It’s Never Too Late to Begin Again | Personal Growth and Courage with Lindsey Goldstein

Posted in thelifeoftryTagged , , , , , , , ,

“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:

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/
  1. How to Celebrate the Try
  2. How to Reclaim Fun in Adult Life; Michael Rucker, PhD on Joy, Burnout, and The Fun Habit
  3. Reinvention, Resilience and The Courage to Try| Lindsey Goldstein on Gap Year
  4. 51: Letting Go of Outcomes: The Mindset That Keeps You Moving
  5. 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers)

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)

49 thoughts on “It’s Never Too Late to Begin Again | Personal Growth and Courage with Lindsey Goldstein”

  5. When I read the post I couldn’t help but have a pang of envy at our heroines freedom to take a year off. Often what happens with huge life changing events is just getting thrown into managing all the aspects of the new changes. I’ve been through a few of those types of events, and there was the obligation to just keep going, to put one foot in front of the other to put out the most pressing fires. I had people relying on me, so it felt necessary to keep moving forward even when the path was murky and not clear.

    Liked by 2 people

    Reply

  8. That was a nice conversation. I like what Lindsey said about finding any time available to write, even if it’s just 30 minutes, instead of scrolling through social media. That’s so true. I’m doing that with reading, and it’s incredible how much you can accomplish in those few minutes throughout the day.

    Liked by 1 person

    Reply

  10. Wonderful conversation, Wynne. So much to take inspiration from – most of all, finding the courage to try rewards us with built confidence.

    I love Lindsey’s sense of humour and what a blessing to balance work, parenting and writing. It’s the dream!

    The idea of a Gap Year – regardless of the circumstances that led to it – sounds so appealing, more so the ability to get to spend it hunkered down somewhere away from home, doing something that makes me feel alive – like writing.

    Thanks for the inspirational kick this morning!

    Liked by 1 person

    Reply

    1. Love your takeaway about trying building confidence. Isn’t that true? And your vision of spending time writing — may it be so!! I’m so grateful to you for listening and circling back to tell me what inspired you. Thank you, Ab!

      Liked by 1 person

      Reply

  11. I think Lindsey is living her best life! Mom, author, marathon runner; I do love how she got into the specifics of the emotional side of running the NYC marathon with it ending in Central Park with the sunlight dabbling on the leaves. She truly felt inner joy. I felt that. And you are 100% right about how trying one thing leads to another. Young or old, it’s baked into our learning curves; what works – what doesn’t. Try the next thing. I’m going to have to mull over my fantasy gap year, hahaha. Thanks, Wynne.

    Liked by 1 person

    Reply

    1. Your fantasy gap year — I can’t wait to hear what you come up with for that, Melanie! And you are so right about Lindsey’s description of the NYC marathon — wasn’t that touching?? I love how she traced the thread from tennis to trying out for crew to running — and that was the icing on the cake. Love your comment, Melanie. I’m so grateful for you!

      Liked by 1 person

      Reply

  15. I took a gap year once. Err…unintentionally (damn corporate downsizing). And it was actually a gap year and nine months. I didn’t climb any mountains, but I did take a two-week solo trip to Ohio and back, which laid the foundation for my future move(s) east, so it turned out to be a pretty fruitful adventure after all. Even if I had to borrow from my retirement savings to afford it.

    Liked by 1 person

    Reply

    1. That is so interesting that your solo trip had bearing on your future in a way that you didn’t know. Downsizing is no fun but I love how it led to both your career as a writer and your midwest moves. Fascinating!

      Liked by 1 person

      Reply
  18. Pingback: The Danger of a Frictionless Life – Thoughts about leadership, history, and more

  19. Loved the interview with Lindsey, Wynne which you do so well, making people feel right at home and comfortable. Sounds like a great read and the 2 of you both are doing such a great job at teaching your kids what it’s like to “try“, practice and set your mind to do something you aspire to and lead by example! Kudos to that and to her new book Gap Year. One of my daughter’s went to London to study abroad for a year and it was a pass/fail grading system. Let’s just say it was an expensive lesson for us but she did learn a lot about the pubs 🙀. I could use that money around now to see what a gap year might be like. 😜😂💗! Best of luck on the book and when I get through my stack it would be one to read for sure!

    Liked by 1 person

    Reply

    1. Oh wow, Cindy – that’s a good story! Sometimes the best learning is outside of a classroom, huh? 🙂 I so appreciate you tuning in. Lindsey’s book is great so I hope you enjoy it! XOXO!

      Liked by 1 person

      Reply

      1. I’ll say it was and is! Some things are more laughable flicking back years later lol
        No doubt I will love it, but I still have to read. Do you remember that right lol.!😎

        Like

  21. It’s never too late to begin again is such a powerful reminder because so many people think growth only counts if it happens early or follows a perfect timeline. Real healing and personal growth often begin the moment someone decides they are still worthy of becoming more.

    Like

    Reply

Leave a comment