
There’s a moment in business growth that’s hard to name, but you feel it everywhere. Your offers still sell. Your systems still work. From the outside, nothing looks broken at first. And yet, showing up feels heavy. Your confidence wanes as you start to question everything… and that’s when things start to break. Your business feels harder to work within because your brand message no longer aligns with you as the founder.
Writing content takes more effort than it used to. Selling feels awkward, even though you know your work delivers real results. You might even find yourself wondering, quietly, Do I actually want to keep doing this?
This is the point where most founders assume they need a new offer. Or a rebrand. Or a completely new direction for the entire business.
But in my experience—both personally and with clients—that’s rarely the real issue.
More often, the problem is simpler and deeper at the same time: Your brand message is still speaking for a version of you that no longer exists.
Business is human, and humans grow, so your story naturally needs to grow too.

In this post, I cover:
If you’d prefer to watch or listen, tune into the video: Signs it’s time to shift your brand messaging strategy and tell a new story.
As personal brands, we don’t always realize how easily we keep ourselves small.
We squeeze ourselves into familiar boxes because they used to fit. A certain way of doing things worked well once, so we keep repeating it… even when it no longer reflects who we are, how we think, or the depth of work we’re actually doing.
Over the last year, I had more space than ever in my business. And with that space came an uncomfortable realization: something had to give in order to build the next version.
My business had evolved. I had evolved.
But my brand messaging strategy hadn’t.
When you grow and your messaging doesn’t, it starts to feel like you’re performing a role you’ve already outgrown. You’re overqualified for the performance, and the words you’re using can’t keep up.
That disconnect shows up as:
That urge is understandable. But it’s also usually pointing you in the wrong direction. Instead of starting fires everywhere, let’s get to the root cause so you can realign your brand strategy with your personal goals, vision, and direction.
Before we go any further, we need to pause in the semantics because these terms are often used interchangeably, and that confusion causes a lot of unnecessary stress.
Your brand strategy is the growth plan for your business including how you want to be perceived by customers. It’s everything—your mission, vision, audience insights, logo, colours, visuals, and messaging.
Your brand message is the core story you’re telling about:
It’s the through line that connects all the dots. Typically a single sentence you can say and people will get it. For me, that message is helping good people make more money online so they can live their lives on their terms.
Your brand messaging is how that story shows up everywhere—your website, content, offers, sales conversations, and internal decisions. It’s the pillar perspectives that support your through line.
For me, that looks like:
There’s more, but this should give you an idea to start. It’s the supporting brand messaging that you use to show up on your marketing channels, website, and pipeline.
Your messaging strategy is the intentional plan that connects that story to growth: how it reaches the right people, attracts the right buyers, and supports your goals.
Think bigger picture direction of what key messages you need to communicate, where, when, and how.
When something feels off, founders often jump straight to tactics:
But if the story itself no longer fits, no amount of tactical optimization will fix the friction. So we step back to basics and realign the brand message first to meet you where you are now.
Yes, messaging is absolutely a marketing task. But it’s also a self-awareness task for founders and freelancers. As much as we try to detach ourselves from the business brand, it’s an extension of our vision therefore feels close.
When done well, brand messaging requires you to look honestly at:
Of course it’s how the answers to those questions reflect into the business, but it starts with you. So no wonder things feel off when you’re disconnected from the brand message.
It’s also just as importantly how you want people to feel when they interact with your brand. Branding is really about perception—it’s what other people think of you, not a tangible product like a logo. Elements like logos and colours and brand messaging shape that perception, but the weight lives in other people’s perspective of you.
Historically, clients come to me for all the marketing work:
That’s all real, necessary work that normally you’d have a marketing team manage or you hire out. But with founder-led businesses and personal brands, there’s always another layer.
We end up talking about:
Over the years, clients have told me my intake process feels more like therapy than marketing. I’ve had people cry in kickoff calls. I always say, “What happens in the Zoom room stays in the Zoom room,” because messaging work is that personal.
When someone asks you to unpack the stories that shaped you and turn them into something buyers can resonate with, it feels personal.
Feeling resistance doesn’t mean you’re doing it wrong. Feeling emotional isn’t a red flag.
It’s proof there’s integrity in the work you’re doing, which already sets you apart from the competition.
For me, the first sign wasn’t that things weren’t working. It was that I couldn’t get behind the words anymore. The work I was doing felt so far different from the work I was selling. Those 2 lists above show the divide. Outwardly, I was talking about marketing and funnels. With clients, we were digging into their personal growth and philosophies.
I struggled to make content. I didn’t feel like selling—even as someone who thought she’d already worked through the mindset blocks around showing up and talking about her work.
Something felt off.
I felt complacent, like I was moving through the motions because this is what works, instead of showing up with intention and expressing what I actually believe. Instead of showing my full self and the full transformation I facilitate for clients.
