The goal was within reach, but somewhere along the line, something fractured. He caught a glimpse of himself he couldn’t unsee: he cared more about disappointing his boss than his wife.

Ryan had spent 23 years in corporate leadership doing what high-achievers do, setting targets, hitting them, and setting bigger ones. He was good at it. The path to president was right there. And then one Tuesday morning, after a run-in with his boss that made it clear where Ryan ranked in his own hierarchy, he knew he no longer belonged there.

So he left.

He didn’t slow down. He took everything he’d built, all that drive and discipline and relentless forward motion, and poured it directly into his own businesses. They grew fast. Too fast. And in late 2019, before the world had any idea what was coming, the weight of it all came crashing down.

Then COVID hit. Then his mother-in-law died in the early days of the pandemic. And then, as Ryan describes it, his entire worldview collapsed.

What followed wasn’t a tidy reinvention. It was the slow, disorienting work of figuring out who you are when achievement is no longer the answer. Successful on the outside. Disconnected on the inside. That’s how he describes the version of himself he’d been performing for decades; numb, lost, checking every box that was supposed to lead to fulfillment.

It didn’t.

Crying Ryan

Ryan grew up being called “Crying Ryan” — a nickname that rewired his relationship with himself for decades. He learned early that the path to acceptance was performance. Be what people need you to be. Stay ahead. Don’t let them see you struggle. “I became what I needed to be,” he says, “or so I thought.”

That belief drove a lot of his success. It also cost him a lot of his life.

One of the things Ryan speaks to most honestly is presence, or the lack of it. For most of his adult life, he was mentally three steps ahead, running calculations, managing outcomes, trying to stay ahead of whatever was coming. He was in the room, but he wasn’t there. “I was so identified with my thinking,” he says, “that I was mentally time-traveling. Missing the tiny, seemingly insignificant moments that make life special.”

He watched his wife walk through postpartum depression and realized, with painful clarity, that achievement couldn’t fix what was actually happening. He sat in a church pew one day and felt the full weight of being completely out of alignment with his own life. These are the moments he calls “2x4 moments.” The hits you keep absorbing until you finally stop and pay attention.

The Unglamorous Practice of Listen to Himself

The work Ryan has done since then is the daily, unglamorous practice of learning to listen to himself. Journaling. Reflecting. Asking hard questions. Naming the gap between who he intends to be and how he’s actually showing up. “What am I protecting right now?” is one he comes back to often.

The shift that changed everything, he says, was learning to accept himself. Not perform. Not achieve. Just accept. Once that started to settle, the comparison faded. The judgment of himself and everyone else began to drop away.

He named his Substack Chasing Maximus, and the name says everything. It’s not about chasing more. It’s about finding what was buried underneath — what so many sacrifice in the pursuit of success rather than happiness.

He still runs businesses. He still has a full life — 26 years of marriage, five kids, two grandkids. But he experiences it differently now. He’s in it. Present.

What Ryan’s story makes clear is that the messy middle isn’t one moment. Sometimes it’s a decade of accumulated pressure finally giving way; the slow erosion of presence until one day you look up and realize you’ve been somewhere else this whole time. And sometimes the hardest part isn’t leaving, it’s sitting in the ambiguity of what comes next.

“Breakdowns and breakthroughs are inextricably connected,” Ryan says. “What doesn’t kill us has the potential to make us stronger. It all depends on how we make meaning of it.”

That distinction is what embracing the messy middle is all about.

If this story resonated with you, there are more conversations like this one. Notes from the Messy Middle features mission-driven leaders, entrepreneurs, and caregivers navigating the self-led life and building something that actually fits. New episodes release monthly. Be sure to subscribe wherever you listen.

Erin Gregory is the founder of Erin Gregory Creative, a strategic communications and brand consultancy serving mission-driven organizations. She writes the Self-Led Life on Substack and hosts Notes from the Messy Middle, a podcast exploring meaningful work, pivots, and the messy reality of building something that lasts. She lives in Columbus, Ohio with her three daughters.

She quit to build something with her hands — a home restoration business alongside her husband Kyle, stripping walls, reclaiming old things, and making them worth something again. She’d been planning it for a while. She had a date. She had a vision. She had a plan.

Then she walked out the door on March 13, 2020, and the world closed.

The same day Jenn left her job, Kyle got a text. School was going virtual. Their elementary-aged boys needed help navigating this new, disorienting thing that nobody really understood yet. And Kyle, a high school principal, was suddenly responsible for shepherding an entire staff and student body through it too.

The restoration business went on hold. Not because the dream died, but because Jenn did the math — the financial math, the family math, the what-does-this-moment-actually-require math. Material costs were about to skyrocket. Her boys needed her home. And forcing something that wasn't ready wasn't the answer. So she got quiet. And she got creative.

She started making candles.

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Specifically, wooden wick candles — the kind that burn clean, that don’t fill your house with toxins, that crackle just enough to make a room feel like somewhere you want to be. She tested them on honest people, family and friends who would tell her if they were bad. They weren’t bad. They were really good.

By November 2020, Rusted Root Co. was open for business online.

Here’s what I love about Jenn’s story: she didn’t pivot because she gave up. She pivoted because she paid attention.

She noticed what her family needed. She noticed what the market was doing. She noticed what lit her up creatively and what she could actually build into something sustainable. And she moved — carefully, methodically, authentically — toward that thing.

Within a year of launching online and doing markets in the cold with cut-up gloves so she could work the sales platform, she had a brick-and-mortar shop in Rockville, Indiana. The kind of shop that feels like it was always supposed to be there.

She told me she reached a sustainable point around year four. That’s the word she used — sustainable. Not massive. Not viral. Sustainable. And she said it like it was exactly enough, because it is.

Jenn Kersey, Founder, Rusted Root Co.

Now she and Kyle are circling back to that original dream. They’re restoring the 1893 building that houses Rusted Root Co. — an old Irish pub — through a new venture called Rusted Root Co. Properties. The plan didn’t disappear. It just waited.

This is the first episode in the Working Mom Series, running through Women’s History Month. These aren’t stories about having it all. They’re stories about making choices — sometimes hard ones — and building something that lasts.

