3 Signs You’re Stuck in the Planning Loop

A few weeks ago I was cleaning out my Google Drive.

I wasn’t looking for anything in particular. Just one of those admin tasks you do when you want to feel productive without doing the actual thing you’re supposed to be doing.

And then I found them. Files from ten years ago. Ideas I had saved. Business concepts I had mapped out. Names I had brainstormed. Frameworks I had built. A full decade of attempts sitting in folders, neatly labelled, colour-coded, completely untouched.

Ten years.

I sat with that for a long time.

Because here is what struck me: I had not been doing nothing. I had been very, very busy. I had been planning, refining, saving, organising. I had been doing a version of moving forward that somehow never arrived anywhere.

That’s the planning loop. And if you’ve been carrying an idea for a while, there’s a good chance you’re in it.

I’ve written before about the research loop, which is a close cousin. That one is about gathering information as a way of waiting for permission. The planning loop is subtly different. It’s about the work you do that feels like preparation but never quite reaches the point where a real person has to respond to it.

Here are three signs that usually give it away.

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Sign 1: You’re doing real work. It just doesn’t involve a real person.

This is the most convincing sign, because you genuinely are working.

You’re choosing brand colours. Thinking about your logo. Writing your About page for the third time. Researching which platform makes more sense. Making decisions about fonts, and tone of voice, and what you want people to feel when they land on your site.

I did all of this. At length.

And here’s the thing: it’s not wasted work. Those decisions matter. A clear brand and a considered identity are real parts of building something. I’m not going to tell you they don’t count.

What I will say is that all of that work is still aimed at you feeling ready. It hasn’t touched the market yet. Brand work is important about three steps further down the road than most of us are when we’re doing it. What you need at this stage isn’t a cleaner logo. You need a signal. And logos don’t produce signals. People do.

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Sign 2: Your plan is detailed. Your audience is entirely theoretical.

I’ve spoken to women who can describe their ideal customer in extraordinary detail. Age, background, the career she’s leaving, the thing that keeps her up at night. Personas so specific and vivid you’d think they were based on someone real.

And then I ask: have you spoken to anyone like that?

Often the answer is no.

The plan gets more complete over time. The audience stays hypothetical. Because building out a persona is something you can do alone, at your desk, without risking anything. Actually reaching out to a real person means they might say something you weren’t expecting.

If your ideal customer exists only in a document, that’s worth sitting with.

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Sign 3: Your next step keeps moving.

Six months ago your next step was to finish the website. Then it was to nail the positioning. Then to sort out the brand. Now it’s to understand the market properly before committing to anything.

Each step is real. Each one makes sense in the moment. And somehow, the actual testing stays just out of reach.

This isn’t a failure of discipline and it isn’t laziness. It’s what a careful, thoughtful mind does when something matters and the stakes feel high: it finds another legitimate reason to wait.

The loop is very good at disguising itself as progress.

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The one move that breaks it

I came across a concept recently from a book called Tiny Experiments by Anne-Laure Le Cunff, and it’s shifted how I think about this.

The idea is straightforward: instead of committing to a launch or a full plan, you design a small, structured test. You decide in advance what you’re looking for. You go find out. Then you make a decision based on what actually came back, not what you hoped might be true.

That’s it.

Not a business plan. Not a polished offer. One contained experiment with real people, built to give you a single clear signal.

I find that word, experiment, genuinely useful. Because experiments are supposed to be uncertain. An experiment that doesn’t produce the result you expected is still a good experiment. You learned something. You adjust and run another one.

That’s a completely different relationship with uncertainty than the planning loop offers. The loop treats uncertainty as a reason to keep preparing. The experiment treats it as the point.