I looked up the definition, I couldn't find the example you quoted. It was neither in definitions nor in suggested synonyms, examples, and recent examples on web. In any case, I was contemplating to use "bypass" instead of "transcend" but it has a strong connotation with cheating. The image in my head was something along the lines of not senselessly bumping into the wall of paradox but going around it.

As for "comfortable (free from doubt)," I see it as the direct result. Going past the paradox (w/o engaging with it, i.e. trying to solve it) makes it make sense, solves it so to speak, and that removes doubt.