Ever since Socrates debated Thrasymachus in Plato's Republic there has seemed to be a potential conflict between morality and self-interest. Paul Bloomfield is a contemporary philosopher who has recently written a book contributing to this debate. He thinks he has arguments which show that the moral skeptic or selfish egoist (who thinks that a life of immorality focused on her own narrow self-interest leads to the Good Life) is wrong even on the basis of assumptions that she herself holds. A life of immorality is really self-undermining since it works against the individual being happy and living the Good Life. This is similar to Plato's argument in the Republic, though he makes the connection through the harmony of the soul and the discord that immorality brings. Bloomfield thinks that a more Kantian argument that makes the link through self-respect will fare better. He argues that immorality is always damaging to the self-respect of the individual, where self-respect is necessary for happiness. I will argue that Bloomfield does not succeed, at least in the sense that his arguments do not show the egoist to be wrong in a completely non-question-begging way as he claims. I also sketch a reconstruction of this argument meant to be an improvement in response to my criticisms of Bloomfield. Where the original argument focused on humanity as the ground of self-respect, I think the skeptic can regard this as a fact external to her life without being self-defeating. However, she must regard rational agency as internal to her life and necessary for her self-respect. So if we can show that immorality damages one's self-respect, then the skeptic has reason to avoid it even if she only cares about her own self-interest.