G'Day Gbrew,

You can not readily do this with Outlook - however, please
see: http://www.cs.umd.edu/hcil/datelens/.

I urge you to watch the streaming video (link on that page) -
it's the ONLY "User Guide" you will get.

Datelens is a PDA product that offers a very cool view
into the Outlook Calendar, and for the PDA you must buy it.

Two variants of the Desktop version are FREE, though
unsupported:
   An addin version that pops a button onto the Outlook
       Toolbar. I have this working well - Outlook minimised
       and a small Datelens Window onscreen.
   A standalone version that fires up a hidden instance of
       Outlook and therefore (to me) has no advantage over
       the Addin (though it also works well).

Either may occasionally crash - although the latest version
does seem very stable.

Make sure that Outlook is NOT running when you install
either.