Why does encoding specificity fail?

The most common reason encoding specificity fails: Evaluating past decisions using information you only acquired after the outcome. You'll know you're in this failure mode when your judgment of a decision changes based on what happened next rather than what was knowable at the time. The phrase 'I should have known' is almost always a signal that you're judging with reconstructed hindsight, not reconstructed context.

The fix: Pick a decision you made in the past six months that didn't turn out as planned. Before evaluating it, write down everything you can remember about the conditions at the time: what you knew, what you didn't know, what pressures you faced, what alternatives you considered, and what evidence supported each option. Then — and only then — evaluate whether the decision was reasonable given that reconstructed context. Notice how different the evaluation feels compared to your initial judgment.

The underlying principle is straightforward: When evaluating past decisions reconstruct the context that existed at the time.