Sometimes it does not matter, you can be in the wrong place at the wrong time no matter when you were born as well.
I remember seeing posts on this board saying they would have been much better off buying a home at the top then leaving their money in the stock market in 2009.
I saw people downsize and put the money in the stock market in 1999 only to have most of it evaporate into thin air when what seem like very solid investment went BK (enron, worldcom etc…)
You can always make the wrong choice, in fact it is very very hard to make the smart choice as they always seem like the most bone head move at the time, like taking your stock money and buying a home in 1999.