My view for every season is make the playoffs. Anything after that I consider a bonus, with a WS title as the ultimate cherry on top.
If they don't make the playoffs, well I have watching a few games of the Patriots to get me through October. Then it's FA season(one of the funnest time's of year around here:)) and the wait for pitchers and catchers to report to get me through until 2010:D
I used to get really upset and bummed when the Sox didn't make the PO or exited badly for whatever reason. Now, not so much. Yes I am disappointed when they don't win. But it last's a lot less these days:D