Reading philosophy can be difficult especially if you're reading the classics which may have been written hundreds or thousands of years ago. Having difficulty doesn't mean that there is anything wrong with you or the readings. Having difficulty just means you'll be a much better reader and smarter person after you've mastered the material. After all, if reading textbooks was like reading a newspaper, there would be no need for colleges! The following are some basic tips for better understanding readings in philosophy (and anything else, for that matter!)
 
 

Reading Once is Never Enough.

A useful strategy is to do the following:

Initial reading (before the material is discussed in class):

1. Place a dictionary within reach. (However, do not use it for philosophical jargon because the dictionary will be wrong - only use the definitions given in class.)
2. Skim the assigned chapter, section or article. Read the first and last sentence of each paragraph and the summary or last paragraph. What is the article about? What view does the author defend?
3. Start at the beginning and read carefully, slowly re-reading any confusing sentences after you have read the paragraph in which they occur.  What reasons does the author give for their view? What opposing views does the author discuss? What reasons are given for rejecting them?

Second reading (after the material has been discussed in class).

1. Have your class notes relevant to the material open and in front of you.
2. Read the material again, comparing it with your class notes. Can you see where the instructor has explained the concepts in the readings? Can you better understand how the author of the reading explained them?

Organize the reading.

In the margins, note (in pencil) where the author states their view and each of the reasons they give for their view. Also note each opposing view and each reason the author gives for rejecting each opposing view.

Highlight or underline key points only.

The highlighting or underlining should allow you to locate every key point made by the author. Don't highlight or underline everything - this is pointless (and besides, it's not a coloring book!)

Make an index.

Many texts don't have an index. Making one as you read through can make it much easier to find material later on in the course. This could be done by writing entries in the back of the book or writing entries with a computer.

Additional Resources

How to Read a Philosophy Paper - some helpful tips from Professor James Pryor.

Some Tips for Reading and Highlighting Texts -  from a variety of experts

McGraw Hill Publishing Company has a series of books which are guided tours of philosophical classics, edited by Christopher Biffle. They include the original texts incorporating extensive exercises designed to help you understand the reading. This series includes:
1. A Guided Tour of John Stuart Mill's Utilitarianism
2. A Guided Tour of Rene Descartes' Meditations on First Philosophy
3. A Guided Tour of Selections From Aristotle's Nichomachean Ethics
4. A Guided Tour of Five Works By Plato: Euthyphro, Apology, Crito, Phaedo (the Death Scene) and The Allegory of the Cave