The Courage to Stop Trying

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“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:

49: Personal Growth Pivot Points: Pause, Quit or Keep Going? – The Life of Try: Personal growth, one try at a time.

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, Wynne Leon explores 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, she draws lessons from Marion Jones, Olympic figure skater Alysa Liu, Oprah Winfrey, and Andre Agassi, plus insights on harmoniousvs. obsessive passion.If you’re wrestling with whether to push through or letgo, this conversation offers language, perspective, and permission to choose what’s healthy—and what’s next.The Life of Try podcast: 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 or clarity—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 a change 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 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 Fun Habit: How the Pursuit of Joy and Wonder Can Change Your Life: Mike Rucker, PhDOpen: An Autobiography by Andre AgassiMarion Jones Reflects on Her Kids Living with 'Reality' of Her Doping ScandalFrom Oakland to Olympic gold: Alysa Liu takes figure skating crownAlysa Liu's Olympic figure skating comeback is golden, true to herselfHow Alysa Liu Found Her Love for Figure Skating AgainWinfrey Announces Show's End in 2011 – CBS News
  1. 49: Personal Growth Pivot Points: Pause, Quit or Keep Going?
  2. 48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive
  3. 47-From Stuck to Momentum: Thomas Edison’s Method for Progress (Try, Learn, Improve, Repeat)
  4. 46: The Quiet Transformation That Changes Everything
  5. 45: The Life of Try: Alex Honnold Case Study

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)

38 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! ❤️

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  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. 🤣

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

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  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!

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  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.

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  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??!!)

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    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!

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      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.

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  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.

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    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!

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  17. I love this, “The Life of Try,” listening to the heart, trusting your instincts, when you know you know. Life is such a fabulous journey and in some small way, we’re all trying. Hugs, C

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  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!

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