Cartesian Questioning

You think you want something. You’re pretty sure about it. You’ve set the goal, maybe written it down, maybe even told people about it.

But have you actually thought it through? Not just the exciting parts. All of it, including the parts that make you uncomfortable.

Most people haven’t. They set goals based on surface-level thinking, then wonder why achieving them doesn’t feel the way they expected, or why they keep finding reasons to delay. Cartesian Questioning is the tool that fixes this. Four questions. Properly answered, they’ll tell you more about whether your goal is right for you than months of thinking about it.

Where the tool comes from

Cartesian Questioning takes its name from René Descartes — not for his philosophy, but for his mathematics. Descartes gave us the Cartesian coordinate system: two axes crossing to create four quadrants. That’s exactly the structure of this tool. One axis is achieve or don’t achieve; the other is will happen or won’t happen. The four quadrants are the four questions below.

A version of it is standard practice in motivational interviewing, which is what your GP might be doing when they ask what you’d gain and what you’d lose by changing. Most people, when they consider a goal, think in only two directions: what happens if I do this, and what happens if I don’t. Cartesian Questioning opens up two additional quadrants that most people never explore, and those unexplored quadrants are precisely where goals fall apart.

As Descartes himself put it, it is not enough to have a good mind. The main thing is to use it well.

The four questions

Apply these four questions to any goal you’re seriously considering before you commit to it.

Question one: What will happen if you achieve this goal? This is the easy one. The benefits, the rewards, the positive outcomes. It’s what you’ve already been thinking about. The reason you want it in the first place.

Question two: What won’t happen if you achieve this goal? This is where it gets uncomfortable. Achieving one thing almost always means giving something else up. More money might mean less time. A new business might mean less security. A transformed body might mean losing the identity of someone who’s been struggling. If you don’t consciously name what you’re giving up, your unconscious mind will quietly sabotage you.

Question three: What will happen if you don’t achieve this goal? What are the consequences of staying where you are? If those consequences aren’t significant enough to motivate change, the goal may not be as important to you as you thought. That’s useful information, not failure.

Question four: What won’t happen if you don’t achieve this goal? This is the hardest one. What are the negative things that won’t occur if you stay where you are? What difficult conversations won’t you have to have? What uncomfortable growth won’t you have to do? These are the hidden benefits of not changing, and they’re powerful. If you don’t acknowledge them, they’ll work against you whether you like it or not.

The smoking patient

I once had a patient who sat down and said, I bet you’re going to tell me I need to give up smoking.

Actually, no, I said. I was going to ask you what wouldn’t happen if you did give up. And then what wouldn’t happen if you didn’t.

There was a pause. A genuine moment of blankness, because question four genuinely stops people in their tracks. It interrupts the normal thinking pattern and takes you somewhere unfamiliar. In that hesitation, I handed him a leaflet on our smoking cessation clinics. He took it.

Sometimes getting someone to think differently, even just for a moment, is enough to crack open a door they’ve been keeping firmly shut. That’s what question four does. It creates the pause. And in the pause, something shifts.

Why the uncomfortable questions matter

Your unconscious mind is remarkably good at protecting you from discomfort, even when that protection keeps you stuck. If you have hidden reservations about a goal, if there are costs you haven’t acknowledged or benefits to staying where you are that you haven’t examined, your unconscious will find ways to undermine your efforts.

You’ll procrastinate. You’ll self-sabotage. You’ll find perfectly reasonable explanations for why now isn’t the right time, or why circumstances have changed. None of it will feel like sabotage. It will feel like common sense.

Cartesian Questioning brings all of this into conscious awareness before you invest significant time and energy in a goal. It forces you to look at the full picture rather than just the parts you find motivating.

A worked example

Say your goal is to start your own business. Here’s how the four questions might play out.

What will happen if you achieve it? Freedom, flexibility, the satisfaction of building something, better income potential, work that feels meaningful.

What won’t happen if you achieve it? You won’t have the security of a salary. You won’t be able to avoid difficult decisions. You won’t have colleagues to share the load. You won’t have the excuse of a bad employer for why your work life isn’t what you want.

What will happen if you don’t achieve it? You stay in a role that doesn’t fulfil you. Your income stays capped. The idea keeps nagging at you. Regret accumulates.

What won’t happen if you don’t achieve it? You won’t have to take the financial risk. You won’t have to work the long hours of a startup. You won’t have to face the possibility of public failure. You won’t have to become someone capable of doing something you’ve never done before.

Look at all four answers together. Does starting the business still make sense? Are you willing to accept the costs and address the hidden benefits of staying put? If yes, you have a goal that’s survived proper scrutiny. If no, you’ve saved yourself months of frustrated effort on something that was never going to work.

How to use this

Before committing to any significant goal, draw a two-by-two grid and work through all four questions in writing. Be honest, especially with questions two and four.

If you discover the costs are too high or the hidden benefits of not changing are too attractive, that doesn’t mean you’re weak or lacking commitment. It means the goal isn’t properly aligned with your values and circumstances. Adjust the goal, address the barriers, or choose a different goal entirely.

Either outcome moves you forward. Neither is failure.

Your first step

Pick a goal you’re currently working on or seriously considering. Work through the four Cartesian questions, write down your answers, and be honest, especially with the uncomfortable ones.

Then ask yourself: knowing all of this, is this still the right goal for me?

If yes, you’re ready to move forward with your eyes open. If no, you’re ready to set a goal that’s actually aligned with who you are and what you’re genuinely willing to do.

In the next article, we’re going to look at a mindset for the goals that need persistence through failure and rejection — including why “no” might be exactly the target you should be aiming for.

Further reading

1. Descartes, R. (1637). Discourse on the Method of Rightly Conducting One’s Reason. Jan Maire.
2. Miller, W.R. & Rollnick, S. (2013). Motivational Interviewing: Helping People Change (3rd ed.). Guilford Press.
3. Prochaska, J.O. & DiClemente, C.C. (1983). Stages and processes of self-change of smoking: Toward an integrative model of change. Journal of Consulting and Clinical Psychology, 51(3), 390-395.
4. Gilbert, D. (2006). Stumbling on Happiness. Alfred A. Knopf.