Why Your Marketing Feels Hard (Even When You’re Doing Everything Right)

[00:00:00] If you've ever found yourself thinking, I'm doing everything that I'm supposed to be doing to market my business and to be more visible, so why does it still feel so hard then this episode is for you? Because the real problem isn't that you're bad at marketing. The problem is that most of the marketing advice that you've been given was never designed for the kind of business.

That you're actually building. Let's get into it.

Hey there, CEOs, Rachel Cook here, founder of the CEO Collective and host of Promote Yourself to CEO. I'm so excited to be back behind the microphone. I am here in the podcast recording studio at Common House in downtown Richmond, Virginia, which is where I have been a member and have been coworking ever since.

I. Closed down my office at the end of 2024, and it has been a minute since I have recorded new content for you. If you weren't aware, if you hadn't seen the updates, um, I have shared a lot about my journey last year and how challenging 2025 was. I've shared on the podcast how I had to basically put everything on.

Autopilot on cruise control. While I was prioritizing taking care of my aging parents, their needs radically escalated last year, and even though I have been managing their care and making sure that my mom had full-time care at home, 24 7 nursing care, a team of nurses all day long, all night long for the last five years, we got to the point where it was just no longer.

Sustainable in a lot of ways, and ultimately I had to move them both closer to me because I could no longer manage the last minute cancellations where a nurse is sick or their child is sick, or they got hurt, or you know, we had a gap in someone taking care of her, and so I would have to. Jump in my car and drive an hour and a half there and an hour and a half back to fill in or to meet them at the hospital or to take a shift.

You know, it just got to the point where it was really, really challenging logistically to be that far away from my mom, especially because she was fully wheelchair bound and needed so much help. And ultimately last year I had to make the really hard call, especially since dad started to need more help.

That it was time to move them closer to us here in Richmond, Virginia. And so that's what I did last year and I moved them both to assisted livings close by within 15 minutes of me game changer. As far as logistically keeping up with being able to help your parents spend time with your parents, still take care of, you know, my kids, all these kids I've got.

16-year-old twins and a 13-year-old, and of course they take a ton of time and energy and try to, you know, continue working on my business and being present at home and all of the things, right. This is what the sandwich generation is all about, is trying to juggle raising kids and taking care of parents and living your life and working.

So last year was the hardest year of my life. It really was. It turned out that my mom needed to ultimately move into memory care and she passed away, um, December 19th, which I hadn't shared on the podcast. You might have heard that. If you follow me on social media, I've been writing a lot about this on my personal Facebook page.

Um, and I had announced it via my email newsletter, but I hadn't talked about it here 'cause I haven't created anything new on the podcast in quite a while. And I'm sharing that because one, I know a lot of people who listen to the podcast have been wondering what's going on. Probably haven't had any new episodes in a while.

Um. And two, there's a business reason behind me sharing some of my own story, what's been happening, [00:05:00] um, is because this is something that I think is so relatable to a lot of other women entrepreneurs. A lot of women entrepreneurs are in the sandwich generation. A lot of women entrepreneurs are juggling.

You know, raising a family and taking care of elderly parents, you're also juggling, like I am maybe chronic health conditions. Like we have so much on our plates, and I think it's important for me to share my lived experience because one, I want you to know you're not alone and trying to handle all the things, trying to keep things moving in your life, keep things moving in your business and deal with.

Things kind of outta your control, especially if you're raising kids or taking care of parents. And I want you to know you're not alone. And I also wanna share from my lived experience, like this pressure tested everything that I talk about, I talk here on promote yourself to CEO about building a sustainable business.

And the honest truth is building a sustainable business as a woman entrepreneur. And small business owner as a mom who is working at the same time as a caregiver, as someone with multiple chronic illnesses. Everything that I talk about building a sustainable business has been pressure tested. 'cause last year was rough.

