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Episode 74: Unbecoming and Recalibrating with Leslie Bailey
Hosted by Katelyn Calhoun
Leslie Bailey and I were building businesses in Indianapolis at the same time. She had Indy Maven, a media company for women, and Maven Space, a coworking space where so many solopreneurs and business owners found their people. I was growing my former business, and our circles kept overlapping.
We both ended up stepping away, leaving the city, and slowing way down.
I’ll be honest... I didn’t plan for this conversation to land here. I swapped it at the last minute with my episode with Jessie Wilde, a fellow boat dweller who gave me a peek at what my future might hold. Only after did I realize this one is the perfect final interview for the show.
Leslie is fresh off a move back to her childhood home in Michigan, recalibrating, and talking about it openly while she’s still in it. She’s writing about the whole thing on her Substack, Unbecoming.
What we really get into is how you know when it’s time to step away from something, and how you find your way back to the reason you started. For Leslie, that’s writing. For me, it’s editing video. Same love for storytelling, different tools.
In this episode, we talk about:
A few moments that stood out:
If you’re somewhere in the messy middle, maybe not quite ready to say it out loud yet, I hope this one feels like company. And if someone came to mind while you read this, send it their way.
After 20+ years in media, marketing, and hospitality, Leslie walked away from all of it, and she’s writing about what comes next on her Substack, Unbecoming. If this conversation stirred something up, her writing is a good place to sit with it for a while.
substack.com/@thelesliebailey
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 73: SOLO - 4 Things Closing my Former Business Gave Me
Hosted by Katelyn Calhoun
For a long time, the question I kept asking about burnout was how do I get past this? Recently, that question changed. Now I’m asking something different... what’s here now that wouldn’t be if everything hadn’t fallen apart?
So I made a list. And when I looked at it, it sorted itself into four things: deeper friendships, letting go of control, making things out loud, and room to move.
This isn’t a silver-linings episode, exactly. It’s more about not letting the hard things be the whole story. I also share what’s next for me, because Crafted Connections is wrapping up, and I’m putting my energy where my life is headed.
In this episode, we talk about:
I started this show in that same backyard duplex, trying to find my way back to creating. By the time we wrap at 75 episodes, it will have done its job. I’m proud of the number, but I’m prouder of the heart I put into it and the healing that resulted.
So here’s what I’ll leave you with: what’s on your list? What wouldn’t have happened for you if a hard thing hadn’t? If you’re in the middle of something that feels like failure right now, maybe this is a gentler question to sit with.
Two more episodes to go.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 72: The Magic of Moving Through Uninformed Optimism with Jessie Wilde
Hosted by Katelyn Calhoun
People ask me all the time how boat life is going. The honest answer is… it’s a lot less adventurous than you’d think. Right now we dock in a marina on the Great Lakes for the summer, put the boat in storage for the winter, and I can count on my fingers how many times we’ve actually taken her out. So this week I brought in someone who’s really living it.
Jessie Wilde and her husband Josh have lived on the water for over ten years, and they’ve spent six of those sailing up and down the East Coast. A friend from the film world introduced us when Phil and I were just starting our boat plans, and our overlap is a little uncanny. Boat life, documentary work in the natural sciences, a near-sacred morning routine... she’s who I hope to be, about six years down the road.
This one is a turn in our burnout recovery series. After a few weeks in the valley, this conversation is about finding the joy again. It’s about adventure, the slow and unglamorous parts of chasing a dream, and what you learn about yourself when you keep going anyway.
In this episode, we talk about:
A few moments that stood out:
If you’re sitting at the dock on something right now (not quite what you signed up for, not ready to give it up either), I hope this one reminds you that the timeline was never really the point. We’re always in process. That’s kind of the whole thing.
Connect with Jessie Wilde on LinkedIn and Instagram at @jessiewilde
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 71 - SOLO - Be Open to Creative Solutions
Hosted by Katelyn Calhoun
“I’m open to creative solutions.” That one sentence helped me move through my most challenging career experience yet, and today we’re digging into how.
Two weeks ago, I left you in the valley in fall 2023. This week is the climb. It’s the baby steps and the small, unglamorous things I did to slowly inch my way out. It wasn’t a straight line, and it took a lot longer than I wanted. Honestly, I’m still pitter-pattering up the mountain, stopping for water breaks along the way.
