Life's Too Short for Someday
What are you waiting for? How many times have you told yourself you'll get around to it someday? Someday you'll pick up the guitar again. Someday you'll take that trip. Someday you'll start the business, write the book, learn the skill, or pursue the passion that's been quietly waiting in the wings. But what if life's too short for someday? My guest is musician Ray Toole, the creative force behind The Yellow Room, a musical community that brings together talented musicians from multiple g...
What are you waiting for?
How many times have you told yourself you'll get around to it someday?
Someday you'll pick up the guitar again.
Someday you'll take that trip.
Someday you'll start the business, write the book, learn the skill, or pursue the passion that's been quietly waiting in the wings.
But what if life's too short for someday?
My guest is musician Ray Toole, the creative force behind The Yellow Room, a musical community that brings together talented musicians from multiple generations to perform live, connect through music, and celebrate the joy of making music together.
Ray's story is a powerful reminder that it's never too late to reconnect with what you love. After spending more than 30 years working as a train conductor, Ray picked up his guitar again during COVID and began playing more seriously than ever before. And here's the remarkable part: he believes he's a better musician today at 65 than he was at 25.
In our conversation, Ray takes me back to his early days growing up during the golden era of rock and shares how music became a lifelong passion.
We talk about balancing creativity with careers and responsibilities, the joy of mentoring younger musicians, and the unexpected opportunities that can emerge later in life when you continue to follow what lights you up.
One phrase came up again and again during our conversation: "Life's too short." In fact, Ray once hosted annual "Life's Too Short" parties! His philosophy is simple but powerful: don't wait for someday.
Whether you've always loved music, have a passion you've put on the back burner, or simply need a reminder that it's never too late to create, connect, and contribute, I think you'll find inspiration in Ray's story.
This Episode
🎸 How Ray fell in love with music and the electric guitar
🎸 Growing up in the incredible music culture of the 1970s
🎸 Keeping a lifelong passion alive while navigating careers and responsibilities
🎸 Why picking up the guitar again during COVID changed everything
🎸 The story behind The Yellow Room
🎸 The joy of bringing musicians from different generations together
🎸 Why Ray believes he's a better musician at 65 than he was at 25
🎸 What aging has taught Ray about creativity, performance, and purpose
🎸 Why mentorship matters at every age
🎸 Ray's advice for anyone thinking about returning to music—or pursuing a long-forgotten dream
If there's something you've been wanting to do, create, learn, or experience, maybe this is your sign to stop waiting.
Connect with Ray Toole and watch his fab music videos on these platforms:
Facebook, Instagram, YouTube, TikTok
Songs mentioned during our delicious conversation:
Desmond Dekker & The Aces – Israelites
Led Zeppelin - Over the Hills and Far Away
Keep On Smilin' - The Wet Willie Band
Coca-Cola's Ad - I'd Like to Teach the World to Sing
If you found inspiration from this conversation, please rate, review and share this episode.
I’d love to hear your thoughts, so be sure to hop on over to Don’t Be Caged By Your Age on LinkedIn or Instagram. Or leave a message on the website here.
☕ Love listening to Don’t Be Caged By Your Age? Join the movement to end ageism and celebrate pro-aging!
For just $5 a cup, you can sponsor the podcast and help:
✨ Amplify inspiring voices
✨ Break age-related stereotypes
✨ Reach more listeners worldwide
💻 Visit: Buy Me A Coffee
Every cup makes a difference - thank you! 🧡
Waving from Boston – cheers!
Ande ♥
CONNECT with me online - I'd love to learn how you're shattering ageism!
https://www.linkedin.com/in/andelyons/
https://www.instagram.com/dontbecagedbyyourage
SPONSORSHIP
If you resonate with the show’s mission of shattering ageism and age-related expectations so folks can thrive after 65, please reach out to me to learn more about making an impact through sponsoring the Don’t Be Caged By Your Age podcast – ande@dontbecagedbyyourage.com.
Creator - The Yellow Room
Ray Toole is a Massachusetts-based musician, lifelong music lover, and the creative force behind The Yellow Room, a musical community that brings together talented musicians from multiple generations to perform, collaborate, and share their passion for music.
Although music was always an important part of Ray's life, he spent more than 30 years working as a train conductor while playing guitar and other instruments primarily for his own enjoyment. During the COVID pandemic, Ray picked up his guitar again and began a remarkable new chapter—one that would eventually inspire thousands through live performances and social media.
Known for his belief that "life's too short for someday," Ray is proof that it's never too late to pursue a passion, develop new skills, and create meaningful connections through creativity. Today, he continues to bring people together through music, mentorship, and the joy of collaboration.
When he's not making music, Ray can be found inspiring others to dust off their instruments, follow their curiosity, and embrace the possibilities that come with every stage of life.