It was the hardest year of my life, but my business did exactly. What I designed it to do. The systems that I have built ran exactly the way they needed to run the team that I have managed everything exactly the way they needed to keep things moving and take care of our clients and make sure that the business kept on keeping on, right.

I put it all on cruise control and that was an option because of all the work I have done and that. I teach with implementing the 90 day CEO operating system into my own business. So I'm really proud of that. It's the one huge silver lining out of a really, really hard year out of grieving my mom, um, is that I know without a doubt everything I talk about is tried and true.

It is pressure tested because my business was able to do exactly what I decided it to do. Okay. We continued to grow. We continue to bring on new clients. We continue to make sales, uh, marketing continued to attract and nurture new potential clients. The team continued to onboard new clients, to take care of all of our existing clients, to offboard people, to renew people.

Like all of that was able to happen even though I had to take such a massive step back. Now, I'll be honest, I didn't hit my revenue goal that I had set at the beginning of 2025 before I realized I was gonna have to. Take over everything for my parents. So I was about a hundred thousand dollars short of my revenue goal, but a hundred thousand dollars short's, not nothing.

I'm not gonna act like it's not nothing. But I was able to continue paying my team. I was able to continue to pay myself and pay my husband, who also works behind the scenes in the business. And if you weren't aware, this is our sole income, like this business is our livelihood. I don't have some other, you know, massive pile of money sitting somewhere that's taking care of the bills when I'm not working.

This business has been our sole income as a family since my husband quit his job in 2014, so 12 years now. This has been our full time source of income has been this business. So I am extremely serious when I say this business did what I designed it to do. I designed it to take care of myself and my family.

I designed it to have the type of flexibility that I needed knowing that. You know, with a disabled parent and parents who had escalating needs, I knew that I was gonna have to have the ability to take a major step back and let the business operate on cruise control, let the team keep the business going, and me step back to only the most essential things that only I could do, which really was working with a handful of clients and managing our calls and the retreats that I do.

But. Stepping back from about my average of 25 hours a week to maybe five hours a week for most of the year. I'm pretty proud of [00:10:00] that. And I share this because I know from talking to so many women entrepreneurs, when they ask me, how are you able to keep it all going? Is your business still running? Is your business still making money?

And I'm like, yeah, it's doing exactly what I designed it to do. This is unusual. For a lot of us and a lot of small businesses cannot handle just a couple weeks of disruption. Must let, uh, must much less a year or more. Right. And this has been. Five years of me having to be on call for everything for my parents, managing my parents' care, and that was only taking, you know, for a long time, maybe 10 or 15 hours a week of my time.

Again, not nothing, but last year, I mean, it was a full-time job. It was a full-time job. Going and checking on my parents every day, calling to make sure they had everything they needed, checking in with their healthcare teams, talking to the doctors, coordinating care, making sure all the medical stuff they needed, ordering stuff, you know, there's just so much, even when your parents are in an assisted living or memory care, it's not like you don't see them.

Like you have to be there to show up and handle all sorts of things. Is, and I want that kind of story to be shared more often because I know that I'm probably getting it a lot earlier in life than a lot of my colleagues. Um, a lot of people don't deal with this stuff in their early forties, but my situation is just a little bit d.

And I know for a lot of women entrepreneurs, this is like their greatest fear is that they have some massive life disruption and their business can't sustain them. And then not only do you have the stress of handling that life disruption, but you're also stressed because it's like, well, where did, how do I keep paying for my life?

How do I afford to keep going? So I know this is a major challenge for a lot of women entrepreneurs, and I'm gonna be talking a lot more about it. This is why here at the CEO Collective, our biggest value is life before business. It's the number one of our values that we share, and that's because I've known my whole life, right?

That having a disabled parent, I knew that this was going to be something I needed to build around. And having kids, I knew that would be something I needed to build around. I needed my business to be built around my life. Not the opposite, but one of the things I hear from so many women entrepreneurs is that when life happens, when they have a major disruption, it feels like everything stops.

