The #1 Reason Your Marketing Isn’t Converting

Let’s be real—marketing your coaching business can feel like pushing a boulder uphill.

You’re showing up, you’re posting content, maybe even batching it in advance. You’re trying all the tricks, following the formulas, maybe even joining a dozen Facebook groups or grabbing every “freebie strategy” you can get your hands on.

But despite all that effort, the results just aren’t there.

And here’s the hard truth most people won’t say out loud:

It’s not because you’re lazy.
It’s not because you’re missing the latest tool.
It’s not even that your strategy is broken.

It’s because of something I call Doubts Over Data.

What Is Doubts Over Data?

Doubts over data means your self-doubt is running the show. Your fear of whether your content will “work” is taking up more of your mental bandwidth than simply putting out the best message you can, right now, and letting the data teach you what’s next.

We obsess. We tweak. We hesitate.
And while we’re spinning in that fear loop, we’re missing the opportunity to practice. To improve. To connect.

As my mentor Brendan Burchard says:
“We’re not afraid to change. We’re afraid to be seen starting small.”

And ohhh is that ever true for coaches. We look at our numbers and instantly feel behind. We compare ourselves to someone else’s 6-figure funnel or perfectly lit Instagram Story and forget:

✨ Everyone starts with a first follower.

You’re Judging the Ones Who Already Showed Up

This might sting a bit, but it needs to be said:

A lot of coaches are dismissive of their early audience.

They post something… someone actually likes it… and instead of building that relationship, they wait for someone “more important” or “more ideal” to show up.

That mindset? It’s costing you.

You’re building a service-based business. Which means relationships are everything. And if you can’t value the first few people who are raising their hands, how are you going to hold space for the hundreds who come later?

You don’t need a massive following to build momentum.
You need connection—and that starts by showing up now, imperfectly, and learning as you go.

The Fear of Telling

Another huge block I see is what I call the Fear of Telling.

It’s not just fear of selling (though that’s real too).
It’s the fear of telling—telling people what you do, what you know, what you believe, and what they need to hear.

Because what if you get it wrong?
What if someone disagrees?
What if you get rejected?

And so you stay vague. You stay silent. You wait.

But here’s the thing: authenticity isn’t just about vulnerability.
It’s about leadership. It’s about telling the truth and telling the path.

People don’t just want your story—they want to know what happened after. They want to know the steps. The insight. The lesson.

If you don’t tell them, they won’t trust you to guide them. Period.

You’re Skeptical of Your Own Value

This one breaks my heart, because I’ve seen it in hundreds of coaches:
Deep down, they’re not sold on what they do.

They wonder if what they’ve learned is really good enough to help someone. They second-guess their pricing, their experience, their value.

This isn’t a strategy issue—it’s a personal development issue.

If you’re skeptical of the transformation you offer, your audience will feel that. Confidence comes from competence—but that means you need to do the work to build and own that competence.

One of the best things I did for my confidence wasn’t more marketing—it was practicing my craft. I got feedback. I built muscle. And I learned to integrate my wins instead of skipping right over them in search of perfection.

Confidence is something you stack. One win, one action, one moment at a time.

You’re Imitating Instead of Leading

Let’s be honest—sometimes it feels safer to copy what other coaches are doing.

You see someone crushing it on TikTok or launching a new program and think, “Maybe I should do that too…”

But you didn’t become a coach to follow trends.
You did it to lead.

So yes, draw inspiration. Learn what works. But bring it back to you—your message, your mission, your audience. Otherwise, your content becomes a watered-down version of someone else’s success story.

And nobody’s hiring you for that.

You Feel Entitled to the Sale

This one’s tricky—and honestly, I blame the industry a bit.

There’s this myth that once you get certified, launch a website, or post a few times… the clients should just roll in.

But here’s the reality:
Most people don’t even know what coaching is.
They don’t understand the transformation, the ROI, or the process.

And if they don’t get it, they’re not buying it.

Sales is a relationship.
It’s education.
It’s leadership.

You have to be willing to explain, to listen, to build trust—before you ever ask for the sale.

The Real Work? It’s Showing Up Anyway.

Every coach I know who’s built a business they love had to move through this.

They didn’t wait until it was perfect.
They didn’t wait for the numbers to look good.
They didn’t wait for “important” people to follow them.

They chose data over doubt.
They practiced. They told the truth. They led with service.

