Notes from the Messy Middle

PODCAST · business

Notes from the Messy Middle

Tune in for honest conversations about the challenges of business, life, parenthood, and relationships — and what we learn along the way. Because the most beautiful progress comes from the messy middle. eringregorycreative.substack.com

  1. 8

    🎙️Let’s Get Unstuck x Erin Gregory🎙️

    Get full access to The Self-Led Life at eringregorycreative.substack.com/subscribe

  2. 7

    Typing It Real: The Gorge, Facing Yourself & Finding Your “Y” With Erin Gregory

    Get full access to The Self-Led Life at eringregorycreative.substack.com/subscribe

  3. 6

    Leaning on Community and Grit in the Hard Seasons

    Building something meaningful rarely looks like a straight line. More often, it’s a winding path, the part where the work feels heavy, the growth is slow, and the uncertainty lingers. It’s a season that can be both exhausting and formative. It’s also where the real story begins to take root.That’s where we find Jamie Szanati, the owner of Groovy Sunshine Co., a colorful, joy-filled shop tucked in the heart of downtown Delaware, Ohio. Part boutique, part gathering place, Groovy Sunshine offers a mix of vibrant home goods, gifts, and locally-made treasures that reflect Jamie’s playful, optimistic style. Step inside and you’ll find shelves lined with handmade candles, retro-inspired décor, and quirky novelties that make people smile. For many, it’s more than a shop, it’s a dose of light in their day, a reminder to slow down and enjoy the little things.But behind the cheerful displays and warm atmosphere, Jamie’s first year as a business owner was anything but easy.Thanks for reading! Subscribe for free to receive new posts and support my work.The Weight of the First YearJamie is honest about how hard that first year felt. There were days she sat in her shop nestled in the second floor of an old brick building, wondering if anyone would come in. She admits she wasn’t sure she’d make it to the one-year mark, and that uncertainty weighed on her.It’s a familiar story for many entrepreneurs. One boutique owner once told me she’d spend entire afternoons refolding the same sweaters just to keep busy while waiting for a single customer. Another recalled sitting in her car crunching numbers on her phone, trying to figure out if she could cover rent. Jamie felt those same pressures: the quiet, empty hours, the financial stress, the constant question of should I keep going?Still, she showed up. Small wins, quiet routines, and little moments of gratitude became her anchor. “You’ve got to get up every day and make it happen,” she says.A Community that Shows UpWhen the one-year anniversary finally came, Jamie worried it might slip by unnoticed. Instead, her community showed up in force. Neighbors, loyal customers, and even fellow business owners from down the street joined with encouragement and adoration for what she had built. The celebration reminded her of something crucial: she wasn’t doing this alone. And what she was doing…was in fact working.That kind of support is what sustains many new business owners. I’ve seen it play out again and again: a coffee shop that survived its first winter thanks to referrals from the bookstore across the street, or three shop owners who teamed up for a “Sip & Shop” event that brought record-breaking sales for each of them. In Jamie’s case, the love and loyalty she felt that day reinvigorated her vision for Groovy Sunshine. What might have been the end of a hard season became a fresh beginning.Looking AheadNow, she’s excited about her next steps: expanding her hours and eventually bringing on help so she can stay open later and more fully participate in community life. These are practical, sometimes difficult decisions every small business owner wrestles with. But for Jamie, they’re filled with new energy because of the people who have walked with her along the way.Whether you’re running a business, pursuing a creative dream, or navigating a transition, Jamie’s story is a reminder that grit and gratitude can carry us through uncertainty. Surround yourself with community, look for those daily glimmers of hope, and keep showing up.Keep the Conversation GoingThis post only scratches the surface of Jamie’s story. For the full conversation, including her reflections on collaboration, resilience, and what’s next for Groovy Sunshine Co., listen to our in-depth episode of Notes from the Messy Middle, hosted on Substack. You can listen to it almost anywhere you get your podcasts.And if you’d like more stories like this, along with behind-the-scenes glimpses from colleagues, community members, and fellow creatives, as well as updates on my own writing and creative process, you can follow along on Substack or visit me at ErinGregoryCreative.com.Connect with Groovy Sunshine Co: [email protected] groovysunshine.com/FacebookInstagramErin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven organizations. She’s also the host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living. Her work connects personal growth with strategic storytelling, helping people and brands speak with more clarity and purpose.Read more at www.eringregorycreative.com or connect on LinkedIn. Get full access to The Self-Led Life at eringregorycreative.substack.com/subscribe