Jenn’s is a good place to start, because her story isn’t about a dramatic reinvention. It’s about a woman who left one door open, found another one, and walked through it with her eyes open.

Find more clips from our conversation on YouTube.

Listen to my full conversation with Jenn Kersy of Rusted Root Co. on Notes from the Messy Middle. Find her candles at rustedrootco.com (shipping to Indiana and surrounding states) and on Instagram and Facebook @RustedrootCo.

This article is part of a larger series.

I’m featuring real women in the thick of it — founders, freelancers, corporate climbers, and everyone in between. Reply here or send me a note. Your story belongs in this series. Find other stories from this series below.

Two books nearly ready.

Living on Purpose is for the woman who is tired of fitting her life into the margins of her work. Own Every Minute follows two people who said enough, walked away from debt and expectation, and built something nobody saw coming. More soon.

Erin Gregory is the founder of Erin Gregory Creative, a strategic communications and brand consultancy serving mission-driven organizations. She writes Communicating with Purpose on Substack and hosts Notes from the Messy Middle, a podcast exploring meaningful work, pivots, and the messy reality of building something that lasts. She lives in Columbus, Ohio with her three daughters.

Here’s what most organizations miss: middle donors, those giving between $1,000 and $10,000 annually, represent only 1% of donors but provide 30 to 40% of revenue. Yet research shows that only 8% of organizations even call these donors to thank them. They fall into what fundraising experts call a gray area, too generous for broad campaigns but not quite at the level for major donor treatment.

David Golaner, Director of Gift Planning at the American Jewish Joint Distribution Committee (JDC), spent 25 years learning that the middle is exactly where you should be investing.

“Middle donors are where the real opportunity lives,” David told me on a recent episode of Notes from the Messy Middle. “The problem is, they require real relationship-building without the immediate ROI that makes it easy to justify. That’s why so many organizations ignore them. But invest in a handful strategically over five years, and you’re building your next generation of major donors.”

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What the Messy Middle Taught Him About Donor Strategy

Now at JDC, David describes his role as being on an “all-star team” where top professionals from various organizations come together. Working globally has taught him that cultural intelligence matters as much as fundraising expertise, and that the world isn’t as broken as media coverage suggests.

His most valuable insight comes from understanding the power of the middle in donor portfolios.

“The middle has the worst ROI compared to mass fundraising or major donor gifts,” David admits. “But it’s also where most organizations underinvest, and it’s messy to manage.” As a middle donor himself, he understands the tension of giving to a large organization where your contribution barely registers versus a small one where the same amount prompts a parade.

His solution? Relevance and impact reporting. Show donors why they matter and what their investment accomplished. Make the case for your organization’s relevance in their lives, whether they’re deeply engaged or only interact occasionally.

This matters right now because so many nonprofits are chasing major gifts while neglecting the donor segment that could sustain them through volatile funding cycles. The middle is messy, but it’s also where stability is built.

When Stepping Back Means Moving Forward

Understanding the power of the middle didn’t come from theory. It came from David living it. After years in executive leadership, he made a move that puzzles most people in our field: he deliberately stepped back into middle management. Not because he had to, but because he wanted to make a bigger impact.

His transition started when the senior center he led in Baltimore merged with a larger organization. Rather than viewing this as a loss, he saw it as an opportunity to scale up his learning. He joined the Associated Jewish Federation of Baltimore in middle management, working on a centennial campaign at an organization with a $50 million annual budget and a $200 million campaign. The nonprofit sector operates differently at scale, and David knew that to expand his impact, he needed to understand how larger systems work, even if it meant a smaller title.

The shift required an identity reset. David had spent four years working for a Jewish funeral home, and he knew that role had started to define how people saw him professionally. So he made a deliberate choice to rebrand himself, right down to changing his wardrobe to wear bow ties as a visual marker of his evolution. “I needed to separate that chapter from what came next,” he explained. “Sometimes you have to actively signal that you’ve moved on.”

He’s in what he calls “the middle of his professional story”, hoping for another 25 years of meaningful work. That perspective, that willingness to embrace the messy middle of his own career, taught him everything he knows about why that same territory matters in fundraising.

While he rebranded his style, his core values remained consistent. When I asked David about those values, he didn’t hesitate: humility, amenability, and curiosity.

“Curiosity is a great value for growth,” he said. “Amenability is just being nice. And humility and amenability together make you someone people want to work with, regardless of their role or level.”

These principles allowed him to step back without ego, to learn from colleagues after decades of leadership, and to adapt when the pandemic forced everyone to pivot from relationship-based, in-person philanthropy to remote donor engagement practically overnight.

For nonprofit professionals navigating funding uncertainty, staff turnover, and donor fatigue, these values are survival skills.

What Nonprofit Leaders Can Learn

David’s insights apply whether you’re rethinking your donor strategy or navigating your own career transition. Here’s what matters most:

1. Diversify your revenue streams beyond traditional fundraising. David’s experience as the first director of auxiliary revenue at the Park School of Baltimore taught him that income from assets like summer camps and facility rentals creates organizational resilience. This makes for “a healthier organization in good days and a viable organization in the not-so-good days.”

2. Invest in your middle donors strategically. Don’t try to steward everyone equally. Pick a handful of middle donors with the right combination of involvement and capacity for growth. Philanthropy is a long game, and developing even a few of these relationships over five years can yield significant returns.

3. Use your donors as a focus group. Ask them directly what type of communication they respond to and what would move them from liking your organization to loving it. David notes the old fundraising adage: “Ask someone their opinion and you’ll get a gift. Ask for a gift and you’ll get an opinion.”

4. Learn to say no so you can say yes to what matters. David’s ability to balance a demanding role with family life and board commitments came down to one skill: prioritizing ruthlessly so he could live up to the expectations that truly mattered.

5. Embrace the fact that there’s no escaping the messy. Whether you’re navigating a career transition or managing a donor portfolio, the middle is inherently complicated. The leaders who succeed are the ones who stop trying to avoid the mess and start learning from it.