And you can too.

Let this be your reminder: you don’t need to be perfect to make an impact.
You just need to show up and do what matters.

And hey—if this resonated with you? DM me “DWM” and I’ll personally invite you to our Clients Over Chaos community.

You’re not doing this alone—and you’re more ready than you think.

Chapter List:

00:00 Understanding Marketing Challenges for Coaches

03:02 Overcoming Doubts and Fears in Marketing

05:24 The Importance of Authenticity and Value

08:23 Building Confidence and Competence

10:57 Navigating Competition and Sales Mindset

Full Transcript

Amanda Kaufman (00:00)

Doubts over data. So what is that? Well, it means that your doubt about whether your marketing is gonna work or not is occupying more of your mental bandwidth, more of your obsessive time, more of your planning than

putting together the best answer that you have right now and putting it out there.

Today we're talking about what makes marketing so hard for coaches. You know, we're gonna talk about some of the biggest challenges that most coaches have when it comes to marketing their business and most importantly, what we can do about it instead. I am broadcasting live

for our clients over chaos community.

I'm really excited about today because I've been getting a lot of questions from my community about what is the most effective place to put my time when I'm marketing my business. so what we're going to do today is we're going to unpack five of the top ways that people kind of encounter that struggle, we'll say, with marketing or even if you are marketing and you're posting really regularly.

why you may not be seeing the kinds of results you hoped for by now. And I want to be able to leave you with an ability to diagnose what you are doing today and what your opportunities might be for tomorrow. And also to get past this perfectionism streak that I am seeing across a lot of service-based businesses. You know, in 2025, we've got to let the perfectionism go. We've got to let it just...

go so that we can do good things that can become great things through deliberate practice, deliberate execution and deliberate know-how. So if this is super helpful for you, let me know and I'll make sure to do more trainings like this. Let's see. So today is a holiday as well. So I'm not expecting a ton of people to come on today, but I think that that's actually the first thing.

How many times do we work up the nerve to write the post, to post the blog, to join the social network? We work up that nerve to do the thing, and then we're afraid that because we won't be seen immediately and getting that instant feedback from people that we're doing things so perfectly. I just realized I don't even have my microphone on. that's funny.

He don't let the perfect be the enemy of the good. OK, so now we're broadcasting live and you can actually hear me and hey, we're off to the races. OK, so why does marketing content actually fail for most coaches, even if they're posting like a maniac, even if they're joining a lot of Facebook groups, even if they've downloaded all the posting schedules and they're doing the thing. Why do they not see more success over the long term?

Well, this is a really good question and it matters because I know that most of you that would be watching this and watching this on replay, you want to manage your time. You want to be able to have a business that pays you whether you are sitting there to receive the payment or not. You're wanting a business that can be automated. And here's the truth. We've got to be able to walk before we can run. So the first...

The first thing that I noticed that a lot of people really struggle with when it comes to the marketing piece is doubts over data. Doubts over data. So what is that? What does that mean, doubts over data? Well, it means that your doubt about whether your marketing is gonna work or not is occupying more of your mental bandwidth, more of your obsessive time, more of your planning than

putting together the best answer that you have right now and putting it out there.

know, Brendan Burchard often says, we're not afraid to change, we're afraid to be seen starting small. And what he's talking about is that people are generally more afraid of the opinions that other people have of them. And we take so many different markers of whether somebody is gonna think that we're cool or not, you know, it's like,

our physical appearance, do we look like the cover of a cosmopolitan magazine? People looking left and right and seeing whether there's hundreds of people tuned in or not. You know, we look at these numbers and we compare to people that we admire. And when we do that, we're never, I'm noticing, we rarely pay attention to how long have they been compounding their success.

So what do I mean by that? Well, there's a first for everything. There's a first follower for everything. And if you're not willing to put yourself out there to get the first follower, if you're just, this is what I really see most of the time. Most of the time coaches are really dismissive of their first followers. They have judgment for the people that are actually following them. And so because of that judgment, the coach doesn't.

reach out that coach doesn't try to build a relationship with anybody. They just keep playing, hoping that someone more important and more interesting is going to come along their feed. And I think that a lot of coaches are getting exactly what they deserve because that's kind of jerkish behavior. Don't you think? I mean, let me know. You know, the doubts over data problem is pretty much people thinking about doing the thing instead of just doing the thing.

