Things About Parenting That I Think I’ve Learned So Far, Part 3

The role of a leader is not to come up with all the great ideas. The role of a leader is to create an environment in which great ideas can happen.” – Simon Sinek

I don’t expect any great applause for this but I’ve solved the sock problem I’ve been complaining about since Things About Parenting That I Think I’ve Learned So Far Part 1. Let’s be clear — the socks still go missing, get tucked in between coach cushions and get carried around by Cooper the dog. But I’ve figured out a brilliant strategy: they don’t need socks when they wear Crocs. <ba dum tss!>

So it’s time to update my Things About Parenting That I Think I’ve Learned. My kids are 11 and 7 years old so I still have a ways to go. But I believe we’ve turned the corner. Parenting now is more psychological than physical. It looks a lot like leadership.

So here are the things I’ve learned so far:

It’s a great responsibility being responsible for someone else; pack treats for yourself…and them
Knowing what you are and are not responsible for will save your sanity

Teaching values is done one small act at a time
They are always watching… like when you
– Wave when someone lets you in
– Say “hi” or smile to strangers
– Admit you don’t know it all
– Call the homeless people by their name
– Bow to a Higher Power

There is a time when you just have to say “yes” to the McDonald’s drive-thru

Rarely will the three of us all see something the same way
But we can still exchange stories of what we see while looking in the same direction

Melt downs and spin outs happen
You will be judged by strangers and your kids alike by how you react
Digging deep to respond from your inner calmness usually works better

This generation will never not know life without Amazon and smart phones
That doesn’t mean that they need to get everything instantly or always be connected
But it does mean we will need to let them navigate the world differently than we did

Wear Crocs…without socks!

You can stall for time by time by responding, “That is a great question.” to a kid’s good question.”
If you don’t know the answer, just say, “I don’t know.”
They won’t hold space for not knowing if you don’t.

Good friends make the world go round
Your friends
Their friends
And if you are very lucky, siblings as friends.

Parenting is hard work
It’s okay to lie on the couch and let them paint your toenails now and then

Kids are different
They will likely not like the same foods
Not be calmed by the same things
Have unique capabilities
But still care about the same people, value each other, and respect differences

On the subject of chores — I frequently forget to enlist help for what would be really helpful to me
Overestimated what I need to teach and what they’ll eventually learn on their own
Miscalculated how long it will take
And have plenty more chances to get it right

You will screw up
They will learn more from how you react than if life had gone perfectly

Correction without judgment and anger is more effective
Use fewer words

Respect goes two ways

There is no substitute for being genuinely interested in and liking your kids
Listen to understand not evaluate

How you show up is as important as what you show up for

Life is not fair
We all want it to be… especially kids.
Demonstrate how to reach for hopes and dreams
And if you can, show how to navigate the messy middle.

(featured photo from Pexels)

If my work has encouraged, inspired, or helped you try something new, consider supporting it with a small “cup of coffee” donation. Your support helps me keep creating conversations, stories, and resources that cheer people on as they do brave, meaningful work.

You can find me on LinkedIn: https://www.linkedin.com/in/wynneleon/ and Instagram wynneleon

Please check out the The Life of Try podcast Where trying becomes the spark for personal growth, discovery, and re-invention!



Support Without Pressure: Why Effort Matters More Than Results

Give light and people will find the way.” – Ella Baker

The other day, my six-year-old son, Mr. D, announced that he wasn’t going back to finish out the last 12 days of first grade. After some delicate probing, I discovered he was worried about a math test.

It’s hard to know what to say to help in a situation like that, isn’t it? And what does real support actually look like—especially when someone is struggling, failing, or figuring things out?

So in this episode of The Life of Try, I explore how to support others without adding pressure, and why focusing on effort instead of outcome can make all the difference.

Whether you’re a parent, coach, friend, or teammate, it’s easy to unintentionally turn encouragement into expectations. But research—and stories from figures like basketball coach John Wooden and psychologist Carol Dweck—show that when we shift our focus to effort, persistence, and growth, we help people stay in the process longer and build real resilience.

