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.

Here’s the YouTube video of this episode:

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Click this link to watch in a browser: Letting Go of Outcomes: The Mindset That Keeps You Moving
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How to Stop Procrastinating and Start: The 10-Minute Rule for Taking Action – The Life of Try: Personal growth, one try at a time.

What if the key to overcoming procrastination isn’tfinishing—it’s simply starting? In this episode of The Life of Try,Wynne Leon shares a practical 10-minute strategy for beginning before you feel ready, taking imperfect action, and building momentum when a goal feels overwhelming.Explore why starting can feel so difficult, how the Zeigarnik effect may keep unfinished tasks active in your mind, and why one small first step can help you move forward with greater clarity and confidence. You’ll leave with a simple challenge: set a timer, make one imperfect move, and give yourself a clear next step.If you’re ready to stop procrastinating, get unstuck, and take action on something that matters, this episode is your invitation to begin. Then continue building momentum with How to Build Habits That Stick featuring Dr. Mike Rucker.What will you start today?