You know, when I was going live just this morning and I'm talking about this particular topic, I was like, I don't know if this is gonna resonate or not. I had doubts. I had lots of doubts about it. And my data is showing that not a lot of people have really like tuned in yet. And that's okay. That's okay. I still go live on Mondays. Why do I do it? Because I want to progress my practice. I want to progress my ability to deliver value. And I also know that somebody catching this on the replay,

may just decide to tune in next Monday at 9 a.m. or join the Clients Over Chaos community to watch the replays at their discretion. I know that success does not always look like immediate gratification. And I know this because I have data. I have the data. I know that a large percentage of people who receive emails from me open them. I know that a significant number of people will show up to live events when I host the live events when they're more formalized.

I already know that most people don't make time for live streams. Live streams are a lot out of fashion compared to what they were doing. So what the heck am I doing? Like, why am I even here? Well, because I also know, and there's other pieces of data here, I know that the more that I speak live, the better I get at it. And that piece of data, I think, really matters. So choose your data over your doubts.

The second big piece of why people's marketing is not as effective as they could be is what I call the fear of telling. So a lot of people will tell you that people have a fear of selling, but I would say that most churches that I talk to, they actually have a fear of telling. They have a fear of telling everyone that they want to be a coach. They have a fear of telling everyone what they know. They have a fear that they're gonna tell.

They're going to tell the wrong thing and then they're going to get rejected for it. It's just this fear of opening your mouth. And when you're not telling your truth, when you're not telling people the answers to common questions that they have, when you're not telling them what the pitfalls and the risks are of what they're doing, this fear of telling, I think, really hurts a lot of people's marketing. And in fact, people know this.

They know this because we're always talking about authenticity and we're always talking about being more expressive online. But the problem is, is that we only seem to in practice apply it to those really dramatic stories that are personal in nature. So when you're talking about your personal struggle and your pain point and your, your issues and your challenges, like people kind of share the negative experience that they have, but

That's not enough. You've got to tell people what you did about it. You got to tell people that it turned out okay, that you're still here. You got to tell people that there were mistakes that you made, but you also need to tell them what you did to overcome the challenge. People want to hear what the path to success looks like. And if you don't tell them, then they don't trust you.

They don't trust you to guide them in a coaching session. They don't trust you to follow a curriculum in your course. They don't trust you to join your membership because you're not telling them anything that they need to know to be able to do it. So the fear of telling, okay. The third thing, and this is really, really huge and kind of sad, but it's the skepticism of the value that you're offering. So I've worked really closely with hundreds of coaches at this point on their

positioning and I would say that the number one issue is actually the skepticism that what they have learned is going to help somebody else. That what they have learned is good enough for somebody else to want to pay for it. That what they have what they've what they've experienced has value to other people. This skepticism, this cynicism is I think rooted in a general

in a general avoidance of personal development. That's what I think it is. I think it is. Because when I think back to my own experiences with feeling the most cynical, the most skeptical, the most doubtful about my own value, I hadn't done the work. I hadn't done the journaling. I hadn't learned from mentors. I hadn't addressed what my mindset was supposed to be. I wasn't creating space for it.

I just had kind of, well, it's gonna be the fifth thing that I talk about. But the point is is that if you are skeptical of the value that you offer relative to what other people could offer them, then you're sunk before you even started. So the other reason why we feel really skeptical about the value is because we haven't had the validation of other people telling us that it is valuable yet.

So one of the most important things that I did in my journey is I got a coaching certification. Now, if you've paid any attention, I've talked to you about some of the problematic things that the coaching industry does to trick you into needing to have way more qualification than you need. However, my first coaching certification, I will tell you that the practice that I got in that certification and the validation I received from the people who were receiving my coaching in that environment,

was just like one more layer of confidence because I had developed a level of competence. There's something called the competence confidence loop. And if you develop more skill, more competence, more ability, more capability, then naturally your results are gonna be a little better than they were before you developed that competence. And when your results are a little better than they were before, you tend to be a little more confident.

