I propose a novel view on hard choices. It broadens the concept to include not only ‘classic’ hard choices but also transformative and aspirational choices. I argue that a choice is hard when an individual does not have an all-things-considered reason to choose an option over another and the objects of choice are ultimate ends. Construing hard choices thusly supports and explains the widely held assumption that, when faced with hard choices, it is impermissible to choose arbitrarily. More specifically, it shows that it is impermissible to choose arbitrarily by plumping and, yet, legitimate to do so by picking. Understanding hard choices as I propose illuminates that there are moral and agential constraints that limit the space of permissible decision-making procedures when confronted with ‘classic’ hard, transformative, and aspirational choices. Delineating these constraints, in turn, can provide guidance to critically appraise current theories of practical rationality.