We talked a lot about how literally no one on earth is capable of seeing an understanding your flaws as well as you, but also most humans on earth are infinitely less interested. The lens you view yourself with is totally unrelated to the lens with which the rest of the world sees you; you'll drive yourself insane if you think you and the world interpret you the same.
The point is, I think he did a phenomenal job at blasting my self deprecating brain into reality, but his initial spin of "Stop treating yourself like you're an idiot, because you're not and I can prove it" was just a slight misstep.