David’s journey proves that growth doesn’t always look like climbing the ladder. Sometimes it looks like choosing the bigger pond, even when it means you’re no longer the biggest fish. The most strategic move can look like a step backward to everyone watching from the outside.

You can find David on social media at @bowtiedg, and listen to our full conversation on Notes from the Messy Middle.

I believe the life you design on purpose is the one worth living — and the same is true for your organization's story. I'm a brand strategist and storyteller helping mission-driven organizations and entrepreneurs clarify their message and communicate their impact. Learn more at eringregorycreative.com.

But more than that, I wanted to show my kids what it actually looks like to live out your passions. So when they grow up, they feel not just capable, but compelled to do the same.

That’s been the driving force behind everything I’ve built over the past decade — my freelance practice, my independent consulting business, this newsletter, the podcast. It’s all been in service of one question: What does it mean to live intentionally?

Living intentionally isn’t about having it all figured out.

It’s about making conscious choices with your time, your energy, and the impact you make while you’re here.

I think about this constantly in my work with nonprofits and mission-driven organizations. The best leaders I know aren’t the ones with perfect five-year plans or flawless execution. They’re the ones asking the right questions:

Is this good for us?

Does this align with what we believe in?

Are we setting an example for our team and our community?

If the answer isn’t clear, it’s time to reevaluate.

For me, living intentionally is about promoting what I believe in and hopefully helping people along the way. That choice has been wonderful — and very humbling at times. There have been slow seasons where I questioned everything. There have been moments when I wondered if I should just get a “real job” with benefits and a steady paycheck.

But then I remember why I started this in the first place.

I wanted my girls to see that you don’t have to choose between stability and passion. That you can build a life that serves you while serving others. That work doesn’t have to drain you, it can energize you when it’s aligned with what you actually believe in.

The same principle applies to your organization’s story.

When you make conscious choices about how you communicate your mission, your message resonates more deeply with the people you’re here to serve. You stop trying to be everything to everyone and start speaking directly to the hearts of the people who share your values.

You stop second-guessing every decision because you have a clear framework for evaluating what aligns with your purpose and what doesn’t.

You build something that feels authentic — not because you’re following a template, but because you’re making choices that reflect who you actually are and what you actually care about.

That’s what I help organizations do. I work primarily with nonprofits, health and wellness ventures, and mission-driven entrepreneurs who are scaling, pivoting, innovating, or seeking brand refreshes. Organizations that care about their communities as much as their bottom line.

Because here’s what I’ve learned over 10+ years of freelancing and running my own consulting business:

The organizations that make the biggest impact aren’t the ones with the biggest budgets or the flashiest campaigns. They’re the ones that know exactly what they stand for and communicate it clearly.

They’re the ones asking the hard questions and making conscious choices about where to invest their time, energy, and resources.

They’re the ones living — and working — intentionally.

Three ways to start living more intentionally this week:

1. Audit one decision you’re facing right now. Ask yourself: Is this good for me? Does this align with what I believe in? Am I we setting an example? If you can’t answer clearly, that’s your signal to pause and dig deeper.

2. Identify one thing you’re doing out of habit, not intention. Maybe it’s a weekly meeting that no longer serves anyone. Maybe it’s a messaging angle that worked three years ago but doesn’t reflect who you are now. Name it, then decide if it stays or goes.

3. Write down what matters most to you right now — not five years ago, not in some idealized future, but right now in this phase of your life or your organization’s journey. Let that list guide your next three choices. See what shifts.

So here’s my question for you: What questions do you ask when evaluating if something aligns with your mission?

Hit reply — I’d love to hear from you.

P.S. If you or your organization is in a transition — scaling, pivoting, or seeking a brand refresh — and you’re struggling to articulate what makes you different, let’s talk. I help nonprofits, health and wellness organizations, and mission-driven entrepreneurs clarify their message and communicate their impact. Learn more at eringregorycreative.com.

Thanks for reading Erin Gregory Creative! Subscribe for free to receive new posts and support my work.

When Marissa Malson’s company was acquired and layoffs began, she could see the writing on the wall. “It was clear that their vision for my role and mine didn’t match up,” she said. “They continued to lay off members of my team… and eventually, in the fall of 2024, they let me go.”

For many of us, that kind of ending brings fear, and the instinct to scramble for the next job and some sense of stability. But for Marissa, the layoff became something else entirely: a chance to stop, breathe, and reevaluate.

“Leaving that job wasn’t something that upset me,” she told me. “The way they handled it was less than kind, but once I let that go, I was free to move on to finding my true passion.”

After fifteen years in marketing, from sports and retail to manufacturing and software, Marissa realized that none of those roles quite aligned with the kind of work that lit her up. She wanted something more creative and meaningful. So instead of rushing into another corporate role, she did something she’d never done before: she took time for herself.

“I’ve never not had a job lined up after leaving a company,” she said. “So this was new territory, but I wasn’t scared.”

A Pivot Toward a New Purpose

What she did next might sound familiar to anyone who’s ever felt the pull toward a more creative existence. Marissa had started writing a mystery novel months earlier, not quite sure where it was heading. After the layoff, she decided to finish it.

“I began writing The Not So Average Life of Average Jane in early 2024,” she said. “I took this opportunity to finish and publish my book.”

She also enrolled in the UCLA Extension Writers’ Program in Editing and Publishing, completing her certificate later that year. What could have been a year of stress and anxiety became a time of growth and opportunity.

Today, Marissa is a published author with a sequel due out in 2026 and the founder of Just A Good Book Publishing, a company that helps independent authors publish, market, and share their work. “I’ve connected with readers all over the world who’ve shared how much they love my book,” she said. “I’m more involved in my own community through book clubs, markets, and other reader events. I’m happier being on my own schedule, and even though owning your own business has its challenges, I’m determined to stay on this path.”

When we spoke, Marissa talked about the divine timing that guided her along the way. “I happened to be at my alma mater, the University of Dayton, for a basketball game when I saw an ad for the Erma Bombeck Writers’ Workshop,” she said. “I was just looking for coffee that morning and wandered into the library, where they had an Erma exhibit on display. That one decision kickstarted my publishing path.”

