Nov. 8, 2026

The Courage to Change: Weekly Preview

Is there something you want to try, but you keep waiting for the right time? It’s week two of my 30 Days of What’s Next experiment, and we’re talking about the courage to change when you’re still figuring things out. Here's what's coming up in the next few days.

On Monday, I talk with Western fashion storyteller Jane Stewart about grief and finding her way back to herself and something she loved. After Jane lost both of her parents, a question in therapy took her back to who she was at 16. She remembered how much fashion had meant to her. Jane reminds us to Wear the Clothes! Inspired with Jane.

On Tuesday and Wednesday, behavior design expert Stephanie Weldy joins me for a two-part conversation about making a habit small enough to fit the day you already have.

Then on Thursday, come with me to Georgetown, Texas. I sat down with artist and master hatter Nate Funmaker in his shop near the square. We talk about how a favor for a friend turned into his life’s work. Nathaniel's Custom Hats.

On Friday, I’ll share one idea you can use from BJ Fogg’s Tiny Habits. I’ll be back Saturday with what stayed with me and Sunday with a look at what’s coming next.

Questions we explore

How did Jane Stewart reconnect with herself and something she loved after loss? A question in therapy got Jane thinking about who she was at 16. It helped her remember how much she loved fashion. Note: This conversation is about much more than fashion.
What is the movie test for understanding behavior design? Stephanie asks whether a film director could show the action on screen. “See my friends more” becomes something you can picture, like picking up your phone and texting one friend to meet for coffee.
How did Nate Funmaker become a master hatmaker? A friend asked him to help, and Nate figured he’d stay a few months. Years later, he builds hats in his Georgetown shop using equipment that’s more than a century old.

One idea to take with you

Pick one change you’ve been putting off. Now try Stephanie’s movie test. If someone filmed your first step, what would they see you do today?

Stories of Change: Helping You Navigate What’s Next
Hosted by Judy Oskam

Navigating a change or wondering what comes next? Hear real stories from people who have faced unexpected turns, made important choices, and figured things out along the way.

A little wisdom to help you find your own way forward.

Explore more at StoriesofChangePodcast.com.

00:01 - Waiting For The Right Time

00:16 - Start With A Closet Question

01:02 - Week Two And Courage To Change

01:35 - Tiny Habits And The Movie Test

03:06 - An Old School Hatter’s Craft

04:16 - Book Pick And One Thing Today

Waiting For The Right Time

Judy Oskam 0:01

Is there something you've been wanting to change, but you keep waiting for the right time? This week I've got more interviews. I can't wait for you to hear. We'll talk about what it takes to try something different when you're still figuring out what's

Start With A Closet Question

Judy Oskam 0:16

next. On Monday, Western fashion storyteller Jane Stewart has a place for you to start. Your own closet. Just wait till you hear this interview.

Jane Stewart 0:27

I think a small step is to walk into your closet and ask yourself why you're not wearing something. Why is it sitting on the hanger? And that is before something's telling you, oh, it's too bold. I can't wear it. I'm waiting for the special occasion. It's it's a very small question that could lead you to slipping on that jacket and just going quickly to the store. And then so what you start to discover is again that question, why did I wait so long to wear the pants, the jacket, the scarf, the hat?

Week Two And Courage To Change

Judy Oskam 1:02

I'm Judy Oskam, and this is Stories of Change Helping You Navigate What's Next. Well, it's week two of my 30 days of what's next experiment. And this week we're talking about the courage to change. After losing both of her parents, Jane went to therapy. One question took her back to who she was at 16, and she remembered something she'd almost forgotten, how much she loved fashion. This was a really great uh conversation.

Tiny Habits And The Movie Test

Judy Oskam 1:35

Then on Tuesday and Wednesday, you'll hear my two-part talk with behavior design expert Stephanie Weldy. We talk about making a new habit small enough to fit into the day you already have. In part two, we'll talk about putting that idea to work. Say you want to see more of your friends. Stephanie gets right down to what she'd say in the group chat. It's a detailed conversation that I think you might find helpful.

Stephanie Weldy 2:05

So as you think about specific behaviors, think who is doing what. So it's like Stephanie's texting April to get coffee. Judy's inviting her friends over on Thursday night at 8 p.m. for a fireside, and s'mores hang by the fire pit, right? Um, I think that helps you think more clearly. So if you hear yourself say behaviors, one thing we don't we say is like think of a movie test. Could a director on a set could what are you seeing play on the screen? Oh, I love that. And if you can't see it play out, you know, Stephanie picks up her phone, Stephanie texts April, Stephanie hits send. It's a coffee emoji. Think of the details here, okay? Then it's not probably really a behavior. It's probably some version of that. Like Stephanie asks April to coffee. Well, is it via text? Is it the postal mail? You know, we're back to that problem.

Judy Oskam 3:03

Everything. Yes.

Speaker 3 3:04

Exactly.

An Old School Hatter’s Craft

Judy Oskam 3:06

On Thursday, come with me to Georgetown, Texas. I sat down with Nate Funmaker, an artist and master hatter in his shop just near the square. Nate got into hat making because a friend asked for help. He thought he'd stay a few months, but years later, it's his life's work. And I wanted to know how that happened.

Nate Funmaker 3:29

I use hundred-year-old equipment. I mean, my fitter is 140 years old. So that's what blows people's minds, and that's what would blow my mind is like this guy still uses that. It's not like he's um opening a box and the open crown flat brim has his name in it and he shapes it, and I should do that. I at the end of the day, that's what I should be doing. I mean, I build a hat.

Judy Oskam 3:51

So why do you why do you use the original?

Speaker 3:54

I just love that. I I want more of that. I want more of the old school.

Judy Oskam 3:59

It's I love talking with Nate about his journey and his shop and where he's going. And I stumbled into his shop looking for a hat. And I'm still looking, but he and Carrie are are helping me find out the right hat just for me.

Book Pick And One Thing Today

Judy Oskam 4:16

Now on Friday, I'll be sharing one idea you can use on that segment. Uh the book will be BJ Fogg's Tiny Habits, The Small Changes that Change Everything. And then I'm back Saturday and Sunday with some perspective about what stayed with me and what's coming up for next week. So take me along on your way to work or on the drive home this week. And if there's a change you've been putting off, what's one thing you could try today? Well, I'll see you back here tomorrow. Thanks for listening.