I think the song "The Dreaming Tree" has many different meanings to it, all of these are intertwined to make one song. I have found this to be characteristic of The Dave Matthews Band. It is a song about change, about the course of life, it's about the world and it's dangers when you are no longer a child with no worries, and about people who lose their sense of imagination as they grow old. .
There are a lot of things we take for granted in our lives, such as our childhood. In the song he says "Conquered fear to climb, a moment froze in time, when the girl who first he kissed, promised him she'd be his" meaning when you are young, you are more sheltered from the realities of life, and you believe every dream you have will come true. It also keeps referring back to the parents and family, it makes me think that he is saying things were easier and simpler in the past, when you could easily dream of what you wanted in life, perhaps he was dreaming of past times that were simpler than dealing with his life then. In another part he says "standing here the old man said to me, long before these crowded streets, here stood my dreaming tree. Below it he would sit for hours at a time, now progress takes away what forever took to find." This shows how some people treasure the things that are important in life, while other people take those same things for granted, not realizing what is truly valuable. The bystander didn't really care about the tree it had no significance to him, but the old man treasured it for it reminded him of so many memories for him. I also think the dreaming tree represented life. The old man loved his life and lived it to the fullest. When the tree finally died, he realized that the tree was what gave him life, and that there was no longer a need for him to live either.