I started actually earning decent money when I took a job at Origin Technology in Business back in 1997. Since everyone was doing it at the time, I put some money into the stock market, buying shares in Apple, Microsoft, and various other tech companies I knew about from reading Red Herring and the like. Since it was the Web 1.0 bubble, I actually made enough return to buy myself a fancy new PowerBook G3 when I moved back to Canada in mid 1999.
Getting 40% on my investments over two years made me feel like I knew something about stocks, so when it came time to set up my first RRSP investments in February 2000, I put almost all of my allowable amount into the CIBC Global Technology Fund and waited for the returns to roll in.
Here's a quote from Michael Arrington from today:
Web 1.0 effectively ended on Friday, April 14, 2000, when the Nasdaq lost about 10% of its total value. Between March 10 and April 17, 2000, the Nasdaq lost over 37% of its all time high of 5,133 (and it fell far further later on). The Nasdaq was practically an index of Web 1.0 companies v. the "old economy" NYSE, and it got hammered.
Notice the earliest date: March 10, 2000 - a week and a half after I got back into the market. Now that's timing!
But my best timing would be a year and a half later, when I saw that things had bottomed out and figured they couldn't get much lower. There were murmurs of an improving economy and business activity was beginning to pick up. I had been doing well with some contract work and so decided it was time to put some more money - about half of my yearly limit - into my (now a bit more diversified) RRSP funds. I called up the bank on Friday afternoon and they said that trading was closed for today, but that they would finish the transaction next Monday ...
... Monday, September 10, 2001.
Now I just have an index fund and have the bank automatically invest the same amount every month for me. I've read a lot lately about how regular investment over time in an index fund is actually a much better investment plan than trying to play the market - even for people like professional fund managers who do this kind of thing for a living.