The Life of Try Podcast

What happens when trying becomes more important than getting it right?

The Life of Try is a personal growth and self‑help podcast about getting unstuck, navigating uncertainty, and choosing to try—even when it’s uncomfortable, inconvenient, or not your idea.

Hosted by Wynne Leon, the show explores how real growth, reinvention, and discovery often begin not with confidence or clarity—but with a single attempt. Through thoughtful interviews, reflective conversations, and real‑world case studies, each episode examines what it looks like to keep going when doubt shows up, plans fall apart, or life forces a change you didn’t ask for.

This podcast is for anyone who:

  • Feels stuck or uncertain about what’s next
  • Is navigating change, burnout, or reinvention
  • Wants to live more intentionally without pretending growth is easy
  • Believes progress starts by trying—again and again

The Life of Try isn’t about hustle or perfection. It’s about learning as you go, surfacing what matters, and sharing what you discover along the way. If you’re ready to surf the uncertainty, outlast the doubts, and step into your own try‑cycle, you’re in the right place.

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
  2. 51: Letting Go of Outcomes: The Mindset That Keeps You Moving
  3. 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers)
  4. 49: Personal Growth Pivot Points: Pause, Quit or Keep Going?
  5. 48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive

Here’s where you can find our podcast:

Please listen, watch, provide feedback and subscribe! Questions? Email thelifeoftry@avitiva.com