Later, while still working full time, she discovered a love for fiction writing she hadn’t known was there. “The idea for my book came to me after one of my regular yoga classes,” she said. “The words were just in my head, and I had to get them out. I wrote the first three chapters in the Notes app on my phone.”

The Power of the Pause

When I asked Marissa what she would say to someone navigating their own “messy middle,” her answer was simple:

“Take a deep breath and step back. It can be hard to see what the right path is, so get advice from friends and family and let them support you. Go for a walk or do an activity where you can let your mind wander, that’s when the inspiration comes and you can clearly see your path. Then keep going and don’t give up.”

For Marissa, healthy practices like yoga, long walks, and disconnecting from electronics helped her find clarity. So did the encouragement of others. “Sometimes the people around you can see the progress you’ve made better than you can,” she said.

Her story is a reminder that losing what we thought we wanted often makes room for what we truly need. Because the middle, the uncertain, messy, in-between, is where we stop performing and start figuring out who we are.

Listen to my full conversation with Marissa Malson on Notes from the Messy Middle, wherever you get your podcasts, or at eringregorycreative.substack.com.

Thanks for reading Erin Gregory Creative! 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 leaders.

As host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living, Erin 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.

Over the next two decades, that leap grew into a multi-million-dollar success story. Portfolio Creative continues to help marketing and creative professionals find meaningful work and to connect companies with the right talent to tell their stories. Catherine led the business with equal parts creativity and grit until, one day, she realized it was time to move on.

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“Every creative person works on something continuously until they are done. They know they are done when they can no longer do anything else with it, or they become tired of working on it.”

That growing awareness, that sense of completion, became the turning point. Catherine sold her company, not to retire but to evolve. Her next chapter would focus on reflection, mentorship, and the lessons she had learned from two decades of building something from the ground up.

From Founder to Author

After stepping away, Catherine didn’t rush into the next thing. She gave herself time to pause, but she also felt a responsibility to share what she had learned. “It would be selfish to walk away without sharing,” she says. The result is her first book, The Rules of the Game for Women in Business, now available wherever books are sold.

Unlike many business books that rely on abstract motivation, Catherine’s approach is practical and personal. The book offers strategies and scripts drawn from real experience, a field guide for women navigating ambition, uncertainty, and self-doubt in the professional world.

“Get it in your head that this will work. Manifest it and walk toward the dream. Be relentless.”

That combination of optimism and realism defines Catherine’s voice. She is honest about the challenges that come with entrepreneurship but equally clear that persistence and confidence make the difference.

The Power of Asking

Looking back, one of Catherine’s biggest early lessons was realizing she was not alone. “Don’t be afraid to ask for help or new ideas,” she says. “Join groups with like-minded people so you start thinking like them.”

That advice applies to any creative pursuit, from starting a business to writing a book. Catherine credits her progress to surrounding herself with people who challenged and encouraged her. When she decided to write, she invested in a strategist group that kept her accountable, another reminder that structure and support are forms of self-belief.

Even with experience, doubt crept in. “I faced a wall of self-doubt. Is this good? Will this be helpful?” she admits. Her solution was discipline and distance: stepping away when needed, returning with fresh eyes, and trusting that clarity would come with time.

For Catherine, writing was not just about creating a product; it was about reclaiming her creative rhythm after years of leading others. The process reminded her that growth often looks like slowing down, reassessing, and rebuilding with intention.

Advice for Creatives and Entrepreneurs

Catherine’s perspective on business and creativity is refreshingly grounded. She encourages entrepreneurs to investigate how others found success but to accept that failure, frustration, and rejection are part of the work.

“Don’t take things personally. Writers and creatives are trying to sell a talent that is so profoundly a part of them. Rise above the frustration because you are not always in front of the people who see and appreciate you.”

Catherine describes herself as an above-average student who came from modest beginnings, proof, she says, that ordinary people can do extraordinary things when they combine resilience with purpose. “Regular people can do great things because we have learned survival skills,” she says. “We know how to work hard, and we can also see the prize if we work toward it.”

Her story is one of persistence, reinvention, and the confidence of knowing when its time to begin again.

About Catherine Lang-Cline

Catherine Lang-Cline is the author of The Rules of the Game for Women in Business and former CEO of Portfolio Creative, a creative staffing firm she co-founded and led for 20 years. Through her writing and mentoring, she continues to empower women to navigate the business world with clarity, confidence, and courage.

Thanks, as always, for being here.For listening.For showing up in this messy middle with me.

If this post hit home, give it a share, a like, a comment. I greatly appreciate your support in my mission.

Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven leaders.

As host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living, Erin 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.

If you’ve been listening to Notes from the Messy Middle for a minute, you’ve heard stories from entrepreneurs, creatives, and leaders sharing their journeys. They’ve been raw, honest, and wonderful.

And in conjunction with their stories — and really, why I started this podcast in the first place — was to share pieces of my own writing journey with you.

I haven’t done a solo episode in well over a month because, as my friend Traci from Let’s Get UnStuck would say… I was stuck.

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I’ve been sitting on this story for a while, quite literally, because for more than a month, I’ve had my book edits just sitting in my inbox.

Every day, those edits stared back at me, an obnoxious taunting reminder I wasn’t ready to face. The document itself annoyed me, like it knew the answer I was searching for but refused to tell me.

When I started writing this book, the story was supposed to be about building a successful investment portfolio, a practical, journalistic exploration of financial independence. I’ve been a journalist for over 20 years, so this was comfortable. I knew how to write this.

The story followed a couple I met in Indiana who left their six-figure jobs to live off twenty thousand dollars for a year with their three daughters while they built their business.

Shocking, right?

So, with their permission, I followed them. Took notes. Observed. Documented. I thought I was writing their story. And somewhere along the way, they invited me to share mine.

And that’s when everything went a bit wonky.

Somewhere between their confidence and my hesitation, I realized I wasn’t chasing financial freedom — although that does sound nice.I was chasing creative and emotional freedom.

What compelled me to tell their story was the same thing that’s guided me through every phase of my work: a deep desire to make something meaningful.Something that matters.Something that’s mine.

