Promote Yourself to CEO | Small Business Strategy for Women Entrepreneurs

I go on CEO dates with myself. Once every month (as well as on a weekly basis), I take some time to check in on my business and ensure I’m continuing the progress toward the goals I’ve set. This is how I create business plans that I follow through on and adapt as circumstances arise. And in this episode, I discuss how you too can build in self-accountability so that your plan isn’t just another document you’ll never open again.

On this episode of Promote Yourself to CEO:

2:59 - I talk about my monthly CEO date and dive into my check-in process.

7:48 - What kinds of questions can you ask yourself as you look back on the previous month?

11:28 - I reveal another reason why I absolutely love working with The CEO Planner.

14:15 - What are the consequences of not tracking and documenting things in your business on a consistent basis?

20:07 - Your business metrics and revenue help you predict your company’s future. I reveal how I check on mine every month without obsessing over them.

27:20 - What if you discover that you’ve fallen behind (even way behind) on your projected goals? Here’s how I handle it.

32:24 - One of the most crucial things you need to do with your team while setting your top business priorities for the next month.

34:10 - What’s the last thing I do at the end of my monthly CEO date?

• Plan Your Best Year Ever Challenge
• The CEO Collective
• The CEO Retreat
• The CEO Planner
• Racheal on Instagram and TikTok
• Rate and review on Apple Podcasts

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!

Every new year feels like a new chance to go after the big, audacious goals of your dreams. But as recent years have shown, you need to have adaptable plans for your business so that it can have the flexibility it needs while still getting the results you want. That’s why I love running my quarter through 90-day plans. Today, I talk about how to actually dig in and start creating these plans for your own business.

On this episode of Promote Yourself to CEO:

3:34 - Why go for 90-day plans? Entrepreneurs love setting big, ambitious goals, but it can be overwhelming.

7:27 - How do you break down big goals into more manageable chunks to fit your time, energy, and resources? You can make your best guess, or do this instead.

11:24 - As an example, I quickly walk through how you can launch a new group program within a year (or sooner).

16:03 - How do you actually create your first 90-day plan? I dig into it and discuss the kind of goals you want to focus on during this process.

19:50 - Start the process by looking over your sales and marketing with this 5-part marketing strategy framework.

27:01 - Most people think of this part of the framework when they think of marketing and can get it confused with the first step. I reveal why it’s different and necessary.

34:08 - What’s next after you have your systems in place? I discuss the difference between process vs. project goals and breaking them down in your 90-day plan.

38:38 - Asking yourself these questions as you work through your plan can really help ensure you avoid major challenges.

• Plan Your Best Year Ever Challenge
• The CEO Collective
• The CEO Retreat
• The CEO Planner
• Get Paid Calculator
• Racheal on Instagram and TikTok

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!

I need you to meet Michelle Mercurio. She's one of those rare people who refuses to pick a lane—and that's exactly what makes her brilliant. In this conversation, we dig into why the traditional business advice to "niche down" might actually be killing your ability to show up as yourself. Michelle's built a career that spans branding, community building, teaching, and yes, witchy practices—all tied together by two powerful threads: understanding who we are and how we relate to one another.

What I love most about this episode is how Michelle reframes growth itself. We're so conditioned to think growth means up, up, up—more revenue, bigger team, next level. But what if growth is actually a spiral? What if coming back to familiar patterns isn't regression but evolution? We explore how to shed decades of conditioning that taught us to smooth out our edges and fit in, why elevator pitches actually kill connection, and what it really takes to build authentic community (spoiler: it requires showing up even when it's uncomfortable). If you've ever felt like you're supposed to be further along or you're doing it wrong because you don't fit the mold, this one's for you.

In This Episode of Promote Yourself to CEO:

• Why Michelle describes growth as a spiral rather than a ladder—and what that means when you feel like you're revisiting the same challenges you thought you'd already overcome

• The real danger of trying to fit in as a small business owner—how smoothing out your edges to belong actually makes you invisible in the marketplace

• What neuroplasticity research reveals about conditioning—and why it takes intentional effort to break free from the patterns that keep us playing small

• How elevator pitches kill connection instead of creating it—Michelle shares her "Ditch the Pitch" approach that uses questions as hooks instead of titles and credentials

• The truth about successful people that nobody talks about—hint: they're just the ones who didn't quit (but Michelle draws an important line about what you should quit)

• Why you can't just show up once and expect community to happen—what it really takes to find your people and build genuine relationships in business

• The one action you can take today to build authentic community—Michelle's practical suggestion for anyone feeling isolated in their business journey

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!

The best entrepreneurial stories rarely start with a grand vision. They start with a rug being pulled out.

That's Ashley's story. A layoff. A pandemic that destroyed her in-person business overnight. So she did what many of us do in crisis—she picked up watercolors and created. A hundred days worth. Except it took two years to finish.

When Ashley came to me, I saw what she couldn't see herself: a hundred pieces of unique, marketable content in a space flooded with generic coaches. She resisted. Hard. Tears and all.

But here's what changed everything: clarity isn't something you force. It's something you create conditions for. Once Ashley stopped waiting for perfection and started building in public, the momentum came fast. Seven months from a wine bar idea to four finished books.

If you've got something incomplete sitting in your files, or you're wondering if your "weird" skill could be your real differentiator—listen in.

On this episode of Promote Yourself to CEO:

• The accidental entrepreneur — Ashley's family had three generations of business owners. She wanted nothing to do with it until a layoff left her no choice.
• When crisis creates clarity — A pandemic wiped out her revenue overnight. She started painting. Two years later, she had 100 finished watercolors and no plan.
• What I saw that she couldn't — A hundred pieces of unique, ready-made content. Ashley saw uncertainty. I saw her competitive advantage.
• The two-year gap between finishing and knowing — Completed the paintings in 2022, knew her path in 2024. Here's what she learned about waiting for clarity.
• Building in public before you're ready — Ashley announced her journal plan on LinkedIn, tagged 200 people, took pre-orders before writing a word.
• Why smaller commitments actually work — Instead of writing all four at once, she took pre-orders for volume one, wrote it, then repeated. The structure got it done.
• Your market is telling you something — People kept asking about her art, not her coaching. She listened to that signal instead of resisting it.

