Have you ever made a choice that seemed perfectly reasonable at the time, only to torture yourself about it later? Maybe you turned down a job offer, ended a relationship, or invested in something that didn't pan out. Now you're stuck replaying the decision, convinced you should have known better.

Here's the uncomfortable truth: you're probably judging past decisions unfairly. Your brain is playing tricks on you, using information you didn't have at the time to evaluate choices you made with limited knowledge. The good news? There's a way to make decisions that hold up to scrutiny—even when outcomes disappoint. It starts with changing what you measure.

Imagine two people who each bet $100 on a coin flip. One wins, one loses. Did the winner make a better decision? Obviously not—they made identical choices with identical information. Yet we constantly fall into this trap with our own decisions, praising ourselves when things work out and beating ourselves up when they don't.

This is called resulting—evaluating a decision based on its outcome rather than the quality of thinking that went into it. The problem is that good decisions can have bad outcomes, and terrible decisions can get lucky. A doctor who correctly diagnoses a rare condition but sees the patient worsen anyway made a good decision. A drunk driver who gets home safely made a catastrophic one.

When you judge decisions only by results, you learn the wrong lessons. You might abandon a sound strategy because it failed once, or double down on reckless behavior because you got away with it. Instead, ask yourself: Given what I knew at the time, did I think through this carefully? Did I consider alternatives? Did I account for uncertainty? If yes, that was a good decision—regardless of what happened next.

Takeaway

Before criticizing a past decision, ask: 'What information did I actually have when I made this choice?' Judge your process, not your luck.

Your memory is not a video recorder—it's more like a creative writer who revises the script based on how the story ended. This is hindsight bias, and it's remarkably powerful. Once you know an outcome, your brain reconstructs the past to make that outcome seem obvious and predictable. Suddenly, you 'knew all along' that the startup would fail or the relationship wouldn't work.

The antidote is simple but surprisingly rare: write down your reasoning before you know the outcome. Document what you knew, what you were uncertain about, what alternatives you considered, and why you chose what you did. Include your confidence level—are you 60% sure this is right, or 90%?

This creates an honest record that hindsight can't corrupt. When you revisit the decision later, you'll see your actual thinking, not a reconstructed version. You might discover you made a reasonable choice with the information available, even if things went sideways. Or you might spot genuine mistakes in your process—not just bad luck—that you can learn from. Either way, you're working with truth instead of distorted memory.

Takeaway

Create a 'decision journal' for significant choices. Write down your reasoning and confidence level before outcomes are known. Review it later to learn what you actually thought versus what hindsight tells you.

Most people are dramatically overconfident about their predictions. Studies consistently show that when people say they're 90% certain about something, they're right only about 70% of the time. This confidence gap is dangerous because it prevents you from preparing for alternatives and makes negative outcomes feel like personal failures rather than expected possibilities.

The counterintuitive insight is this: embracing uncertainty actually reduces regret. When you acknowledge upfront that your decision might not work out—that you're maybe 65% confident, not 95%—you're mentally prepared for different outcomes. You've already accepted that this is a bet, not a guarantee.

Calibrating your confidence means getting honest about what you don't know. Before a decision, try assigning an actual probability: 'I think there's about a 70% chance this job will be a good fit.' This forces precision and reveals overconfidence. It also changes how you feel later. If you acknowledged 30% odds of disappointment and disappointment happened, that's not a failure of judgment—that's the minority outcome you knew was possible. You can stand behind a well-reasoned bet even when it doesn't pay off.

Takeaway

Before major decisions, explicitly state your confidence as a percentage. If you find yourself saying '95% certain' frequently, you're probably overconfident—and setting yourself up for unnecessary regret.

Making decisions you won't second-guess isn't about being right more often—it's about thinking in ways you can defend later. Focus on process quality, document your reasoning before outcomes are known, and get honest about your actual confidence levels.

When you do this, something remarkable happens: you can look back at choices that didn't work out and still respect the person who made them. That person did the best they could with available information. That's all any of us can do.