There is an unresolved debate about whether the ways of being currently identified by the DSM-5-TR as Cluster B personality disorders (henceforth PDs) should be considered genuine mental disorders or normal (if often serious) problems of living. This issue is a microcosm of a larger debate about whether psychiatry is overextending itself and overmedicalizing many of life’s hardships. We show that the resolution of the first debate can inform the second, larger, question. To this end, we examine Louis Charland’s influential arguments that Cluster B PDs are moral, not medical, conditions. Although Charland’s arguments fail to support this conclusion, Charland’s focus on mental healing to inform what ways of being are properly considered “mental disorders” is promising. We argue that skilled metacognitive self-regulation is necessary for mental healing and show that a focus on the role played by self-regulation in healing partially vindicates Charland’s argument: Cluster B PDs are not necessarily “moral conditions,” although some instantiations will be. We also show that current definitions of PDs are both overly inclusive and overly exclusive, allowing moral judgments to drive diagnosis. We conclude by showing that a focus on self-regulatory skill can help distinguish between mental disorders and normal problems of living.