This book is a pretty good idea: now that we are getting into the second or even third generation of classical education, have someone from the first generation write to the current generation trying to get them on board with the project. In execution, it turns out pretty OK: there is definitely a lot here that might help get current students on board.
Alas, as Kierkegaard warned, life, which can only be lived forwards, can only be understood backwards, and so I fear a lot gets lost in translation across time and experience. Proclaiming that the aim of classical education is to make you a "leader" seems like a sop to adolescent vanity, particularly when it gets translated in terms of "success," and "success," it is strongly suggested, will show up on balance sheets. (And if we tried to put the Beatitudes on a balance sheet, would they be what anyone would describe as "success"? Was Jesus a "successful" teacher, having no place to lay his head, no assets to speak of, a paltry number of students, by one of which he was betrayed, abandoned by the rest?)
The trouble is trying to communicate the value of something which is not really of instrumental value to people (that is, young people) who think almost exclusively in terms of instrumental value, if not in more explicitly hedonic terms . Though it can be done, trying to convey the importance of cultivating the soul to someone who is motivated by superficial things is not easy. To try to enlist a sanitized version of the will to power (Nietzscheans 4 Jesus) to try to motivate young people to cultivate their souls is an understandable move, given the circumstances, but I am not really sure it is productive.
There are some other assorted issues here, though none very major. Though I am as skeptical of the mainstream education system as anybody, some of Merkle's descriptions of it are pretty dismissive, and few of them seem to be based on firsthand experience. There are also some embarrassing rhetorical gaffes here -- words used with indifference to their meaning and register (has nobody ever told Merkle what "schmuck" means? It is hardly a polite word), confusion about terminology ("case" is used where "tense" is meant in a discussion of Latin grammar), and a colloquial tone that sometimes comes across as patronizing ("She wrote 'wait a sec'? OMG! Merkle is one of us!!"). In a typical book targeted at high school students all this would be de rigeur, but in a book that claims to prize eloquence and precision it is somewhat disappointing.
For reasons best explained at length in a different medium, I also do not particularly find the emphasis on "worldview" helpful. However, Merkle's discussion of it is more nuanced than one often finds. Her comments about other subject areas are also often helpful and even insightful. (Her ebulliently optimistic attitude about the power of logic to make us more rational is almost certainly wrong, however: abundant evidence seems to show that pretty much anybody behaves very rationally when discussing topics on which they are well informed and predictably irrational elsewhere, in spite of formal training).
Overall, a good attempt and a worthy project. Hopefully it will inspire further efforts at talk about education across generations.