regret – Surprised By Joy

“Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable.” – Sydney Smith

I’ve told this story before but it still cracks me up. When my daughter was three-years- old, I asked her how many houses she could see when she looked out the ground floor window of our house, it was about three.

Then I took her up to the floor above and ask her how many she could see and it was about seven.

Finally we went out onto the little deck on our rooftop and I asked her how many she could see and it was more than she had numbers for. “Miss O” I said “this is the perspective that you get when you are older, you know that everything fits into a larger picture and you are able to see more of it.”

Miss O’s eyes got wide and she looked at me like I was a crazy lady. I admit, that lesson was a little before it’s time. But I love a good dose of perspective. It’s one of the reasons I enjoyed this latest How to Share podcast conversation with author and educator Andrea Simon about her wonderful book, Did You Live the Life You Wanted?

We talk about perspective, regret and the meaning of life. She tells us why she choose to write this story as a novel and how the course she taught about how to write about family plays into her writing.

There are so many fantastic female friendships and characters in this book that spans 50 years. Andrea talks about how she asked men and women if they lived the life they wanted and what she learned differs when women and men answer that question.

We talk about the meaning of life and how writing plays into that. Andrea’s incredible experience as an educator and facilitator shines through as we dig into the depth of life and how we share it.

This is a great episode full of perspective and wisdom with a thoughtful guest. I know you’ll love it.

Takeaways

The novel spans 50 years, highlighting female friendships.
Writing about family requires sensitivity and respect.
Men and women often have different perspectives on life choices.
Older women may feel they had fewer options in their careers.
Regret can lead to personal growth and new opportunities.
It’s important to pursue personal desires as we age.

Here’s Andrea’s fabulous elevator pitch for her novel Did You Have the Life You Wanted?:

Here are some ways you can watch or listen to all of this insightful and helpful episode:

The podcast player embedded below
Click this link to watch in a browser: How to Share Perspective
Subscribe to How To Share on Spotify, Amazon Music, or Apple Podcasts
Subscribing to the YouTube channel: https://www.youtube.com/@howtosharepodcast

Please listen, watch, provide feedback and subscribe.

How to Celebrate the Try – The Life of Try: Personal growth, one try at a time.

When should we celebrate progress—only at the finish line, or all along the way?In this episode of The Life of Try, Wynne Leon explores the power of small wins, tiny habits, and incremental progress. Drawing from a personal story about preparing her home for an Airbnb experiment during the World Cup in Seattle, Wynne reflects on what it means to keep going when growth is messy, nonlinear, and full of setbacks.Along the way, she connects insights from BJ Fogg, creator of Tiny Habits and director of Stanford’s Behavior Design Lab, with the long-term philosophy of Toyota’s Kaizen culture, where small daily improvements add up over time, and the practical courage found in the checklist mindset associated with Captain Sullenberger. This episode is about personal growth, habit formation, celebrating small victories, and learning to recognize that progress doesn’t have to be dramatic to matter.In this episode, we discuss: → Why celebrating small wins can help you stay motivated even when progress feels slow or messy → How BJ Fogg’s Tiny Habits approach shows that tiny celebrations can reinforce lasting behavior change → What Toyota’s Kaizen philosophy teaches about the long-term power of small, consistent improvements → How checklists and small-step courage can help you keep going when you feel overwhelmed or stuck → Why growth often looks nonlinear, and how to recognize progress before the final result arrives → How honoring effort along the way can help you build resilience, confidence, and momentum If you’ve ever felt stuck, overlooked your own progress, or wondered whether the little steps count, this conversation will remind you that they do. Small wins matter. Tiny steps matter. And trying counts, even before the big outcome arrives.🌍 Show notes and more inspiration: https://wynneleon.com🔔 Subscribe for more: Subscribe to The Life of Try for more conversations on: personal growth, creativity, reinvention, resilience, writing, and mindset.ABOUT ME: Hi, I’m Wynne Leon — host of The Life of Try, a personal growth and self-improvement podcast exploring resilience, reinvention, uncertainty, and the courage to keep trying. Through thoughtful interviews, reflective conversations, and real-life stories, I share insights to help you navigate change, get unstuck, and move forward with more intention.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ Letting Go Of Outcomes: The Mindset That Keeps You Moving➡️ 48: How to Get Unstuck: Michael Yang on Saying Yes, Resilience and Coming Alive➡️ How to Reclaim Fun in Adult Life | Mike Rucker, PhD, on Joy, Burnout and the Fun Habit🔗 CONNECT WITH ME:• Website:→ https://wynneleon.com/• Instagram:→ https://www.instagram.com/wynneleon/• Facebook:→ https://www.facebook.com/wynne.leon/

Links for this episode:

How to Share Perspective transcript

Andrea Simon’s website

Did You Have the Life You Wanted? on Barnes & Noble, and Amazon

From the host:

My book about my beloved father: Finding My Father’s Faith

(featured photo from Pexels)