3 Simple Questions to Ask Yourself When Making Big Decisions

Read time —
5 Minutes
Last updated
March 19, 2024

“So, what do you want to do?”

Here I was, fourteen, acne-ridden, and faced with a big decision. At the time, I didn’t see it as a big decision, with the game of football I was missing occupying my mind. My mum and the deputy-head thought otherwise.

“I’ll stay where I am” I stammered. “Are you sure” challenged the deputy-head.

Assurances tumbled from my mouth that the lower maths set was right for me, convincing them with my words.

Two years later as I sat on the steps of the fire escape, smoking, and hiding from the office manager, I knew I had made the wrong decision. The lower maths set trapped me. It put a cap on me, rooting me in the below-average performance of my fellow students. No one cared. We didn’t study, we didn’t do homework, and we didn’t pay attention in class. As a result, I entered the set as a high average student and left with an exam qualification of a low average student.

The fire escape belonged to a building surveyor company. One, who up until my poor exam results, had a job offer for me. Now, a future of work combined with a college placement swiftly disappeared.

This article covers:

Why did I get my big decision wrong?

Thirty years on from that decision and I still live with regret.

‘What if’ is an easy question to dwell on when you know you’ve mucked up. Don’t get me wrong, I’m happy with the life I now have, with the wife I have, and the children we have in our lives. And I know I wouldn’t have those if I hadn’t lived the life I have.

What troubles me is my decision-making.

I was more worried about what my friends might think of me for choosing to move to the higher set. I certainly wasn’t thinking of my career, or even of my exam results. My lack of maturity, which comes when you’re fourteen and gripped by adolescent sensations, was a factor in my choice. The stigma attached to moving to the ‘top’ set wasn’t one I wanted.

I will never know what exam results I would have gotten moving to the top set. Some might see it as an irrelevant thought, but it forces me to accept my decision was the wrong one. Now, I have a learning opportunity. I have a chance, should I find myself in a similar position, to at least not repeat the decision-making steps I took.

My big decision errors

As I look back, I can see the following errors.

  • I was blind to the cap I was putting on my grade by staying in the lower set. Probability factors would have shown the grade value coming from being in the top set were vastly increased. I ignored what I knew to be true.
  • The only thought in my mind was now. There was consideration of the long game, of my career and life ahead. Consequently, I had no perspective on the upsides of moving to the top set. There was no thought about how I might feel about this decision in the future.
  • I didn’t consider the negatives of not moving. I had little thought on the risk of doing nothing. All I could see were the upsides of staying in the lower set.

I assumed my grades would be okay in the lower set. I didn’t challenge my assumptions. My emotions locked me into a position of focusing on how my friends would react, and lastly, my inbuilt biases prevented me from assessing the risks of my decision.

3 questions for big decisions

What I needed were three questions, which when we ask them, will question our assumptions, challenge our biases, and check our emotions.

In short, they are as follows.

  1. What do I know to be true?
  2. How will I feel about this decision in six months or six years?
  3. What is the risk if I do nothing?

My approach is to give your decision-making three points of information to consider; they are facts, an alternative perspective, and a view into the window of entropy.


Every decision comes with a myriad of information surrounding it. Facts are the principles of truth on which you can build your decision. Assumptions are not facts, therefore, they are assumed truths and left unchallenged, they will ruin your decision. Asking why and how questions will give you a first principles view of the fundamental truths in your situation.

At the same time, you will also become aware of incomplete information. Seeing this for what it is will improve how you decide.


Perspective is a superpower when making big decisions. It’s like superman’s ability to fly, it changes everything, separating him from the rest of us. Perspective enables you to see a different view of your options. When you’re faced with a big decision, losing perspective is the last thing you want, but often the first thing that happens.

Perspective, whether it be from changing your period or seeing it from someone else’s eyes helps you see the decision before you differently.


We think doing nothing risks nothing. This is not a fundamental truth. Seven billion people let alone countless organisms, and the forces of nature make this world what it is. We feel their impact through chance, through serendipity, and if we do nothing, entropy. The fact is, all these elements are beyond our control, and although you’ll never irradicate them when you do something, you’re potentially distancing yourself from their influence.

The risk of doing nothing is an invitation to the forces of chance and luck, and then entropy to rule over your decision.

Concluding thoughts on making big decisions 

At the age of fourteen, the concepts of fact, perspective, and entropy weren’t in my mind. But they should have been. Making better decisions should be a life goal. Making our dreams or ambitions a reality comes down to the quality of our choices.

Even as adults, I know we don’t focus on making better decisions. Most of us don’t anyway – and that’s the point of this article. It doesn’t matter whether your fourteen or fifty-four, the big decisions are the ones we should ensure we get right.

Of course, you can’t predicate the outcome.

But, by finding fact from fiction, from shifting your view from now – to the future, and by being aware that doing nothing risks far more than first appears – you stand a chance of getting your big decision right.

The purpose of these three questions is to lead you towards those crucial concepts of fact, perspective, and entropy. Making the process of thinking easier, is a path to better decision making. So, the next time you’re faced with a big decision, ask yourself:

  1. What do I know to be true?
  2. How will I feel about this decision in six months or six years?
  3. What is the risk if I do nothing?

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