The Courage to Stop Trying

Posted in thelifeoftryTagged , , , , ,

“The important thing is to not stop questioning.” – Albert Einstein

We have a strong ethos of trying in my household. There’s an example that we often joke about. When my daughter was about 9, my friend Eric asked her to help deflate a rubber raft so we could take it home from vacation. When she went to put it back in the box, he said it’d never fit.

Her response was something like, “It won’t fit back in the box with that attitude!”

Safe to say, we are primed to try. But sometimes that overshadows the wisdom of when to stop trying. How do you know when to stop trying—especially when you’re someone who prides yourself on perseverance?

In this episode of The Life of Try, I explore the moments when quitting isn’t failure, but wisdom: when our efforts are overly controlled, when something deep inside says “it’s time,” or when passion turns obsessive and starts costing more than it gives.

Along the way, I draw lessons from Marion Jones, Olympic figure skater Alysa Liu, Oprah Winfrey, and Andre Agassi, plus insights on harmonious vs. obsessive passion.

Here’s a short section about mining the deep knowledge of when you know, you know:

If you’re wrestling with whether to push through or let go, this episode offers language, perspective, and permission to choose what’s healthy—and what’s next.

Here are some ways you can listen and watch this motivating episode:

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
  1. 51: Letting Go of Outcomes: The Mindset That Keeps You Moving
  2. 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers)
  3. 49: Personal Growth Pivot Points: Pause, Quit or Keep Going?
  4. 48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive
  5. 47-From Stuck to Momentum: Thomas Edison’s Method for Progress (Try, Learn, Improve, Repeat)

Links for this episode:

Personal Growth Pivot Points: Pause, Quit, or Keep Going? transcript

The Fun Habit: How the Pursuit of Joy and Wonder Can Change Your Life: Mike Rucker, PhD

Open: An Autobiography by Andre Agassi

Marion Jones Reflects on Her Kids Living with ‘Reality’ of Her Doping Scandal

From Oakland to Olympic gold: Alysa Liu takes figure skating crown

Alysa Liu’s Olympic figure skating comeback is golden, true to herself

How Alysa Liu Found Her Love for Figure Skating Again

Winfrey Announces Show’s End in 2011 – CBS News

(featured photo from Pexels)

57 thoughts on “The Courage to Stop Trying”

  2. Love this episode, Wynne. Especially the points you’ve made about pursuit…and retreat. When to pause, stop…listen to head and heart. We, the people who commit and are ever steady, ever ready—sometimes need reminders to take action for change. For our own good. Xo! ❤️

    Liked by 2 people

    Reply

  3. Wonderful and inspiring episode, Wynne! I love the wise nugget of how the mind helps inform the heart and to always listen to our hearts. The hardest but often most necessary thing to do is to stop trying – even pausing.

    The skater story also reminded me of Simone Biles, who bravely in front of the world, stopped – regrouped and came back stronger in the Olympics. The heart just knows.

    I’m going to look at the stapler supply at work today and follow your dad’s lead. I’ll keep you posted on how that goes. 🤣

    Liked by 2 people

    Reply

      1. yes, I like more positive terminology instead of ‘giving up’ —- words like ‘ease back’. ‘recalibrate,’ ‘interrogate design’ …..

        Like

  5. There are those who will keep on going even if everything points to failure (a stubbornness not necessarily admirable!) It does take wisdom to know when to keep on going and when to stop. Good stuff!

    Liked by 1 person

    Reply

  7. Your soliloquy was both beautiful and wise. I might add that we should realize which efforts are worth the try because they are virtuous and in line with humanities needs. Thanks, Wynne.

    Liked by 1 person

    Reply

  10. This is such a timely episode for me, thank you, Wynne! So many good points for me to consider, in my writing I feel like I’m “running out of staples,” but yet other days I feel energized (or is it obsessed?) Lots to think and pray about! (How did you do that in 11 minutes??!!)

    Liked by 1 person

    Reply

    1. Thank you for this wonderful compliment, Dana. I know what you mean about the running out of staples days…and I think that’s important to note if even just for the day. Thank you for the thoughtful comment!

      Liked by 1 person

      Reply

      1. Yes. I went out to dinner with my former board members last night. Our charitable organization that I resigned from is now defunct. The residential facility still exists and is running strong. Our group that volunteered to help them doesn’t exist.

        Like

  14. I’ll admit that I was caught off-guard when I realized this episode was all about stopping the process of trying…what?? 😊 But it’s actually incredibly insightful and smart. It’s the flipside and it matters. You offered great examples of being aware of when to stop such as fear of change (I’m so with you on staying longer than we should!) Plus, it’s a fascinating idea that stopping the effort actually opens a door where you should be! (I think that was Marion Jones.) That is a truly compelling reason to stop. Thanks, Wynne.

    Liked by 1 person

    Reply

    1. The flipside — I love how you put things, Melanie. Right! I stay longer than I should so I think this (and maybe most of what interests me) is researched and written for me… 🙂 Thank you so much for listening, my friend!

      Liked by 1 person

      Reply

  18. Isn’t it a tricky balance to pick ourselves back up again and again, yet have the wisdom to realize that there comes a point when taking a break, trying a new approach, or admitting that it’s healthier to stop makes more sense? I wish I had a dollar for every time I heard a student say, “It’s too hard,” only for them to say, “This is so easy!” five minutes later.

    I think I’ve heard you write about Miss O’s anecdote of giving the “improve your attitude ” speech to Eric before. I love it!

    Liked by 1 person

    Reply

  19. Love your analogies Wynne and comparisons. Beautifully shared and articulated. It’s so very true. We need to know what our threshold is and what is truly important if we are banging our head against the wall as well. There is no failure. Try till you can’t and then try again and when it’s time to hang your hat… do that too❣️

    Liked by 1 person

    Reply

  20. Looking forward to this episode! I tend to stop trying when I hit the combination of not enjoying the process and a lessening in my perceived satisfaction with achieving the goal. Or in some cases-exhaustion and/or injury! 😁

    Liked by 1 person

    Reply

  21. Interesting subject, my friend. I just listened to it this morning, and it got me thinking about when it’s the right time to stop, not just trying, but other things we do in life, like working and deciding on retirement. My mandatory retirement from the Army was set for 2030, but I decided to go for it in 2023. Seven more years would have meant two or three more moves, maybe a deployment or two, so I didn’t see the benefit of staying longer. Yes, I might have received a bit more money, but I would have missed more important things in life. So there is definitely nothing wrong with stopping early, even when people want you to keep going.

    Liked by 1 person

    Reply

  22. Sassy one, that Miss O! But I approve, because she’s absolutely right: no task is impossible unless you don’t give it a try. Reminds me of the scene in Apollo 13 where the engineers at Mission Control were tasked with making a square peg fit inside a round hole. Whaddaya know, they did it!

    Liked by 1 person

    Reply

  24. What a tough topic, Wynne. The point of pausing is different for everyone, but I love your analogies. And listening to your heart is great advice. “What our gut tells us is usually right.” Thanks for this helpful post, and have a good weekend! 💞

    Liked by 1 person

    Reply

Leave a comment