Not coincidentally, I first started paying attention to my investments around the time Moneydance gained support for tracking them. Keeping all of my investment records in Moneydance forced me to pay attention to the transactions, fees and securities. Alan Haft has posted a nicely written set of guidelines for investing that I think are very helpful.
My favorite, predictably, is this one:
5. Watch your money
No one else will ever keep track of your money like you will. Don’t get lazy and stop paying attention. Read your statements every month and monitor your progress and returns. This is your hard earned money we’re talking about, and don’t ever forget that.
via boboroshi, who also happens to have designed moneydance.com and is an incredibly enthusiastic Moneydance user.