He Spent 23 Years Chasing the Top Before Realizing He'd Been Running from Himself

He Spent 23 Years Chasing the Top Before Realizing He'd Been Running from Himself

Ryan Maxwell was 11 months away from becoming president of his company when he quit. 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 [https://eringregorycreative.substack.com/podcast] 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, [http://www.eringregorycreative.com] 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

She Left Her Job on a Friday. By Monday, Everything Had Changed.

Jenn Kersey didn’t quit her job to start a candle company. 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. Thanks for reading Erin Gregory Creative! Subscribe for free to receive new posts and support my work. 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. [https://www.youtube.com/@eringregorycreative] Listen to my full conversation with Jenn Kersy of Rusted Root Co. on Notes from the Messy Middle [https://eringregorycreative.substack.com/podcast]. Find her candles at rustedrootco.com [https://www.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 [http://www.eringregorycreative.com], 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

Why This Gift Planning Director Chose the Messy Middle

Nonprofit leaders are stretched thinner than usual right now. Funding is unpredictable, major donors are harder to land, and the middle of your donor base (the people who could actually sustain you) keeps getting ignored because the ROI feels impossible to justify. 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, [https://www.linkedin.com/in/bowtiedg/] 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.” Thanks for reading Erin Gregory Creative! Subscribe for free to receive new posts and support my work. 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. [https://eringregorycreative.substack.com/podcast] 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

🎙️Let’s Get Unstuck x Erin Gregory🎙️

Get full access to The Self-Led Life by Erin Gregory Creative at eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4] This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

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

Get full access to The Self-Led Life by Erin Gregory Creative at eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4] This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit eringregorycreative.substack.com/subscribe [https://eringregorycreative.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2]