When Rebbe Nachman discusses his disfavor with philosophy he explains it like so: Philosophers take a question and its answer and then rephrase them collectively in the form of a question, which then has no answer, because the answer is already part of the question.
Part of the reason I think most people don't understand themselves is because just like a philosophical question, (as defined by Rebbe Nachman) a person is a combination of two opposites whose union defies explanation.
A person has many parts, overall we can categorize them into three: a body, an animal soul, and a Godly soul. As long as a person looks at these three parts and assumes they are one part, it's impossible to make sense out of all the contradictory elements of the human condition.
The best place, I think, to begin to understand the structure of a person is to learn the first twelve or so chapters of the Tanya; the manual for self-awareness and fulfillment written by Rebbe Shneur Zalman of Liadi, the first Lubavitcher Rebbe.