  4. 5

    Notes From the Messy Middle: Sticker Companies and Spilled Waffles

    Hey friends, welcome back to Notes from the Messy Middle.Thanks for reading! Subscribe for free to receive new posts and support my work.I was so encouraged by the response to my very first episode yesterday that I couldn’t help but come back and keep sharing. There’s something powerful about being at a stage in my career where I not only have lived experience to draw from but also get to connect with fellow consultants, writers, and small business owners who are on their own creative journeys. Your support means so much. It gave me the push I needed to hop back on after a long, busy day of work.If you’re new here, I’m Erin Gregory. I am a writer, strategist, storyteller, and, on most days, a referee between children. When I’m not working or writing, you’ll usually find me in the garden for a little dirt therapy, sneaking in a run with my dogs, cheering on one of my three girls at softball, or hanging out with my main squeeze (who also happens to be the producer of this show).This podcast is about the down and dirty process of creating work that matters. It is about the stumbles, the tears, the late-night doubts, and the tiny wins that eventually lead to moments of clarity. In the first episode, I introduced my book Living on Purpose and shared the opening section, the wake-up call that made me realize I did not even recognize my own life anymore. Chaos had taken the wheel, and I was caught in the middle of it.Before I dive back into the book, I want to pause on something that keeps coming up for me. The messy middle is not just the stretch we rush through on our way to something better. It is the place where the real work happens. It is where progress is made. It is where we uncover who we are, what we value, and what kind of life or business we want to build.So if you are in the middle of something right now, whether overwhelmed, exhausted, or simply in that unfinished in-between, I want you to hear this: there is light ahead. The process is messy and slow, but showing up matters. Even when it feels impossible. Even when it is loud and sticky and covered in spit-up. That is the work that counts. My children are living proof that something beautiful can grow in the middle of chaos. That is how this book was born.A Glimpse from Living on PurposeHere’s a piece of what I shared on the podcast this week:Down the hall, I hear the shower running. Mike is in the bathroom, getting ready for his workday. My workday started an hour ago. He will walk out in clean clothes, smelling good. I am already covered in spit-up and syrup. I am not bitter. Not really. I chose this life. But my need to control everything works against me… [listen to the podcast for the full excerpt]When I read back the section I shared today, I felt it all over again: the chaos of mornings with little ones, the exhaustion of trying to keep it all together, the guilt of handing a crying baby to child watch so I could squeeze in work or exercise, and the relentless pressure to do it all and to do it well.But looking closer, I can also see the growth that was hidden there. That version of me did not feel strong or certain, but she was learning. She doubted herself, and because of that, she struggled to trust others. She tried so hard to carry everything alone. And yet every burnt waffle, every YMCA morning, and every tearful drop-off was shaping her. Teaching her. Forcing her to look in the mirror and rediscover who she was. Preparing her to become someone new, someone who could finally give herself grace and lead with purpose, not perfection.And that is why I keep sharing these stories. Because your mess matters too. Even when you feel like you are unraveling. Even when you cannot see the bigger picture yet. You are building something with every step, every stumble, and every small victory. One day you will look back and realize the very moments that felt like breaking you were the ones that were building you.This show is produced by Mike Gregory at https://www.undergroundfunkmonk.com.Thanks for reading! This post is public so feel free to share it.Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven organizations. She’s also the host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living. Her work connects personal growth with strategic storytelling, helping people and brands speak with more clarity and purpose.Read more at www.eringregorycreative.com or connect on LinkedIn.. Get full access to The Self-Led Life at eringregorycreative.substack.com/subscribe

