They build things that matter.

Yes, they matter to me, obviously, or I wouldn’t be supporting their work. But they matter to the world I want to see my daughters work in.

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Staffing firms that open doors for people who’ve been overlooked because their resume didn’t fit the algorithm. Journalism and marketing teams that shape how we talk about workplace culture. Nonprofits doing the unglamorous, necessary programs that fill the gaps for the underserved. A construction company that decided being a good partner was a competitive advantage in an industry that doesn’t expect it.

Mission-driven and workforce-centered, every one of them. That’s not a coincidence.

Neither is why I do this.

If you’re new here, hello! I’m Erin.

I spend my days helping leaders navigate change, building brands for organizations doing work that matters, and writing about what it looks like to design a career around your life instead of the other way around. I’ve been doing this work for twenty years, and the thing that keeps me going is pretty simple. I have three daughters, and I want the workforce they walk into to be better than the one I did.

Whether they end up working for someone else, building something of their own, or figuring it out somewhere in between — if I can’t change it at scale, I can build tools that help them think about it. Frameworks. A fresh perspective. A way of seeing their career like a puzzle to be solved instead of a course to finish first.

That’s what I’m building here. For them, for my clients, and for the version of me that needed it twenty years ago.

I didn’t set out to specialize in this. It happened because the people I kept being drawn to were doing similar work from different angles. Finding their voice. Getting clear on what they were actually built for. Deciding what mattered, personally, not just professionally, and building from there.

Partnering with so many of them has been the most beautiful discovery of this work. It’s also put personal practice behind what I do every day in my professional life. I’m not teaching something I figured out once and packaged up. I’m living it.

Case in point: I spent part of this week project managing a phone call with my sister. She’s getting married in August, and as we walked through the run of show I asked questions, helped her find the gaps, kept bringing her back to the goal, which is not to execute a perfect wedding. It’s to be organized enough beforehand that on the day of, she can just have fun and be in the moment.

That’s a brand strategy conversation. It’s also just a life conversation.

What I teach isn’t about putting together a compelling sentence, although there is a bit of that (communication matters, after all). It’s about being strategic — with your business, yes, but also with your time, your relationships, your decisions. When you look at everything through a values-interests-natural advantages lens, you stop compartmentalizing. Life informs work. Work informs life. You start living more holistically, and you don’t have to force it. It’s what happens when the framework actually fits.

Here’s what I know now that I wish I’d known earlier: change management isn’t simply a project management discipline. It’s a life skill. Understanding what sits at the core of resistance, transition, and transformation changed how I see almost everything. Workforce challenges. Client friction. My own career pivots.

Most of us are looking for steady. We think if we can just get the right job, land the right client, reach the right milestone, then things will settle.

They won’t.

Not because you’re doing it wrong, but because steady isn’t the destination. Change is the constant. The sooner you stop fighting that, the more interesting everything gets. On the other side of change is something you haven’t seen yet and that discovery is the whole point.

The race is long. The obstacles shift. The opportunities shift. The version of you that gets there won’t look exactly like the version of you that started.

Be strategic. Look at it like a puzzle and learn to move with it.

You always have something to look forward to if you’re willing to stay in the game long enough to find out what it is.

What’s Coming Up:

Join me and tomorrow (Tuesday, June 16) at 1:30PM for a free live conversation about pitching strategy and earned media. If you've ever wanted to get published and didn't know where to start, this one is for you.

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This week in Building a Meaningful Brand, the paid tier of this work, I’m walking through the thought process that took me from a consultant scrambling for assignments others were handing to me, to going after it on my own. This is the first summer I’ve felt like I have full ownership of my time, and it’s strange. I still catch myself thinking I should be working. Then I remember that time was the whole point.

If you’re trying to figure out how to create more ownership in your life and work, this one’s for you.

Thanks for being here.

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Pitching isn’t about having the best writing. It’s about understanding what a publication needs right now and making it easy for them to say yes to you. Those are two different skills, and most people only develop one of them.

This week inside Building a Meaningful Brand I’m sharing a one-page worksheet to help you land your next pitch, plus office hours to review yours with me directly.

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is a published poet and a publicist with 25 years in PR and journalism. He started his Substack nine months ago with zero following, no email list, and a story about his son he had to tell. He’s at 1,600 subscribers now, because he understood how to make it easy for people to say yes.

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I found Chris the way you find any of your friends and collaborative partners on Substack: through the writing. He writes about caregiving for his son with the kind of honesty and authenticity that makes you stop scrolling. We started talking and realized pretty quickly we were working from a similar place. Advocacy for people who get overlooked. Raising kids who pay attention to the world around them. And a shared belief that personal, thought-provoking writing isn’t self-indulgent, it’s the whole point.

