Philosophy is a lot to take in all at once. There are many philosophers, many areas, many methods and many beliefs. Since this is true, there is more than one way to teach philosophy. Some teach philosophy using history, and start at the beginning. Others teach philosophy by topic and discuss what various philosophers have said about that topic. Still others believe that as long as you have studied the great philosophers, you have covered everything right.
I believe that there is some value in all of these methods. However, the average person must start at one place. I suggest beginning with the philosophy of Aristotle, particularly with his introductory works in philosophy. From there you can branch out to various topics in Aristotle and later on discuss what people believe today and where modern philosopher’s ideas come from.
I have currently begun to commentaries on Aristotle’s Topics and his Categories. The Topics provides an introduction to Aristotle’s thought and also teaches how to argue. The Categories provides an understanding of Aristotle’s metaphysics. At the present time, both of these are incomplete.
I have also written a number of series on my blog. I have one practical series on how to argue and the nature of expert opinion. I also discuss the existence and nature of the world by examining what exists in the world, exploring the nature of free will and proving the existence and attributes of God. I discuss our knowledge of the world by determining what philosophy and religion are and demonstrate that naturalism is false. Finally, I spend a bit of time on ethical and political issues: what education is, what ownership is and why freedom is such a good thing. Currently I am exploring the nature of knowledge, how to gain happiness and the relationship and nature of words and concepts.