When it comes to liberty, whether it be free speech or something else, I tend to think about in terms of what has been done to me by previous generations, and what I should do for future generations. If, let's say, a man from the 19th century risked death, risked violence, risked revolutions, to fight in favour of free speech, despite everything encouraging him not to, what's my excuse to not elaborate upon that right and push it even further?
I mean, what are we risking nowadays? Hurt emotions? People shaking because of reacting negatively to something that's usually taken off context? Corporations losing money from customers because of a backlash to what their employer has said? These are not the same kind of dangers that our ancestors faced, when they fought in favour of the liberties that we now have. Not even close.
Keeping that in mind, I don't see any reason why we shouldn't do our absolute best to elaborate upon any freedoms that we have, to their fullest extent. Being trolled on the internet is not the same as being strung up by an angry mob who felt like you insulted God or whatever. We are not dealing with these sorts of consequences any more, and in spite of those consequences, people fought for liberty nonetheless.
We have to atleast try to retain the same toughness of mind and spirit, which drove the previous generations to push the boundaries of liberty, despite all seemingly "common sense" which spoke against it, the constant presence of violence, outraged reactions, lynch mobs being formed, government oppression, loss of social status and family. Otherwise we run the risk of stagnation, of accepting things as they are, "fine the way they are", a mentality which would have produced absolutely nothing for us, had it been applied centuries earlier.