And this is the major pain point for a lot of women entrepreneurs in their business. Is that they feel like they just can't get away from the feast or famine trap. If they have to take a break, if they have to pause, if they have to go handle something in their life, everything stops. And this happens even when they feel like they're spending all their time trying to figure out, how do I keep marketing my business?

And there's such a correlation for a lot of people where when you are super busy doing a lot of marketing, being super visible, doing all of the marketing activity, you start to see results, but it still feels fragile. You get this feeling of, I can't take a pause. I can't take a break, I can't rest because the minute I slow down.

Even if it's not to take care of other people, even if it's just to take care of yourself, there is a correlation between how consistently you can market your business and be visible for your business and the ability for your business to bring in that revenue and to pay the bills, and it's a very scary place to be.

It's exhausting. Because you start to feel like you can't take a break and you always have to be on. There is an emotional toll behind this, right? There is a huge emotional weight behind this because then you always feel like you can't take a break, you can't rest, and it's on you. Everything is on your shoulders to keep showing up.

And if you're like me, you're a small business owner with a small but mighty team, or maybe even it's just you. You probably don't have a huge team behind you who can keep all this stuff going for you if you take that break, right? And there's such a massive challenge with this. So I know that if you're listening to this [00:15:00] podcast, you're not new at what you do, like you're a true expert at what you do.

You. Have clients coming to you not only for your experience and your education and your expertise, but because you have a proven track record getting results. But you didn't start your business knowing all of the businessy stuff, right? So you started learning about, well, how do I become a business owner?

How do I make sure I can get clients in the door? How do I keep this business growing? And so I know if you're listening to this podcast, you value self-education. And self-growth because you're listening to my podcast, I am pretty sure you're listening to other podcasts, which is awesome. You're listening to podcasts about business and marketing and sales and all of the things that go into being a business owner.

You're probably buying books. You've probably taken some courses or attended some workshops or gone to some conferences, so you've gotten a lot of input into all the ways. That you can market your business, that you can be visible in your business, that you can grow your business so you know what you should be.

And I'm saying that with the little, you know, air quotes, what you should be doing, you've got a laundry list of things you should be doing right. But it's probably frustrating that it hasn't like clicked into place yet. And you know, it hasn't clicked into place because. You know that if you step back for a couple of weeks, everything will slow down and if it doesn't slow down immediately, it will slow down pretty quickly after that.

That's exhausting. That's not sustainable for a lot of us because the reality is for a lot of us, there are gonna be things that show. That need our time and attention and our businesses must be sustainable enough that we can step away for a couple weeks, if not a couple of months at a time, whether it's to go on a sabbatical, which I've had a lot of clients who've prioritized that over the last few years to take a month off so that they can pursue another project or a.

Creative outlet or travel or just take time to really be present with their families, or you have an emergency come up where you gotta take care of your family, you gotta take care of yourself, you get sick and suddenly you don't have the capacity to do these things. So I know how frustrating it is 'cause it feels like you're on this nonstop hamster wheel that you can't quite get off of.

And the reason is, the reason businesses aren't sustainable, even if you are doing all the things that you should be doing, is because it feels harder when there is no clear strategy underneath it. And that's the gap that I see for so many. Business owners, especially women business owners, is that they have a laundry list of marketing actions that they're taking, but those things are not connected.

There's no clear alignment with all the actions they're taking and building a sustainable business. And without that clarity, without that clear strategy and those clear systems. You are going to be exhausted 'cause you're never able to get off that hamster wheel. We have to get the clarity to understand what the right things are for our business and understand why they are the right things for our business and that is really the key here.

Right. So the disconnect is we all end up with these laundry list of things we should be doing that we hear from all these different places. Each time you listen to a new episode on a podcast or read a new post on social media, or watch a new video or take another course, you get more and more things you should be doing.

