I can see that... for the first books. Though consider that at the time the main character hasn't gone to college yet and does have a childish view of life and is using the 'merit badges' as a goal. Give Milk Run a try, or if you're ok with jumping ahead, Double Share.

Thinking back to my own college days, the "merit badge" model and the planning guide for a major (first three books, Ishmael is pre college... the beginning of Double Share has a summary of his time in college that takes a fe paragraphs).

The more adult life choices all happen in the later books (and while he still has some focus on "the certification that allows him to do X" (steward's certification for carrying passengers) its a minor thing rather than the "what he does all day").