It seems to me that the Carleton administration has been getting more and more heavy-handed during my last few years there, and especially after I graduated. Drinking rules are becoming stricter, impromptu art is treated as vandalism, and fines are becoming heavier. Consequently, a great deal of student cleverness and creativity (stuff that would be revered as "hacking" here at MIT) is in danger of dying out.
Carleton has a longstanding tradition of irreverence, and that should be directed toward the Carleton administration as well. The Administration's principal threat to oppose student unruliness is monetary fines. Now, a $300 fine for climbing the water tower to paint a giant Saturn on it would be crippling for a Carleton student, but would be peanuts for a group of young urban professional alums.
I propose a highly informal (and probably illegal) "Carleton Anti-Fascism Endowment", to allow alums to encourage bad behavior on the part of Carleton students. Fines incurred by students would be reimbursed, and students disciplined by the administration would be looked upon favorably for hiring in alums' companies, letters of recommendation, etc. Of course, the Endowment would have its own standards; unruliness leading to injury or harrassment of others or significant property damage, or impromptu art which doesn't meet the Endowment's exacting standards, will not be reimbursed.