One big grain of salt to take with that NYT graphic is that they took taxes into account. If you are investing in a retirement vehicle (401k, IRA or Roth IRA), your tax obligations are going to be very different. Not to mention that tax laws have changed greatly over time.
Another think to remember is that if you are saving for retirement, you are very likely doing dollar cost averaging, i.e. making deposits on a regular basis. So you aren't buying all your stocks in one year, you are buying them across a multitude of years. That greatly mitigates the risk of starting at the wrong time.
For example, I started saving for retirement in 1999. It was ugly for a while but I was positive for good as of 2009, despite all the red in that graph.
Another think to remember is that if you are saving for retirement, you are very likely doing dollar cost averaging, i.e. making deposits on a regular basis. So you aren't buying all your stocks in one year, you are buying them across a multitude of years. That greatly mitigates the risk of starting at the wrong time.
For example, I started saving for retirement in 1999. It was ugly for a while but I was positive for good as of 2009, despite all the red in that graph.