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I feel like this question gets posed a lot in different ways and was curious if it might be possible to formulate it narrowly enough to get answered here.

For the most part I think the answer is determined by the question -- in other words, you find someone who does understand and get them to explain it to you.

Of course even with a pair -- or ideally a mentor -- one still must tackle a text in isolation. The "someone who understands" is finally the author themselves.

How to prepare yourself to evaluate and interpret a philosophical text? I'm looking for a strategic vision here.

Beyond tactical things like reading secondary sources or finding a pair/mentor to study with; and even beyond spiritual qualities (a certain patience, caution, charity, &c). Although ideally strategies for evaluation/interpretation will have an impact on the tactics and spirit of a reading.

What long-term sort of critical practices can help support the structured, rigorous reading and evaluation of philosophical texts?

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    Purchase a good armchair, particularly of a rocking nature, and a good pipe. ;) – stoicfury Dec 7 '14 at 20:10
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    Stay away from alcoholic drinks to keep a sharp mind. Cut sugar and avoid too much meat in your diet. – infatuated Dec 7 '14 at 22:22
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    Try to imagine the inner voice of the author which was whispering author what to write and how, but itself did not get onto the paper... Inverse read. – Asphir Dom Dec 8 '14 at 1:37
  • Do you mean to evaluate based on the author's context, or a modern one? – Rex Kerr Dec 8 '14 at 10:33
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I've found the best way to truly understand a work is to be a part of the ongoing discourse surrounding it -- i.e. try to find an opportunity to write about the work for an audience. Reading with the goal of communicating with others opens the opportunity for a much more rigorous approach.

This written dialectic is one of the fundamental activities of the philosophical community across history.

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