R. M. Hare is pessimistic: “Nothing is so difficult in philosophical writing as to get people to be sympathetic enough to what one is saying to understand what it is. Perhaps nobody will ever understand a philosophical book [or view] of any depth without, initially, believing it, or at least suspending his disbelief. Otherwise he will never grasp what the writer is trying to convey.” [1]
Ernest Nagel, then, pays a great compliment to Rudolf Carnap: “He is one of the rare people with whom one does not have to agree in order to be understood by him.” [2]
René Descartes thinks that “almost all philosophical controversies arise simply from the fact that we don’t understand each other properly” (“quasi toutes les controverses de la Philosophie ne viennent que de ce qu'on ne s’entend pas bien les uns les autres”) [3]
[1] R. M. Hare Moral Thinking, Oxford: Clarendon Press, 1981, p. 65.
[2] E. Nagel ‘Impressions and Appraisals of Analytic Philosophy in Europe II’ The Journal of Philosophy 33: 29–53, 1936, p. 45.
[3] R. Descartes, Letter to an unknown recipient, written in 1645 or 1646, in The Philosophical Writings of Descartes Volume 3, trans. J. Cottingham et al., Cambridge University Press, 1991, p. 281.
Schopenhauer says something—unsurprisingly—very pessimistic indeed on this matter. Perhaps even to the point of rudeness or arrogance towards the layperson: “Sometimes I speak to men and women just as a little girl speaks to her doll. She knows, of course, that the doll does not understand her, but she creates for herself the joy of communication through a pleasant and conscious self-deception.” - Arthur Schopenhauer
It seems that Schopenhauer often not only did not expect to be understood but he, at least sometimes, completely gave up on it.
Of course, he had his own faults but that’s another matter.