That’s what pitching actually is. A way of thinking about what someone else needs and whether you can give it to them.

Check out some of Chris’s successful pitches:

Chris B. Writes

Pressed Send on a Whim

I didn’t arrive to Substack with a strategy. No funnel. No growth plan. Just a moment…

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2 months ago · 106 likes · 59 comments · Chris B. Writes

Chris B. Writes

The Believer, An Award-Winning Poem About The Daily Grind of Caregiving

There is nothing more humbling as a poet and a writer than when people truly see you. I am honored to share that my poem The Believer has won the 2025 BREW Poetry Award - Community Poem of the Year…

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9 months ago · 115 likes · 64 comments · Chris B. Writes

I came up in PR through the nonprofit world. At the Y, earned media wasn’t optional, it was the strategy. Tight budgets, big missions, and a community that needed to know you existed. You learned to pitch or you went unnoticed. Those years taught me that a well-placed story does something a paid ad never can. It says someone else decided you were worth amplifying.

When I started writing bylines for Forbes Health, the work compounded. Those pieces led to ghostwriting roles with Nationwide Children’s Hospital and Wexner Medical Center. That work led to executive writing roles. One of those led to a position with the Department of Veterans Affairs, advocating for equitable healthcare for veterans. All of it eventually led to launching Erin Gregory Creative.

My latest pitch success story can be found here:

None of that chain exists without the pitch. And for those of us who can’t stand traditional selling, pitching is a more attractive way to get your voice out there and get your brand noticed.

Earned media is having a moment right now because everything else is getting harder. Algorithms shift constantly. Paid reach is more expensive. Audiences are searching for more honest, authentic brands. And AI engines cite earned media at a rate of 84%. Paid and advertorial content accounts for 0.3%. A byline in the right publication doesn’t just reach human readers anymore. It’s how you show up when someone asks an AI what you do.

The skill just matters more now.

So, Chris and I decided to share our insights and experiences with all of you.

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We’re going live together on Tuesday, June 16 at 1:30 PM. Here’s what you’ll walk away with:

Why fit kills more pitches than quality does. Most writers assume rejection means the writing wasn’t good enough. Chris will walk through how to read a publication the way a publicist reads it: as someone asking whether this piece fills a gap for that audience right now.

What a subject line is actually doing. One sentence opens a door or closes it. Chris has written them and received them for 25 years. We’ll talk about the difference.

How to handle rejection without losing momentum. 180 rejections. 20 acceptances. A 5-10% win rate in a competitive space. His mindset on that ratio is worth showing up for alone.

What your pitch says about you before anyone reads your work. The writers who get published aren’t always the best writers in the room. They’re the ones who made it easy to say yes.

Free and open. Come ask us something.

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If you want to take a stab at your own pitch before we go live, this week inside Building a Meaningful Brand I’m sharing a pitch positioning framework for mission-driven founders: how to think about your content before you write a single line of the actual pitch. And I’m holding office hours to review yours with you directly.

If you’re a paid subscriber, you already have access. If you’re not, this is a good week to change that.

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It’s about why mission-driven organizations are turning to fractional leaders and why the relationship works as well as it does when the fit is right.

Read it below.

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I did not set out to become a fractional worker. I didn’t even know that was a thing until my mid-30s. I had been a freelance writer for years, which I thought of as a nice side income to support my measly nonprofit salary. Then an opportunity to dabble in consulting came my way, and I learned how to step in and out of an organization, how to coach and advise, how to respond quickly to needs. The pace was a natural fit. The clients were aligned with what I really enjoyed supporting. The structure just needed my attention, so I built one that fit my life.

A business began to form around what had started as a side hustle, and the market was shifting around me while it happened. LinkedIn profiles mentioning “fractional” roles grew from 2,000 in 2022 to over 110,000 by early 2024, and the FRAK State of Fractional Industry Report found the number of fractional professionals doubled from 60,000 to 120,000 in the same window. It’s not freelance transactional consulting or temp junior talent filling gaps. It’s senior professionals choosing a different career architecture, and companies choosing a different staffing model.

The organizations drawn to fractional support are disproportionately the ones with vital communications needs and limited budget for a full-time senior hire. Nonprofits, health ventures, and purpose-led companies all have campaigns to run, boards to brief, donors and funders and patients and staff to keep connected. A full-time director of communications would solve the problem and bankrupt the budget, where fractional solves both at once. But the longer I worked with these organizations, the more I realized the financial piece was only part of the reason it worked so well.

