A few weeks ago, I shared an Instagram post about spending eight weeks on an Ionian island in Greece with my family this summer. Something that over the last five years has become our ordinary, but might sound quite extraordinary to others.
The response completely caught me off guard. It’s been viewed by over 165,000 people (and counting!), led to over two thousand new followers, and the comments revealed something deeply profound… a yearning from creative business owners who saw themselves in that story and wanted to know: “How can I create this too?”
The messages under the post are so heartfelt. People sharing their own dreams of freedom, of designing their businesses around their lives rather than the other way around. I realised that many of you are exactly where I was several years ago – knowing there’s something more possible, but not quite sure how to get there.
The Coffee Conversation Approach
Today I want to have a different kind of conversation with you. Imagine we’re sitting together right now… perhaps at my kitchen table back in Dorset, or at the taverna overlooking the Ionian Sea where we spend our summers. I’d pour you a coffee, and I’d ask you five questions.
These are the same questions I ask every creative business owner who feels stuck between where they are and where they want to be. They’re the questions that took me from delivering bud vases of flowers to rural pubs and not really knowing if I was cut out for business, to building a seven-figure creative brand with clients like Vogue, the Royal Family, Chanel, and Dior.
But more importantly, they helped me build all of that while creating real freedom – eight weeks in Greece every summer, work that energizes rather than exhausts me, and so much more.
Why Traditional Business Advice Falls Short
Before we dive into the questions, I want to tell you why I believe in this approach so deeply.
For years, I followed traditional business advice. I read the books, tried to fit my creative business into conventional frameworks. While some of it worked, much of it felt forced, exhausting, and completely disconnected from why I started my business in the first place.
The breakthrough came when I stopped looking outwards for answers and started looking inwards for the questions that would show what I actually wanted and needed.
Most business advice assumes we all want the same things – more revenue, faster growth, bigger teams, wider reach. But what if your version of success looks completely different? What if you want four-day weeks? What if you want to work from different countries? What if you want summers off to spend with your family?
In the guide below I share the five questions, plus a few extra thoughts and ideas for you. It’s completely free and I think you’ll find it a helpful addition to this post:
My Answers to the Five Questions
Let me share how I answered each question, because seeing the process in action often helps more than theory.
Question 1: What would your ideal ordinary Tuesday look like three years from now?
My answer revealed something crucial. I didn’t want a Tuesday filled with back-to-back meetings or constant email checking. I wanted spacious mornings for creative thinking, meaningful work that energized me, and the freedom to step away when family needed me. That Tuesday vision became the blueprint for how I structure everything.
Question 2: What do you naturally do that feels so easy you assume everyone can do it?
For me, it’s seeing patterns and possibilities that others miss. I can look at a creative business and immediately see where the disconnect is between what they’re offering and what their ideal clients actually need. For years, I undervalued this because it felt too easy. Now it’s the foundation of everything I do.
Question 3: What part of running your business makes you feel most like yourself?
The one-on-one conversations. Whether it’s coaching calls, interviews, or even responding to emails, I come alive when I’m having genuine conversations about what’s possible for people’s businesses and lives. Everything else supports this core work.
Question 4: If you knew your way of doing things was the RIGHT way for you, what would you stop doing tomorrow?
I’d stop trying to post on social media every day just because that’s what the experts say. I’d stop attending networking events that drain my energy. I’d stop offering services that don’t play to my strengths just because there’s demand for them.
Question 5: What’s the real reason you haven’t taken the next step?
The honest answer? Fear that people would think I was showing off or being unrealistic. Fear that wanting both business success and lifestyle freedom was somehow selfish or impossible. Once I admitted this, I could address it instead of letting it unconsciously control my decisions.
What Your Answers Reveal
Going back to the five questions – the answers you come up with already contain everything you need. The vision, the strengths, the direction – it’s all there. You just need someone to help you see it clearly and give you permission to build from it.
That Tuesday you described? It’s not a fantasy. It’s a method for how to structure your business and your life.
That thing you do naturally that feels so easy? It’s more valuable than you realize, and it should probably be the foundation of your entire business.
That feeling of being yourself in your business? That’s your business trying to align with who you really are. It’s showing you where to focus your energy.
The permission piece – if you knew your way of doing things really was the right way? That’s showing you all the energy you’re wasting on things that don’t fit, energy that could be redirected toward what does.
And that real reason why you haven’t taken the next step? Now that it’s in the light, it can be addressed rather than unconsciously controlling your decisions.
The Simple Truth About Success
The gap between where you are and where you want to be is almost never about working harder or learning more tactics. You’re already a hard worker and you’re open to new ideas.
Instead, it’s about recognizing what you naturally do brilliantly and building everything around that. It’s about trusting what comes naturally to you instead of forcing yourself into someone else’s formula.
I’ve watched this simple shift transform hundreds of creative businesses and lives. When you stop trying to fit into generic advice and start building from your own answers, everything changes.
Your Next Step
Pick one thing from your ideal Tuesday. One small element. And find a way to add it to your real Tuesday this week.
Maybe it’s working from a more inspiring location. Maybe it’s blocking out time for the work that makes you feel most like yourself. Maybe it’s saying no to something that doesn’t fit so you have space for something that does.
Start small, but start. Because your impossible dream? It starts with believing it’s possible.
The clarity you’re seeking is already inside you. You just need the right questions to bring it to the surface.
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