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:

How Writing Helps Us Survive Chronic Illness and Loss – The Life of Try: Personal growth, one try at a time.

What does it means to keep showing up when life asks more of you than seems possible?In this episode of The Life of Try, Wynne Leon talks with Kathryn M. B. Johnson, author of Invisible, Until I’m Not, a memoir-in-essays about chronic illness, caregiving, grief, and resilience. Together, they explore what it means to live with fibromyalgia and invisible illness, how caregiving reshapes identity, and why being seen matters so deeply when pain is hard to explain. This conversation offers honest insight, emotional validation, and hope for anyone navigating chronic pain, caregiver burnout, loss, or the daily work of endurance. If you’re looking for a thoughtful podcast episode about chronic illness, caregiving, trauma, faith, and finding strength in difficult seasons, this episode is for you.In this episode, we discuss: → Chronic illness can reshape identity, relationships, and daily life in ways that are often invisible to others. → Caregiving is an act of love, but it also carries grief, exhaustion, and the need for self-compassion. → Writing can become a lifeline—a way to process pain, preserve connection, and reclaim a sense of self. → Being believed and truly seen matters deeply for people living with chronic pain or complex health conditions. → Rest is not laziness; caring for yourself is part of being able to care for others.📘 Order Invisible, Until I'm Not: https://www.amazon.com/Invisible-Until-Im-Not-Illness-ebook/dp/B0GSB7QQMH/🌍 Show notes and more inspiration: https://wynneleon.com🔔 Subscribe to The Life of Try for more conversations on: personal growth, creativity, reinvention, resilience, writing, and mindset.📌 Subscribe & Stay Updated: → https://www.youtube.com/@thelifeoftry?sub_confirmation=1ABOUT ME Hi, I’m Wynne Leon — host of The Life of Try, a personal growth and self-improvement podcast exploring resilience, reinvention, uncertainty, and the courage to keep trying. Through thoughtful interviews, reflective conversations, and real-life stories, I share insights to help you navigate change, get unstuck, and move forward with more intention.🎥 Watch Next➡️ Letting Go Of Outcomes: The Mindset That Keeps You Moving➡️ 48: How to Get Unstuck: Michael Yang on Saying Yes, Resilience and Coming Alive
  1. How Writing Helps Us Survive Chronic Illness and Loss
  2. Near Death, Deep Faith, New Life | Liza Anderson’s Extraordinary Story
  3. Encouraging Effort, Not Outcome: The Secret to Helping People Keep Trying
  4. How to Celebrate the Try
  5. How to Reclaim Fun in Adult Life; Michael Rucker, PhD on Joy, Burnout, and The Fun Habit

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! ❤️

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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.

    Liked by 1 person

  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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  15. that is a whole other side of trying, know when to stop trying and giving yourself permission to do so because it’s the best thing for you to do – love this

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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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  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❣️

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  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! 😁

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  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.

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  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!

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  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! 💞

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  25. Wynne – I loved the wisdom about taking a risk – and all that insight that then led you to the wisdom of when to stop trying – was really powerful

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