The Path Most of us Took to Get Here

Most people who end up in fractional work got there through the intentional restructuring of their life. Fifteen or twenty years inside organizations, and a series of moments that made the traditional workforce structure unattractive. For me it was motherhood and the realization that the career and life I had built was not the one I wanted to keep building. The traditional 9-to-5 was never designed to accommodate working mothers. I wanted a presence at home and with clients. I wanted work and a lifestyle that reflected who I was. I wanted to show my daughters that they didn’t have to live a life that didn’t fit who they are just because someone designed it for nineteenth-century factory floors. I wanted them to see they can have it all without losing themselves in the process.

I left a full-time marketing and consulting career to do work that fit who I am and who I constantly strive to be: a present mom, a strategic partner, a garden-loving health-minded woman. FRAK’s research shows 72.8% of fractional professionals have 15+ years of experience, and 30.4% have 26 or more. This is a path people take after they know what they are doing and who they are, not before. Those early years in the workforce are vital. And since the vast majority of jobs in the current marketplace are still entry level, and will continue to trend in that direction, the economy is supporting this change whether it realizes it or not. Gain that early experience, figure out what kind of life and work you want to own, and start building on the side. When the time comes, the opportunity will be there.

That also impacts what I look for in clients. I want to work with people who are building something, creating something, doing something that makes this country a little less broken than they found it. Work that uses everything I know and matters to someone on the other end of it. Mission-driven organizations are constantly navigating uncertainty. That’s our economy. Senior operators think across functions anyway, and mission-driven work lets me use that range instead of asking me to stay in my lane.

In a given week I might shape donor communications for a foundation, coach a nonprofit CEO through a board presentation, or help a purpose-led founder decide what her company actually stands for. One of my clients is going on maternity leave in a few months and asked me to tag in for project management while she is out. Fractional work gives me the flexibility to plan for her. That’s work that matters to me. Supporting the people, not just the organization.

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The Partnership Approach

Most mission-driven organizations already have mid-level talent who can execute. What they need is someone to guide that team, ease the burden on the CEO, and collaborate on direction, while also delivering on the tactics. That combination of senior judgment and execution isn’t the norm in fractional work, but it’s what these organizations need more than senior availability alone.

There is also a trust layer that matters in this sector and gets underestimated everywhere else. Mission-driven organizations have been burned by consultants who show up with impressive decks, frameworks, and high budgets, then disappear after the project is complete. The people they keep are the ones who learn the staff by name, treat the work like their own, and stay long enough to see change happen. The fractional leaders I know who left full-time work for value reasons (like yours truly) tend to show up that way by default, building relationships they intend to keep for years rather than firms designed to scale.

Full-time roles inside mission-driven organizations still matter. For a significant share of nonprofits, health ventures, and purpose-led companies, fractional is simply the structure that fits the work, the budget, and the people who do it well. The senior operator a mission-driven organization assumed it couldn’t afford is often available on exactly the terms it needs, and just as invested in the outcome as a full-time hire would have been. Sometimes, even more.

This shift is happening in the choices of experienced professionals who walked away from the traditional structure and the mission-driven organizations who figured out how to work with them. The 9-to-5 was designed for a different economy, and what’s replacing it is being built by people who know what the work actually requires alongside the organizations willing to meet them there.

Read the Original on Fractional.io

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What makes Mud Girl different is that it is built to be achievable by all. The whole ethos is simple: we can, we will, we are. That felt right for what we were trying to show our daughters. Also worth noting: since 2017 the Mud Girl community has donated over $554,000 to organizations fighting breast cancer, a cause that is personal and important to us. Showing up for yourself and showing up for others at the same time. We are here for all of it.

Side-by-side, we launched ourselves into pools of muddy water, traversed high climbs, and carried heavy weights across the landscape. There was a lot of screaming and laughing, often at the same time. It has been a few years since I have done anything like this. Once upon a time I completed half marathons, sprint triathlons, and trail runs multiple times a year. Injuries and life got in the way and forced me to shift my approach to fitness. Sunday was a wonderful step back into that world.

Kelly and I swam together at Ball State University. Fitness has never been just a physical health factor for either of us. It has been a vital emotional one, too. It has been our way of coming back to ourselves time and time again, through children, life changes, transitions, and career ups and downs. When life gets complicated, we move through it. Literally.

This was the first time we invited our daughters into that world. And watching them take it on was something else entirely. Proud doesn’t even begin to explain how we felt at the end of it.

We keep health and fitness at the forefront of their lives, not as an obligation but as an operational reality. They go on bike rides and runs with us, hike trails, play sports, and we help them train, building their confidence and capability along the way. It is a lifestyle, not something they have to do. It is how we operate as humans. Even our vacations, while full of relaxing elements, often include physical activity. Hiking a new course in a place you have never been is just what we do.

So when we showed up to that starting line on Sunday, they were ready.