Fast-forward a year later, and a manuscript was born. Polished. Heartfelt. Complete.

Or so I thought.

Then came the rejections.One after another.Each one chipped away at my confidence.What was I missing?

That’s when my friend and client, Christie Dawson of Dogwood & Quill, reached out.She needed help with her brand. I happily agreed to assist, but I also asked for something in return — help figuring out what the heck was wrong with my book.

Christie is an English professor and an executive speechwriter. The girl knows how to put two and two together.

And she saw it immediately. The writing was strong. The story was clear. But my why was missing.

First video episode of Notes from the Messy Middle!

Finding Freedom in the Messy Middle

Over the past year, and especially these past few months, as I’ve building my brand and sharing more of my stories — the messy middle ones, the honest ones — I began to see what I’d been creating all along.

I wasn’t just creating a platform. I was creating permission. A space where I could be as unfinished, uncertain, unshowered (yes, you read that right), and human as everyone else I write for.

Launching my platform gave me the freedom to figure it out in real time — to be both the writer and the experiment.

I value honesty and authenticity above almost everything, and that’s what I promise my readers. I share the down-and-dirty reality of building a business, the challenges, the sleepless nights, the doubt.

But somewhere along the way, I also got tired of watching people I love — friends, family, clients — get swallowed by the struggle.

It’s everywhere. We’re glued to the news, to the drama, to the constant reminder that everything is broken.It can consume you if you let it.

I needed a change in perspective.And honestly, I wanted the world to have one too.

Because there’s still so much good here.So much worth noticing, worth creating, worth sharing.

And that’s when it clicked.

That’s what this is all about, embracing that phase, the in-between, the messy middle, because that’s where it all happens.It’s also where we spend so much darn time, we might as well embrace it.

In the book, I chronicle the journey of this couple. Yes, they achieved financial freedom, but the real story is about how they got there and why.They, too, were seeking a life that was truly theirs. They wanted to own their time.

I won’t go into it any deeper here because I want you to read the book when it comes out (and it will, I can finally say that with confidence).

This weekend, after a sleepless week, it finally clicked. I texted Christie first thing Saturday morning, and bless her, she answered, happily.Before I could even explain, she already knew.She’d given me the space to uncover it in my own time.

Now, I’m deep into those edits, finally seeing the end in sight, and more importantly, seeing myself in the story.Because I didn’t know what I was building until I built it.And sometimes, that’s exactly how it’s supposed to happen.

What the Work Taught Me

What’s so fantastic about this process is that this is exactly what I help other creatives, entrepreneurs, and mission-driven brands do.I find clarity in the chaos.I help them uncover what their work is really saying and why it matters.

And as a tortured empath, having to look inward and discover it for myself has been invaluable.I’ve learned so much through this process.

I believe in the power of our stories, not just to promote our journeys and purpose, but to heal, to reflect, to grow.

I’m happier today than I’ve been in a long time because I took the time to bet on myself, to figure out my story, and to find my community through storytelling.

To my followers, thank you for your support, your belief in what I do, and your patience with this messy, evolving process.I hope you find value in the stories, comfort in the honesty, and community in your engagement.

We’re all in this together.And I’m so glad I found this group of creatives and innovators who not only understand that, but encourage it.

For the Brands Still Figuring it Out

First of all: keep figuring it out. Your entire brand life. Don’t stop being curious. Because everything changes, including you. So your brand should evolve with you.

If you’re building something, or you know deep down it’s time to start, here’s what I’ve learned:

One: Start with where you are and who you are today. Don’t leap ahead or wait until everything feels polished. Ask yourself: What do I want to say today? Start there.

Two: Clarity comes from action. You can’t think your way into purpose; you have to create your way there. Start small, stay consistent, and let the work guide you forward.

Three: Give yourself permission to evolve. The brand you start with won’t be the one you finish with — and that’s the point. Keep moving in the direction that feels right, even when it shifts.

Four: Stay human and share the process. People don’t connect with perfection; they connect with progress. Let them see behind the curtain. Be transparent, be real, and grow alongside them.

Five: Leverage your community. Any successful entrepreneur will tell you they didn’t do it alone. Surround yourself with people who advise, support, and add value. Find your people and lean on them — they’ll be there when you need them most.

And if you’re sitting in that uncertain, creative in-between, wondering what you’re building or how to find your voice, I’d love to help you find clarity in your own chaos.

Send me a DM or reach out through my site at www.eringregorycreative.com.Sometimes, all it takes is an outside eye, and a little patience and experience, to help you see what you’ve been building all along. And if you need an editor or speechwriter, I will happily connect you with Christie.

And remember, you can also find clarity through the chaos of others.That’s what my stories and this podcast are all about — honest conversations, real moments, connection, and the courage to keep building even when you don’t know exactly where it’s headed.

It’s all free, and it’s all here to help you on your journey toward freedom, whatever that looks like for you

Thanks, as always, for being here.For listening.For showing up in this messy middle with me.

If this post hit home, give it a share, a like, a comment. I greatly appreciate your support in my mission.

Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven leaders.

As host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living, Erin 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.

For Chris B., a poet, caregiver, and dad to his son Brayden (“Bray Bray”), that moment came on the eighth day of a 28-day hospital stay last May.

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Before the Hospital

Bray Bray’s story began with challenges most parents can hardly imagine. At six months old, he started having seizures that doctors diagnosed as Infantile Spasms, a rare and severe form of epilepsy that strikes in infancy. Medication stopped the seizures, but as Bray Bray grew, it became clear his journey would look different from most.

Over the years, doctors added more to his chart: global developmental delays, hypotonic cerebral palsy, microcephaly, and legal blindness. He can’t walk and he doesn’t speak, though he vocalizes. But his smile, a radiant, billboard-bright smile, became his language. It’s how he tells the world he’s here. That joy still exists.

For nearly a decade, he remained medically stable. Then, in May 2024, the seizures came back.

Within days, he was in the pediatric ICU, where he would spend 26 of the next 28 days. His blood pressure was low. His heart rate was low. His oxygen was low. And Chris’s reserves were nearly gone, too.

