The Two Questions Your Choices Need You To Ask

Read time —
4 Minutes
Last updated
March 6, 2024

Big decisions are often hidden from us.

We make seemingly small decisions which feel inconsequential at the time. And then, sometimes days or months later, they bite us.

We fail to think about the future. No, that’s wrong. It’s not that we don’t think about the future. It’s that we don’t ask ourselves the right questions to consider what the future might look like. Our minds are full of the expectation of what could happen now.

This short-term thinking has a name; present bias. The future is just a glimpse, not a consideration.

Questions can change the information we consider before we decide.

So, in this article, I want to look at a two-question combo.

  1. Where will this decision take you?
  2. And then what?

This article covers:

Where Will This Decision Take You?

Decision-making could be — and often is — like a formula.

Information + action = outcome

It is the foundation of every decision we make.

Every choice begins with information. Facts define where we are. Desire through imagination gives us information about an outcome. All manner of stories, both true and false, add to this perception.

We see our decision as this; if I take this action, what outcome will it give me?

Yes, there is a whole world of trouble lying in the assessment of information. Confirmation bias, loss aversion, and recency bias all affect our judgement of what we think we know.

But, what we must do is look forward.

We need to ask ourselves, where will this decision take us?

It’s a question that forces us to think about the outcome, to think about the gravity of information and our actions, and to see how they combine.

Importantly, this question doesn’t hold one answer.

It is a naïve view to think if we do x – we get y.

We do not live in a binary world. The consideration of asking where this decision will take you has to stretch your thinking into considering outcomes you might not want.

And Then What?

This second question, like the first, requires our imagination.

What it does is alert us to the fact that decision-making isn’t an isolated event. It’s a data point in a chain reaction of events we call life.

One decision leads to another and then another.

The process is endless until you die.

The ‘and then what’ question opens your mind to consider the second and third-order effects of the decision. It takes your ‘small decision’ and then makes you think about the consequences of the outcome you’re chasing.

If you then stack these two questions together and ask them again and again, you give yourself a glimpse of a future few see.


I was seventeen.

There is something to be said of the tone coming from a summer sky. It has an inviting hue. A warmth you can’t touch but one that draws you outside.

The sun — and the beach was calling me.

Being a year younger, Toby had finished his exams. I was at college, lost to the calling of the sky through the rusty window.

The sun won, so I finished college early and walked to Toby’s house.

By mid-morning, we were on the beach loving the sun and splashing in the sea.

That summer, I spent my days on the beach — jumping waves in the morning and chilling under the sun in the afternoon. It was far more appealing than sitting in a hot classroom.

I didn’t think about where this decision would take me.

If I had, well then, I would have thought of the impact of getting a low grade. I would have considered there was a risk of expulsion. If I had asked, and then what, I might have considered the career I wanted was slipping away from me. The more time I spent at the beach, the more I was changing my future.

The long-term impact of that summer was significant.

I left college the following autumn. I was so far behind I couldn’t catch up with the others. The career I wanted was gone — no qualifications meant very different job prospects.

Concluding Thoughts

Hindsight always makes this look obvious after the event.

But that’s the point.

Hindsight allows us to learn. Memories give us this — and we shouldn’t shirk the chance to dig into our decisions and think of ways to make them better.

My summer of fun was great at the time.

Did it align with my long-term goal of becoming a quantity surveyor?


Consequences aren’t events we go looking for when making decisions. But they should be something we treat as another piece of the information pie we need to consume.

The two-fold question — which can run and run, opens up a view to challenge whether your small decisions are the right ones to be making.

It seems like those are questions worth asking.

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