Before you ask, yes, it is weird that I’m reading a bunch of “management” books.
You can watch Michael Lopp’s career by following his various books. Start with “Being Geek” [affiliate link], the software developer’s career handbook. The move into management resulted in “Managing Humans” [affiliate link]. And his promotion from manager to director and executive gets you “The Art of Leadership” [affiliate link] which is the book I recently finished.