“At one point, the chaplain, as kindly as possible, asked us about administering last rites. I always said nothing really phases us, because we’ve accepted Bray Bray for the inspiration he is. But this… this phased me.”

The Eighth Day

Chris did what caregivers do when there’s nothing left to control: he showed up. He cried when he needed to, then took notes through the night so he could advocate for his son at every hospital round. He stayed present — exhausted, hopeful, and terrified.

And then, on the eighth morning, something shifted.

“Bray Bray scoots himself up, sits up, and smiles. I cried and cried and cried. He was telling me, in his own way, I’m gonna be okay, Dad. That smile saved me.”

That moment marked a turning point, not just in Bray Bray’s recovery, but in Chris’s faith. It reminded him that real strength isn’t about holding everything together. It’s about breaking open and finding light inside the cracks.

After: Writing Through the Messy Middle

A year later, Chris began writing about their journey on Chris B. Writes — his Substack community where poetry and caregiving connect. His award-winning poems, including The Believer, Happy Hands, and What I Still Bring, explore love, loss, and the quiet courage it takes to keep showing up.

He’s shared deeply personal reflections like:

* His One Smile

* Less Than, A Caregiver’s Poem… And Why Assessments Piss Me Off

* Writing As Healing: A 90-Minute Workshop for Caregivers — co-hosted with Jeannie Ewing. (You can register directly here.)

Through his words, Chris reminds us that the messy middle isn’t something to avoid, it’s where the meaning lives.

“The messy middle is inevitable,” he says. “You can either embrace it and learn from it, or run away from it and have it turn even messier.”

Because healing isn’t perfect. It just takes presence, asking for help, and one miraculous smile that reminds you: I’m still here.

About Chris

Chris B. was born and raised in Long Island, NY. He attended Binghamton University in Upstate New York in the late ’90s and early 2000s, earning a BA in Creative Writing with a specialization in poetry. His father once told him, “If you can write a memo, you’ll always have a job.”

By day, Chris works in PR and content writing/editing, but raising Bray Bray is a full-time vocation in itself. He and his wife, Melanie, have been together for 20 years and married for 16. They’re profoundly grateful for their strong family unit and the “army of supporters” who help care for Bray Bray — family, therapists, friends, nurses, and teachers alike.

Today, Bray Bray is 11 years old. For nearly every one of those years, he’s been a warrior — battling Infantile Spasms, global developmental delays, hypotonic cerebral palsy, microcephaly, legal blindness, and a rare genetic disorder called GNAI1.

And yet, through it all, he keeps smiling.

Listen to the Full Interview

Chris and I talked more about caregiving, creativity, and how his understanding of strength has changed over time. You can listen to our full conversation on the Notes from the Messy Middle podcast.

Thanks for reading Erin Gregory Creative! This post is public so feel free to share it and provide your network with a little inspiration today.

Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven leaders.

As host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living, Erin 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.

But before she built Let’s Get Unstuck, her blog and storytelling platform, Traci went through a chapter that shook everything she thought she knew about herself, her work, and the people she trusted most.

Thanks for reading Erin Gregory Creative! This post is public so feel free to share it.

The Messy Middle

Before becoming a writer and entrepreneur, Traci spent ten years building her career alongside a mentor she admired deeply, a woman she described as family. Together, they grew a company from two employees to a thriving business. Traci poured her energy, creativity, and loyalty into it.

Then, one day in 2019, it all fell apart.

Her boss, the woman who had taught her everything, was revealed to be running the largest female-led Ponzi scheme in U.S. history. Overnight, Traci lost her job, her stability, and what felt like her identity.

“Reality is, I’ve been stuck for years,” she says. “When that happened, my world came crashing down. I relied on her for so much that I struggled to stand on my own two feet. I doubted myself and my abilities to ever repeat the great work I once did. The imposter syndrome was unreal.”

What followed was a long, quiet season of grief, shame, and self-doubt. Applying for new jobs only added to the pain as rejections piled up, deepening the sense of lost confidence. “Every ‘no’ just reinforced that I wasn’t good enough,” she admits.

The Shift

Then, one ordinary day, she heard a podcast episode about being stuck.

“I didn’t even realize that was a thing…being stuck,” Traci says. “But something about that word clicked. It named what I’d been feeling for years.”

That moment became a catalyst. She started to write, at first, just for herself. What began as private therapy slowly turned into purpose. Her words gave shape to feelings she couldn’t speak out loud, and over time, she realized that if she was feeling this way, others probably were too.

So she started sharing her writing publicly. And from that leap of vulnerability came Let’s Get Unstuck, a blog and storytelling platform where she now turns pain into connection, helping others navigate their own moments of paralysis and self-doubt.

“I decided to take this painful period of my life and turn it into power,” Traci says. “After five years of silence, I finally opened up to tell my story. It’s been uncomfortable, it’s reopened old wounds I didn’t realize were still there, but it’s also brought growth and healing at the same time.”

Through her writing, she’s learned that healing isn’t linear and that the power of vulnerability lies in the ripple effect it creates. “When someone DMs me or comments on my Substack, I can feel the connection my writing brings,” she says. “If I can reach even one person who’s struggling, then I’m serving my purpose.”

For Traci, stuck isn’t a permanent state. It’s a sign that something needs to shift, that growth is waiting on the other side of discomfort. She’s passionate about helping others recognize their own stuck points and move through them with honesty and self-compassion. “Write,” she says. “Write it all down. It’s how you start to untangle what’s inside. And if you see red flags, in work, in people, in yourself, don’t ignore them. They’ll burn you worse later. Learn how to walk away. Don’t lose yourself.”

The Now

Today, Traci continues to build her platform, write for multiple outlets, and share her story with raw honesty. She’s still on the journey, still healing, still growing, but that’s exactly the point. She’s proof that getting unstuck isn’t about bouncing back to who you were before. It’s about becoming who you were meant to be next.

Listen to my full conversation with Traci Edwards on the Notes from the Messy Middle podcast, where we talk about betrayal, rebuilding, and how writing became her way out of stuck.

