To understand The Philosophy Of Freedom the most important thing is to study the book. It is amazing how many "experts" have barely read it. You can tell by the terms they use when commenting on it, as they usually are just attaching their own views onto the book, as you see in the way Christians use the bible. One needs to take into the mind concepts in the book without projecting in one's own familiar beliefs. If you do that your reading will merely extract the concepts that you already have inserted into the text. More than a philosophy book, it contains descriptions of the cognitive process that you can check out within yourself.
What is required is an emancipation of knowing from past preconceptions, such as Steinerism; the century of built up institutional belief of what Rudolf Steiner believes and stands for. The Philosophy Of Freedom is the result of independent thinking and complete in itself. This means it can only be understood within itself, and perhaps with some help from the three books that lead up to POF when Steiner struggled with his questions of knowing and developed his philosophy of life. (It must be keep in mind that even though he began his work with an analysis of Goethe he went on to develop his own independent view.) Note: I put together a page that contains the whole text plus insertions from his other related books to help with understanding POF. Key word searches can be done from one's browser page search that will include POF and parts of 3 reference books. It is on the reference page and here.
The answer as to how you work with the book is called reading comprehension. Simply put, reading comprehension is the act of understanding what you are reading. There are two elements that make up the process of reading comprehension: vocabulary knowledge and text comprehension. In order to understand a text the reader must be able to comprehend the vocabulary used. If the individual words don’t make sense then the overall conception will not either. In addition to being able to understand each distinct word in a text, one has to be able to put them together to develop an overall conception of what it is trying to say. One way to practice text comprehension is to boil a short section down into a few words. George O'Neil recommends Mastering the Content and then discovering new relationships.
Master of Content
We first must become master in the highest degree of content, utterly eliminating the arbitrariness of personal preference and emphasis. Says Goethe: To have the whole in your heart, you must have conned its every part. To which Rudolf Steiner has added: First read for substance, then read again for form.
Contemplative Comparison
In contemplating the totality of a living thought-organism, correspondences and symmetries, previously unseen, begin to emerge, each illuminating the other. Meanings come forth, never before expected, revealing interdependence and mutual support. The whole is experienced as weaving interplay of single thoughts, each reflecting the whole as experiencable from its single aspects.
book of answers?
The Philosophy Of Freedom is not intended to be a book of answers, because it is not interested in gathering together a group of passive followers. Individual inner freedom is respected by allowing room for the reader to gain knowledge through their own insight. To struggle with the way Steiner presents his ideas is exactly how the book was meant to be studied. The intention of Steiner's writing style is to provoke thought. Once one works through it one finds that it actually is clear, makes sense and is even kind of simple.
Some clues to understanding are that he is describing experience, so you can always compare what he says with your own experience.
The book is a whole so each piece fits within a specific context of the whole book.
The book evolves through stages of development so he describes experience suitable to the level of development of the chapter.
It is independent thinking so he may use more unusual words to describe something rather than more familiar terms which keeps us thinking rather than falling into our standard definitions.
He continuously changes his choice of words to explain similar things rather than sticking to a set nomenclature
In short, you are continuously challenged to think. He brings in many many views which develops broadmindedness, and his thoughts rise as you move through a chapter which develops an ascending thought training. He presents a point through many view-points. One view evolves out of the previous view, even though you may have to look sometimes to see how. The thinking stimulated can produce new insights each time you read the same passage, so you are never done with the book and can never really say I know the book.
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