“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:
Here are some other ways you can listen and watch this episode:
- The podcast player embedded below
- Click this link to watch in a browser: Letting Go of Outcomes: The Mindset That Keeps You Moving
- Subscribe to The Life of Try on Spotify, Amazon Music, or Apple Podcasts
- Subscribing to the YouTube channel: https://www.youtube.com/@thelifeoftry
51: Letting Go of Outcomes: The Mindset That Keeps You Moving – The Life of Try: Personal growth, one try at a time.
- 51: Letting Go of Outcomes: The Mindset That Keeps You Moving
- 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers)
- 49: Personal Growth Pivot Points: Pause, Quit or Keep Going?
- 48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive
- 47-From Stuck to Momentum: Thomas Edison’s Method for Progress (Try, Learn, Improve, Repeat)
Links for this episode:
Letting Go of Outcomes: The Mindset That Keeps You Moving transcript
Sir Alexander Fleming – Biographical – NobelPrize.org
How to Regulate Your Emotions and Mental Chatter When Bad Things Happen | Maya Shankar
Penicillin Wasn’t Alexander Fleming’s First Major Discovery | Scientific American
This really hit home. I love how you showed the shift from “trying” to “needing a specific outcome”—I see myself in that more than I’d like to admit. The Little League example made it so real, too. Learning to stay open when things don’t go my way is something I’m actively working on, and your reminder about reconnecting with the “why” felt grounding. Also, the idea of naming expectations to avoid silent disappointment… so good. Thank you for this gentle, honest perspective.
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I like Brené Brown’s mindset, and I’d like to read her book. This is an interesting episode, Wynne.
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It is heartwarming to hear your story, Wynne, and how it benefits and consoles you. Your mom’s Bible verse is a complicated one, as I have witnessed in my therapy practice and among others who felt their pain and loss was hard to rationalize. I am glad you have found a way to find hope in it.
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Looking forward to tuning in! Thank you, Wynne! ❤️
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