Knowledge is necessary for certain moral obligations. In learning something new, one sometimes triggers a moral obligation. This paper argues that the existence of these knowledge-based obligations poses a problem for the view that we are not only free to choose the course of our own lives, including our careers and personal projects, but also free to change our minds and quit at any time to pursue something else. For if our choice of life path has generated knowledge-based moral obligations that we must fulfill, then it is apparently not true that we can quit at any time. To resolve this tension, this paper proposes a relatively demanding set of conditions under which it is permissible to swap one career or life project for another. The resulting compromise reconciles the moral force of knowledge-based obligations with the basic freedom to choose less-than-optimal careers and projects. It also highlights the distinctive role played by knowledge and expertise in generating the intractable problem of morality’s demandingness.