I started an e-commerce website with one of my friends the year I graduated highschool (way back in '97) and had to learn, mostly the hard way, how to maintain our 2 servers. I grew up in a Linux-friendly household, so there were some things I already knew and it was mostly policy and best-practices things I had to pick up on. Fortunately there was a friendly usenix group nearby that were willing to help me out with that. Later, at college, I enrolled in a major that catered specifically to network and systems administrators.
I think most of the practical stuff I picked up via trial and error and the occasional o'reilly book, but I think that my most-utilized resource now is forums. Those long nights reading SAMS, Deitel&Deitel, and fat Cisco books is mostly history.
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