The Consolations of Philosophy is a curious introduction to philosophy, if that is what it is intended to be. The subject matter is at least ostensibly philosophy and the writing style is certainly introductory, but it is certainly not a good choice for an introductory philosophy course, unless one would like to assign a chapter or two as "recommended reading" left on reserve at the library.
The title is, of course, derived from Boethius's great work The Consolation of Philosophy. The Consolation of Philosophy was written while Boethius was in prison, waiting to be executed. It remains perhaps the greatest piece of death row literature of all time. Its literary form is a dialog between Boethius and a lady figure personifying philosophy. Philosophy makes the case that Boethius's condition does not justify complaint and that nothing has been taken from him that is the basis for true happiness. It is through the thoughtful examination of one's circumstances (through philosophy) that one can come to this realization and be consoled in the face of misfortune.
De Botton's Consolations of Philosophy, broadly speaking, attempts to make roughly this case, but it does so through the examination of the thought and works of six philosophers: Socrates, Epicurus, Seneca, Montaigne, Schopenhauer, and Nietzsche. De Botton attempts to show how the thought of these philosophers can help us overcome (respectively) unpopularity, poverty, frustration, inadequacy, a broken heart, and difficulties in general. The structure of the work and the selection of the philosophers has some reason behind it, but at times it appears that de Botton has cobbled together a string of mostly lesser philosophers and mined their works for passages that fit his purposes. This is not to say that he has misread these philosophers, but that his project was mostly to write a book -- not to explore an important theme or thesis among philosophical debates. By the end of the book one is left wondering, "so what?" Certainly there were a number of interesting anecdotes (along with some clever illustrations), but was it really worth the time?
The Consolations of Philosophy is less an examination of the philosophy of six (mostly minor) philosophers and more a curio cabinet of objects collected from their biographies.