And I really love this idea of confidence stacking, that the more that you do something and the more that you get these positive results. Now, here's a really key thing. It's a high performance coach, me to you. It's so important to integrate your success. know, so part of your skepticism in your own value that you're bringing to the marketplace is rooted in this, rooted in this lack of integration.

of your progress and lack of integration of your intentionality around what you did and then the result that you actually achieved from that. And boy boy, I can do a whole live based on that, but essentially a lot of people end up feeling really...

they end up feeling really down on themselves even though they don't deserve it because you're operating more from a place of perfectionism. You're operating more from a place of it could be better and it always could be better. Oh my God, it could always be better. I was actually watching a little clip from one of my mentors this morning and I was thinking to myself, I'm like, hey, he could...

position the camera a little higher. He could have had better lighting. He might have wore a nicer outfit. you know, I, I, wasn't judging him. I was observing that there were all of these opportunities to enhance the performance that that particular day, that particular time he didn't do those things. And I was like, wow, if somebody who's like a literal world, world's best performer can show up with a level of casual to the task sometimes, right? What if you gave yourself more permission to do the same thing?

What if you give yourself permission to do great and good instead of always like holding out for this perfection thing? And what if you integrated the good thing that you did? What if, what if that happened? Okay, so thing number four is actually you're intimidated by your competition and you keep copying them. This drives me really wackadoo because...

One of the reasons you're drawn to being an entrepreneur in the first place and to coach other people is you know what it's like to break out of molds. You know what it's like to break past these boundaries. But what happens is we break past the boundary. We say, I'm going to do the thing. I'm going to post the thing. I'm going to host the thing. I'm going to do the thing. And we do it like the one time. And then we tend to snap back to our standards. We tend to snap back to what

we already knew in the past. Fifth thing, fifth thing is we feel entitled to a sale. And I see this in the coaching industry and I think it's the industry's fault, but also just society, right? We think that because we got a certification or two in my case, that people should automatically be excited to compensate us for what we know.

And the truth is, that most people just don't know what coaching is. They don't know that coaching is an option. They don't realize the return on the investment in coaching. I read a study recently that showed that over 70 % of people who participate in the study, over 75 % of the people surveyed who were

executives who received coaching said that the benefit of the coaching far outweighed the investment in the coaching. 70 % of the people who went through it felt that the return on their investment was way greater than the investment that they made. And yet a lot of people really still feel very entitled to the sale. And the thing that I've realized, and I realized very quickly, is that I need to slow down.

and understand the challenges and dilemmas that the person that I want to serve is facing so that I can invite them to the next step that's going to make the big impact. Well, thank you so much for joining me today. Those five things I'm just going to recap. Doubts over data. So get data, get data, right? Get information. And if you want more details on like what data, how do I get the data, all those kinds of things, be sure to join my clients over at Chaos Community.

or even reach out to me just directly and let's have a chat about what data matters with your content based on where you are in your journey. The fear of telling. Look, I'm the first to tell you that this is not easy, but it's possible. And when you have structure and you have a plan, your likelihood of success goes up exponentially compared to winging it. So definitely...

Don't be afraid of telling people in your respective space the truth about the challenge, but also the truth about the possibility, right? You gotta balance that out. The third thing is the skepticism and the value. Hey, you are your first customer. You've gotta be sold on what it is that you do, and if what you do is amazing for the value, then you're gonna feel great about selling it. If you feel like it's not a great use of value or it's not...

not a great use of somebody's money, then you you got to fix that and you've got to you've got to be developing the value. If you're intimidated by your competition, right, really examine why like and also I would say a good stoic perspective here is just what's in your control and what's not in your control, right? Or what's in your immediate control? What's in what's in your longer term control? What's in your control? Because the only thing that you can actually affect right now is the habits.

and your decisions that you're making today, right? Wishing that you were Cindy Crawford or wishing that you were Jim Carrey or wishing that you were Ellen or Oprah or something like that. It's useful in the visioning stage, but then after that, you've got to take things down to the level of your day and you've got to make decisions that are new and different for you. And then finally, be careful of being entitled to the sale. Sales is a communication, it's a connection, it's a relationship.

When people trust you and they know that you are likely to provide them with a thing that has been missing in their life, they will hire you, they will pay you. But never be entitled to the sale. Don't be above explaining what you do. Don't be above exploring the conversation with your people because when you do that, your content is gonna connect in a much deeper way and you're gonna find greater success.

All right, y'all, I hope you love this. And like I said, just say DWM if you're not in the Clients Over Chaos community already. We're gonna make this replay available to everyone in the Clients Over Chaos group. And until then, I will see you next week. And my name is Amanda and I love helping coaches to have businesses they love.