This is the part of the story I couldn’t find anyone talking about when I needed it: what you actually do while you’re in it. It covers selling our house, moving onto a boat, losing two dreams at once, and learning that slow really is fast.
In this episode, we talk about:
A few moments that stood out:
If you’re somewhere in the middle of your own climb right now, this one’s for you. You don’t need the giant leap. Just the next small step… and a little openness to whatever creative solution shows up.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 70: Ego Off, Value First with Jill Trimmel
Hosted by Katelyn Calhoun
In November 2023, I was a brand-new solopreneur with more debt than I knew what to do with and just enough in the gas tank to get to Muncie. My friend Brittany Scott of GROW had gifted me a ticket to her very first women’s leadership conference, and I wandered into a breakout session on failure... and how to make a fail plan. That’s where I met Jill Trimmel. I’ve held on to her as a mentor ever since.
Jill is the CEO of Elevate Claim Solutions. She came up through the corporate insurance world, often as the first woman in the role and the only woman at the table. She knows her numbers in a way that’s honestly a little dazzling. But underneath all of that, she’s a people person through and through. We recorded this conversation back in the spring, and it’s actually the one that sparked this whole fall series.
We talk about choosing experience over the bigger paycheck, how to hold onto your value when it’s time to negotiate, and why sometimes the goal is just to still be in business at the end of the year. Then Jill gets really honest about her own burnout, and about Margaret, the business partner who wouldn’t accept her resignation.
In this episode, we talk about:
A few moments that stood out:
If you’ve been keeping score against yourself lately, I hope this one feels like permission to ease up a little. You’re doing better than you think.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 69 - SOLO - When the Thing You Built Falls Apart
Hosted by Katelyn Calhoun
What do you do when the thing you built your whole identity around falls apart?
The burnout series officially starts today, and I'm going first. This is my most recent story of burnout. I say "most recent" on purpose, because I'm a full-throttle kind of person and I'm not going to pretend it won't happen again. It's the story of Teardrop Pictures, the business I started in 2016 and poured everything into, and the season where I tried to grow it faster than it could hold.
This one's a little heavier. I talk about chasing a seven-figure business on a timeline I picked up from a podcast, assembling a team I'm still proud of, and then having to let them go. But mostly it's about the moment when nothing fit anymore and I had no idea what to do next... and the fact that I kept waking up anyway.
In this episode, we talk about:
A few moments that stood out:
If you're in your own valley right now, or you've been in one and never quite said it out loud, I hope this one keeps you company. You don't have to know the whole way out. You just have to keep waking up and trying.
Next week, I'm sitting down with a mentor of mine to talk about her own business stories, and how this is a season so many of us move through.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 68: SOLO - We're Back!
Hosted by Katelyn Calhoun
We're back! After a summer away, Crafted Connections returns, and it feels good to be here.
I stepped away in July because I was chasing Thursdays… producing every week without ever stopping to ask what this show was really about. When people asked me, I couldn't explain it. So I gave myself Q3 off, leaned into another Slow Girl Summer, and let the answer find me.
In this episode, I'm walking you through why I took the break, what the summer actually looked like, what you can expect from the show now, and a first look at the series starting next week. It's the story of the hardest experience of my working life, and I'm finally ready to tell it.
We talk about:
A few moments that stood out:
Before next week, sit with this for a minute. Where have you been feeling a little burnt out? And what would your own recap of this summer look like? We're going to dig in together.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...BONUS Episode! - We're Taking the Summer Off (Back October 1st)
Hosted by Katelyn Calhoun
Short and even sweeter this week: I'm taking a summer break from the podcast. After Slow Girl Summer aired, I kept thinking about it. What if I actually gave her a run for her money?
Pausing the podcast felt like the perfect way to do that. I love this show. I love getting on the mic, asking questions, hitting people up to be guests. And I've also spent a year and some change chasing that Thursday 7 AM deadline. It's time for a little breather.
After more than a year of interviews and solo episodes, I want to step back, look at everything I've made, and come back with a clearer, more defined mission. The original plan for this podcast was to reignite my creativity and it frickin worked, y'all. Now I want it to have even more purpose behind it.
I'll be back — October 1st, just in time for Q4
If you've been listening for a while, or you're pressing play for the very first time...thank you. Truly. Your support means everything, and I can't wait to come back this fall with some really thoughtful episodes and some really cool people.