Connect with Traci:Let’s Get Unstuck | Substack

Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven leaders.

As host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living, Erin 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.

Erin Gregory Creative is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

All those moves had always been part of a bigger plan: to find a permanent place that gave us room to grow. We’d hopped from small town to small town with jobs, always searching for the right mix of community, opportunity, and home.

When we lost our jobs in 2020 due to the pandemic, we took it as a chance to start fresh in Columbus, a city equidistant from our families and home to an economy that matched our passions. We packed up our Indiana home, sold off a ton of stuff (which is quite cathartic) and moved to a small condo while we got our footing. With the housing shortage in full effect, a new build turned out to be the best financial option. Since neither of us had stable jobs at the time, we were conservative with that purchase, and “cozy” would be the generous way to describe it.

Our house was beautiful, and the girls loved the neighborhood, but it was tight. Every square foot was spoken for, and as they got older, it started to feel smaller by the day. I was still hopeful that our forever home, the one that would finally let us put down roots, was out there.

We weren’t in a rush. Our 2.9% mortgage rate made it easy to stay put, especially with the market climbing back up to 6%. But Michelle, being the savvy REALTOR® she is, got my attention right away. I met her at an open house in our neighborhood, and before I knew it, she was sitting in our kitchen talking strategy and possibility.

Fast forward a year, and we were unpacking boxes in a new home, with more space, a great neighborhood, and a 3% mortgage rate. The process of making that move (and navigating an assumable loan) is a story for another day, but Michelle was the one who made it happen. We’re forever grateful for her persistence, expertise, and the way she turned possibility into reality.

The Messy Middle

Before becoming one of Central Ohio’s go-to REALTORS® for creativity and strategy, Michelle Cosner built her business the hard way: through trial, resilience, and a lot of passion. Like many success stories, hers started off a bit rocky, in the messy middle.

There was a time when Michelle was juggling all the things: family, work, big dreams, and even bigger doubts. She said yes to everything, convinced that doing more meant doing it right.

“I was saying yes to everything, trying to prove myself in a business that rewards volume over value,” she says. “But somewhere in the middle of it all, I realized that I didn’t need to do more, I needed to do me.”

The real-estate world can be noisy, fast-paced, and unforgiving. But Michelle’s journey, and the lessons she learned in her messy middle, remind us that the most powerful thing we can build is an authentic life and business.

Her experience taught her resilience, clarity, and a truth she still lives by today: the right people will always find you when you show up as yourself.

The Shift

Michelle’s transformation didn’t happen overnight. It came through long days, solo decisions, and the courage to trust her instincts.

“I learned that I’m tougher than I thought and more creative than I gave myself credit for,” she says. “I realized I don’t need to have it all figured out to move forward. I just need to keep showing up.”

That mindset changed everything. She began leading with both heart and strategy, focusing less on competition and more on connection. She invested in coaching, community, and creativity, even when others told her she couldn’t do it. Those choices became the foundation of the business she leads today: consistent, grounded, and real.

For Michelle, success isn’t about being the loudest or flashiest. It’s about being consistent, kind, and values-driven. She believes authenticity beats perfection every single time. “Confidence doesn’t come first,” she says. “Consistency does.”

That lesson extends beyond real estate. It’s relevant to anyone learning to build a career on their own terms.

The Why

Michelle’s love for real estate began long before it was a career. As a child, she’d wander through open houses just to imagine what home could feel like. Growing up in both a loving and an abusive home, she learned early on that home isn’t just a structure, it’s a feeling.

“I used to wonder who lived there, what their lives were like, and what it must feel like to feel safe within those walls,” she says. “That’s where my passion for homes and for people was born.”

For Michelle, helping others find that sense of safety, peace, and belonging is deeply personal. It’s not just about transactions; it’s about transformation.

Today, Michelle shows up for her clients and her community with heart, humor, and an incredible amount of hard-earned wisdom. She’s built a business that reflects her values of authenticity, service, and creativity.

And when things get tough she goes back to the same truths that carried her through her own struggle: discipline, consistency, and a refusal to quit.

“I used to think confidence had to come first,” she says. “But really, it’s consistency that builds confidence. Keep showing up, even when it’s hard. That’s how you find your strength.”

The Connection

Michelle’s story is a reminder that your messy middle isn’t the part you have to hide, it’s the part that shapes you. It’s the space where you find clarity, courage, and the confidence to build something real.

🎧 Listen to my full conversation with Michelle on the Notes from the Messy Middle podcast, where we talk about resilience, creative business-building, and what it really takes to “do you” in a world that’s always telling you to do more.

Connect with Michelle:Website | Instagram | Facebook

Thanks for reading Erin Gregory Creative! 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 leaders.

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.

The news didn’t come with a conversation. It came through a sterile message: bureaucratic language delivered via portal, signed electronically, and sent into inboxes like any other memo. “That’s how we learned,” she said. “One line that changed everything.”

Behind those lines were real people, communicators, analysts, project leads, suddenly erased by a restructuring plan few could explain. And layered on top of that loss was something else entirely: the stigma.

In the wake of the announcement, social media lit up with opinions about federal “contractors,” a term often misused as shorthand for waste or redundancy. “There’s this idea that contractors are the problem,” Christie told me, “but the truth is, we’re the ones holding the work together. We’re the continuity. We’re the storytellers who make sure institutional knowledge doesn’t disappear.”

For many, the layoffs felt like both an ending and an erasure. But for Christie, it became a reckoning, and eventually, an opportunity.

“You can shred documents,” she told me, “but you can’t change hearts and minds.”

That single line stayed with me. Because it speaks not only to the resilience of the people behind the policies, but also to the deep truth that stories, our stories, outlast systems.

The Work Behind the Words

Christie spent her career shaping messages for leaders at every level: senators, executive directors, deputy secretaries… the people who live under constant pressure to say the right thing, in the right way, at the right time. She was the steady voice behind the scenes, the editor who made ideas coherent and kept communication grounded in integrity.

That work requires both precision and compassion. “It’s the people at the top of the group where I’m usually assigned,” she explained. “I think the buzzword now is ‘C-suite,’ but for me, it was always about helping people find the words that matched their intent.”