This episode dives into:

  • Why it’s often harder to watch someone try than to try ourselves
  • How subtle signals can create pressure without us realizing it
  • The difference between encouragement and expectation
  • How to support kids, friends, and colleagues in a way that builds confidence and persistence
  • Practical ways to reinforce effort, not just results

And fortunately this research helped provide me a roadmap to help with Mr. D’s math test. I reminded him that he’d already done the work and practice and so the test was just like a baseball game. All he had to do was do his best.

If you’ve ever wondered how to truly support someone you care about—especially when things aren’t going well—this episode offers a powerful reframe. Because sometimes the best support isn’t helping someone succeed… …it’s helping them keep going.

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

How To Tell Relatable Stories About Life The Life of Try: Personal growth, one try at a time.

What makes a story truly relatable? In this episode of The Life of Try, Wynne Leon explores how the smallest moments in life can become the most powerful stories — from a beloved Seattle raccoon named Jimothy to a little boy celebrating soccer goals with his grandmother. Through humor, heart, and the idea of narrative transportation, this episode looks at why specific, human stories help us feel seen, connected, and inspired to keep trying.If you’ve ever wondered how to tell better stories about everyday life, how to make your experiences more meaningful, or why small moments can carry big emotional truth, this episode is for you.Key takeaways:• Relatable stories often begin with small, specific moments rather than big life lessons.• Details help listeners see, feel, and remember a story.• Everyday stories can reveal courage, connection, confidence, and support.• The most powerful stories do not need to be perfect — they need to be honest and human.• Living The Life of Try means celebrating small wins, showing up for each other, and trying again from wherever we are.🔔 Subscribe to The Life of Try for weekly conversations about resilience, courage, creativity, reinvention, mindset, and living with intention.ABOUT MEHi, 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ How to Overcome Burnout & Build an Upward Spiral of Growth, Fun & Resilience➡️ Near-Death Experience with Jesus | Liza Anderson on Faith, Healing and Recovery➡️ How to Embrace What Makes You Different | Finding Your Purpose with Kym Gordon Moore
  1. How To Tell Relatable Stories About Life
  2. Why Second Place Might Be Preparation, Not Failure
  3. When Your Plan Falls Apart | How to Stay Resilient and Keep Trying
  4. Barbara Nickless on A Voice In The Dark, Online Gaming and The Power of Story
  5. Embracing What Makes You Different | Kym Gordon Moore

Links for this episode:

Other Episodes you Might Enjoy:

⁠ Letting Go Of Outcomes: The Mindset That Keeps You Moving⁠

4⁠8: How to Get Unstuck: Michael Yang on Saying Yes, Resilience and Coming Alive⁠

⁠How to Reclaim Fun in Adult Life | Mike Rucker, PhD, on Joy, Burnout and the Fun Habit⁠

(featured photo from Pexels)

Fun Is a Practice, Not a Reward

“If you’re not having fun, you’re not learning. There’s a pleasure in finding things out.” – Richard Feynman

What if fun isn’t a reward for getting everything done—but a skill that helps us live better right now?

Recently as I was driving ten-year-old Miss O to a rehearsal for a musical, she said, “I always have fun at rehearsals.” Six-year-old Mr. D had a similar answer as I was bringing him home from baseball practice the other night. I asked what he liked best – the base running practice, the scrimmage, the throwing contest? His answer was, “I like all of it.

What kids know and grown-ups seem to forget (speaking for myself) is that fun is a day-to-day practice, not a reward only to be savored when we get everything else done. Fortunately, my guest for The Life of Try podcast this week, Mike Rucker, PhD, reminded me that parents have some agency in this too. We aren’t just Uber drivers getting our kids to the places they need to go. And that prompted me to put on my mitt and take part of the scrimmage at Mr. D’s baseball practice. The ball didn’t come to me but I enjoyed standing in the field and being part of the fun immensely for a couple of innings.

In this episode of Life of Try, I talk with Mike Rucker, PhD author of The Fun Habit, about the science-backed value of fun and why it matters for stress relief, resilience, creativity, relationships, and well-being. We discuss positive psychology, the “sandwich generation,” burnout, parenting, savoring joyful moments, and how to create simple systems that bring more play, rest, and connection into daily life.

