Welcome back to the tenth issue of Wayfinder, your fortnightly compass for navigating life’s toughest decisions.

Have you ever caught yourself thinking, "If only I had taken that job, moved to that city, or even chosen that restaurant, things could have been so different"? That's counterfactual thinking at work.

Many of us engage in it frequently, perhaps unwittingly, and often unproductively.

Missed the train by a minute? You might think, “What if I’d left home just 60 seconds earlier?” A relationship ends, and the mind drifts to, “What if we’d met at a different time in our lives?”

Counterfactual thinking revolves around the very human act of imagining alternative scenarios to events that have already occurred — a mental revisiting of "what might have been".

It's like having a time machine that you can only use to travel back to the alternate realities on the other side of every decision.

The road not taken

The poet Robert Frost once mused about two roads diverging in a yellow wood and the choice that made all the difference.

The paths we don't take, the choices we don't make — they can haunt us, shaping our perceptions and feelings, often more profoundly than the actual choices we make.

But, when wielded carefully, counterfactual thinking can be a powerful weapon.

A 2012 study published in Nature suggests that counterfactual thinking, especially focused on how outcomes could have been better, helps improve learning and future decision-making.

Our brain is wired to dissect past events, extracting lessons to better navigate the uncertain terrains of the future.

From Regret to Resilience

Picture the last mistake you made. Or even your last lucky break. By mentally simulating how things could have gone differently, you can discover valuable lessons for the future.

Let's dive into ancient Greece for a moment. The Stoic philosophers were known for their mental exercises, one of which, 'premeditatio malorum', or the premeditation of evils, was a sort of counterfactual thinking in reverse.

Instead of looking back, they would envision future challenges or adversities, preparing themselves emotionally and mentally. This practice cultivated resilience and equipped them to handle life's unpredictabilities.

What if things were the opposite?

While watching an apple fall, Sir Isaac Newton didn’t just see fruit meeting the ground. He pondered, “What if the apple doesn't merely fall - what if it's being pulled? what if there’s an invisible force pulling objects towards each other?”

This counterfactual thinking led to the foundational laws of gravity, changing the trajectory of science.

Philip K. Dick’s The Man in the High Castle, was built on a counterfactual: “What if the Allies had lost WWII?” Such explorations offer fresh lenses to understand our world and reflect on societal structures and norms.

In the context of fiction, it makes for an interesting story. But in reality, thinking back on outcomes helps us in multiple ways:

  1. Create empathy: Thinking about how things might have changed if the other team won can create a sense of empathy.

    We realise how fickle history is, and the extent to which we mistakenly judge our morals or decisions based on our perspective of the 'relevant context'.
  2. Unravel sunk costs: Sometimes it's easy to stick to a path simply because it's consistent with a pre-existing set of events.

    Asking questions like 'Would I still do this thing / think this way if [preceding event] had gone differently? What if I wasn't already in this position?' can help us step out of our own shoes and make objectively robust decisions, rather than biased ones.
  3. Escape tilt: this is a variation of the previous point. Tilt is an emotional sunk cost. It's what happens when you lose a bet and suddenly want to double down to 'get your money back'. Or when you make a mistake and suddenly want to scramble for a quick fix.

    We don't think clearly when we're tilted. Sometimes the follow-up action just makes things worse. Step back. Consider the counterfactual. 'How would I act if I was feeling differently?'
  4. Evaluate weaknesses: You can use counterfactual thinking like a torch to hunt down 'near misses' you might otherwise ignore.

    When things go well, it's easy to ignore how easily things could have gone the other way.

    Ask: 'If this decision hadn't paid off, why would that be? Where did I take too much risk? Was that objectively a good decision? Would I still feel confident about it if things had gone differently?'

    You can even ask this question before knowing the outcome: 'If this project failed, what would be the most likely reason?' This way you can guard against weaknesses in advance.


Charles Darwin once penned a letter expressing gratitude for not having read certain philosophy books. His reasoning? Reading them might've clouded his original ideas.

This counterfactual thought—imagining a reality where he had consumed those ideas—allowed Darwin to appreciate the unique trajectory his theories had taken.

Here are some questions worth asking yourself today, as you begin to engage proactively in counterfactual thinking:

Purpose Over Pity: Am I using this ‘what if’ to learn and grow, or simply to wallow in regret?

Direction Not Destination: Does this thought propel me forward, or does it chain me to an unchangeable past?

Reality Check: How can I use insights from an alternative scenario to shape my current reality?

Each ‘what if’ we entertain is a doorway to an alternate universe, a realm of endless possibilities. While it's tempting to linger there, sometimes it's best to peek, ponder, and then return to the present.

In the words of Voltaire, “Doubt is not a pleasant condition, but certainty is absurd.” While we may never attain surety over the 'road not taken', we can derive wisdom, humility, and a sprinkle of wonder from the journey.

Stay decisive.

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