Subscribe so the October return lands right in your feed, and come hang with me on Instagram @CraftedConnectionsPod in the meantime.
Have a wonderful Slow Girl Summer.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 67: SOLO - Bring Back Slow Girl Summer
Hosted by Katelyn Calhoun
A year ago, I set an intention for a Slow Girl Summer and I shared it with you publicly. I had no idea it would become my most downloaded solo episode. But here we are, a summer later, and I'm thinking about it all over again.
In this episode, I'm replaying that original Slow Girl Summer episode in full, and then coming back to share how the last year actually went and what I'm doing differently heading into summer 2026.
Because here's what I've learned: intention doesn't mean perfection. It means iteration. And the fact that I can look back at last summer and say "it was better" feels dang good.
IN THIS EPISODE, WE TALK ABOUT:
- The original Slow Girl Summer intention: what it meant, why it resonated, and why I needed it
- The difference between setting goals and setting intentions
- What "intentional and aspirational" actually looks like in practice (and in real life, not just in the journal)
- The old pattern of working 12+ hour days and how I've genuinely started to let go of it
- Three gentle practices I'm bringing into summer 2026: considering ROI (not just financially), receiving support, and letting myself get lost in the work
- Letting creativity run without spending all your energy worrying about whether it will work out
- Life on the boat and the significance of slow mornings on our back deck
A FEW MOMENTS THAT STOOD OUT:
- "Slow Girl Summer is both intentional and aspirational." That line from my journal still gets me. Room to grow, not a standard to meet.
- The Latin test story: I've been postponing joy in service of productivity since high school.
- Receiving support is its own skill. Whether it's letting Phil handle the boat projects, or finally sending a voice note to a friend asking for support.
If you've been waiting for a sign to slow down this summer, this one's for you.
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...Episode 66: Why You're Already Braver Than You Think with Julie Kratz
Hosted by Katelyn Calhoun
This one digs deep into my entrepreneurial origin story. Julie Kratz, founder of Next Pivot Point and a thoughtful voice on allyship and inclusive leadership, has been in my life for over 10 years. She ran a goal-setting workshop in January 2016 that set me on the path to working for myself. So getting to sit across from her (virtually) and dig into both our journeys was simply magnificent.
We talk all about pivot points. Julie is someone who has lived this work, not just taught it, and that comes through in every single thing she says. This conversation goes deep on what it means to be an ally and why mid-career feels so heavy for so many women right now.
IN THIS EPISODE, WE TALK ABOUT:
- How one workshop in 2016 helped shift the trajectory of my career (and why it still resonates a decade later)
- Julie's own pivot from corporate America to building Next Pivot Point and what prompted it
- What is the definition of "ally" from Julie's experience and expertise
- The mid-career reckoning so many women are hitting and "what's next?"
- The connection between relationships, belonging, and happiness (backed by real research)
A FEW MOMENTS THAT STOOD OUT:
- "What's happening on your very best days?" - Julie's reminds us that the right reflection questions are often the simplest ones
- The sunk cost conversation
- The honest admission that she doesn't know exactly what her next pivot is yet and how that feels like a relief to hear
If this episode landed for you, send it to someone who's been in a pivot point lately. Or someone who's helped you through one. That feels like the right move.
Connect with Julie:
LinkedIn: Julie Kratz
Newsletter + free allyship starter kit: nextpivotpoint.com
P.S. If your videos are stuck in your camera roll, head over to @calhounedits for quick editing tutorials, or book a free 30-minute consult here: [link]
Community Co-Working Monthly Kick-Off
Start the month with me! Once a month, we get together on Zoom to review the past month, set intentions for the next, and work on something that matters. Quiet focus, community, and accountability to keep the momentum going all month long. It's free. It's monthly. 👉 Sign Up!
Need Help Clarifying Your Story?
Story Strategy Sessions are designed to help you uncover your narrative, refine your messaging, and build a visibility strategy that actually feels like you.
🎥 Book your session: HERE
Join the Conversation
📲 Send a DM on Instagram: @CraftedConnectionsPod
Crafted Connections is produced by Calhoun Creative Consulting, a strategic storytelling firm helping people and brands tell stories that resonate.
🌟 Subscribe and don’t miss an episode. Keep creating. Keep connecting.
...From the publisher's feed
We talk to folks in our community about how they use storytelling to build their community