Timing is very difficult, I've been told over and over again. I personally think it's easier to time the top rather than the bottom. The reason: the fall is always preceded by lots and lots of people forecasting doom and gloom. I got out of Sun Microsystems stock (and some others) at the end of 1999 for that reason. Sold at $150+. Months later it was at $5. Now, I'm no prognosticator. I was looking to buy a house in the future and knew I needed to convert to cash at some point. So, I was sort of hyper aware of what was going on and at the end of 1999 I just couldn't take it anymore.

I'd love to hear how people timed the upswing from 2008.