The Power of Small Wins

One of the secrets of a happy life is continuous small treats.” – Iris Murdoch

I learned this reflective practice from my meditation teacher, Deirdre: before stepping out of a space at the end of the day (the office, a studio, the kitchen), pause for a moment to think about what you did, who you saw, any breakthroughs (or breakdowns, for that matter) you had. It’s a chance to absorb the day before you turn out the lights and leave.

I’m not very consistent in remembering to do this practice. But when I do, I find that it helps me to savor the day as well as to honor the small steps that mark progress. It counterbalances my inclination to be focused on the next thing and helps to answer a question that I struggle with: when should we celebrate progress—only at the finish line, or all along the way?

In this episode of The Life of Try, I explore the power of small wins, tiny habits, and incremental progress. Drawing from a personal story about preparing my home for an Airbnb experiment during the World Cup in Seattle, I reflect on what it means to keep going when growth is messy, nonlinear, and full of setbacks.

I offer some insights from Director of Stanford’s Behavior Design Lab, BJ Fogg, PhD, plus the long-term philosophy of Toyota’s Kaizen culture, where small daily improvements add up over time, and the practical courage found in the checklist mindset associated with Captain Sullenberger.

This episode is about personal growth, habit formation, celebrating small victories, and learning to recognize that progress doesn’t have to be dramatic to matter.

Here are some takeaways:

  • Why celebrating small wins can help you stay motivated even when progress feels slow or messy
  • How BJ Fogg’s Tiny Habits approach shows that tiny celebrations can reinforce lasting behavior change
  • What Toyota’s Kaizen philosophy teaches about the long-term power of small, consistent improvements
  • How checklists and small-step courage can help you keep going when you feel overwhelmed or stuck
  • Why growth often looks nonlinear, and how to recognize progress before the final result arrives
  • How honoring effort along the way can help you build resilience, confidence, and momentum

If you’ve ever felt stuck, overlooked your own progress, or wondered whether the little steps count, this episode will remind you that they do. Small wins matter. Tiny steps matter. And trying counts, even before the big outcome arrives.

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

When should we celebrate progress—only at the finish line, or all along the way?In this episode of The Life of Try, Wynne Leon explores the power of small wins, tiny habits, and incremental progress. Drawing from a personal story about preparing her home for an Airbnb experiment during the World Cup in Seattle, Wynne reflects on what it means to keep going when growth is messy, nonlinear, and full of setbacks.Along the way, she connects insights from BJ Fogg, creator of Tiny Habits and director of Stanford’s Behavior Design Lab, with the long-term philosophy of Toyota’s Kaizen culture, where small daily improvements add up over time, and the practical courage found in the checklist mindset associated with Captain Sullenberger. This episode is about personal growth, habit formation, celebrating small victories, and learning to recognize that progress doesn’t have to be dramatic to matter.In this episode, we discuss: → Why celebrating small wins can help you stay motivated even when progress feels slow or messy → How BJ Fogg’s Tiny Habits approach shows that tiny celebrations can reinforce lasting behavior change → What Toyota’s Kaizen philosophy teaches about the long-term power of small, consistent improvements → How checklists and small-step courage can help you keep going when you feel overwhelmed or stuck → Why growth often looks nonlinear, and how to recognize progress before the final result arrives → How honoring effort along the way can help you build resilience, confidence, and momentum If you’ve ever felt stuck, overlooked your own progress, or wondered whether the little steps count, this conversation will remind you that they do. Small wins matter. Tiny steps matter. And trying counts, even before the big outcome arrives.🌍 Show notes and more inspiration: https://wynneleon.com🔔 Subscribe for more: Subscribe to The Life of Try for more conversations on: personal growth, creativity, reinvention, resilience, writing, and mindset.ABOUT 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.🌍 Website: https://wynneleon.com━━━━━━━━━━━━━━━🎥 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➡️ How to Reclaim Fun in Adult Life | Mike Rucker, PhD, on Joy, Burnout and the Fun Habit🔗 CONNECT WITH ME:• Website:→ https://wynneleon.com/• Instagram:→ https://www.instagram.com/wynneleon/• Facebook:→ https://www.facebook.com/wynne.leon/
  1. How to Celebrate the Try
  2. How to Reclaim Fun in Adult Life; Michael Rucker, PhD on Joy, Burnout, and The Fun Habit
  3. Reinvention, Resilience and The Courage to Try| Lindsey Goldstein on Gap Year
  4. 51: Letting Go of Outcomes: The Mindset That Keeps You Moving
  5. 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers)

Links for this episode:

Tiny Habits by BJ Fogg, PhD on Amazon

The Tiny Habits Toolkit from BJ Fogg, PhD

How I recovered from a bout of anxiety-induced paralysis by Dan Harris

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)

Celebrating Getting To Stay

The capacity to learn is a gift; The ability to learn is a skill; the willingness to learn is a choice.” – Brian Herbert

I have two young kids with summer birthdays so I’m well steeped in the high expectations that come with celebrating our entry to this life – gifts, parties, songs, cakes. They are just so darn proud of all the growing up they are doing.

I get it because I’m so proud of them too. The expanded perspectives, vocabulary, abilities, smarts, empathy, and maturity are incredible to watch bloom.

But at some point it switches, doesn’t it?

