Your Past Isn’t the Only Path: Explore Alternative Histories
Every day you live one version of your life, but dozens of invisible paths lie just out of sight. In reality, you might have accepted that overseas assignment, started a side business, or said no to a risky investment. Thinking only in terms of actual outcomes narrows your view and leaves you blind to better strategies. By deliberately sketching these untraveled routes, you expose the hidden driver behind your decisions and discover options you never noticed. Picture each alternative history as a branching road on a map—some routes look tempting, others risky, but none should be ignored.
This exercise isn’t about regret or dwelling on the past; it’s a tool to sharpen your future moves. When you see a potential detour that could have led to a better outcome, you gain the courage to test it. The science of counterfactual thinking shows that reflecting on what might have happened teaches you more about your world model than repeating the same stories. You’re not trapped by the single timeline you lived—you can peek behind the curtain and learn from every possible ending.
Next time you face a choice—big or small—imagine three “what if” versions of your decision and assign each a realistic probability. This habit rewires your brain to spot neglected risks and opportunities, giving you a broader, clearer lens on the next fork in the road.
Imagine yourself in a quiet corner of your day—drinking coffee, waiting at a bus stop, or early in the morning before emails arrive. Pull out your notebook or phone and write down two big events you’ve lived through. Then, let your mind wander: “What if I had taken a different job? What if I avoided that deal?” Assign a number to each alternate history—your gut estimate of how likely it would have been. Finally, jot one lesson you’ll apply this week. Give it a try tonight.
What You'll Achieve
You will develop a habit of counterfactual analysis that broadens your perspective, teaches you hidden risks and opportunities, and leads to more resilient, creative decision-making.
Map Your Could-Have-Beens
List key turning points
Choose two or three major events from your past—promotions, big wins, or setbacks—and write them down in a notebook or on your phone.
Brainstorm “what if” scenarios
Next to each event, ask “What if I had done the opposite?” Sketch two or three alternate outcomes, however wild they seem.
Estimate plausibility
Give each alternate scenario a probability from 1% to 99%, just your gut reaction. This helps you see which versions merit more attention.
Record hidden lessons
For the scenarios you rated most likely, jot down one lesson you can apply today—maybe a new risk buffer or backup plan.
Reflection Questions
- When have you assumed there was only one way things could go?
- Which ‘what-if’ scenario scares you the most—and why?
- How might assigning probabilities to alternate paths reveal blind spots in your plans?
Personalization Tips
- – At work, a project manager lists key pitches they’ve lost and imagines how a different negotiation tactic might have changed the result.
- – A student writes down major exam failures and creates “what if I studied differently” scenarios to fine-tune next semester’s study plan.
Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets (Incerto)
Ready to Take Action?
Get the Mentorist app and turn insights like these into daily habits.