There was a disconnect between:
I know so many founders hit this point, especially during major life shifts. I see it often with the moms I work with—pregnancy and postpartum are massive identity shifts, layered on top of running a business.
When your internal reality changes, your brand message has to change too.
If you’re unsure whether this is what you’re experiencing, here are the clearest signs your messaging needs to evolve.
That “off” feeling is usually misalignment. You’re struggling to show up, to sell, or to feel excited about what you’re building even though nothing is technically broken.
Your identity expanded, but your messaging stayed the same. You feel stuck in offers or roles that no longer reflect your capacity or skill.
You might still be selling copywriting packages when clients rely on you as a strategist. You downplay your role saying things like “I’m just a copywriter” even when you’re doing much more.
Everyone is selling the same promise. You know your approach is different, but you don’t have language for it yet.
This is the moment to sell your method, not just your offer.
A $2k buyer and a $10k buyer are not the same person. When your rates and audience evolve, your messaging must evolve with them.
The point to remember here is that if your messaging feels too small, it’s because you’ve gotten bigger. It’s time for you to expand.
I shared this post on LinkedIn, but it deserves a place here too.
Good messaging stalls when it’s built for who you were—not who you need to be next.
Here’s what needs to change for 2026.
A lot of founders assume their messaging is “off” when:
So they start tweaking. Hooks, CTAs, formats… even pivoting to new offers. But no viral hook is going to save messaging that no longer matches the depth of your audience.
Your offer isn’t unclear—your messaging is unfinished. It creates agreement, not actions. They nod along because they get it, but take your quick tip and go back to tweaking on their own. Not choosing you. Here’s what to do when this happens to you.
The old way:
“I help women entrepreneurs”
“I help service providers”
“I help founders in X industry”
2026 reality: You’re not talking to a broad market. You’re talking to one person in one moment. If your reader can’t see themselves, they won’t move.
Industry-based niches used to be enough. Now it matters more where someone is stuck, what decision they’re avoiding, and what phase they’re transitioning out of. Mirror their situation and headspace back to them, so they recognize themselves.
Messaging converts when it meets someone mid-decision. That’s deeper than demographics.
Most “helpful” and “valuable” messaging doesn’t work in the way you want it to. Information should be free, but the solution for you to close more isn’t by teaching more for the sake of adding more value.
Instead, you need to show where information isn’t enough.
At a certain level, the issue isn’t better copy, more funnels, or more content. It’s realizing that what worked before can’t carry the next version of you.
Your messaging has to reflect how you think, decide, and lead now. Otherwise you’ll keep attracting people from your old level.
That’s why your messaging that used to work isn’t anymore.
2026 messaging isn’t louder, or more, or about keeping up with trends. You just need to be more clear and more decisive of who you’re for… and who you’re not for.
You already know the shifts you need to make after reading this. Next, you need to acknowledge who you are now, then actually follow through.
There’s a reason messaging shifts feel so uncomfortable.
Behavioral science shows us that humans make decisions based on identity first, logic second. Your buyers do this. You do this. We all do.
Frameworks that support this:
As people, our stories change. As founders, our brand stories need to change too. If your identity evolves, your behavior evolves. And if your behavior evolves, your messaging has to evolve with it.
That’s why this work isn’t about “better copy.” It’s about accepting that you’re not the same person who wrote your last website. Professionalism doesn’t come from blazers or academic language. It comes from integrity, follow-through, results, and how you treat people.
Business is human—because you are human.
If brand strategy is the highest view of a business’ direction, the messaging strategy is the part of the story that focuses on words. But how should a brand speak? What’s the tone of voice? What are use case examples? That’s where brand personality and brand voice come into play.
A brand messaging strategy needs to outline the brand’s personality and brand voice. These are essentially the rules of engagement. The language style and tone. How your business communicates. It’s less about the what—the specific messages—and more about the how. How you sound. Common phrases. Off-limits words. All those details are helpful to nail down so you know what’s on brand and off brand.
Your brand personality will also help you connect better with your audience. If you look at business as being human, then we know humans naturally gravitate towards some humans more than others. Often that’s because of shared values, interests, and how we show up in the world. Your brand message can model this too.
Many founders reach this point of feeling off and assume they need to start over.
If it’s not working, you burn it all down… right?
In my experience, personally and with clients, that instinct usually isn’t true. If your mission is grounded, it doesn’t disappear when you outgrow your message. It guides you through the messy middle.
Most of the time, the changes required aren’t massive. They’re small, intentional shifts that bring everything back into alignment.
You’ll find the through-line. But you need clarity on your long term vision to get back to there. That’s why I have most clients kick-off working together with deep reflection on their vision for themselves and their business. We get granular into how they want to spend their days, who they want to work with, what type of work are they doing. When your vision is solid, it can guide you through the messy parts of life.
