A lot of language is subtle.
On this case, the use of the word “obviously” is a backhanded compliment. It’s like seeing someone come last in a race and say “well they obviously tried”. I
I don’t really think if this (the subtlety of language) as a bad thing. If you want to improve as a writer you have to begin dissecting words and meaning and underlying context. It’s part of emotional and social intelligence.
When taking to people, it’s not as easy as “everything is the opposite”. If that were true, then it would be easy since everything is the opposite. Learning the subtlety of language is a skill—you might argue in every way as important as learning to code or learning maths or learning how to walk.
This subtlety of language governs how you treat others, how you write letters, how you give talks, how you parent, etc.
Check out his podcast with Podcast P. I’m not sure how the book compares but you gain a lot of respect for his career.