10 Playful Prompts for Midlife Joy

Are the Questions You're Asking Keeping You Stuck? with Larry Robertson

creativity curiosity Jun 10, 2026
Late Bloomer Living podcast Episode 277 promotional graphic. Teal background with white daisy illustrations. Text reads: "Are the Questions You're Asking Keeping You Stuck?" Polaroid-style photo of guest Larry Robertson, author of Great Question, smiling in front of a bookshelf.

Are the Questions You're Asking Keeping You Stuck?

Episode 277 | Late Bloomer Living | 6th Anniversary Episode

 

 

It’s been Six years?  How is that possible?  I have to stop and say thank you — to those of you who have been here from the beginning, and to those of you who are newer to this little corner of the internet. Either way, I'm really glad you're here.

When I started this podcast six years ago I had no idea where it would take me. And for this anniversary episode, I want to tell you something: I thought I had a pretty good handle on the power of curiosity.

And then Larry Robertson showed up in my inbox and changed everything.

I didn't even plan to have a guest for this episode. I had a solo topic all ready to go. But when Larry reached out — through our mutual friend Lynn Borton of the Choose to Be Curious podcast — I got on a call with him, and that was that. Some conversations just tell you where they need to go.

Larry is an innovation advisor, Fulbright Scholar, and author of four award-winning books. His latest, Great Question: The Art of the Ask and Getting More of What You Really Want, is the result of years of research and interviews with some of the world's most original thinkers — Nobel Laureates, neuroscientists, educators, and entrepreneurs.

His central argument is one I find both humbling and exciting: asking great questions might be the most underrated human skill we have. We're born doing it. And somewhere along the way, most of us stopped.

Well maybe we didn’t stop asking questions, but we stopped asking “great questions” - the kinds of questions that involve genuine curiosity and lead us to even more interesting questions.  The questions we tend to ask are utilitarian and functional.  We ask to answer an immediate need. What about the questions that lead to wonder and awe? How do we get back to those types of questions? 

In this conversation we explore:

— Why jumping straight to "why" can actually shut down your thinking before it gets started

— What intellectual humility really means and why it's the key to asking better questions

— The specific trap midlife sets for our curiosity — and how to get out of it

— The difference between reinvention, rewiring, and renewal

— The five elements of what Larry calls "the art of the ask"

— The one question he comes back to every time he's navigating uncertainty

I have a confession to make... After six years of hosting a podcast about aging playfully, I'm still catching myself having ageist thoughts. Turns out that's not a failure. It's just proof that the most important questions never really end.

This episode feels like exactly the right conversation to mark the occasion of the sixth anniversary of this podcast. Six years of asking what's possible as we age — and it turns out I've only scratched the surface.

You can also Watch this episode on YouTube

 


Connect with Larry Robertson:

Website: lrspeaks.com

LinkedIn: Larry Robertson

Instagram: @larryrobertsonauthor

Book: Great Question: The Art of the Ask and Getting More of What You Really Want — available wherever books are sold

 

Mentioned in this episode:

Lynn Borton — Choose to Be Curious podcast

Angus Fletcher — Primal Intelligence

Simon Sinek — The Infinite Game

Braver Angels — braverangels.org

 

Want to take your curiosity further?

Come explore play and curiosity with real humans in my Playshop. Get all the details at latebloomerliving.com/play.

 

 

In Full Bloom: a guide to aging playfully 

a little book of inspiration with big impact

Whether for yourself or a loved one, this guidebook is a reminder that midlife is an opportunity for growth, adaptation, and celebration.

Order Your Copy

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