How Carolyn Leasure Designed a Business That Fits Real Life with the Staying Solo Squad

When Carolyn Leasure, Founder of Maypop Creative Studio, joined the Staying Solo Squad in late 2024, her business wasn’t failing, but it was changing in ways she hadn’t yet fully figured out.

After years of steady referral-based work, she found herself at a decision point. She had recently shifted her niche slightly, but the referrals she was receiving no longer aligned with the type of clients she wanted to serve. At the same time, the broader business environment looked very different from what it had been when she first launched in late 2019.

“For a few years, business was booming. I didn’t have to work to get clients,” she explained. “Because of that, I had to think about the strategy and systems and structuring my business a different way.”

Marketing also felt like a major gap. Carolyn wasn’t active on social media, rarely emailed her list, and had largely relied on inbound client leads rather than intentional visibility.

What drew her to the Staying Solo Squad wasn’t just tactical help; it was the promise of community and strategic support.

“I thought it was a great way to both be involved in a community of peers, as well as having Sara and Maggie help figure out some of the stuff that I was really on my own with.”

The Unexpected Shift: From Isolation to Belonging

One of the biggest surprises for Carolyn about the Squad wasn’t a specific framework or tool; it was how deeply connected the community felt.

“When we all get together and have a call, everyone’s very open and very much themselves,” she shared. “I felt this pressure to show up as having everything all together when I was on my own. There’s so much grace and openness in the group.”

That openness made it easier for her to ask for real help, not just polished, surface-level feedback.

“The best way to get help in the group is to be very vulnerable and honest about where you are in your business,” she said. “It’s an open and honest place to be.”

Carolyn summed it up simply: “It’s a sense of belonging.”

Getting Paid for Strategy Work

One of the most concrete business changes Carolyn made inside the Squad was formalizing and selling strategy work.

Before joining the Squad, she already knew something wasn’t working with her custom projects. Thirty-minute discovery calls weren’t enough to understand what clients truly needed, and they often left her guessing.

“I always found it really difficult to figure out exactly what they need in a half-hour discovery call,” she explained.

With the Squad’s focus on strategy-first services and paid discovery, she built a new process:

• An initial discovery conversation.
• A paid strategy session.
• A detailed strategy document that clients could either use with her or take elsewhere.

“I’ve already used it twice. It was very effective, and it awed my clients,” Carolyn said. “We can get so much deeper into what they’re looking for and what’s actually going to help them.”

Just as importantly, it protected her time and expertise.

“I also get paid for the strategy work. And if they don’t end up booking with me, I’m disappointed—but I got paid for the work that I did.”

Designing a Schedule that Works for Real Life

While revenue growth wasn’t Carolyn’s headline result for 2025, largely due to personal circumstances that reduced her available working time, her capacity planning and energy management improved dramatically.

“I’ve always had trouble with time management. I overload my schedule so much,” she shared. “But I’m so much better at understanding my capacity in terms of time and energy.” 

A key shift: consolidating all client calls into a single day.

“I realized that having all of my calls on one day is really helpful,” she said. “Doing that has really preserved my energy.”

The Squad also helped her slow down her natural tendency toward idea overload.

“I would just go full throttle into all my new ideas and let everything else go by the wayside,” Carolyn admitted. “Now I can ask: what’s the minimum viable option? Or should I put this on hold?”

The Community Impact: Support That Actually Shows Up

For Carolyn, the Squad became more than a business resource; it became a lifeline during a difficult season.

“When I was going through so much with my youngest child in the spring, I felt like a failure as a parent and a business owner,” she shared. “Having everyone’s support really gave me a lifeline.”

She also emphasized how rare it is to find a community that balances honesty, generosity, and trust.

“There’s room for disagreement without it becoming toxic,” she said. “And people are so giving with their knowledge. If you have a question, you can ask an actual person who’s experienced.”

Over time, that trust extended beyond advice into referrals.

“There’s a group of people I really trust. We’ve built that trust over the past year, and I can freely recommend them.”

Sustainable Support for Solo Business Owners

When asked what she’d say to someone considering the Staying Solo Squad, Carolyn didn’t hesitate.

“For someone looking for support as a solopreneur, I can’t think of a better community, in terms of business support and personal support,” she said.

She summed up the experience this way:

“Being part of the Squad gives you a whole group of people in the trenches with you. It’s the best.”