But we don't step back and really look at the big picture, the real strategy underneath it, and even stepping back a little bit more. We're not seeing. The big picture of why things do or do not work for our businesses, because we rarely have the context of what our business actually needs. So the truth is not all businesses grow the same way.

Not all businesses grow the same way. There's so many different business models out there, and the worst thing we can do is try to force someone else's model on our business when they're completely different. [00:20:00] That is like trying to go put on someone else's jeans and hoping they're gonna fit you perfectly.

It's just not gonna happen. Right? Sisterhood of the traveling pants. It's not a business concept. Why would we try to squeeze ourselves into someone else's business model and not think about the context and the nuance and discern between what they're telling you is a great marketing idea or a great way to grow your business and what actually works for us.

So there's really two major things here that I want you to think about. Two major differences. In business models, and I'm gonna say this is based on what I hear out there in the world as far as the advice we get, right? So a lot of the advice we are getting is based on high volume businesses. These are business models that are built on high volume and high transactions.

So a lot of sales coming in, high volume of sales. This could be. Hundreds or thousands or tens of thousands of sales every single month, every single year, and often these super high volume businesses are selling things, products that are lower price point. So think about this e-commerce. Information, products, apps, a lot of the tech startups out there, even if you think about high volume, like any mass retail, those are all high volume businesses.

They depend on being able to go out there and make a lot of sales in order to generate revenue. It's a very different model from my model. And I'm sure from your model, because a lot of our businesses are highly relational businesses. We are not high volume businesses. We are highly relational businesses.

We are more boutique style businesses. We are your regular, everyday day small business. And in these highly relational, high trust businesses, we don't need thousands of clients a year. In fact, thousands of clients a year would be really challenging, right? We don't have a massive team to handle that many people.

That is not our business model. You might only need 10 clients a year. You might only need 20 or 50 or a hundred, but even a hundred. It is kind of on the high end for a lot of us as far as the volume of clients we're working with at a time for a lot of our regular, everyday small businesses, we are selling programs.

We are selling services, and whether they are done for you or done with you or a hybrid, these are generally a higher price point, right? These are going to be services where we are working closely. With our clients, you know the people who are paying you, they're not just, uh, another transaction in your Stripe account, like you actually know their name.

You've actually communicated with them. For us, we are generally gonna be running coaching, consulting, service businesses, creative services businesses. More boutique style businesses, maybe health and wellness. I have a lot of different types of businesses that work with us at the CEO Collective, but the through line for most of them is that they know their clients and their businesses are built on relationships.

So why is this so important? Because most of the advice out there in the business space assumes that you have the first model, that you have a high volume business even when you're running the second. And that is a really dangerous and confusing place for us. Because high volume businesses require high volume marketing, and I want you to think about this.

Think about the high volume businesses that you interact with on a regular basis, whether it is a big, massive company or a personal brand who is still a high volume business. Those businesses require huge content teams to keep up with the volume of marketing. So a great example of this is, let's think about Gary V and I feel [00:25:00] fine talking about him because I'm not calling him out or anything.

He's, he's great. I think Gary's great. I love a lot of his advice, but. His model is high volume, right? His business model is around him growing this massive agency. In addition to all the other things that he's doing. He's selling books and he has an entire content team. And I remember realizing this years, years, and years ago when he made this shift to the big content team.

I was like, oh my gosh. He has full-time people with cameras and microphones just following him around every day because yes, Gary makes some of his own content, but his team is there all the time. And I think this is really important for us to understand because even the people that we're following.

That are the quote unquote business experts out there right now. Um, a lot of them might have higher volume businesses now, but they did not start that way. And so they're often sharing what they're doing now, strategies they're doing now, and those tips and tricks and tactics are incredibly difficult for us to pull off sustainably without the massive team they have behind them Now.

Right, so you have to consider the source. When you are getting this type of information about how to grow your business, you have to consider the context and discern what actually makes sense for where you are right now. There might be a point maybe if your goal is to grow a multimillion dollar business.