  5. 4

    Welcome to Notes from the Messy Middle

    Welcome to Notes from the Messy Middle, where we talk about storytelling, strategy, and the real-life process of creating work that matters. I’m Erin Gregory, a writer, strategist, and storyteller—and right now, I’m also a woman deep in the editing process of my first book.Thanks for reading! Subscribe for free to receive new posts and support my work.This space is about pulling back the curtain. The messy drafts, the hard edits, the lessons I’ve learned from helping nonprofits and purpose-driven businesses tell their own stories—and now, from telling my own.So grab a coffee, settle in, and let’s walk through this together. Because stories don’t just connect us. They shape us.I didn’t know how much this book would pull from me. Writing was one thing. Editing is something else entirely. It forces me to face myself and my life, to ask if the words are honest enough.Just this week, my editor and I spent nearly two hours on the introduction. The goal wasn’t to polish sentences but to help me see the truth. This book, which I thought was a dedication to a couple who changed my life, is in fact about me.In these final stages, I’m going to start sharing small pieces of my story with you. The pains, the accomplishments, and the lessons I’ve learned along the way. My hope is that by letting you in, the words will carry more weight than they could on the page alone.I’d love your input on these inserts as I go. Here’s one of them:Living On PurposeIt starts before the sun.Always before the sun.The first sound is the creak of the hallway door. Then the slap of little feet on the hardwood floor. A whisper that turns into a whine. And then Mia’s cry. My alarm clock for the past year. Sharp, insistent, with no snooze button.I open my eyes, and the dark room already feels heavy. My body aches from yesterday. Shoulders tight. Back sore. Eyes dry and scratchy. I can’t tell if the pain is from the classes I taught at the Y this week or from the ongoing conditioning that is motherhood. Probably both.I swing my legs out of bed and sit there for a moment, listening. My left foot shoots back at me with sharp pain. The plantar fasciitis I keep ignoring is catching up. Every step feels like I’m walking on broken glass, but there’s no time to deal with it.The house is never really quiet, not even at this hour. The heater hums through the vents. Pipes groan in the walls. From down the hall comes the faint rustle of little feet, a whisper that means the morning obligations are approaching.I close my eyes, rub my temples, and take one deep breath. Then I push myself up. Coffee first. Always coffee.Not a delicate cup. A vat. I fumble with the machine, scoop too many grounds, and press start. The sound of it dripping is like salvation. I close my eyes just to inhale. Bitter, rich, hot. The only thing between me and collapse.I grab a box of Frozen waffles from the freezer and pop a few in the toaster. Again.I used to care about stuff like that. Once upon a time, I was the mom who made everything from scratch. I steamed organic carrots, froze them in tidy little ice cube trays, labeled the bags with dates and descriptions. I read blogs about cloth diapers and ordered every recommended baby bottle. I wanted to be that “crunchy” mom. I thought I would be.Then came my first child. Colic. A milk protein allergy. Failure to thrive. Torticollis. Suddenly survival became the priority. Organic be damned. Anything she could keep down was the goal. By the time daughter two arrived, I was already stretched thin. Daughter one was still a handful. Feeding her felt like a full-time job. Parenting her felt like a full-time battle.Then daughter three came along, and at that point, I stopped pretending. I became a robot in the kitchen, serving up whatever was convenient and checked the bare minimum nutrition boxes. If it filled their bellies and got us to the next thing, that was enough.“Homemade” started to mean a box mix where I tossed in eggs and milk and called it good. Pancakes from Bisquick? Close enough. Banana bread from a packet? Sure. At least it smelled like I had baked something from scratch. I’d watch them eat and tell myself it counted. And most days, that small lie was what kept me moving.Down the hall, I hear the shower running. Mike is in the bathroom, getting ready for his workday. My workday started an hour ago. He will walk out in clean clothes, smelling good. I am already covered in spit-up and syrup.I am not bitter. Not really. I chose this life. But my need to control everything works against me.This show is produced by Mike Gregory at https://www.undergroundfunkmonk.com. Thanks for reading! This post is public so feel free to share it.Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven organizations. She’s also the host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living. Her work connects personal growth with strategic storytelling, helping people and brands speak with more clarity and purpose.Read more at www.eringregorycreative.com or connect on LinkedIn. Get full access to The Self-Led Life at eringregorycreative.substack.com/subscribe

