I avoided reading philosophy books for a long time. Since you,
  like me, are the product of a computer age (we're using
  computers), and I believe humans work best with analogies, I
  would start with:

  a) a basic book on computers and computer logic. A lot of
  philosophy involves logic.
  b) a book on common terms you will find in philosophy. A lot of
  information can be gotten by definitions: They often represent
  "distilled wisdom", that is - the experience of thousands of
  years of thinking can be compressed into a few words by a good
  definition that is well written.
  c) look up several definitions of some of the words.
  d) Then I would start with books on early philosophers. If you
  are studying Western Philosophy, which a lot of philosophy you
  might want to study will be based on, I would go back to the
  ancient Greeks.
  There's no need for the original books at first; youtube videos
  should be fine.

  *then* you can start diving into some books on other
  Philosophers.

  You can get used to the family of names as well. There are
  charts you can find on Google images that will show you "this
  philosophy influenced that philosopher who influenced that
  philosopher".

  There are "schools of philosophy", different groups that
  philosophers are often categorized in.

  You might want to consider some books on different forms of
  logic, especially as they are used in Philosophy.

  It's not that that logic is more important than philosophy.

  Rather, it's so you will be familiar with the "terms" that are
  used in philosophy a lot. They can be very confusing. Philosophy
  has its own special unique coded language that's a little
  different.