Evil Genius and Evil Twin
If you really intend to examine your life, you need them both. Absent your own personal/internal Socrates, of course (Socrates in the dialogues not being a real Socrates in this sense.)
The best the other side(s) have to offer: the intellectually honest, learned, clear, sane, cant-free: your Evil Genius, the Moriarty to your Holmes (or the Holmes to your Moriarty). If you don't think anyone who thinks very differently from you fits this description, then...
Hmm, I can't even think of what to suggest you do. Because I don't care about you.
Don't go to the easy and the popular and the cheap on the other side. You don't have to set up straw men - this lowest-common-denominator world will offer them first. But go to your Evil Genius, and gaze into the Abyss, and see if the Abyss gazes into you. Don't approach them as a debater, an advocate, looking for their weaknesses - not at first, or only in passing. Look to their strengths and assent to everything you can. Now see where you are.
And go to the worst of your ideological allies, your Evil Twin, your doppleganger. The Half-Orc you. Look at them caricature your principled stand and cheapen it with fallacies and bathos. See them take your most cheished thoughts ad adsurdum, and realize that if you remain consistent you'll be heading down that path as well. Convex make-up mirrors don't just distort - they magnify, so you can see your blemishes. Look at who you might be. Tolstoy talked about not arguing with the opposite side, because the rhetorical acts inherent in it tend to falsify and exaggerate your arguments. You lie. I say: let someone else do it for you, before you get tangled in your own rhetorical web.
Rinse. Repeat. The rest of your life.
Late thought: if you can't think of anyone on your side who strikes you as despicable and/or moronic, I hope the implication about you is both obvious and somewhat troubling. Even if you believe, as R.A. Lafferty ironically put it: "Salvation is better than smart answers."
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