Among the most crucial decisions (or at least, the first of many) surrounding graduate school is the decision to even start. Here are the thoughts of several academic bloggers considering the decision from many points, as potential student, recent student, and advisor.
Howzerdo at Gully Brook Press talks about the decision as it's being made.
Though she writes largely about the experience of professional music, Terminal Degree's perspective at Metamorphosis Complete, applies broadly.
Dr. Crazy, currently at Reassigned Time and formerly at The Chronicles of Dr. Crazy, considers, considers and reconsiders her experience, and her take on the advice to go to grad school.
Finally, Bardiac offers a useful list of things to know and consider, items which are useful for surviving graduate school as well as making this initial decision.
Updated 2008: Undine offers these considerations.