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.