  6. 3

    Building Stability in a Chaotic Market

    We’re a bit over halfway through 2025, and if I had to sum up the year so far in one word, it would be: chaotic.That’s exactly what I found myself saying in a recent conversation with Jon Heise, founder of Covert Recruiting and one of my trusted recruiting partners over the years. We met back in 2020 on LinkedIn—proof that sometimes those random connections actually do turn into real, lasting partnerships.At the time, I was transitioning—like so many of us were during that strange post-COVID window—looking for meaningful work, first as a full-time employee and eventually as a consultant. Jon didn’t know me. He didn’t owe me anything. But he saw potential in my story, in my work, and in what I could offer his clients. Whether it was a writing contract or a strategic comms role, he consistently showed up with honesty, insight, and kindness.He’s the type of partner you keep close—not just for the opportunities, but for the perspective. So when we reconnected on LinkedIn earlier this month, I requested a call to pick his brain about what is going in on our workforce today.Whether you’re a full-time consultant like me, a business trying to find the right talent, or a gig worker figuring your next move, here are a few reflections from that conversation to help you navigate what might come next:1. Candidates Want Stability. Clients Want Precision.The fallout from the Great Resignation, layoffs, and economic chaos has created a candidate pool that’s craving something solid. As Jon put it, “People want to hold on to something good and see it through.” We’re all a little tired of the constant transitions—and I get it. I’ve had to pivot more than once in the last few years myself.On the other side of the table, clients are more selective than ever. With roles often pulling in hundreds or even thousands of applicants, companies can afford to be choosy. They're looking for people who solve very specific problems—and fast. That means both candidates and hiring teams need to get clear: Who are you? What do you need? Why now?2. Interviews Are Discovery Calls—Not AuditionsI never really minded having to do interviews. It was a skill I had honed throughout my 20s. I could say the right thing, at the right time. And to be fair, those skills served me well. But even as someone who’s been comfortable in that traditional interview format, I’m as happy as anyone to see that the game has changed.Jon and I talked about how interviews today feel less like high-stakes auditions and more like discovery calls. Yes, clients still want to hear about your experience, your education, and how you’ve navigated challenges—but that’s just one part of it. They’re also trying to get a real sense of you.Can they see you thriving on their team? Do your values align with their mission? Are you adaptable, collaborative, and clear in how you think and communicate?Today’s interviews are more about chemistry, curiosity, and clarity than they are about performing. Clients want to see how you approach problems, not just how you describe past successes. They’re looking for someone who fits—not just on paper, but in the room (or the Zoom).So if you’re preparing for an interview, don’t just rehearse answers. Practice being present. Be honest about your strengths. Be thoughtful about your questions. And show up as the person who will not only do the work, but do it with them.* Can you solve today’s problems?* Will you take initiative without needing micromanagement?* Are you someone they’ll actually enjoy working with?I’ve approached every consulting opportunity I’ve taken as a collaborative strategy session. The more I share how I think, not just what I’ve done, the better those conversations go. The priority is making that connection.3. Be a Persistent, Present Problem SolverJon’s biggest advice? “You have to be your own multi-channel marketer.”And he’s right. These days, sending your resume isn’t enough. You need to:* Know your value and articulate it clearly* Build a target list of companies or people you want to work with* Follow up, show up, and stay visible—especially onlineAs someone who built my consulting business from the ground up over the last 10 years, I can tell you: that trust is everything. You don’t need to be loud, but you do need to be present, honest, and accountable.4. The Power of Partnerships Over TimeWhen I began my consulting journey back in 2020, I started with what I do best: networking. I leaned on relationships, reached out to past colleagues, and said yes to the work that came my way. Over time, something beautiful happened—I carried several of those partners with me from one contract to the next. Together, we supported clients, built trust, and created value. Slowly, steadily, I built my own roster.People like Jon weren’t just connections—they became collaborators. They referred me, trusted me, and allowed me to grow alongside them. That long-game approach to relationships is something I now bring to every client engagement of my own.5. Specialization > Generalization—Most of the TimeDuring the pandemic, generalists like me thrived because businesses just needed help. One day I was leading strategy; the next I was writing donor emails or sketching out a landing page layout. I still love the variety—but even I’ve found that the more I lean into my strengths (storytelling, strategy, emotionally-driven messaging), the more aligned and fulfilling my projects become.Clients are now looking for specialists. As Jon said, they want people who’ve “been in the industry, have a track record, and know how to solve that specific problem.” The more clearly you can articulate what you do best, the easier it is for people like Jon—and folks like me—to advocate for you.6. Honesty, AlwaysJon’s not the guy who’ll hype you up for a role you’re not right for. And thank goodness for that.When I was on the job hunt, he always kept it honest—whether that meant telling me I wasn’t the right fit, or prepping me with clarity and encouragement when I was. He treats clients the same way. That honesty has shaped how I show up for my own clients. When I pitch myself, when I lead trainings, or when I help teams navigate messy messaging challenges, I take that same approach: truth first. It builds better partnerships every time.Final Thoughts: Prepare Like You Might PivotJon called it: “This is the hardest market I’ve seen in 15 years.” So if you’re feeling overwhelmed or uncertain—you’re not alone. We’ve all had moments this year where the ground felt a little shaky.But you can build something stable in the chaos. Whether that’s your personal brand, your client base, your creative work, or your internal compass—just keep going. Keep listening. Keep reaching out.If you’re a gig worker or consultant:* Know your niche* Stay ready* Keep your network aliveIf you’re a client or hiring manager:* Get specific* Offer real value* Remember you’re hiring humans, not checklistsAt the end of the day, the work still matters. The right people are still out there. And the best partnerships are built not just on skills, but on trust, timing, and the courage to show up as your full self.Looking to build your brand, tell your story, or hire someone who gets it? Subscribe to my Substack, or connect with me at eringregorycreative.com. If you’re hiring and want a trusted guide on your side—Jon’s your guy. Tell him I sent you.Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven organizations. She’s also the host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living. Her work connects personal growth with strategic storytelling, helping people and brands speak with more clarity and purpose.Read more at www.eringregorycreative.com or connect on LinkedIn. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit eringregorycreative.substack.com Get full access to The Self-Led Life at eringregorycreative.substack.com/subscribe

Type above to search every episode's transcript for a word or phrase. Matches are scoped to this podcast.

Searching…

No matches for "" in this podcast's transcripts.

Showing of matches

No topics indexed yet for this podcast.

Loading reviews...

ABOUT THIS SHOW

Tune in for honest conversations about the challenges of business, life, parenthood, and relationships — and what we learn along the way. Because the most beautiful progress comes from the messy middle. eringregorycreative.substack.com

HOSTED BY

Erin Gregory

URL copied to clipboard!