s not just about music.
It’s about noticing the things that still call to us - the ideas, dreams, and passions we may have quietly put on the shelf while life moved forward.
We all have decades of lived experiences to know that there will always be a reason to wait.
The timing isn’t perfect. There’s not enough time. I’m not sure where to begin. And do I really want to be a beginner?
But every person I’ve met through this podcast has reminded me of the same thing: our next chapter doesn’t arrive on its own. We have to step into it.
So as you listen to Ray’s story, I’d love for you to think about this:
What’s one “someday” you’d like to turn into a “today”?
Mine is salsa dancing.
And thanks to a comp ticket I just received to try an Arthur Murray dance class (thanks a lot Mary!), it looks like someday is becoming today.
Look out, people - these hips are going places! 💃
I’d love to hear your answer in the comments.
Who knows? Your someday might be the spark someone else needs to begin theirs.
