1. What I believe mark manson is saying is more of a lifestyle choice than talking about the holocaust or slavery lol .
I do understand your thinking though.
Logically, to gain social proof everyone should like you right? being controversial would make poeple hate you.
But,
2. Think back to when you were in high school. Think about the really popular guys.
If you're like me and weren't really social at all, you probably don't like them. They seem arrogant and just dicks to lots of people, so why were they the most popular? They didnt give a damn what anyone thought about them.
They 'stood for what they believed in'
(which for the most part is why all the cool people seem so grounded imo) .
They didn't really care about offending anyone by swearing, making jokes that could make people mad, etc.
This comes into play with being a leader. deciding what to do with your best friends. say you want to go to the club and someone makes a suggestion you go to the movies. if you really want to go to the club you would express how much FUN it'd be and saying how extremely BORING a movie would be, right?
but if youre invited by some new friend you made to meet with all his friends, you wouldnt express your opinion in the same situation for fear of rejection (etc. "who does this guy think he is")
This is one of the most subtle ways of being controversial.
3. In a club environment telling a girl how much you hate whatever state she lives in (too much gangs, everyones creepily friendly) can be offensive to her, or ( sometimes you gotta say it with enough belief and cocky/funnyness! ) she will find it extremely funny because its true!
you leave yourself open to disagreements, or people disliking you. (most people wont even argue with you if you really believe in what your saying)
as you quoted;
"You have to be willing to sacrifice some
people’s approval in order to live life on your own terms."
These are just a few small examples, you gotta think in other ways how it may apply. Basically it means "dont give a damn"
I personally only replied to this because this happened to me last night. Getting driven home by one of my friends sibling and two guys i have never met before (they're all best friends)
It could've been a looonnng journey where i only laughed at a few jokes and sat looking out the window, because i wasn't comfortable with these new people. I felt it hard to let go and talk about what I wanted to talk about (in contrast to the conversation) but i did it, and once you get going it comes naturally.
The real lesson is freedom from caring what others think. Mark Manson phrases it in a way where you can use it in a lot of situations in life. (sales, job interviews, etc.)
I really hope I helped, I never wrote a big reply to anything and I'm afraid you won't understand or think i'm just crazy, but give me a reply!