Maya shankar – 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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Who's In Your Corner? The 5 People Who Shape Who You Are – The Life of Try: Personal growth, one try at a time.

Who’s in your corner? Discover the five people who shape who you are and how the right support system helps you take bold tries, chase big goals, and grow.Neuroscientist David Eagleman suggests we’re shaped by the people we spend the most time with.In this episode of Life of Try, Wynne Leon shares stories from climbing Mt. Rainier, mentors who cheer from the sidelines, and hiking with her kids to reveal the five people everyone needs:The Yes’ers who turn crazy ideas into plans. The Guides who share their notes. The Counterpoint who gives you the gift of a pause. The Foundation who shows up when things fall apart. The Visionaries who remind you that you can do great things.This week’s challenge:Name your five, thank one of them, and be that person for someone else. Because you were never meant to try alone.For a companion listen, check out The Power of Saying Yes with Natasha Dillinger.Follow Life of Try on Spotify and tap the bell so you never miss the next try. Topics:personal growth, motivation, friendship, mentorship, courage, support systems, and adventure.