I used to have a sign pinned up on my wall that read: "Only to the extent that we expose ourselves over and over to annihilation can that which is indestructible be found in us." Somehow, even before I heard the Buddhist teachings, I knew that this was the spirit of true awakening. It was all about letting go of everything.
Nevertheless, when the bottom falls out and we can't find anything to grasp, it hurts a lot. It's like the Naropa Institute motto: "Love of the truth puts you on the spot." We might have some romantic view of what that means, but when we are nailed with the truth, we suffer. We look in the bathroom mirror, and there we are with our pimples, our aging face, our lack of kindness, our aggression and timidity—all that stuff.
This is where tenderness comes in. When things are shaky and nothing is working, we might realize that we are on the verge of something. We might realize that this is a very vulnerable and tender place, and that tenderness can go either way. We can shut down and feel resentful or we can touch in on that throbbing quality. There is definitely something tender and throbbing about groundlessness. - From the book When Things Fall Apart by Pema Chodron