Then there will be a point where you'll have maybe that content team where you'll have the resources to do a higher volume of marketing, but if you are earlier on in the journey, or your revenue is under a million dollars a year, then. Chances are you don't have the capacity, you don't have the team to do high volume marketing in a sustainable way.

To do it as a one woman show is pretty much impossible. So it's not your fault, right? It's not your fault. It is this disconnect where we're hearing tips and tricks and tactics from businesses that have massive resources and teams. Behind them. And we have to really understand what works right now for your business, where it currently is, the resources, the capacity that you have to grow right now.

But the good news is highly relational businesses don't need you to always be on. They don't need you to turn into an influencer. And I think there has been this huge misunderstanding in, in the business space that if you are running a small business, you have to be a personal brand, which a lot of us are, but you don't have to be.

And the other part of that is that you now have to be the influencer who is constantly sharing everything, every part of your day, every part of your life. And that is not realistic or sustainable. And I know most of us honestly don't want that. Like I don't wanna share every single part of my life.

There are parts of my life that are for me that are private, and I don't want to have to talk about everything. I want to have my life be my life for me and my family. Right. And I know you're probably listening and going, yeah, I don't wanna have to share. Every little detail about what's going on with my kids or the challenges I'm having in my marriage or the whatever it is that you wanna keep private, right?

So there has been this disconnect that has told us we have to be something we're not. We all have to turn into influencers and content creators and be on this hamster wheel of constantly marketing ourselves. Doing this laundry list of tasks that we should be doing and that we always have to be on.

Always posting, always creating something new. And I want you to know that's not true. If you have a highly relational business, a high trust business where you don't need thousands of clients, you actually know who your clients are. You are doing more high touch, high trust services where you're doing coaching, consulting, creative work, service based work, anything like that, more high touch work with your clients.

Then you just need a real strategy and [00:30:00] you need your marketing to align with what actually works for you and your business. So you're not behind, you're not behind, you're not broken. It's just that we are all caught up in this trying to force a square peg in a round hole, trying to force advice, trying to force tips, tricks and tactics that just don't fit the business that we're actually building right now.

It feels hard because the strategy doesn't match the business, not because you're bad at marketing. So that's what we're diving into in this series. Uncomplicate Your Marketing. I'm gonna be talking about why all of the marketing tips, tricks and tactics just feel so mismatched right now because they do.

They just feel like God, is there something else I have to do that I should be doing? There's so much already on my list. This is getting insane. It is insane. Like it doesn't fit us, it doesn't fit, it's not sustainable. We're gonna talk about the myths that make it all harder than it needs to be. So you can see those coming and have more context and nuance to think through as you are making these strategic decisions for your business.

And we're gonna talk about how to simplify everything. Because the reality is when you have a real strategy, it can be really simple and your business will still grow, and you will have the sustainability to be able to step away for a few weeks at a time, for a month at a time, and know that you're still bringing in new clients.

That's a game changer. I'm here to tell you, it is a game changer to know. That I can step away and my business will run itself. I love that and I want more of us to have that. So I want you to think for a minute and sit with this question and maybe pop over to Instagram and share your thoughts on this.

Where in your marketing are you working really hard, spending a lot of time in this area. But it feels uncertain or unstable. Or unsustainable. I think this is a really important question. We need to ask ourselves. We need to really question everything that we're doing, and if it doesn't help you feel more certain about your business and more sustainable.

About your business, then it might not be the right strategy for you. So over the next few episodes this month, I'm gonna break down all of these things. We're gonna talk about why it happens and how to fix it, and ultimately how to have a smarter, simpler, more sustainable strategy that doesn't require you to do more.

It just requires you to do less with more focus. So make sure you have subscribed to the podcast so that you don't miss what's coming next. If you like this episode, please make sure you rate and review, and if you want to connect with me, come on over to Instagram. I'm pretty active over there. Message me at Rachel dot Cook.

I would love to hear your insights or ahas from this episode.