What is philosophy? How is it possible? This essay constitutes an attempt to contribute to a better understanding of what might be a good answer to either of these questions by reflecting on one particular characteristic of philosophy, specifically as it presents itself in the philosophical practice of Socrates, Plato and Wittgenstein. Throughout this essay, I conduct the systematic discussion of my topic in parallel lines with the historico-methodological comparison of my three main authors. First, I describe a certain neglected aspect of the Socratic method. Then, exploring the flipside of this aspect, I show that despite the fact that both Socrates and Wittgenstein understand their philosophical approaches as being essentially directed at the particular problems and modes of understanding that are unique to single individuals, they nevertheless aspire to philosophical understanding of the more ‘mundane’ kind that is directed at the world. Finally, interpreting parts of Plato's dialogues Phaedrus and Laches, I further develop my case for seeing the role of mutual understanding in philosophy as fundamentally twofold, being directed both at the individual and what they say (the word), and at things that are ‘external’ to this human relation at any particular moment of philosophical understanding (the world).