I love the idea of this book because stories are such a powerful form of inspiration. I would have wanted something like this as a teenager, and still think it wouldn’t hurt!
To build on the great idea you have here, I would especially like to see this as an interactive book or website. You could partner with a career or motivational coach to develop activities that the reader could complete—so sort of part how-to employment manual (your pathway case studies), part journal/activity book. Asking the reader to brainstorm their own first steps toward accomplishing something similar could make them more inclined to act, and give them a sense of immediacy and empowerment.
For example, Matt Faraday was a pro-bono cat sitter, and that helped him get a leg up applying to work at the pet store. An example activity that could follow might ask the reader to list everyone she knows for whom she might be able to provide some service (e.g. neighbors, relatives, teachers, coaches). The next activity might be to narrow the list and develop a proposal for how to complete an interesting project for that connection over the next month.
I think this could exist in book form and on the web. Downloadable PDFs could be a simple way to supplement class curricula with relevant, career-oriented material, and start bridging that gap between education and real world work. There are some great ed/tech teacher bloggers out there who would very likely love to adopt this in their classrooms and write about their experiences.
Sital, I really like how you emphasize that "these are not one-off experiences, but done regularly so the lessons become engrained." That's so important to successfully educating kids about career opportunities, and to building their engagement, confidence, and skills. I remember having a “career day” once a year or so in school—these events were never useful or meaningful because the conversation did not persist alongside other parts of the curriculum.
I also really like how you propose we change the way we teach kids to think about their career prospects. “The focus should start on whether they like fixing problems, discovery, dealing with people, or building things.” That is a great place to start! I believe it would help a lot of teenagers view a career as an expression of themselves, their desires, and the things that bring them joy. Framing work in a very positive light could make a huge difference.