The Planning Trap
Why Confidence and Clarity Emerge from Doing (Not Strategy Docs)
I’m sitting here feeling disorganised. Everything needs rebuilding. I could start in 27 different places, and so I don’t start anywhere.
Sound familiar?
After rebranding to The Unremarkable Entrepreneur, I stopped the events I was running. The podcast recordings dried up. The content and client pipeline went quiet.
Not because I don’t know what to do - I’ve built audiences, closed clients, generated revenue doing this exact work. But because I needed to spend some time behind the scenes, reimagining the structure behind the business you all get to see. Creating space for what works, and closing off energy sink holes.
But over the last few weeks I’ve grown restless.
I’m making energetic down payments in my future, but I’ve felt increasingly stuck in planning mode. Stuck thinking about the work, instead of doing it.
And that’s the trap, isn’t it? Because planning can feel enough like progress without actually moving anything forward.
So, writing this article is an act of rebellion.
It’s my attempt to stop spinning around my ideas and do something with them. Even if that doing is simply an act of open reflection.
In short, I need to remind myself that no structure will bring momentum. I cannot plan my way to clarity. There’s no ecosystem I can shape that brings life if I don’t fill it with life.
And that goes for you too.
The Messy Middle
When a peer asked me what was going on, I had to be honest: “I think I just need to lock in a weekly starter cadence so it feels like I’m living the work instead of feeling stuck planning it.”
They didn’t let me off easy. “You’ve just diagnosed yourself perfectly. You’re stuck in planner mode. How about you just get on with the work instead.”
It was like looking in a mirror. This is EXACTLY the kind of stuff I say to my clients. I’ve built a business around the act of closing the gap between planning and practice.
I’ve been acting like a strategist, when I was born to be a practitioner.
And the first casualty has been my content. I’ve stopped saying stuff about what I do. The truth? It doesn’t need a complex system, cleverness, or crisp editing. What it actually needs is consistent practice and contact with the world.
In other words: say the stuff and make it clear what people do with the stuff.
And when I close the tabs, resist the LinkedIn scroll, ignore the Substack clickbait, and tune out the gurus, what I want to talk about is crystal clear:
The Authority Lab: my 1:1 programme for those ready to build a practice, not a business
The Unremarkable Entrepreneur: weekly articles about how to build with intention and scale without limits
The Unremarkable Entrepreneur Podcast: interviews with Unremarkable clients and creators who’ve been there and made it happen
Here’s my challenge to myself: if what you’re about to create doesn’t directly serve one of those, DON’T DO IT!
I believe in the power of constraints - time being the most sacred. Before I chase any shiny idea, I ask: will this cost me an hour with my son? Does this help build the future I want to own? If the answer to either is no, it doesn’t matter how clever the idea feels.
So I know what I want to say, but actually saying it? Well that’s a different practice entirely.
The Unemployable Reality
Here’s what I know about myself: having experienced five redundancies in a decade, the idea of going back into a full-time role feels like I wouldn’t be living my potential. But I still get tempted by the benefits: the security, the freedom of someone else’s to-do list, the team camaraderie. It’s catnip to a lonely entrepreneur.
But honestly, I’m unemployable now. Not because I lack skills - I have real depth across everything needed to succeed. But because the promise of working in alignment with who I actually am is like catnip for the soul!
My bills are paid, and there’s food on the table. But I still carry stress about whether this will work, especially with a 4-month-old son and a house purchase that’s running behind schedule. There’s pressure. Plus those redundancies have done my nervous system no good: I’m hard-wired now to expect that the rug will be pulled.
Despite this, my normal state is pretty confident.
I close most of my sales calls. I’ve grown an audience to nearly 10,000 on LinkedIn without ads or viral tactics. I’ve made this work before by simply serving the work instead of worrying about the outcome.
So why have I been feeling stuck?
The Forward-Thinking Curse
My friend nailed it: “One of your greatest strengths is that you are a forward thinker. You can see the entire process and all the potential before you start. But that can lead to overthinking every possible option, which feels overwhelming.”
And they’re right. I can see all the potential paths. I understand frameworks before I implement them. I’m intelligent enough to spot the whole journey from the starting line.
But that same intelligence can paralyse. When you can see everything that could work, choosing one path feels like closing doors. And when you’re carrying stress about whether this will actually provide for your family, that weight gets heavier.
The irony? I’ve watched people I’d consider less capable than me succeed by taking what might be considered dumb action. They just get on with things with the full belief that it will work, and often it does. Imperfect action is still action, and action creates opportunity.
They’re not smarter. They’re just not stuck in the planning trap.
The Starter Cadence
What I teach people is this: Your unfiltered self is your opportunity magnet. Don’t worship the outcome. Serve the work and take action. When you do, you’ll discover what wants to happen to you, through you, and for you.
And right now, I’m deciding to take action.
Here’s what I’m committing to in order to liberate myself: a weekly starter cadence that feels doable with a 4-month-old.
Monday: Write one Unremarkable Entrepreneur article. Just write what wants to be written and let it rest
Tuesday: Release one post about my 1:1 offer, The Authority Lab
Wednesday: Publish the article and record a video read-through. Post it to the podcast
Thursday: Reserved for business tasks and admin
Friday: Write x5 short posts linking back to the article and schedule them for the following week
Of course, I’ll be working on guest podcast episodes, and let inspiration lead from time to time, but otherwise, that’s it!
One content pillar and one offer post. The long form drives almost everything, and one offer post solves my greatest weakness as an entrepreneur - telling people how I can actually help them.
Everything else - podcast recordings, events, social posts - orbits around this core practice. They’re not separate content pillars to manage. They’re extensions of the writing.
And if they can’t justify their existence, they’ll get cut. Without mercy.
Why this cadence and not another? Because I tried the ‘post daily’ approach. I tried the ‘batch everything monthly’ method. Both made me feel like I was performing rather than practising. This rhythm gives me space to think on Monday, take action on Tuesday, share on Wednesday, breathe on Thursday, and prepare for the next cycle on Friday. It’s not the perfect system - it’s simply the one that fits my life right now.
I Give Myself Permission
I have lived the experience of starting a business from absolute zero. Most people think they need to know the outcome, to understand where they’ll land.
But here’s what I know: things rarely go to plan. So whilst I’ve designed a rhythm, now it’s time to learn to dance. To establish the practice that generates the raw material.
I don’t need to know ‘what’s next’ beyond next Monday’s article. I’m going to write consistently until Christmas, and let what wants to happen to me, through me, and for me, reveal itself. The writing will deepen, the themes will compound, and what I can offer the world will sharpen through articulation and start cutting through the noise.
And here’s the thing I keep forgetting: I already have proof this works. I built 10,000 followers by running events, recording podcasts, and reaching out to people. One or two leads would always emerge naturally.
Not because I had perfect positioning, but because I was doing the work in public and people could see themselves in it.
The Path Forward
So I’m done planning. I’m done trying to see the whole journey before I take the next step.
Starting this week: One article. One offer post. One video. Repeat.
Starting from tomorrow: THIS article. Published. Recorded.
And it will work. Not because I’ve architected the perfect system, but because I’m serving the work consistently enough for patterns to emerge and in public enough for the right people - the 1% who are ready to build differently - to find me.
That’s the practice. That’s serving the work instead of worshipping the outcome.
And if you’re stuck in the same trap - overthinking, over-planning, waiting for the perfect structure - this is your permission slip: You already know enough. Start Monday. See what emerges by Friday. Do it again the next week.
The universe will show you what it wants from you. But only if you’re actually in conversation with it.