Here is my monthly plan for May. I used to do these on my own but lately I've been writing them up for the Tower so I figured I'd start posting them here too.
May 1 - 8: Finish swatch and post OWL proposal. (done!) Knit four dishcloths for Mom and Susan by the end of the week. (half done.) Knit and felt three mice for Selena. Begin working on herbology purse. Begin knitting OWL once approved.
May 9 - 15: Finish herbology purse and add a rose to it. Submit to Ravenclaw Tower's May Flowers contest. Begin and possibly finish Monkey socks for Ravenclaw Monkey KAL. May 15th - knit test beanie pattern for Quidditch challenge. Continue working on OWL.
May 16 - 22: If socks aren't finished, finish them. Start a Jayne hat for Potions. Begin working on the first of three regular Quidditch items. Continue working on OWL.
May 23 - 31: If any classes aren't completed, finish them. Finish Quidditch item 1. Get OWL to 33%.
This is as much as a monthly plan as I can have. It's always subject to change, depending on how much knitting I get done in a week. The OWL (aka, my sweater) must be at 33% by the end of the month so that I can get to 50% by the end of June.