I was standing at the airport yesterday, saying goodbye. Hellos are wonderful—there’s anticipation, happiness, a lift in the chest. Goodbyes are the opposite. They leave you in a blue funk until the routine swallows you back up. Arrivals and departures may bookend the same event, but emotionally they live in different countries.
Decisions are like that too. We make hundreds of them a day—most small and forgettable—and a handful that shape the arc of our lives. The trouble is that a decision that looks good today can look very different years later. Sometimes it curdles. Sometimes it surprises us by turning out better than we imagined. And sometimes it simply meets a version of ourselves we hadn’t yet become.
Take the move to the coast. You sell the inland house, buy near the sea, and for a while it’s everything you wanted. Then your health suffers—the damp, the pollen, something in the air that doesn’t agree with you. Or the reverse: the move was about lifestyle, but coastal property values climb, and the loss on the inland sale is more than covered. The decision didn’t change. You did. The world did.
This is where Daniel Kahneman’s Thinking, Fast and Slow becomes useful, not as a catalogue of biases but as a way of understanding how we judge decisions across time. Kahneman distinguishes the experiencing self from the remembering self. The experiencing self lives the five years day by day. The remembering self later tells a story about whether the move was a good idea—and it tells that story badly. It overweights the peak and the ending, and it neglects duration almost entirely. You might have had five genuinely good years and one bad one, and remember the whole thing as a mistake. Or five hard years and a redemptive ending, and call it a success. The retrospective verdict is not a clean ledger.
So when we ask whether a decision was good or bad, it helps to make the time frame explicit. Good for whom, for what, over how long? A move can be good for your career for five years and bad for your social life for twenty. Good while you’re single, bad once you have children. Good for your income, bad for your health. Without specifying the horizon and the criteria, the judgment floats free.
There are three different things that can happen when a decision sours over time.
The first is unforeseeable change. You moved for a job, the company collapsed, a pandemic hit, a parent got sick. The original decision may still have been sound given what you knew. That’s bad luck, not a bad decision.
The second is foreseeable change you ignored. You moved knowing you wanted children eventually but didn’t check the schools. You knew the industry was cyclical but assumed the good times would last. You knew you hated cold weather but told yourself you’d adapt. That’s a process failure. The decision was flawed at the time, even if it felt fine then.
The third is changed preferences. You are not the same person who moved. Your priorities shifted. The decision wasn’t necessarily bad—it was good for the person you were, and now it’s wrong for the person you’ve become. That’s not a failure of reasoning. It’s a failure to account for the fact that future selves exist and often disagree with the present one.
There’s also a hidden trap: the move wasn’t one decision. It was a bundle. Move, rent or buy, build a network, stay in a job, have children there. The five-year outcome is the product of many later decisions. If you bought a house and refused to leave because of sunk cost, that’s a later decision problem, not proof that the original move was bad. Kahneman’s work on loss aversion explains why we cling—losses loom larger than equivalent gains—but the point here is temporal: we misattribute the result of a chain to a single link.
Where does that leave us?
Maybe it helps to make the horizon explicit. You could ask whether you’re optimizing for two years, ten years, or a lifetime—and perhaps set a review date. A move might be framed as a three-year experiment rather than a permanent verdict. You could rent instead of buy, keep the network warm, preserve exit options. That changes the decision itself.
It can also help to separate decision quality from outcome quality. A good decision is a good bet under uncertainty. It can still lose. Over long horizons, variance compounds. If the bad outcome was reasonably foreseeable and you ignored it, the original decision wasn’t good—it was lucky for a while, then unlucky. But if the world simply changed in ways no one could predict, the decision can still have been sound.
You might keep a decision journal. Writing down what you expected, why, and what would make you change your mind can be useful. Five years later, you can ask whether your reasoning was sound, whether you updated, whether you confused a bad outcome with a bad process. That’s often more useful than declaring it a mistake and moving on.
And perhaps treat the present as a new decision. If you now realize the move was wrong, the question isn’t “Was I an idiot five years ago?” It’s “What’s the best decision from here?” The past decision is data, not a sentence.
So yes—a decision can be good today and bad in five years. But often that means the time frame was wrong, the criteria changed, or the world moved. The deeper lesson is that good decision-making isn’t about being right forever. It’s about making robust bets, monitoring them, and being willing to revise when the person or the world changes. Kahneman’s remembering self will always try to rewrite the story. The best we can do is keep the ledger honest.
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