All right, I have a lot of points on why you would benefit from Entourage. And because I happen to be in a numerical mood right now, off we go:

Let me be clear: I only use this program for its Calendar feature. That is all. And it’s totally worth the purchase, even for only that one element.
This is my backup system for remembering birthdays, anniversaries, vacations, holidays (I don’t mean Christmas, but moreso the kinds that don’t fall on the same day each year), six month check-up days, bill payment dates, the last time you backed up your laptop, appointments, death days (why is this important? I don’t know, but it gets written down ‘cause it feels important), etc.
You can set up specifically what kind of reminder you want for each event, ie. being reminded of something a minute before it happens or, say, a few days before, whatever.
A reminder box pops up and appears, no matter what window on your computer is open. This is amazing, in my opinion, because it lets me live my life a little easier without having to check my calendar constantly to see what I’m forgetting or missing. (Also, even having a reminder is optional.)
Optional color co-ordination. Everything can (not must) be organized into categories like family, personal, recreation, work, etc.
You have a distinct record of what’s going on in your life past, present and future.

The above photo is just an example of what it looks like, that one shown isn’t mine. Mine is much too precious for your curious little eyes.

I can’t really tell you how much I love using this guy. It’s way too organized, beautiful and I think you probably need it in your life. No pressure.