Here are some of my favorite takeaways from this great book and fantastic, science-backed conversation about fun:

  • Fun is not frivolous — it’s restorative.
    Being intentional about fun can help reduce burnout, restore energy, and bring more meaning into everyday life.
  • Happiness and fun are not the same thing.
    As Mike says, “Happiness is a state of mind, but fun is something we can do.”
  • Agency matters.
    When we feel like we have a say in how we spend our time and energy, life becomes more enjoyable and sustainable.
  • Small “pattern interrupts” can change everything.
    Breaking our routines in creative ways can open up more space for joy, connection, and better habits.
  • Fun looks different for everyone.
    It doesn’t have to be loud, social, or high-energy. Fun can be calm, quiet, and personal.
  • Burnout narrows our thinking.
    When we’re depleted, we tend to rely on autopilot. Renewal helps us think more creatively, flexibly, and expansively.
  • Enjoyment is a powerful predictor of sticking with a habit.
    If you want to build sustainable habits, choose approaches you genuinely like—not just ones you think you “should” do.
  • You don’t need a total life overhaul.
    Reclaiming fun can start with just a few intentional hours, a simple list, or one activity that brings you back to yourself.
  • The “Fun File” is a practical tool.
    Keeping a running list of activities that genuinely light you up can make it easier to choose joy on purpose.
  • Making life better doesn’t always mean adding more.
    Sometimes it means removing, reframing, outsourcing, or rethinking routines that quietly drain you.

Here is a clip of one of Mike’s eye-opening points – that having fun is an upward spiral that creates more capacity for challenge and growth:

This conversation is for anyone looking for better work-life balance, more joy, and practical strategies for living with greater intention.

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

How To Tell Relatable Stories About Life The Life of Try: Personal growth, one try at a time.

What makes a story truly relatable? In this episode of The Life of Try, Wynne Leon explores how the smallest moments in life can become the most powerful stories — from a beloved Seattle raccoon named Jimothy to a little boy celebrating soccer goals with his grandmother. Through humor, heart, and the idea of narrative transportation, this episode looks at why specific, human stories help us feel seen, connected, and inspired to keep trying.If you’ve ever wondered how to tell better stories about everyday life, how to make your experiences more meaningful, or why small moments can carry big emotional truth, this episode is for you.Key takeaways:• Relatable stories often begin with small, specific moments rather than big life lessons.• Details help listeners see, feel, and remember a story.• Everyday stories can reveal courage, connection, confidence, and support.• The most powerful stories do not need to be perfect — they need to be honest and human.• Living The Life of Try means celebrating small wins, showing up for each other, and trying again from wherever we are.🔔 Subscribe to The Life of Try for weekly conversations about resilience, courage, creativity, reinvention, mindset, and living with intention.ABOUT MEHi, 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ How to Overcome Burnout & Build an Upward Spiral of Growth, Fun & Resilience➡️ Near-Death Experience with Jesus | Liza Anderson on Faith, Healing and Recovery➡️ How to Embrace What Makes You Different | Finding Your Purpose with Kym Gordon Moore
  1. How To Tell Relatable Stories About Life
  2. Why Second Place Might Be Preparation, Not Failure
  3. When Your Plan Falls Apart | How to Stay Resilient and Keep Trying
  4. Barbara Nickless on A Voice In The Dark, Online Gaming and The Power of Story
  5. Embracing What Makes You Different | Kym Gordon Moore

Links for this episode:

How to Reclaim Fun in Adult Life | Mike Rucker, PhD on Joy, Burnout and the Fun Habit transcript

The Fun Habit on Amazon and Barnes & Noble

Mike Rucker, PhD’s website

Michael Rucker, Ph.D. on LinkedIn

(featured photo from Pexels)

Hope Without Attachment

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:

How To Tell Relatable Stories About Life The Life of Try: Personal growth, one try at a time.