These girls didn’t overthink it. They trusted the journey because we told them they could do it. At this age, their moms are still stronger, faster, and more experienced, and they leaned into that. That story will change as they get older, more into their own athletic journeys, and more capable on their own. That change is important and something we are already looking forward to. As it does, it will only become more important for Kelly and me to keep challenging ourselves alongside them, to show them that age is not a barrier but simply a part of life. Just as they faced this course young and inexperienced, we will face the next one older and more experienced. Different advantages. Same willingness to show up. But for this race, if one was down, the other picked her up. That is the lesson here. Not just completing the course, but completing it together.

Our mission, as moms and women, is to show our daughters exactly that. It’s not just about good grades, winning the game, or getting from one step to the next. It’s about doing things you didn’t think you could do, supporting one another, and constantly challenging yourself, because what is on the other side of those challenges is incredible.

Both of us took the leap to start our own companies over the last few years. We are each other’s cheerleaders, checks and balances, and thought partners. There is something specific about building a business alongside your sister. She has seen every version of you. There is nowhere to hide, and that’s the point.

That mud run course and the work of building something from scratch have more in common than you might think. There are climbs that feel too high. There are weights you are not sure you can carry. There are moments you are face down in the mud wondering how you got there and whether getting up is worth it. The answer is always yes, but you do not always find that answer alone.

The mentality that got us across that finish line on Sunday is the same one we bring to our clients every day. You lead with your strengths. You build resilience by doing hard things, not by avoiding them. And when someone on your team is down, you pull her out of the mud and keep moving. That is not just how we raced. It is how we are building our businesses, and it is what we try to model for every person we work with.

That philosophy shows up in how approaches nutrition with her clients too. Functional. Lifestyle oriented. Not a fad diet or a quick fix, but a sustainable method woven into your day to day. The same way we move our bodies because it is simply how we live, Kelly helps her clients eat in a way that supports the life they are actually building, not the one they are trying to sprint through.

As for me, going it alone as a solopreneur, as a mom, can be so difficult. You need to find your community. You need that support system. Whether you are navigating your own personal health challenges or struggling to get that business idea off the ground, find your team. That’s what I’m here for.

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Sunday was a physical reminder of something we carry into our work every day. Our daughters saw it. We hope they felt it. We are not raising girls who define themselves by a straight or clean path from one safe step to the next. We are raising girls who know how to get muddy, get up, and keep going.

If you are striving to take your health to the next level, Kelly is your person. Find her at Nutrition.

If you are ready to take your business into your own hands and build a brand that reflects who you are and what you have built, that is exactly what I do. Find me at eringregorycreative.com.

Find your people. Jump in the water. We’ll be the ones already muddy, cheering you on to the finish.

The question this worksheet answers is: how do I connect the dots between everything I’ve done and the offer I’m building now?

The job here isn’t to invent something new. It’s to surface what’s already there. The patterns, the unique capabilities, the position you’re already standing in without quite naming it yet. Work through it in order. By the end you’ll have a working position statement you can start testing in real conversations.

Before you begin: this isn’t about what you think you should be good at or what sounds marketable. This is about excavating what your actual experience shows you’re uniquely positioned to offer. Be honest and specific.

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Somewhere in the middle of the conversation, the program director paused and asked me a question I didn’t expect.

“What would you have done at a younger age to further your career?”

Their students are high schoolers in inner city schools. Kids working hard to move beyond their circumstances, looking for any edge they can find. I’ll be in a room with some of them soon, and I’ve been turning the question over ever since to figure out how I want to incorporate my response into the workshop I’m building for them on safe social media use and building a personal brand.

I thought about it for a second, and then I gave her the answer I’d been sitting with for a while: I would have started a newsletter earlier.

I would have started documenting my journey sooner. I would have shared the career woes, the challenges, the small wins that felt big at the time. I would have started connecting with an audience while I was still figuring it out, instead of waiting until I thought I had something polished to say.

I would have loved to read those entries now.

Here’s what I know on the other side of two decades of work. Every experience you collect along the way contributes to the career you end up building, if you let it. The job you took because you needed the paycheck. The role you outgrew faster than you expected. The manager you left because he didn’t treat you right. The skill you picked up on a side project that turned out to matter more than the full-time job. None of it is wasted. All of it is material.

The trouble is, you can’t see the through-line while you’re inside it. You only see it later, when you look back and realize the seemingly unrelated chapters were actively building the same person the whole time.

That’s part of what I’m doing with the book I’m working on. It’s part memoir, part workbook for people building something of their own, and a lot of what I’m pulling from is that earlier stretch of my career. The seasons I didn’t think to document while I was living them because I was struggling. Struggling inside a system I didn’t understand that I thought I had to fit into. The lessons I had to reconstruct later from memory.

