The Backstory: $100K and Still Anxious
When Courtney and I first started working together, she had been running Palmetta, her brand and web design studio, for just over a year. And on paper, that first year was a win. She’d generated $100K in sales, fueled almost entirely by a “this just has to work” mindset.
But behind the scenes, she was anxious, overwhelmed, and unsure how to keep growing in a way that didn’t feel like white-knuckling it. She had the creative vision down. What she didn’t have yet was confidence in the business side of the business: sales, pricing, boundaries, finances, the actual logistics of running a studio.
She was pricing based on what she saw other designers charging instead of what made sense for her offers, her time, and her expertise. She didn’t have the systems or the clarity to feel like she was actually leading. The business was running her, not the other way around.
“It felt like I had the talent, vision, and drive, but not yet the confidence or structure to fully step into the role of CEO.”
That gap showed up everywhere. Anxious before sales calls. Second-guessing her pricing. Spending too much time trying to make proposals feel “perfect.” Shaping her offers around what she thought people would say yes to, instead of what actually made sense for the business. And because she cared so much about doing great work, she’d overextend herself constantly, absorbing stress that wasn’t hers to carry in the first place.
Courtney had tried to fill the gap on her own before. She’d leaned on an informal mentor, a brand design studio owner she’d interned for in college, who was generous with her time. But because Courtney wasn’t paying her, she often felt guilty asking for too much support. And her business was heading down a different path than her mentor’s had, so not all of the advice fully applied. She needed something more consistent, more intentional, and built specifically around the studio she was trying to create.
The Decision: The Right Message at the Right Moment
For a while, Courtney held herself back with the belief that it was “too soon.” That she needed to prove herself for longer before she’d earned the right to invest in coaching. Looking back, she can see that hesitation for what it was: inexperience and scarcity thinking, not a real reason to wait.
Then tax season rolled around, and she realized she’d oversaved more than she thought. That gave her the permission slip she needed to reinvest in herself and the business. Around the same time, my emails about the mastermind kept showing up, and they felt eerily specific to exactly where she was.
“I don’t remember every exact detail of the emails or messaging, but I do remember feeling like she was somehow talking about me and directly to me at the same time.”
She’d already proven she could make the business “work.” What she could feel was that the way she got through year one wasn’t sustainable, and she couldn’t do it the exact same way again. She needed help moving out of survival mode and into something more grounded and strategic.
What We Worked On Together
The process ended up being a mix of strategy, tactical support, accountability, and genuine emotional support, more than Courtney expected going in.
One of the biggest pieces was the daily conversation she and I had access to. Whatever came up, a tricky client situation, nerves before a sales call, a pricing question, a boundary she wasn’t sure how to hold, we worked through it together. I listened, took notes, remembered what she’d told me before, held her accountable, and helped her knock down the limiting beliefs that kept surfacing.
We also completely restructured her offer suite. She had packages that didn’t fully make sense, and she hadn’t realized how much friction that was creating, both for her and for potential clients. We simplified, clarified, and repositioned so her offers could actually support the business she was building.
And we brought in financial experts to help her get real clarity on the numbers. She learned how to track her expenses, pay herself intentionally, understand her actual profitability, and start building a business emergency fund. That piece alone made the business feel a lot less scary.
“Having someone else affirm you, your vision, and your dreams while also giving you practical guidance is invaluable.”
The Turning Point
There wasn’t one dramatic lightbulb moment. It was more gradual than that. But Courtney remembers noticing, almost out of nowhere, that discovery calls had started to feel completely different.
That shift is what told her the work was actually landing in real time.
“I wasn’t just learning how to ‘be’ more confident… I was becoming more confident!”
The Results
- Grew revenue from $100K to $115K year over year
- When you isolate design services alone, that’s a $43K increase, or roughly 60% growth, since only $72K of her first year came from brand and web design work
- Fully stepped away from outside contract gigs to focus entirely on her own clients
- Simplified and clarified her entire offer suite
- Built a business emergency fund from scratch
- Gained real clarity on expenses, profitability, and how to pay herself
Beyond the Numbers
The confidence shift showed up everywhere, but especially on sales calls. What used to feel intimidating and high-pressure started to feel natural and grounded. Courtney became comfortable leading the conversation, naming her pricing, and trusting that the right clients would see the value without her having to convince them.
More than anything, Palmetta stopped feeling like a business she was trying to survive and started feeling like a studio she was intentionally building.
What She’d Say to You
“It is absolutely worth it, and I can say that confidently because I’m already back working with Olivia again. The way she keeps you focused on the needle-moving work that actually grows the business makes the investment pay for itself.”
Courtney’s advice to anyone sitting where she once was:
“It’s easy to tell yourself that you should wait until you’re more established, more profitable, or more ‘ready’ to invest in support. But the support is what helps you become more ready.”
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