What makes a story truly relatable? In this episode of The Life of Try, Wynne Leon explores how the smallest moments in life can become the most powerful stories — from a beloved Seattle raccoon named Jimothy to a little boy celebrating soccer goals with his grandmother. Through humor, heart, and the idea of narrative transportation, this episode looks at why specific, human stories help us feel seen, connected, and inspired to keep trying.If you’ve ever wondered how to tell better stories about everyday life, how to make your experiences more meaningful, or why small moments can carry big emotional truth, this episode is for you.Key takeaways:• Relatable stories often begin with small, specific moments rather than big life lessons.• Details help listeners see, feel, and remember a story.• Everyday stories can reveal courage, connection, confidence, and support.• The most powerful stories do not need to be perfect — they need to be honest and human.• Living The Life of Try means celebrating small wins, showing up for each other, and trying again from wherever we are.🔔 Subscribe to The Life of Try for weekly conversations about resilience, courage, creativity, reinvention, mindset, and living with intention.ABOUT MEHi, 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ How to Overcome Burnout & Build an Upward Spiral of Growth, Fun & Resilience➡️ Near-Death Experience with Jesus | Liza Anderson on Faith, Healing and Recovery➡️ How to Embrace What Makes You Different | Finding Your Purpose with Kym Gordon Moore
  1. How To Tell Relatable Stories About Life
  2. Why Second Place Might Be Preparation, Not Failure
  3. When Your Plan Falls Apart | How to Stay Resilient and Keep Trying
  4. Barbara Nickless on A Voice In The Dark, Online Gaming and The Power of Story
  5. Embracing What Makes You Different | Kym Gordon Moore

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

Atlas of the Heart: Mapping Meaningful Connection and the Language of Human Connection by Brene Brown

Penicillin Wasn’t Alexander Fleming’s First Major Discovery | Scientific American

The Courage to Stop Trying

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 To Tell Relatable Stories About Life The Life of Try: Personal growth, one try at a time.

What makes a story truly relatable? In this episode of The Life of Try, Wynne Leon explores how the smallest moments in life can become the most powerful stories — from a beloved Seattle raccoon named Jimothy to a little boy celebrating soccer goals with his grandmother. Through humor, heart, and the idea of narrative transportation, this episode looks at why specific, human stories help us feel seen, connected, and inspired to keep trying.If you’ve ever wondered how to tell better stories about everyday life, how to make your experiences more meaningful, or why small moments can carry big emotional truth, this episode is for you.Key takeaways:• Relatable stories often begin with small, specific moments rather than big life lessons.• Details help listeners see, feel, and remember a story.• Everyday stories can reveal courage, connection, confidence, and support.• The most powerful stories do not need to be perfect — they need to be honest and human.• Living The Life of Try means celebrating small wins, showing up for each other, and trying again from wherever we are.🔔 Subscribe to The Life of Try for weekly conversations about resilience, courage, creativity, reinvention, mindset, and living with intention.ABOUT MEHi, 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ How to Overcome Burnout & Build an Upward Spiral of Growth, Fun & Resilience➡️ Near-Death Experience with Jesus | Liza Anderson on Faith, Healing and Recovery➡️ How to Embrace What Makes You Different | Finding Your Purpose with Kym Gordon Moore
  1. How To Tell Relatable Stories About Life
  2. Why Second Place Might Be Preparation, Not Failure
  3. When Your Plan Falls Apart | How to Stay Resilient and Keep Trying
  4. Barbara Nickless on A Voice In The Dark, Online Gaming and The Power of Story
  5. Embracing What Makes You Different | Kym Gordon Moore

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)

How to Get Unstuck: Michael Yang on Saying Yes, Resilience and Coming Alive

Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.” – Howard Thurman

When my daughter was two-and-a-half, I installed a seat on the back of my bike. I strapped her in and we pedaled around our neighborhood. She yelled, “this is fantastic!

A pure jolt of energy and vitality shot threw me. For me, it was such a good example of the fullness of life that surges when we embrace the freedom that comes with getting out on two wheels. As a bonus, it reminded me of how easy it is to get stuck in the humdrum of life. And the cure is just an adventure (big or small) away.

So in this episode of The Life of Try podcast, I talk with tech entrepreneur and author Michael Yang about his memoir Coming Alive on the Ride and the way motorcycle travel became both a literal journey and a powerful metaphor for personal growth. Michael shares how stepping outside your familiar environment can help you hear “life’s invitation” to dream, venture, and rediscover what makes you feel fully awake.

Together we explore resilience through the Korean concept of han—the accumulated weight of difficult circumstances—and how setbacks can become fuel for perseverance. Michael reflects on immigrating from Korea at 14, building a life through gratitude and hard work, and learning (again and again) that rejection doesn’t have to be the end of the story.

