In this edition of "Where's Steve-o", Mr. Sailor pops up in the comments of Yglesias blog posting a variant of an idea I'm supportive of.
My stronger variant of this idea is making the default level of liberty at a level empirically demonstrated to give the best outcomes for populations, but then allow movement to greater levels of liberty through demonstration of qualifications.
This could involve making a level of savings opt out rather than opt in, making full-time work mandatory, for example (unless one demonstrated alternative productivity).
I'm aware of the standard libertarian critiques, but I'd like to note that in some ways this proposal is more libertarian than the current state (most restraints are opt-outable), and any solid libertarian critique should be rooted in empiricism rather than on romantic or mythological first principles.