Digital real estate is one of the most valuable things a young person can build right now. If you can start capturing an audience and honing your writing and digital marketing skills while you’re still in high school or college, that compounds for the rest of your career. It doesn’t matter what direction you end up going. The skill of telling your own story, the discipline of publishing consistently, the muscle of finding the people who care about what you have to say. That work pays off everywhere.

It’s a big part of what I educate clients on, whether it’s a healthcare professional, a workforce-focused nonprofit, or a photographer building a business from the ground up. Share your stories. Share the lessons learned. Help your audience find you.

You don’t need to wait until you’ve made it. The documenting is the making.

Most of you reading this are already past that first hurdle. You’ve started. You’re publishing. You know your story and you know who you’re trying to reach. The question isn’t whether to do the work. It’s whether the work is pointing at the right thing yet.

You sit down on a Tuesday morning. The cursor blinks. You know your story. You know your expertise. You know what you’ve lived through and what you’ve learned. And still, when you try to name what you actually offer the world, the words don’t quite land. The brand feels close, but not yet yours. The business feels real, but not yet sharp.

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That gap is the thing I work on with clients more than anything else. Helping them see that the job from ten years ago, the certification nobody noticed, the volunteer work that taught them how to lead, all of it belongs in the offer they’re building now. Not as a resume. As proof of the person behind the brand. The learning and growth documented along the way.

I help you leverage your lived experience to build a life, brand, and successful business that align with who you are and what you’re naturally good at.

Next week inside Building a Meaningful Brand, paid subscribers get the Experience-to-Offer Mapping Worksheet. It’s the same tool I walk clients through when we’re figuring out what they’re uniquely positioned to offer based on the patterns in everything they’ve already done.

By the end you’ll have:

• A clear view of what people consistently come to you for, across work, volunteer projects, and the rest of your life

• The specific problem you solve better than most, named in plain language

• A defined target so you stop writing for everyone and start writing for the person who actually needs you

• A working position statement you can test in real conversations starting that same week

If you’re sitting on years of experience but can’t quite name what makes your work yours, this is the one to grab.

The work behind a brand that lasts happens inside Building a Meaningful Brand. Come build yours with us.

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Headshots

A lot has changed since I went full time, in such a beautiful way. The podcast. This Substack. A roster of clients doing work that matters, from healthcare, to civic tech, to community development, to nursing education, to purpose-filled employment. The work has been fulfilling and I’m so proud of where it has been and where it has potential to go.

That’s why these photos mattered. They had to show up where I am now, not where I started.

When was the last time you updated yours?

Your photo is doing a job. It’s setting expectations before anyone reads a word you’ve written.

Maybe it’s easy to hold on to. Fewer crow’s feet, darker hair, less gray. But those years are important. They’re experience, patience, competence, grit, understanding.

So what happens when someone asks to meet with you and you’re quite a different person than who they see on your digital platform? Are you hiding behind an older, safer version of yourself?

A few questions to consider:

• Have your service tiers, audience, or positioning changed since the last shoot?

• Are you still wearing the blazer you bought for a job you no longer have?

• Have you started reaching for a cropped phone selfie because the “real” one feels wrong?

Pixelated photos undercut everything else you’re building. If you’re charging premium rates, does the way you show up match the work you deliver? A professionally crafted appearance, brand, and positioning reflects the quality of your delivery.

Now, that doesn’t mean you have to put on a Brooks Brothers suit. It means you need to spend the time developing an image that reflects who you are in a way that resonates with your brand and your client base. For me, that means my office setting, my garden, my podcast. The versions of me that come together to create a holistic marketer. A brand that puts values first.

Here’s what I love about a fresh shoot — you walk away with material. It is immediate gratification. New website hero. New podcast cover. New Substack header. New press kit. One good afternoon can feed a year of brand assets if you plan it that way. My brand is going through a bit of a redesign, more on that in the weeks ahead.

A photo sets expectations. The trouble is that most headshot advice produces the same photo. Neutral wall, blazer, arms crossed, slight smile. It works, in the sense that nothing about it is wrong. It also doesn’t tell anyone anything about you. It checks a box and nothing more.

The photos at the top of this post were taken in my podcast studio, my office, and my garden. Three settings that show up in my actual life and my actual work. That wasn’t an accident, and it’s not something you need a stylist or a creative director to pull off. You need a plan.

Here’s how I built mine.

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The catch is that AI is only as useful as what you feed it. Dump a screenshot of your dashboard and ask “what do you see,” and you’ll get something that sounds smart and says nothing. Pull the right data, ask the right questions, and you can find the the patterns that should be shaping your next quarter.