From riding thousands of miles with a lifelong friend to a memorable run-in with Steve Jobs at Macy’s in 1982, Michael’s stories remind us that courage grows through companionship and curiosity. We also discuss the Korean guiding philosophy of Hongik—living in a way that benefits all humankind—and how our bravest tries can ripple outward in ways we may not expect.

In this episode, we cover:

  • Why “accepting the invitation” is simple—but the road rarely runs straight
  • Han, perseverance, and turning setbacks into strength
  • The immigrant mindset: gratitude, effort, and going for opportunity
  • Friendship as a confidence builder—on the road and in life
  • Curiosity, rejection, and holding onto a vision (plus the Steve Jobs story)
  • Hongik: living for the wider benefit and making a positive dent in the world

Here’s a small taste of Michael’s brave and bold reminder that saying “yes” to adventure often brings out our best selves:

Whether you’re craving a literal road trip or a fresh start at home, this conversation will nudge you toward your next brave yes.

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

How To Tell Relatable Stories About Life The Life of Try: Personal growth, one try at a time.

What makes a story truly relatable? In this episode of The Life of Try, Wynne Leon explores how the smallest moments in life can become the most powerful stories — from a beloved Seattle raccoon named Jimothy to a little boy celebrating soccer goals with his grandmother. Through humor, heart, and the idea of narrative transportation, this episode looks at why specific, human stories help us feel seen, connected, and inspired to keep trying.If you’ve ever wondered how to tell better stories about everyday life, how to make your experiences more meaningful, or why small moments can carry big emotional truth, this episode is for you.Key takeaways:• Relatable stories often begin with small, specific moments rather than big life lessons.• Details help listeners see, feel, and remember a story.• Everyday stories can reveal courage, connection, confidence, and support.• The most powerful stories do not need to be perfect — they need to be honest and human.• Living The Life of Try means celebrating small wins, showing up for each other, and trying again from wherever we are.🔔 Subscribe to The Life of Try for weekly conversations about resilience, courage, creativity, reinvention, mindset, and living with intention.ABOUT MEHi, 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ How to Overcome Burnout & Build an Upward Spiral of Growth, Fun & Resilience➡️ Near-Death Experience with Jesus | Liza Anderson on Faith, Healing and Recovery➡️ How to Embrace What Makes You Different | Finding Your Purpose with Kym Gordon Moore
  1. How To Tell Relatable Stories About Life
  2. Why Second Place Might Be Preparation, Not Failure
  3. When Your Plan Falls Apart | How to Stay Resilient and Keep Trying
  4. Barbara Nickless on A Voice In The Dark, Online Gaming and The Power of Story
  5. Embracing What Makes You Different | Kym Gordon Moore

Links for this episode:

48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive transcript

Michael Yang’s website

Coming Alive on the Ride at Barnes & Noble and Amazon

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 next
  • Is navigating change, burnout, or reinvention
  • Wants to live more intentionally without pretending growth is easy
  • Believes progress starts by trying—again and again

The 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.

(featured photo from Michael Yang — more incredible photos in his book and on his website!)

Creating Without Elbow Grease

Do the difficult things when they are easy and do the great things when they are small. A journey of a thousand miles must begin with a single step.” – Lao Tzu

What if “trying” doesn’t have to mean pushing harder?

I’ve been in a flow state often enough to know it exists but not so often to know how to reliably get there. Is it really possible to regularly create — to write, to connect with others, to co-author life in a way that doesn’t leave me sweaty and tired? My guest on this week’s podcast had some insight about finding flow. Even if it falls into the category of easier said than done, it’s the quietness of the approach that makes me think it’s possible

In this Life of Try episode, I talk with author and New York Insight Meditation Center co-founder Joseph Schmidt about The Torchbearer—a collection of short stories born from an unexpectedly effortless creative process. Together we explore the mindset shift from effort to openness: how letting go of the agenda can create space for insight, transformation, and a deeper, more alive way of meeting each moment.

