I've been writing for some time on how to correctly compute the last record high in stock prices (see link).
Based on this analysis (which uses monthly closing stock prices), the last record high was in September 2000. Today's closing S&P 500 price is the first time that high was crossed in the last 12.7 years.
That means that after almost 13 years, an investor buying the S&P 500 on September 1, 2000 in a tax-free account, then re-investing all dividends along the way, has finally broken even after inflation.
That is one awful 13 year period, only matched by a 12 year period from February 1973 to February 1985. The only thing left for me to actually record this new high is for the S&P to hold or exceed this level when the month ends. Of course nobody knows whether that will happen, but for the moment, the general message of breaking even after 13 years is still the take-away.
This makes me intuitively bullish - it seems the next 13 years have got to be better than the past 13 just based on how unlikely it is for there to be generation-long (25-30 year) periods of zero real returns!