Here’s how I do it.

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Season one of Notes from the Messy Middle had been running, the episodes were getting downloaded, and I had a working assumption in my head about who was listening. Mission-driven professionals. People in the messy middle of meaningful work. A wide net.

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The numbers told a more specific story.

The people actually showing up were entrepreneurs, solopreneurs, and mission-driven leaders. Not the broader audience I had described in my positioning. Not the “anyone building something that matters” version I had written into the early episodes. A narrower, more identifiable group of people who were running their own thing and trying to figure out how to keep it sustainable.

I sat with that for a while. Then I let the data do what it is intended to: help steer the direction for the next phase of work.

Season two is being built around what the audience actually told me it needed.

The conversations are more specifically angled toward people running small operations. The questions I am asking guests are more intuitive. The episodes I am planning solo are about the actual problems entrepreneurs and small leaders are bringing to the work. The positioning is following the people, not the other way around. If you missed season one, you can find it wherever you listen to podcasts.

Check out Season 1

This is the part of building something that you learn along the way. You think the work of clarity is figuring out what you do. Most of the time, the harder work is figuring out who you do it for, and being willing to look at what your audience is actually telling you instead of who you thought they were.

That is why I tell clients to just get started. Put down what you know. Find your audience and tighten your positioning as you go.The honest stock-taking part of any practice is not just an inventory of what you offer. It includes what is coming back to you from the people you are trying to serve. Those two things have to match for the work to keep going.

I am still mid-build on this. Season two is not out yet. The new positioning is still settling into the website and the Substack and the way I introduce myself in rooms. But the data did its job. It told me something true, and gave me the chance to evolve with it.

This is the work every good marketer should be doing every six to twelve months.

Reanalyze the data. Tailor your position to address audience trends and needs. You do not change who you are or what you offer. You shift your presentation so the people you are already serving can find themselves in your work more clearly.

So here is your prompt:

Open your analytics. Look at the last six months. Notice who is actually showing up, what they are responding to, and what that tells you about the work you have been doing. Sit with whatever you find before you try to fix it.

If you want a partner and community in this part of the work, that is what Building a Meaningful Brand is built for.

This month we are inside the starting point with the Brand Inventory. The framing essay this week walks through how to use it. The difference between honest stock-taking and the self-criticism that gets you stuck. What to do when something on the page bothers you. How to mark a tension without rushing to resolve it. If your data is telling you something you have not yet evolved to meet, that is where the practice lives.

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A few things from the conversation to take with you:

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Credentials matter, but they are not the work. I see this constantly with the founders and leaders I work with. They want to chase another certification before they share what they already know. Scott put it bluntly.

Chasing credentials can be a seductive way to hide. You already have enough to start. The work is in showing up.

There is a difference between performing and being. Most professionals I work with feel like they have to lead with the polished version of themselves. The credentialed version. The one that has already arrived. Scott and I both believe the opposite. The people who build trust are the ones willing to be in the middle of it with you. Not performing the destination. Being on the road.

Action is the thing. You cannot think your way to clarity. You take the next intentional step, let it teach you something, and take the next one. I built my whole business this way. Twelve years of small steps. None of them were the perfect plan. All of them were data.

Your brand is not your logo. It is the story other people tell themselves about you, based on what you say and what you do. I have been writing some version of this for years. It hit different hearing Scott say it back. The work of building a brand is not making yourself look a certain way. It is closing the gap between who you are and what people experience when they meet you.

You can build a business that fits your life. Not the other way around. That is the whole reason I do this work. I came to it through my daughters, through realizing the traditional structure was not built for the life I wanted. Scott came to it through 37 years of marriage and two grandsons and a career that funds the life he actually wants to live. Different paths. Same conclusion. It is possible. It is also a design problem, not a sacrifice.

Grateful to Scott for the conversation. The full episode is on Notes from the Messy Middle. Link in comments.

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Join us live!

Last week we worked through the Brand Inventory. The exercise asked you to audit your existing content for three signals: values, advantages, and interests. The overlap of those three is your Brand Foundation.

This week we move from audit to action.

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We’re sitting down at 11:00 AM EST to talk about the space where most mission-driven leaders get stuck. The gap between knowing what you’re meant to be building and actually building it. Scott calls it the Implementation Gap. Here, we call it the messy middle.

A few things we’re getting into.

• Why “fine” is the enemy of aligned. The good-enough career. The good-enough brand. The good-enough version of the work you’re merely tolerating. It’s the biggest obstacle to a self-led practice, and it is difficult for leaders to see.

• How to close the gap between purpose and practice. The honest reason most people stay stuck thinking about it, and what it takes to actually move.

