What if the reason your business feels stuck has nothing to do with strategy, and everything to do with one question you keep asking yourself?
I want to tell you about Kate.
She runs a team, and like many creative business owners, she’d been doing everything conventional business advice tells you to do. She had a detailed CRM system. Follow-up spreadsheets. Tracking when clients last called. All the machinery of “proper” business development.
And her team? They’d started groaning whenever she mentioned implementing another system. They would literally say, “Oh god, please not another system.”
Kate herself was caught in what she called “chasing sales mode” – the constant follow-ups, feeling inauthentic, pushing and pursuing rather than building genuine relationships. Her entire business felt stuck.
Then Kate made one shift. Just one.
Within four weeks, her entire team felt the stuck feeling start to lift.
That shift? She stopped asking “when did the client call?” and started asking “what is the client getting from this interaction?”
She stopped chasing. And she started connecting.
And so many things began to change.
The Pattern I Keep Seeing
Let me paint a picture of what I hear constantly from creative business owners:
“I’m doing all the things. I’ve got the CRM. I’m following up. I’m tracking everything. But it feels wrong, and nothing’s changing.”
There’s this assumption in traditional business advice that if you just implement the right systems, follow the right process, track the right metrics, everything will flow.
But from my own experience and from all the creative entrepreneurs I’ve supported, we’re often measuring the wrong things entirely.
Think about it. When you focus on “when did a client call?” you’re focused on timing, on mechanics, on the machinery of sales. But when you ask “what is the client getting from this interaction?” you’re focused on value, on relationship, on the human element that actually drives creative business forward.
And you’re also focusing on what you’re naturally good at. Most creatives are also very strong empaths. We care deeply. We’re good at forming relationships when they feel easy and natural. And this is exactly what we can focus on in our businesses too.
The first question makes you chase. The second question helps you connect, and feels far less like selling or marketing.
What’s fascinating about Kate’s story – within those four weeks, not only did her team feel different, but her Instagram followers started increasing after being stuck for ages. Her whole business started flowing in ways it hadn’t before.
Not because she implemented a new strategy. Because she changed the lens through which she was seeing her entire business.
Kate told me something afterwards that was so revealing: “I’m sure it’s because we were trying to approach things in this blueprint of traditional business that just didn’t fit with us.”
That phrase – “didn’t fit with us” – is so important. Because what works for a large-scale product business, or a software company, or a traditional service business, often fundamentally doesn’t work for creative entrepreneurs. We’re trying to force ourselves into frameworks that were never designed for how we actually work.
The Real Cost of Wrong Questions
Here’s what happens when you’re asking the wrong questions in your business:
First, you exhaust yourself implementing systems that don’t serve you. Kate’s team groaning about “another system” was their intuition telling them these particular systems didn’t fit their business model.
Second, you lose sight of what actually matters. When you’re tracking response times and follow-up dates, you stop noticing the quality of relationships you’re building. You start treating people like numbers in a spreadsheet rather than humans you’re genuinely trying to serve.
Third – and this is the most subtle part – you start to feel inauthentic. Because you ARE being inauthentic. You’re acting out someone else’s idea of how business should work rather than building from your own strengths and values.
I experienced this myself in my floral business. There was a period where I was trying to do everything the industry expected – too many offerings, following others’ paths, completely losing sight of what made our work unique. I was asking myself questions like “what should I be doing?” and “what’s everyone else doing?” rather than “what actually works for us?” and “what do our clients genuinely value?”
It was only when I stripped everything back to focus on what came naturally that things really felt comfortable and began to work, enabling us to scale our business in a way that made sense and felt right.
I’m not saying ditch systems and processes completely – they are important. We need clarity in our businesses and the right ones will enable us to be hugely efficient. They take the weight of the admin side, supporting us to focus on what’s valuable for our clients. Just make sure you’re choosing the ones that make sense for you, not ones that dictate an approach that doesn’t work for you.
The Questions You Might Be Asking
Let me help you identify what questions you might be asking that are keeping you stuck.
If you’re asking: “How do I get more clients?”
