This is an easy thing to say, but a very difficult one to understand in such a way that it guides one's being in the world. It is probably the hardest thing to imagine that I try to imagine. Yet, I believe it is about the 'truest' thing one can say about Reality, and the surest way to break out of my own insular context. If it seems an incredibly negative thing to say, then I would point out that it is merely the flip-side of All is Well, which strikes me as the most positive thing one can say. Yet even this raises our moral hackles.
Things are not well. In fact, things are incredibly bad. But it does not matter. Does it? If it does, then there is no end to it being so. Humanity is, in my opinion, fundamentally fucked-up. The amount of pain and suffering we inflict on each other is staggering. (At this very moment someone is being tortured to death. Bummer. Have another bite of that bagel. Are those blueberries in there?) That we can function as well as we do, and even sometimes demonstrate practical love and kindness, is quite amazing, though that doesn’t matter either.
When one of the Marys broke an amphora of precious balm at Jesus' feet so as to anoint him in anticipation of his death, Judas protested the waste and declared it would have better been sold and the money given to the poor. The Gospel says he just wanted to embezzle it since it was he who held the common purse. I don't think so. He always gets a bum wrap. What Judas wanted was revolution and justice; he was a zealot, a person of radical political persuasion. He cared. Things mattered. And Jesus was a great disappointment with all his blabber about an other-worldly kingdom. Turn him in, and maybe he'll find his balls and fight back.
But Jesus said, "Chill Judas; the poor you shall have with you always, but I am about to leave you." Yes, there will always be the poor and starving, and thus there will always be a world in dire need of our caring, because these things matter. Our caring is also an expression of our humanity. But there is a larger context; and within this context, all this 'mattering' dissolves into wellness. Dao is the Totality, and within the Totality could anything be other than 'well'? Human antics, whatever they be, may or may not affect the Nameless (and if Dao is Becoming and Emergent, then our antics might be said to 'be' Dao), but in every case, all is well.
Because nothing matters, all that does matter can be pursued without hatred and violence, disharmony and strife. Because nothing matters, all that does matter can be accomplished through wu-wei.
This, too, is walking Zhuangzi's Two Roads. Our insular human context is understood in the context of Vastness, where all is well and equal. We do not abandon the one for the other, but allow that they inform each other.
You can check out Scott's other miscellaneous writings here.