In a world that often rewards volume over value, Christie’s gift has always been clarity. She believes that writing and leadership are acts of service. And when that service was disrupted by forces beyond her control, she did what she’s always done best: she wrote a new chapter.

Writing Her Way Through Change

While awaiting her retirement from federal service, Christie founded Dogwood & Quill, a creative consultancy dedicated to thoughtful communication and storytelling. It wasn’t a pivot so much as an evolution, a continuation of the same mission, just under a new banner.

Dogwood & Quill was born in the quiet between endings and beginnings, that uncomfortable but generative space I call the messy middle. It’s where we start to ask bigger questions: What remains when the titles fall away? When our country abandons us? What stories are worth telling next?

For Christie, the answers came not from social media feeds or political headlines, but from real conversations: in grocery store aisles, over coffee, and in the shared stories that remind us of our common ground.

“We can’t get ourselves out of problems by ourselves,” she said. “And we can’t really create something joyful and good by ourselves either. We’re all meant to be together in the fabric of society.”

Her response has been to step back from the noise, to build a slower, more intentional kind of creative life. Dogwood & Quill became not just a business, but a philosophy; a reminder that meaningful communication is rooted in connection, not performance or the convenience of AI.

As we wrapped our conversation, Christie referenced a lyric from Tom Petty’s American Girl:

“After all, it was a great big world, with lots of places to run to.”

It’s a line that captures both the freedom and the fragility of reinvention; the reminder that even after disruption, there are still new places to go, new work to do, and new people to serve.

Christie’s story is a testament to that truth. It’s about the courage to rebuild when the script changes, and the grace to recognize that sometimes loss isn’t the end of something, it’s the invitation to tell it differently.

In her words and her work, Christie continues to help others do the same: to find the story beneath the structure, to write with heart, and to remember that even in the most uncertain chapters, our voices still matter.

Because the documents may be gone.But the stories, and the hearts and minds behind them, remain.

To connect with Christie, visit www.dogwoodquill.com.

We’re talking about what it means to:

Step into uncomfortable spaces with courage

Find growth on the other side of uncertainty

Remember your “why” when life feels hard

Stay grounded in purpose, even when the path shifts

This episode is a gentle reminder that growth rarely happens in comfort — it happens when we show up, stay present, and keep choosing to move forward.

For many of us, seasons like that send us into overdrive. We bury ourselves in work, numb with busyness, and hope the pain fades. But Lisa chose a different path. She chose presence.

Part of that presence came through yoga. At first, it was simply a way to breathe again, to find steady ground when everything felt uncertain. Over time, yoga became a practice of returning to herself. On the mat, she could listen, slow down, and remember who she was beyond grief, deadlines, or expectations. That sense of grounding began to shape how she showed up in her work, too: calmer, clearer, and more aligned.

“You know, sometimes we choose work because it feels safe. For me, design was a way to avoid being too vulnerable. But the truth is, that’s where the juice is. You really have to get there to be successful in this work,” Lisa said.

She has spent more than 20 years building brands and communication products for clients like the Country Music Hall of Fame and Augusta National. But what I admire most is her refusal to let her skills alone define her. She has learned, often through pain, that the real definition of success is not constant hustle, it is peace. It is the ability to slow down, lean into creativity, and bring her whole self to the work.

And that is where the why comes in.

Your Tools Will Change, But Your Why Will Not

During our conversation, Lisa shared a story from her early years as a design student in the 1990s. At the time, “desktop publishing” was taking over the industry. (For anyone who was not around then, desktop publishing was basically the Canva of the 1990s, only clunkier and on a big boxy computer.) Designers panicked, convinced computers would erase the need for skilled creatives. (Sound familiar in today’s AI conversation?)

“Back then everyone thought computers were going to take all the jobs. But the truth is, the tools will always change. You are always a visual communicator. The role just changes,” she said.

It brings to light an important fact: tools will always change. They did in the 90s, they are now, and they will again. But your purpose, the deeper reason you create, should always remain.

For Lisa, that purpose is visual communication. Not just making something look good but helping people feel something through design. For me, it is storytelling, using words to help people connect to themselves and each other. The medium evolves, but the why does not disappear.

The Takeaway for Creatives

* Do not let fear of change box you in. Lisa admitted she once chose design partly because it felt safe, a way to be creative without too much vulnerability. But over time, she realized real connection only happens when you are willing to bring your full, messy, human self to the table.

* Choose presence over perfection. Whether its grief, transition, or uncertainty, slowing down and honoring the moment often leads to more honest, impactful work.

* Anchor yourself in your purpose, your why. Tools and platforms will change. Algorithms will evolve. AI will keep making headlines. But when you know your why, you can adapt without losing yourself.

Proof in the Process

Lisa’s story is proof that creative resilience is not about working harder, it is about grounding deeper. Yoga reminded her that wholeness matters more than hustle. Even in the perfect storm, she continues to design, create, and inspire.

“If you want to be successful going forward, you have to figure out how to bring your unique voice. Those old ways of hiding from vulnerability, they are going away,” she said.

Not because she is rushing to stay ahead, but because she is rooted in the purpose that brought her here in the first place. And maybe that is the invitation for all of us: to stop chasing busyness as the only indicator of worth, and instead ask,

What does it look like to work from a place of peace instead of pressure?

Because when we lead from that place, our creativity does not just survive change, it thrives in it.

Connect with Lisa at https://www.bigthinkery.com and on LinkedIn.

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.

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.

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The Weight of the First Year

Jamie 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 Up

When 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 Ahead

Now, 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 Going

This 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:

GroovySunshineCo@gmail.com

groovysunshine.com/

Facebook

Instagram

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.

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 Purpose

Here’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.

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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 Purpose

It 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.

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 Auditions

I 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 Solver

Jon’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 online

As 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 Time

When 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 Time

During 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, Always

Jon’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 Pivot

Jon 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 alive

If you’re a client or hiring manager:

* Get specific

* Offer real value

* Remember you’re hiring humans, not checklists

At 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.