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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

Connect with Me:

• Instagram: @racheal.cook
• TikTok: @rachealcookmba
• LinkedIn: @rachealcook
• YouTube: @the_ceo_collective
• Website: The CEO Collective

Subscribe & Review:

If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!

🎤 Thanks for listening! I'll see you next week!

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What if everything you've been told about raising your rates is backwards?

Amy Hayes, founder of The Global Creator, spent a decade building a design business that runs almost entirely on referrals—and she's never touched social media marketing for her client work. In this conversation, she reveals why most creatives are focusing on all the wrong things when trying to command premium prices.

You'll discover why that expensive camera or fancy software isn't what's keeping you from high-end clients. Amy breaks down the real difference between high-end and high-touch services, and why the latter matters more than you think. She also shares her unconventional approach to client boundaries—one that actually strengthens relationships instead of creating friction.

If you've ever felt trapped in the feast-or-famine cycle, constantly chasing new clients, or wondered why your perfectly polished portfolio isn't attracting the clients you want, this episode will shift how you think about service-based business entirely. Amy's insights on the relationship-first approach might just save you years of spinning your wheels on strategies that don't actually move the needle.

In This Episode:

• Why accumulating more skills and certifications won't fix your client pipeline problems

• The "self-concept" shift that transforms how clients perceive and treat you

• How Amy built a decade-long business without social media marketing (and why referrals don't actually "dry up")

• The counterintuitive approach to client boundaries that creates stronger relationships, not weaker ones

• Why high-end services require high-touch experiences—and what most people get wrong about this

• The real reason clients become demanding (hint: it's not about your pricing)

• How to price projects with built-in margins for creativity and collaboration

• Why saying yes to smaller projects from existing clients can be your most profitable decision

• The energy shift from "creative gun for hire" to strategic partner that changes everything

Connect with Me:

• Instagram: @racheal.cook
• TikTok: @rachealcookmba
• LinkedIn: @rachealcook
• YouTube: @the_ceo_collective
• Website: The CEO Collective

Subscribe & Review:

If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!

🎤 Thanks for listening! I'll see you next week!

Send us a text

I've been thinking a lot about why so many of us are running on empty, and this conversation with Amanda Miller Littlejohn gave me language for something I've been feeling for years. We're not just tired—we're operating from a fundamentally broken blueprint about what makes life worth living.

Amanda's new book, The Rest Revolution, cuts through all the productivity hacks and time management systems to get to the real issue: we've been taught to measure our worth by our output. And frankly, it's killing us. What struck me most about our conversation wasn't just her story of severe burnout after having her third child during the pandemic (while not taking maternity leave), but how she traced this pattern all the way back to childhood.

This isn't another "work-life balance" conversation. Amanda challenges the entire framework of ambition in our post-pandemic world. She's a sought-after executive coach, brand strategist, and now Rosalyn Carter Mental Health Journalism Fellow whose work has appeared in the Washington Post and Forbes. But more than that, she's someone who hit the wall hard and found a different way forward.

If you've ever felt like you're supposed to be grateful for being overwhelmed, this episode will shift something in you.

Show Notes

• The childhood origins of overwork - How being rewarded for effort and achievement creates adults who don't know they have limits

• Back-burnering vs. front-burnering - Why we systematically deprioritize health, hobbies, and key relationships for things that "matter" financially

• The breaking point pattern - How burnout manifests when we either get physically sick or lose someone and have no space to grieve

• Machine mindset vs. human needs - Why "I can't afford to take my foot off the gas" is a lie that keeps us trapped

• The village we've lost - How hyper-capitalism destroyed the natural support systems our grandparents had

• Friend-making in your 40s - Amanda's practical approach to "proposing" to potential best friends and showing up consistently

• The three P's of friendship - Proximity, positivity, and frequency (why adult friendships require intentional effort)

• Redefining the measuring stick - Moving from productivity-based worth to relationships, joy, and health as success metrics

• Why this all becomes urgent in your 40s - How decades of bad habits finally catch up and force a reckoning with what actually matters

Connect with Me:

• Instagram: @racheal.cook
• TikTok: @rachealcookmba
• LinkedIn: @rachealcook
• YouTube: @the_ceo_collective
• Website: The CEO Collective

Subscribe & Review:

If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!

🎤 Thanks for listening! I'll see you next week!