Two things make records less remarkable than the coverage of them suggests. The first is arithmetic. Once a series has climbed past its previous peak, every subsequent step up is a new record, so records are not scattered evenly through history. They arrive in runs, separated by long stretches in which none occur because the market is below an earlier peak. A count of record days therefore says more about which regime the market is in than about how unusual any individual record is.
The second is that "the level" is not one number. A price index tracks prices only and leaves out dividends; a total-return index assumes dividends are reinvested and so is always higher over long periods, and reaches its records earlier. An inflation-adjusted series is different again, because prices have to rise faster than the cost of living for a real record to be set. The headline figure quoted in the press is almost always the nominal price index, which is the one that sets records most rarely of the three and the one that corresponds least well to what a diversified investor actually holds.
Individual investors have a fourth version that matters more than any of them, which is their own account's high-water mark. That figure depends on the contributions and withdrawals made along the way, so an account can be at its own all-time high while every index it holds is below theirs, simply because money kept arriving. The reverse also happens in retirement, when withdrawals can keep a balance below its old peak through a market that has fully recovered.
The behavioral question, which is why this page carries the psychology topic, is why a record level feels like a bad moment to invest when the same money invested a week earlier at a slightly lower price felt fine. The mechanism is reference-dependence: the old peak becomes an anchor, and prices above it read as expensive relative to that anchor rather than as ordinary. Our pages on anchoring bias and recency bias cover the mechanism. What this page can say plainly is the arithmetic point: in a series that rises over long periods records recur by construction, so a rule of "wait until it is not at a high" has no stopping condition other than a decline, which makes it a rule about the calendar rather than about value.