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Personally, the philosophy of Martin Heidegger was the most difficult for me. It was still difficult to study postmodernists. As a result, I came to the conclusion that to a large extent their philosophies are artificially overloaded with abstraction, covering up a poor set of basic ideas.
From the continental – Hegel.
We have more than a dozen fundamentally different and contradictory interpretations that are used in different contexts (metaphysical, non-metaphysical, anthropological, Marxist-Leninist, etc.). There is no agreement on anything at all. This year, a volume of Brandom was released – there is again a fundamentally new reading.
In an analytical context, the question does not make sense – disciplines are studied, not philosophers. A person can (and should, because the time of the “renaissance people” has passed) spend all his life studying ethics and not touching formal semantics at all, which requires a colossal mathematical, logical and linguistic apparatus. Aesthetics may be difficult for a philosopher of mathematics, and philosophy of physics may be difficult for a philosopher of consciousness (McGinn's disastrous case). And the continental Derrida will be difficult for everyone.
The words “for study” can mean “for reading without preparation” or “for studying the full corpus”. If in the second sense-then there are philosophers, for example, Leibniz, who have written a lot on special issues, but it is not so easy to relate their ideas to the current state of scientific issues and everyday experience, precisely because of some particulars of argumentation. Hegel and Heidegger gravitate towards this pole. If we talk about complexity for a beginner, then it seems that analytical philosophy is difficult, since it requires accepting many prerequisites at once, existentialism and post-structuralism are difficult, since they also imply a good knowledge of, for example, French fiction, from which these philosophers often take examples and arguments. But any philosopher has his own easy works: for example, Kant wrote Prolegomena for those who find it difficult to read the Critique of Pure Reason right away, Heidegger and others gave lectures and wrote introductions in the spirit of ” What is philosophy?”
I'm a psychologist. Therefore, I think the most difficult question is how to know the soul (inner world) of a person without being able to perceive it sensually.