  • Try smarter, not harder: why forcing outcomes can block creativity—and what changes when you partner with the process instead.
  • Mindset shift to “empty hands”: Joseph’s Zen chaplaincy training and the practice of entering a room (or a moment) without an agenda.
  • Personal growth through discovery: how his characters—and we as readers—find the next move by noticing what’s already here.
  • Feeling alive at the edge of the unknown: mindfulness as the place where consciousness meets what happens next.
  • Belonging as a practice: building a bond of belonging by showing up with curiosity, care, and presence.

If you’ve been working hard but feeling flat, this conversation is an invitation to loosen your grip, step back into the present, and discover a more natural flow—one where growth comes from attention, not strain. Listen in for a gentler (and often more powerful) way to create, connect, and keep beginning again.

Here’s great clip of Joseph describing the lesson he learned from a Zen monk about a powerful mindset shift:

This is a great episode if you’re craving a mindset reset, rebuilding your creative confidence, deepening a mindfulness practice, or simply want to feel more awake and engaged in your everyday life.

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

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How To Tell Relatable Stories About Life The Life of Try: Personal growth, one try at a time.

What makes a story truly relatable? In this episode of The Life of Try, Wynne Leon explores how the smallest moments in life can become the most powerful stories — from a beloved Seattle raccoon named Jimothy to a little boy celebrating soccer goals with his grandmother. Through humor, heart, and the idea of narrative transportation, this episode looks at why specific, human stories help us feel seen, connected, and inspired to keep trying.If you’ve ever wondered how to tell better stories about everyday life, how to make your experiences more meaningful, or why small moments can carry big emotional truth, this episode is for you.Key takeaways:• Relatable stories often begin with small, specific moments rather than big life lessons.• Details help listeners see, feel, and remember a story.• Everyday stories can reveal courage, connection, confidence, and support.• The most powerful stories do not need to be perfect — they need to be honest and human.• Living The Life of Try means celebrating small wins, showing up for each other, and trying again from wherever we are.🔔 Subscribe to The Life of Try for weekly conversations about resilience, courage, creativity, reinvention, mindset, and living with intention.ABOUT MEHi, 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 Watch Next➡️ How to Overcome Burnout & Build an Upward Spiral of Growth, Fun & Resilience➡️ Near-Death Experience with Jesus | Liza Anderson on Faith, Healing and Recovery➡️ How to Embrace What Makes You Different | Finding Your Purpose with Kym Gordon Moore
  1. How To Tell Relatable Stories About Life
  2. Why Second Place Might Be Preparation, Not Failure
  3. When Your Plan Falls Apart | How to Stay Resilient and Keep Trying
  4. Barbara Nickless on A Voice In The Dark, Online Gaming and The Power of Story
  5. Embracing What Makes You Different | Kym Gordon Moore

Links for this episode:

The Transformation That Changes Everything transcript

The Torchbearer: and other Stories of Borderline Redemption by Joseph Schmidt on Amazon

Joseph Schmidt bio – New York Insight Meditation Center

(featured photo from Pexels)

Now I Lay Me Down To Sleep

Faith and prayer both are invisible but they make impossible things possible.” – unknown

About a dozen years ago, a good friend told me a story about her son who was about seven or eight-years-old at the time. Their neighbor’s dog had gone missing and her son was worried. So they looked everywhere they could think of. When they didn’t find the dog, they went home and said a prayer for its safe return. By the next morning, the dog had returned home.

Shortly after, her son was worried about getting a new class seating assignment. He didn’t want to have to sit next to a particular kid. So he prayed about it before he went to bed.

When he came home from school the next day, his mom asked him about the seating arrangement. Did he have to sit next to the kid he didn’t want?

Her son answered, “Of course not. I prayed about it.

Ah, the wisdom of kids.

I love the time talking with my kids right before bedtime. They snuggle in to bed, we talk about the highs and lows of the day, and if there is a nagging worry or hurt, it usually comes tumbling out.

Then we pray, I kiss them goodnight and turn off the light. Rarely does a worry persist to the morning. They turn it over to a Higher Power and then let it go.

Of course they have smaller worries – but they also have a good practice. One that I need to remember for myself.

We need to empty our cups before we fill them.

(featured photo from Pexels)

Lessons from Letting Go: Parenting Reflections

How lucky I am to have something that makes saying goodbye so hard.” – Winnie the Pooh

There’s a lot of grief that comes with parenting, isn’t there? And I’m not referring to the grief the kids give us. I’m talking about the variety that comes with letting go.

