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You requested a book. I strongly recommend _Herding Cats: A Primer for Programmers who Lead Programmers_. It covers the mindset a truly competent manager must develop in order to lead a team of programmers. It's especially geared towards those people who were once great coders and must now...

I once read a fantastic book by Jack Falvey with a title like "Career Strategies After 35." It ponders the same question you posed. Its conclusion was "It is better to have worked for a large company than to work for a large company." Working for a large company does bring several perks...

Usually when someone in IT insists you must have a degree, it's because: 1. They don't know how to determine true competence. 2. They have a degree are jealous of anybody who's accomplished much without one. I knew a lady with 20+ years experience with no degree who used to get challenged on...

I remember years ago reading in a book by Janet Ruhl that at age 22 you may absolutely love technology and detest management types, only to then at age 35 wonder why you didn't consider management. One big advantage going into management has is portability. You may get tired of IT, or IT may...