• How to stay grounded in the middle of a rebrand when everyone around you has an opinion about what you should be doing.

• The anatomy of one bold next step.

If you did the brand audit work last week, this is the conversation that picks up where it left off.

Join us live tomorrow, Tuesday May 12, at 11:00 AM EST on Substack. Bring your questions about alignment, positioning, and the next step you’ve been circling.

Join us Live!

This week inside Building a Meaningful Brand

Last week we worked through the brand audit. The Brand Inventory is in your hands, and you’ve started the honest stock-taking the rest of this work builds on.

This week’s paid essay picks up where the Live leaves off. How to Read Your Brand Audit: How to look honestly at where your brand actually is. How to tell the difference between something that needs to change now and something that can wait. And how to pick the first aligned move so you stop circling the inventory and start using it.

Paid members also get the office hour this Wednesday. Bring whatever your audit surfaced and we’ll work it through live.

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Free subscribers get the thinking. Paid members get the structure, tools, and practices to make it real.

See you tomorrow at 11.

Erin

I hope you’re doing well and navigating the “messy middle” of your week with some grace.

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The freelance and founder world is a strange place. We start our own things because we want freedom and alignment, but it’s incredibly easy to wake up one day and realize we’ve just built ourselves a new “professional costume” to perform in. We get stuck in the gap between the meaningful work we want to do and the “hustle” we think we have to do.

Next Tuesday, May 12th at 11:00AM EST, I’m going Live with to talk about how to take that costume off.

Scott is the founder of Creative on Purpose, and he specializes in helping people “let their lives speak.” Together, we’re going to dig into the Architecture of Alignment—how to move past the “fine” trap and finally build a brand that actually fits the person running it.

Here is what we’re tackling:

• Closing the Implementation Gap: How to move your mission from a “thought” to a “practice.”

• Architecture over Hustle: Building structures that support your life instead of consuming it.

• The Bold Next Step: What one aligned action looks like today.

Mark your calendar: 📅 Tuesday, May 12th ⏰ 11:00AM EST 📍 Meet Here

Save the date!

If you’re ready to stop performing for a narrative that doesn’t fit and start positioning your work around who you actually are, I’d love to see you there.

Best,

Erin

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Nothing in here is new. That’s why we keep coming back.

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There’s something about a used bookstore that makes you stop and pay attention in a way almost nothing else does. You’re not searching for a title. You’re letting your hand land on a spine. You’re reading the first page of something you didn’t know existed an hour ago.

I’ve always connected with this part of myself. Ever since my fifth-grade young authors competition. Ever since falling in love with Bridge to Terabithia. The part of me that wanted to make something a person could walk into and not want to leave.

It took having children to remind me how much that part of me was missing.

That’s why I start every client engagement looking for that part of their own story. The pivotal moment. The inspiration behind the work. The reason they started, before the website and the services page and the pitch.

Because people don’t fall in love with titles. They fall in love with stories. With the person behind the project. With something the founder can’t quite explain but won’t stop showing up for.

Healthcare coach, nonprofit leader, book editor, small business owner. A title is a title. A story takes work.

Most branding work starts with the wrong question. It asks what you do, who you serve, what makes you different. Useful questions. They come second.

The first question is the one most founders skip: what’s the part of you that won’t let this go?

The values underneath the work. The unique capabilities you forget are unique because they come easily to you now. The interests you keep circling back to when no one is paying you for them.

That’s where I start with every client. Not with positioning. With discovery.

A brand built on the right foundation doesn’t have to be defended every quarter. It stands. It solves a problem from an angle nobody else can replicate, because nobody else is you.

If you’re building something and the messaging keeps slipping out from under you. If the strategy works on paper but doesn’t feel like yours. That’s the work we do inside the paid subscription. Frameworks, prompts, and the occasional read of your draft. The work that turns discovery into something an audience will actually invest in.

A title is a title. A story takes work. Paid subscribers get the frameworks and prompts to do that work on their own brand.

I kept coming back to one question.

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Why was it so hard?

Parenting young kids is hard. I get that. Toddlers are little deviants. Sleep is hard to come by. Laundry and dishes are eternal. While all of that came at me like a fire hose, it is the job.

What I couldn’t reconcile was the sense that Mike and I were both failing at something the world kept telling us should be manageable. Two college-educated adults. Two people who loved their kids and each other. And still, we were struggling to keep our heads above water.

I went looking for answers. What I found wasn’t comforting, but it was clarifying.

New here? Start with my story.

The United States is the only wealthy country in the world without guaranteed paid maternity leave.

Childcare in most states costs more than in-state college tuition. A third of American parents spend more than twenty percent of their household income on childcare alone. Fathers who request flexibility or leave face career penalties that no company will ever put in writing. Part-time workers often have no access to paid leave of any kind.

