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Andrew Schroeder
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Concerning the generalization argument, the same concerns (obviously) arise for Kantians thinking about the Formula of Universal Law. It's unsustainable for everyone to act on a maxim of being a banker, but surely it's not wrong to decide to be a banker. The standard Kantian answer (and this seems independently plausible to me) is to say that it is wrong to act on a maxim which says to become a banker, no matter what. But it's not wrong to act on a maxim proposing, roughly, to become a banker, so long as doing so doesn't violate any other duty. In practice, this will amount to an intention to be a banker, so long as society doesn't urgently need you for some other purpose. In your case, we could similarly say that if Betty only intends to pay Alf not to vote, so long as the consequences of his not voting are trivial, that's permissible (though perhaps, as you say, indicative of a bad character). If, however, she intends to pay Alf not to vote, even if his not voting would have serious consequences, then her act is impermissible (even if his not voting in fact has only trivial disvalue). That seems plausible to me.
Jason, I'm not convinced by the prima facie case you make at the end in favor of permitting Betty's action. There seem to be a number of situations in which it would be permissible for someone to do X or not, but impermissible for someone else to pay that person to do X. Arguably: to donate a kidney, to break up with a partner/spouse, to award a prize to some nominee, to have sex, to admit someone to a university, to vote for some candidate (maybe this is why you raise the example?). and so forth. Now, the reason why paying for each of those actions is impermissible (if it is) surely varies from case to case. Some of them -- the honorific nature of a prize or the nature of intimate, personal relationships -- don't apply to supererogatory acts in general (though they will apply to specific instances of supererogation, which means we need to know more about what Alf plans to do). If there's a general case to be made here, I suspect it might parallel the arguments sometimes given for the examples above. For example, we might say that an agent's moral character lies within some relevant sphere of autonomy, and so another agent ought not interfere unnecessarily. That might mean it would be permissible in many cases for Betty to pay Alf not to do something supererogatory, but that it would be impermissible for Betty to [pay Alf not to do something supererogatory because it was supererogatory].