It goes from birthdays being all about being celebrated for showing up and turns into celebrating that we get to stay. At least, that’s the way that it feels to me as I turn 56 years old today.

I am so grateful that I get to be here to love not only my two beautiful kids but also everyone I can. Sure, there are some people and things that challenge my “love wins” perspective but with each year, I understand more that life doesn’t come wrapped in neat packaging. Also, that there is much to learn when uncovering each unexpected “gift” and all I need to do is find the next right thing to do.

So as I unwrap this year, I try to remember to be proud that somewhere along the way I’ve grown into me. My stubbornness has mellowed into tenacious resilience. My faith has evened out the lows and added gratitude to the highs. I’m so delighted that I’ve gotten to stay another year.

Here’s to the next. Thanks for riding along with me!

P.S. I’m writing this while drinking a cup of tea from the Book of Tea. A perfect gift from my co-host Vicki Atkinson of the Sharing the Heart of the Matter books and authors podcast! Thank you, dear Vicki!

(featured photo is mine of my children)

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

I host the How to Share podcast, a podcast about how to share anything – to the appropriate audience, with the right permissions, at the most opportune time.

I also co-host the Sharing the Heart of the Matter podcast, an author, creator and storytelling podcast with the amazing Vicki Atkinson.

Milestone Moment

The difference between winning and losing is most often not quitting.” – Walt Disney

I’m celebrating today. I’ve published a post every day for a year. And since late October of last year, I’ve also written a weekly post on the Pointless Overthinking blog as well. That’s about 400 posts total.

Looking back on the experience, I realize that what happened to me over the year was a far different thing than what I thought going into it.

Write What You Need to Read

I was reminded of this adage somewhere in the middle of this year of posts and connected it to what I’m doing here. I’ve been writing what I need to process and remember this precious time that is so busy it could go by without notice. The posts that I imagined I would write – clean, full of poignant phrases, powerfully evocative – are not at all what came out. But what came out was something like little snapshots of learning, appreciating and searching for the depth and richness of life as it is right now.

Themes

I imagined that I would write a lot more about faith and God because this was going to be my meditation journal for parenting. But it turns out that I can’t easily find the words to describe this core but non-denominational factor in my life. I suspect that because my beloved dad had such a definite view of God through Presbyterianism that I imbibed that deep belief but have trouble intellectualizing the faith, hope, and optimism that keep me going.

Instead I find myself writing about friendship, learning, trying, failing, confidence, feelings, the precious lessons I see unfold in my kids, meditation and breathing, imperfection, healing. And though they are all colored by my faith, hope, and optimism, they reflect life as I process it in all its messiness.

Community

I expected that writing posts would help me practice to become a better writer. But I had no idea I was joining a community. In many ways, the beauty of this experience had very little to do with the keyboard and everything to do with finding a network of interesting, inspiring and invested people. Writing blog posts has helped me remember this year of my life – but commenting on them and other people’s post filled a need I didn’t know I had for daily interaction with grown-ups that I wasn’t getting from my professional or family life.

As an example, in the beginning, I had my Gravitar website pointing to an outdated URL. Fortunately, Ab pointed that out to me, I fixed it and we connected. He has commented on every single post of mine since which deserves its own medal. Thank you for that gift, Ab!

That experience multiplied by many including Alegria, Ally, Art, Ashley, Betsy, Caitlyn, Chaya, Claudette, Cristiana, Deb, David, Dr. Stein, Dutch, Endless Weekend, Fred, Gary, Grace, Jane, Julia, Kathy, LaShelle, Mark, Michael, Michelle, Nancy, Natalie, Rebecca, Rosaliene, Susan, Tamara, and so many more is a treasure trove of goodness for which I’m so grateful. Thank you all!

I’m going to go celebrate. See you tomorrow – because even though my experiment is over, somehow I still have more to say… 😊  

(featured photo is of my kids celebrating a few years back)

Some Things Can’t Be Dropped

If peace comes from seeing the whole, then misery stems from a loss of perspective.” – Mark Nepo

The year after I’d summitted Mt. Rainier for the first time with a guided group, my friends and I put together a team of four of us to make an attempt on our own without a guide. We left on a Friday afternoon, climbed three and a half hours to ascend about 3,500 feet in altitude and started to make our camp.

It was dark by this time and as we hurried around with our headlamps on, I went to pull the tent poles I was carrying out of my pack. One of the poles slipped from my hand and started to slide down the mountain. Panicked by my mistake, I leapt forward and fell on it before it could disappear out of the spotlight of my headlamp.

I was thinking about that pole as I hurried around making Christmas plans yesterday. In a season where it seems like there are a hundred things to do, some things can’t be dropped.

The slipperiest sometimes is the whole point in all we are celebrating. In my family, we celebrate the birth of Jesus and the promise that love, light and kindness spread generously can make a difference in this world. As we celebrate the delight of this year, we also recognize that there are many ways we can do it better next year.

On that climb twenty years ago, fortunately I caught that tent pole because without it, there wasn’t going to be a tent. At 9,000 feet of altitude on a dark night with a whole lot of mountain to search, we weren’t going to find it if it slipped out of sight. But with it, we went on to climb and summit the mountain safely with a warm, dry tent as our base.

I keep coming back to that story as a way to keep me centered this Christmas season. With the point of all we are celebrating in the spotlight, it gives us a solid base from which to attempt everything else we are doing.