A common theme with the new moms or soon to be moms that I work with is that they feel this “off” feeling when they’re early postpartum. That’s normal. If you combine business growth with personal growth with the natural experience of matrascence, of course you’re going to feel disconnected from your business.
Especially if you’re the ex-Girlboss type now navigating how to run a business with littles around. Your priorities have shifted out of necessity and your life looks totally different.
But in this season, with all the clients I’ve worked with, the best plan forward isn’t always to burn things down. Often it’s just to keep making progress towards that vision you wrote down before. Even if it feels off right now, you’ll find your way back to it and thank yourself for the small steps forward even when you were focused elsewhere.
After months of unraveling and reflection, I felt reinvigorated by my business again.
I feel clear. Grounded. Aligned with the work I’m actually doing—not the work I used to do. So much is different, but also so much is the same. I catch myself thinking multiple times a day how lucky I am. How much gratitude I feel for the direction I’m going and the work I’m doing now. Everything I said I wanted is already here—now we lean in to grow.
The moral of the story: Your brand message doesn’t disappear when you outgrow it. It evolves with you.
If you’re realizing your brand messaging has fallen behind your growth, you don’t have to unpack this alone! I created Billie, my AI messaging strategist for this exact moment. She’s trained to ask the deep questions, extract what’s changed, and help you articulate the next evolution of your messaging strategy.
You’ve built something real. You’re allowed to let it evolve with you.
Billie is available 24/7 to help you sort through the mess and get back on track with your brand message. Learn more about Billie and get her help here.

When founders feel misaligned, they often chase tactics. But if your internal story has changed, your external story must change first, or no strategy will stick.
When your sense of who you are evolves, continuing to communicate from an old identity creates friction. The discomfort isn’t a flaw—it’s a signal.
You’ve grown in skill, perspective, and depth. Using beginner language for advanced work creates internal resistance and external confusion.
Past success doesn’t obligate you to stay frozen there. Evolution is part of sustainable leadership.
Sameness signals it’s time to articulate how you do what you do, not just what you deliver.
These shifts aren’t about trends. They’re about alignment.
Brand messaging is the language system that communicates who you are, what you stand for, and why your work matters across your website, content, offers, and sales conversations.
It’s not just taglines or clever copy. It’s the through-line that connects your values, identity, and expertise to how buyers understand you. When your brand messaging is aligned, everything feels easier to say. When it’s off, even “good” marketing feels wrong.
Your brand strategy is the bigger-picture plan including all aspects of the business’ presentation. It defines your positioning, audience, goals, visuals, and how you intend to grow.
Your brand messaging is how that strategy becomes human and visible through a clear story.
Strategy answers questions like:
Messaging answers:
You can have a solid brand strategy and still struggle if your messaging no longer fits who you are.
Your brand message is the core story at the heart of your business. It’s the essence of what you believe, why you exist, and what problem you’re here to solve.
Your brand messaging is how that message shows up everywhere:
Think of the brand message as the foundation, and brand messaging as the system built on top of it.
Brand messaging feels personal because it is. For founder-led businesses and personal brands, your identity is deeply connected to your work. Messaging asks you to articulate:
That’s why resistance, emotion, or discomfort often show up during messaging work. It’s not a sign something’s wrong… it’s a sign the work actually matters.
Most people expect a messaging problem to look like poor results.
In reality, it usually looks like:
If your messaging feels too small, it’s often because you’ve grown.
Not necessarily. A messaging shift doesn’t always mean new visuals, a new name, or burning everything down. In fact, most of the time it’s about realignment, not reinvention.
Your mission often stays the same. Your values usually stay the same.
What changes is how you articulate your work now. There’s more clarity, depth, and ownership. A new take on the stories that shaped you and how you show up now.
Personal branding is how you show up as the face of the business—your voice, values, perspective, and lived experience.
Your personal brand and your brand messaging should reinforce each other. When they’re out of sync, you’ll feel like you’re performing instead of leading.
Strong personal branding doesn’t mean oversharing. It means communicating from a place that feels true, grounded, and integrated with the work you actually do.
Because humans don’t make decisions based on logic alone—they make them based on identity.
When your internal identity shifts but your external message doesn’t, your behavior changes:
Your buyers feel that disconnect too. It’s normal for outdated messaging to stop working for any type of business regardless of how integrated the founder is with the daily operations.
Yes. And most of the time, that’s exactly what’s needed.
Messaging evolution often looks like:
Small shifts, made intentionally, can restore clarity and momentum.
Start with reflection, not tactics. Before you rewrite anything, get clear on:
From there, tools like a messaging playbook or structured brand brief can help you translate that clarity into a messaging strategy that actually fits.
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