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!

Your revenue is down. Sales have slowed. And every time you log into social media, you're hit with another wave of news that makes you want to throw your entire business plan out the window and start over.

But here's what most business owners don't realize: when things slow down, the problem is rarely everything. It's usually just one or two key levers that need your attention. The CEOs who come out stronger on the other side? They're the ones who can diagnose the real issue instead of burning it all down in a panic.

In this episode, I'm walking you through the exact framework I use with my CEO Collective clients to figure out what actually needs fixing in your business. We're talking about the four levers that directly impact your revenue, how to identify which one is causing your slowdown, and why changing everything at once is the worst move you can make right now.

This isn't about working harder or doing more. It's about working smarter and focusing your energy where it will actually move the needle. Because sales slowdowns don't mean your business is broken. They mean it's time to make a strategic CEO-level decision.

On this episode of Promote Yourself to CEO:

• The leaky bucket problem - Why you might be bringing in new clients but still losing revenue (and the one metric that will tell you if this is happening in your business)
  
  
• Product-market fit in uncertain times - The three scenarios where adjusting your offers makes sense, and when a "bite-sized" entry point could be the bridge between hesitant buyers and long-term clients
  
  
• The messaging shift nobody's talking about - Why aspirational content stops converting when the economy gets shaky, and what your audience is actually searching for right now
  
  
• The visibility dilemma - How to stay visible when you're burned out on social media, plus the "Follow-Up Friday" strategy that's working for service-based business owners right now
  
  
• The science experiment approach - Why changing one variable at a time is the only way to actually know what's working (and what's not) in your business
  
  
• Client retention as your secret weapon - The case study of a CEO Collective member whose revenue dropped even though new client numbers stayed the same, and what we discovered when we looked under the hood

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!

You know that feeling when you open your closet and somehow have nothing to wear—even though it's packed full? That's what running your business feels like right now. Not because you lack options, but because you have too many of them.

Fresh off our CEO Retreats, I've been hearing the same thing from small business owners across the country: they're stuck. Not on client work—they're confident there. But on the CEO-level decisions that could make or break their next year. The ones about pricing, team, strategy. The decisions they keep putting off because "what if I'm wrong?"

Here's what nobody talks about: this isn't a confidence problem. It's not an effort problem. It's decision fatigue, and it's eating up your cognitive capacity before you even get to the decisions that matter. Every morning you're starting with a tank of mental fuel, and by the time you need to make the big call, you're running on empty.

In this episode, I'm breaking down why wait-and-see mode is costing you more than you realize, what Steve Jobs and Barack Obama understood about preserving brain power, and the one tool that's going to help you cut through the noise: your CEO decision matrix. If you've been spinning your wheels on a decision you know you need to make, this one's for you.

In This Episode:

• Why small business owners feel economic shifts first—and what that reality means for the decisions sitting on your desk right now that you've been avoiding
• The cognitive capacity trap: I'm breaking down how your morning routine, chronic illness, or last night's sleep actually determines how much decision-making power you have today (and why this changes everything)
• What prolific leaders do differently when it comes to preserving mental energy for strategic decisions—it's not about working harder, and the examples might surprise you
• The real cost of "wait and see" mode—I'm sharing what I've witnessed happen when small business owners delay tough conversations about team, pricing, or strategy, and why your options shrink instead of expand
• How too many options create paralysis—your packed closet explains exactly what's happening in your business, and once you see this pattern, you can't unsee it
• The CEO Decision Matrix framework: I'm walking you through the filtering system that uses your vision and values to help you make tough calls faster and with more confidence

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!

You know that sinking feeling when a client asks for "that document we worked on last month" and you have absolutely no idea where you saved it? Or when you're paying your team to sit idle while you frantically search through folders trying to find the resources they need?

If you've ever felt like the organized, professional front you present to the world is hiding a complete digital disaster behind the scenes, this episode is for you. Tracy Hoth, professional organizer turned business coach, reveals why most entrepreneurs struggle with organization (hint: it's not because you're "naturally messy") and shares her surprisingly simple system that works whether you're a solopreneur or managing a team.

This isn't about buying fancy software or overhauling your entire business overnight. Tracy breaks down the exact five-folder system she uses with clients to eliminate the constant search-and-rescue missions that are quietly draining your productivity and confidence. She also shares the "wonderful one" concept that could save you hours every week and the maintenance habit that takes less than five minutes but keeps everything running smoothly.

Ready to stop being the bottleneck in your own business? Tracy's practical approach might just be the missing piece that transforms your behind-the-scenes chaos into a well-oiled machine.

In This Episode:

• The "Monica's Closet" phenomenon — Why most business owners look perfectly organized on the outside while drowning in digital chaos behind the scenes

• Tracy's five essential business folders — The stupidly simple filing system that works for Google Drive, Canva, email, and every other platform you use daily

• The hidden cost of disorganization — How being unable to find files is masquerading as "bad time management" and costing you money in team productivity

• The "wonderful one" rule — Why choosing a single hub for everything eliminates decision fatigue and stops files from multiplying across devices

• SPASM method revealed — Tracy's 17-year-old organizing process that works for physical spaces, digital files, and even overwhelmed brains

• The maintenance secret — The simple habit-stacking technique that keeps your system running without constant overhauls (spoiler: it ties to something you already do)

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!

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!

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!

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!