Sep 10
38m 25s
Ever feel like you're constantly tweaking your business but nothing quite clicks? Like you're a plant that's outgrown its pot but you keep trying to make it work anyway?
You're not alone. And more importantly, there's a reason why all that surface-level fixing isn't working.
In this conversation with Jessica Sato, we dig into why successful entrepreneurs hit this wall—and what actually needs to happen to break through it. Jessica works with impact-driven female entrepreneurs who've built something good, but know there's something bigger calling them forward.
This isn't about another rebrand or website refresh. It's about the deep work that most people skip because it feels too slow, too introspective, or too "nice to have." But here's what Jessica and I both learned the hard way: you can't shortcut this process.
We talk about the moment you realize your current container is too small, why "good enough" can be the enemy of extraordinary, and how to find that through line that connects everything you've built into something cohesive and compelling.
If you've been in business for 5+ years and something feels off—even if you can't put your finger on what—this conversation will give you language for what you're experiencing and a path forward that doesn't involve starting over.
On this episode of Promote Yourself to CEO:
• The accidental TEDx discovery that shifted Jessica's entire approach to helping entrepreneurs find their big ideas
• Why your "expertise overwhelm" is actually the problem—and the umbrella framework that cuts through the confusion
• The two unmistakable signs you've outgrown your current business model (hint: one involves a lot of frustrated tweaking)
• The root-bound plant analogy that explains why no amount of "window dressing" will fix a foundational misalignment
• Why successful entrepreneurs resist the deep work that would actually solve their problems (spoiler: it's not what you think)
• The difference between copywriters and messaging strategists—and why working with the wrong one keeps you stuck
• Rachel's honest breakdown of her two major business evolutions and what triggered each shift
• The "good enough" trap that keeps mid-stage entrepreneurs from doing the work that would unlock their next level
• How Jessica's Egypt retreat idea emerged from a dream and why discomfort might be exactly what your business needs
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🎤 Thanks for listening! I'll see you next week!