I know what he means.

I know what he thinks he means.

He's conflating "always say what you mean" and "say everything you're thinking," which are two different things. He doesn't stand up for himself or publicly own his beliefs because he's desperate for acceptance and thinks the best way to get it is to pet everyone else. That's different from self-preservation, like not telling your boss off, or not gushing all over your date. The feeling this is based on comes from things he *regrets* not saying in the past because it makes him feel weak now. He will never regret not telling off his boss nor will he ever regret staying cool on a date, so that's not what he's talking about. Those are excuses his scared minds makes up to prevent him from saying what he means when he chooses to speak.

There's a lot of room between talking straight and being a "finger-pointer" or a "self-righteous twerp".

I try to say what I mean, but that's usually boring. Lying is more fun.