The 5-Path Test I Use When I’m Stuck

When I’m stuck on a decision, it’s rarely because I don’t have ideas.
It’s because I keep circling the same few options, just dressed up slightly differently each time.

I think about it. I leave it. I come back. Same answers. Same tension. Same loop.

This is the test I use to break that cycle.

Not to get the answer. But to open the problem wide enough that something new can actually emerge.

Breaking the cycle of stuck thinking

Most stuck problems aren’t solved by trying harder. They’re solved by changing the way you’re thinking about them.

This test works because it forces a pause before solutions. It slows the process down just enough to sharpen the context first, then deliberately opens five distinct paths forward.

AI plays the role of a thought partner here. Something that helps surface options you wouldn’t naturally reach on your own.

How the test works

The first phase is about asking questions, one at a time, until the shape of the problem is actually clear. Constraints, trade-offs, pressures, goals. All of it.

Only then do I ask for five paths forward.

Each path is developed enough to be useful, not just interesting.
What it would take to implement.
What could go wrong.
Where it might fall over.

Where I use this

I use this test whenever I notice I’m looping.

Business decisions that feel stuck.
Strategic shifts that carry risk.
Projects that keep stalling because nothing feels quite right.

It’s especially useful when time and energy are limited and you can’t afford to explore every idea manually.

It gives me a way to move from stuck to unstuck without forcing certainty too early.

The 5-path test template

Copy and paste this prompt into your favourite AI chat:

I’d like you to act as my strategic thought partner for this challenge.

[Briefly describe the situation, including relevant constraints, complexities, and what a good outcome would look like.]

AI’s role: Assume the perspective of [the most relevant expert for this problem (eg. Strategic advisor. Industry specialist. Process or systems thinker).]

Process: Ask me up to ten clarifying questions, one at a time, to fully understand the context. Use multiple choice questions wherever possible to speed up the process. Once you have finished asking those 10 questions, provide five well-developed paths forward. For each path, include practical implementation considerations and potential obstacles, including how those obstacles might be mitigated.

Why this works

This test doesn’t magically make decisions easy.
What it does is replace mental looping with structured movement.

Instead of one fragile plan, you get five grounded options.
Instead of vague ideas, you get paths you can actually assess.

Use it once and you’ll feel the shift.
Not because AI gave you the answer.
But because the problem finally opened up enough for you to choose with clarity.

The prompt above has been adapted from a prompt originally published by Geoff Woods.