You might actually need to ask: “How do I look after and support my existing clients more deeply?”
Often, we’re chasing new business while underserving the people who already trust us. And strangely, when you shift to serving existing clients more deeply, new clients tend to find you – through referrals, through reputation, through the quality of work that comes from not being scattered.
If you’re asking: “What should I really be focusing on that will ensure success?”
You might actually need to ask: “What feels natural to me that clients consistently praise?”
The “should” question keeps you looking outward, comparing yourself to others, trying to fit into moulds that weren’t made for you. The second question helps you identify what’s already working – what you might be taking for granted because it feels so easy to you.
If you’re asking: “How do I scale?”
You might actually need to ask: “What would make this more sustainable?”
Scaling in the traditional sense – more clients, bigger team, complex systems – often doesn’t serve creative businesses. But sustainability? That’s about building something that energises rather than exhausts you, that grows naturally rather than through force. And this is what leads to very successful creative businesses.
If you’re asking: “When did they last contact me?”
You might actually need to ask: “What value did our last interaction create for them?”
This is Kate’s shift exactly. One keeps you in transaction mode. The other keeps you in relationship mode. And relationship mode is where creative businesses thrive.
If you’re asking: “Am I doing enough?”
You might actually need to ask: “Am I doing what actually matters?”
“Enough” is a bottomless pit. There’s always more you could be doing. But “what matters” is specific, achievable, and actually moves your business forward.
How to Identify Your Question
Pay attention to how you feel when you’re working on different aspects of your business.
If something feels like pushing or forcing, you’re probably asking a question that puts you in chase mode. If something feels like connecting or really looking after and supporting, you’re probably asking a question that aligns with how creative businesses actually work.
Here’s a practice that might help: For one week, notice every time you feel stuck, frustrated, or inauthentic in your business. Write down what you were trying to do in that moment.
Then ask yourself: “What question was I trying to answer?”
Were you trying to answer “how do I get them to say yes?” or “how can I help them make the right decision for them?”
Were you trying to answer “how do I compare to competitors?” or “what makes my approach distinctive?”
Were you trying to answer “am I doing enough?” or “am I doing what matters most?”
The questions you’re asking will reveal themselves. And once you can see them clearly, you can start to shift them.
The Question That Changes Everything
Here’s what I want you to take away from Kate’s story:
You don’t need to overhaul your entire business. You don’t need to implement a dozen new systems. You don’t need to work harder or do more.
Sometimes, you just need to change the question you’re asking yourself.
From “when did they call?” to “what are they getting?”
From “what should I do?” to “what feels natural?”
From “how do I scale?” to “how do I sustain?”
These aren’t just different words. They’re actually completely different ways of running your business.
And the brilliant thing? The shift can happen really quickly. Kate’s team felt the change within four weeks. Not months. Not years. Just four weeks.
Because when you’re finally asking the right question, the answers become obvious, and the path forward starts to become much clearer. And thankfully, the stuck feeling begins to lift.
Kate sent me a message after our live session: “I wasn’t expecting the live session to be so in-depth today and I’m coming away from this with so much and I’m incredibly excited.”
That’s what happens when you find the right question. The excitement returns. The possibility opens up. You remember why you started this business in the first place.
What Question Are You Asking?
So here’s what I’m wondering for you:
What question are you asking yourself right now that might be keeping you stuck?
And what question could you ask instead that would help you connect rather than chase, to really look after and share your expertise rather than sell, to build rather than force?
I’m not going to pretend this is always easy. Kate mentioned being aware of “resistance through fear” as she made her shifts. That’s part of the process. Your old patterns will call you back. They’ll feel safer even though they’re keeping you stuck.
But if you can stay with the new question – if you can keep asking “what is the client getting from this?” instead of “when did they call?”, or whichever question is most relevant to you – something shifts. Not just in your metrics, but in how your business feels to you and everyone around you.
And that shift? It can change pretty much everything.
I would love to hear your thoughts on this, what realisations you’ve had just from reading this. You can reach me either on Instagram or via email.
Comments +