It’s not enough to read the results of other people’s thinking nor even books about how one might learn to think for oneself. You have to engage in the process itself, and this is not something for which there are formulas or rules. It’s a living act—unpredictable and (in a sense) uncontrollable. One of course “positions” the mind, but the insights that come always remain a kind of grace or gift.

What you need is someone with whom to engage in real dialectic—elenchos or cross-examination of the Socratic variety, an incredibly rare thing these days, even in so-called “discussion” courses in colleges and universities. Dialogues with oneself, of the kind you envision, aren’t the solution. Supposing they could be would simply prove one’s ignorance of the traditional maxim, “He who chooses himself for a master has chosen a fool.”

The self can never bring about its own aporia or sense of “no exit” , and aporia is the necessary prelude to genuine wisdom.