My 10-year-old daughter< Miss O, changed the wallpaper of my phone to be a rotation of pictures of her and her younger brother. Now every time I tap the phone, I see a picture of one of the two of them, usually as younger kids.

Along with the cute pictures comes the grief. It’s small but I feel a stab of knowing I’ll never hold them on my hip like that again. Or that the era of toddler speak that required Momma interpretation has ended. Or that we don’t have so many moments of un-self-conscious joy anymore. There are all sorts of things to mourn as I get that momentary hit of how much we’ve changed. As neuroscientist Maya Shankar explains, every change comes with a loss of identity.

When I leaned into the grief, I found three things blooming underneath.

Gratitude. My sister-in-law’s mom, Georgia, repeatedly told me a story when I first had kids. She said that when my sister-in-law was six or seven, she asked Georgia to play. Georgia laments that her reply was, “No, Honey, I’d rather read my book.

I learned from that story to say “yes” so that I’m not talking about it when I’m 75-years-old. There have been many moments it has been hard to put down my book or stop progress on something I want to get done. But more or less, when my kids have said, “Mommy, look?” or “Mom, do you want to play ball?” I’ve said yes. So now when I feel the pangs of grief that come with letting go the younger selves of my kids, I also feel the gratitude for all the memories we have made and continue to make.

Learning. My kids have learned to walk, talk, ride a bike, read, play musical instruments, bat a ball and a myriad of other things. But the grief makes me realize how much I’ve learned as well. Things like that I had name my feelings so I could teach them how to name theirs. Also how to pitch baseballs, get grass stains from the ballfield out of pants, make slime, and clean slime from clothes too. These years have not only been full of memories but also lessons and growth too.

Faith. Miss O is heading to middle school next year. The horizon is already changing with boys, more complex relationships, and a wider circle of independent activities. The number of things I can’t control is growing exponentially larger every day.

Of course, I’ve never been able to control much. This whole journey of parenting has helped me lean into faith. To say “yes” to making memories, learning, loving and leading, and then leave the rest to God.

Grief is uncomfortable. Even the small “g” kind that I’m feeling these days. But underneath it is a whole lot of goodness that reminds me to lean in to creating a life worth growing out of.

(featured photo is Miss O and Mr. D in 2019)

Even 10-year-olds Know Better

There is no better test of a man’s integrity than his behavior when he is wrong.” – Marvin Williams

About 10 days ago I was making breakfast for my family on a calm Saturday morning. The news was on in the background and Donald Trump was responding to the Supreme Court ruling about tariffs.

He started, “I am ashamed…”

And then ended the sentence, “…that a couple of members of the Supreme Court don’t have the courage….

I don’t recall saying anything. But the next thing I knew my 10-year-old daughter, Miss O, was standing on the couch with a pretend microphone in her hand offering an alternate response.

I apologize. It was my fault. How can I fix it?”

Miss O is not an expert in the workings of the three branches of the US government. But she does possess the emotional intelligence to know that people should take responsibility for their decisions and actions.

I suspect this US presidency resonates in a unique way for those of us who’ve had significant entanglements with a narcissist.

  • The chaos.
  • The willingness to say anything, believable or not, in order to shift the conversation.
  • The loyalty tests.
  • The genuine belief that they should not be held to the same standard of behavior as normal people.
  • The constant need for more recognition and validation.

Being around people who make up their own rules and then blame others when they lose is exhausting. Even 10-year-olds know better.

When I had a business partner who was a narcissist, I was forced to learn the difference between what I can control and what I can’t. The wisdom of Prentis Hemphill helped me cope, “Boundaries are the distance at which I can love you and me simultaneously.

Not only did I gain a lot of clarity about boundaries, but I also developed a deep appreciation for the people in my life who are trustworthy enough to hold close. I came through that period with a huge amount of gratitude for when life is calm.

There are enough tariffs being levied these days. So I try to remember not to let narcissists tax my energy more than necessary.

(featured photo from Pexels)

You can find me on LinkedIn: https://www.linkedin.com/in/wynneleon/ and Instagram @wynneleon

Please check out the How to Share podcast, a podcast where guests share what they’ve lived and learned!