And the pressure is tightening, not loosening. In the last year alone, JPMorgan Chase, Amazon, AT&T, Dell, and Disney have ended hybrid work and called hundreds of thousands of employees back to the office five days a week. Kroger, Truist, and Home Depot announced the same for 2026. Deloitte is cutting paid parental leave from sixteen weeks to eight, reducing PTO by up to ten days, and eliminating adoption and surrogacy benefits. Zoom is trimming parental leave for birthing and non-birthing parents alike. The work can still be done from home. The benefits were still affordable. The companies chose otherwise.

I was a part-time employee at the Y when my youngest, Mia, was a baby. I had no paid leave of any kind. I came back to work as soon as my body would let me after having my third daughter. Not because I wanted to. Because I had to.

I was one of them. I came back to work as soon as my body would let me after having my third daughter. Not because I wanted to. Because I had to.

And here is the part that took me the longest to see. The system wasn’t broken.

The system was working exactly as designed.

It was designed when one income could support a family of five. When fathers were expected to earn and mothers were expected to do everything else. The housework. The child rearing. The emotional labor of an entire household. All of it absorbed quietly, with no expectation that she might have interests, ambitions, or a life of her own beyond the walls of the home. When one parent commuted to a job with a pension and a gold watch at the end, and the other kept the whole operation running without pay, recognition, or choice.

Maybe that is why I lose patience with the people insisting women belong at home. That this is how it was meant to be. Says who? Whose design are we actually defending?

Wages have stagnated while housing, healthcare, education, and food have not. Two incomes are no longer a preference for most families. They are a requirement. The cost of living in this country has made staying home a luxury most households cannot afford.

But the infrastructure never caught up.

We still act like one parent is home. We build workplaces that assume it. We design school calendars that require it. We make childcare inaccessible enough that it punishes anyone who tries to work around it. And then, when families buckle under the weight of the contradiction, we tell them to go back to a traditional model that the economy itself has made impossible.

That is not a policy failure. That is a choice.

And underneath the choice is a discomfort with what women have become.

This is not a man or woman problem. It is a structural one. Mike was not thriving in the old design either. He was carrying the pressure of being the sole financial engine for a family of five, tied to a job he did not love because it paid the bills, watching his daughters grow up from the margins of a schedule he did not control. The assumption that he should be satisfied because he was the one earning was as limiting for him as the assumption that I should be satisfied staying home would have been for me.

When I went back to work and started building something of my own, something that reflected my values and my skills and the kind of impact I wanted to have, it did not just change my life. It changed his. Watching me chase purpose gave him permission to do the same. And the easing of the financial pressure, two incomes instead of one, gave us the freedom to prioritize flexibility, presence, and each other. We stopped operating as a traditional family and started operating as a team.

Both of us found freedom.

Women are not asking permission anymore. We work because we have to, yes. But also because we want to. Because we have ideas. Because we have knowledge and experience and perspective that the world has needed all along and finally has access to. Because contributing to how this country operates, how companies are run, how communities are built, how children are raised, is not something we are willing to outsource anymore.

Motherhood is not the whole of us. It never was. And the generations of women who silently absorbed that assumption paid a price we are no longer willing to pay.

So when I hear the cultural drumbeat getting louder, the push to return to a traditional family structure, the framing of working mothers as the problem, the obnoxious suggestion that maybe things were better when women stayed home, I recognize it for what it is.

It is not concern for families. It is discomfort with change.

The traditional structure did not fail because women abandoned it. It failed because the economy stopped supporting it and nobody built anything to replace it. You cannot ask both parents to work, refuse to fund childcare, refuse to mandate paid leave, refuse to build flexible workplaces, and then blame families for struggling.

You certainly cannot tell women to go home when home is not economically viable and was never the whole of who we were to begin with.

What Mike and I were feeling that morning was not weakness. It was the weight of carrying something the country refused to hold with us.

I wish I had known that then. I would have been gentler with both of us.

If you are in that season right now, reading this with a toddler climbing your leg or a baby monitor buzzing in the background, I want you to hear me clearly.

You are not failing.

You are doing the work of two generations inside a system built for neither of them. The exhaustion is real. The guilt is misplaced. The question is not what is wrong with you.

The question is what we are finally willing to build.

If this piece resonated with you and you are ready to start building something that actually fits your life, I am opening a free first cohort of my coaching program soon, grounded in the Self-Led Life framework. It is designed for people who are tired of performing someone else’s version of success and ready to reconnect with their own values, interests, and talents.

If that sounds like you, take the free assessment and start building something that works for you and the life you want to lead.

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.

New here? Start with my story.

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.

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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.