“Things falling apart is a kind of testing and also a kind of healing. We think that the point is to pass the test or to overcome the problem, but the truth is that things don’t really get solved. They come together and they fall apart. Then they come together again and fall apart again. It’s just like that. The healing comes from letting there be room for all of this to happen: room for grief, for relief, for misery, for joy.” – Pema Chodron

The troubleshooting method that I’ve taught to new technology consultants is to change one thing at a time. But what happens when life goes sideways and you get a chance to change all the things keeping you rooted? Do you scramble trying to rebuild life as it was? Or lean in to the chance to rethink about where you want to be?

That’s the premise behind Lindsey Goldstein’s delightful novel, Gap Year. When in the span of a few days, Jane’s daughter leaves for a gap year, her husband informs her that he’s in love with someone else, and she’s forced to choose between a promotion or to quit at work, she decides to take her own gap year. She goes to Ecuador to climb the mountain she’s always wanted to, Cotopaxi.

There are many reasons I love this book. Climbing and Ecuador – two of my favorite topics. But also because walking alongside Jane in her adult gap year helps to put in perspective the choices that we’ve made that handcuff our ability to try.

I was lucky enough to sit down with Lindsey Goldstein, the author of Gap Year on The Life of Try podcast, for a conversation about personal growth, self-improvement, and finding the courage to try—even when the path ahead feels uncertain. From writing and running to parenting, failure, and fresh starts, we explore how confidence is built one brave step at a time. If you’ve ever wondered whether it’s too late to try something new, this uplifting episode is a reminder that growth often begins the moment we say “yes” to the challenge.

Key takeaways

• When life falls apart, it can also become an opening.
• Courage often starts before confidence.
• Trying, failing, and learning are all part of growth.
• Small steps lead to bigger transformations.
• You do not always end up where you expected—but you still grow.
• Practice changes what feels possible.
• It is never too late to begin again.

Here’s the YouTube video of our conversation:

Here are some other ways you can listen and watch this episode:

• The podcast player embedded below
• Click this link to watch in a browser: Reinvention, Resilience, and the Courage to Try | Gap Year with Lindsey Goldstein
• Subscribe to The Life of Try on Spotify, Amazon Music, or Apple Podcasts
• Subscribing to the YouTube channel: https://www.youtube.com/@thelifeoftry

Reinvention, Resilience and The Courage to Try| Lindsey Goldstein on Gap Year – The Life of Try: Personal growth, one try at a time.

What do you do when life falls apart? In this episode, Wynne Leon sits down with Lindsey Goldstein, author of Gap Year, for a conversation about personal growth, self-improvement, and finding the courage to try—even when the path ahead feels uncertain. From writing and running to parenting, failure, and fresh starts, they explore how confidence is built one brave step at a time. If you’ve ever wondered whether it’s too late to try something new, this uplifting episode is a reminder that growth often begins the moment we say yes to the challenge.In this episode, you’ll learn: → When life falls apart, it can also become an opening → Courage often starts before confidence → Trying, failing, and learning are all part of growth. → Small steps lead to bigger transformations. → It is never too late to begin again → You do not always end up where you expected—but you still growLindsey Goldstein shares how writing in short windows of time highlight that progress often comes from regular effort, not waiting for the ideal moment. Check out Lindsey's book Gap Year and experience Jane's courage vicariously – but beware, it's contagious!If your kids are leaving for college, you want to try a new hobby, or a travel spot is calling you, this episode is for you. 📘 Order Gap Year on Amazon🌐 Visit Lindsey Goldstein's website🌐 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.📌 Subscribe & Stay UpdatedABOUT MEHi, 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 Finally Write That Book You've Been Dreaming About | Writing Motivation 🔗 CONNECT WITH ME:• Website:→ https://wynneleon.com/• Instagram:→ https://www.instagram.com/wynneleon/• Facebook:→ https://www.facebook.com/wynne.leon/

1. Reinvention, Resilience and The Courage to Try| Lindsey Goldstein on Gap Year 20:35
2. 51: Letting Go of Outcomes: The Mindset That Keeps You Moving 11:33
3. 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers) 23:26
4. 49: Personal Growth Pivot Points: Pause, Quit or Keep Going? 11:02
5. 48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive 24:50

Links for this episode:

Reinvention, Resilience, and the Courage to Try | Gap Year with Lindsey Goldstein transcript

Gap Year on Amazon and Barnes & Noble

Lindsey Goldstein’s website

(featured photo from Pexels)