the life of try – Surprised By Joy

“You never fail until you stop trying.” – Albert Einstein

I have been watching a lot of Little League baseball this Spring. It’s a fascinating mix of young athleticism and skill development peppered with moments of bitter disappointment. In most every practice and game there is at least one example of someone who wants to sit on the ground and pout because things aren’t going as they expected.

But disappointment doesn’t just happen to six and seven-year-olds. It reminds me that expectations can inspire us to try—until they harden into a demand for a specific outcome.

In this episode of The Life of Try, I dig in to how unmet expectations fuel disappointment, why that disappointment can keep us from taking healthy risks, and what it looks like to stay hopeful without clinging.

From a childhood lesson I learned from my mom about “pressing for the answer” to Alexander Fleming’s accidental discovery of penicillin, I trace how openness, curiosity, and faith can turn apparent failures into forward motion.

Along the way, I draw from Brené Brown’s research on disappointment, Maya Shankar’s reframing of identity after loss, and spiritual wisdom about surrender and non‑attachment—so you can keep trying even when the path changes.

Takeaways:

Recognize when expectations are motivating you—and when they’re setting you up for disappointment
Practice openness and curiosity when a try doesn’t go as planned (and why that matters)
Name and communicate your expectations to reduce “unspoken contracts”
Reconnect with your deeper “why” when your “what” gets taken away
Hold onto faith that trying will lead somewhere good—even if it’s not the destination you imagined.

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51: Letting Go of Outcomes: The Mindset That Keeps You Moving – The Life of Try: Personal growth, one try at a time.

Expectations can inspire us to try—until they harden into a demand for a specific outcome. In this episode of The Life of Try, Wynne Leon explores how unmet expectations fuel disappointment, why that disappointment can keep us from taking healthy risks, and what it looks like to stay hopeful without clinging. From a childhood lesson about “pressing for the answer” to Alexander Fleming’s accidental discovery of penicillin, we’ll trace how openness, curiosity, and faith can turn apparent failures into forward motion. Along the way, we’ll draw from Brené Brown’s research on disappointment, Maya Shankar’s reframing of identity after loss, and spiritual wisdom about surrender and non‑attachment—so you can keep trying even when the path changes.In this episode, you’ll learn how to:Recognize when expectations are motivating you—and when they’re setting you up for disappointmentPractice openness and curiosity when a try doesn’t go as planned (and why that matters)Name and communicate your expectations to reduce “unspoken contracts”Reconnect with your deeper “why” when your “what” gets taken awayHold onto faith that trying will lead somewhere good—even if it’s not the destination you imagined.The Life of Try is a podcast about personal growth, one try at a time.What happens when trying becomes more important thangetting 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 orclarity—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 achange you didn’t ask for.This podcast is for anyone who:Feels stuck or uncertain about what’s nextIs navigating change, burnout, or reinventionWants to live more intentionally without pretending growth is easyBelieves progress starts by trying—again and againThe 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.Links for this episode:The Life of Try HomeLetting Go of Outcomes: The Mindset That Keeps You Moving transcriptSir Alexander Fleming – Biographical – NobelPrize.orgHow to Regulate Your Emotions and Mental Chatter When Bad Things Happen | Maya ShankarAtlas of the Heart: Mapping Meaningful Connection and the Language of Human Connection by Brene BrownPenicillin Wasn't Alexander Fleming's First Major Discovery | Scientific American