The Obstacle is the Path.  Zen Saying.  I take this proverb to mean that when something stands in the way of movement in the direction you wish to take that is an indication of what your first steps must be.  The obstacle is the teacher and the guidepost.  When we encounter the same obstacle repeatedly, this is an especially important sign.  My favorite words on this subject are from Paulo Coelho's wonderful book, The Warrior of the Light:

A Warrior of the Light knows that certain moments repeat themselves.

He often finds himself faced by the same problems and situations, and seeing these difficult situations return, he grows depressed, thinking that he is incapable of making any progress in life.

"I've been through all this before," he says to his heart.

"Yes, you have been through all this before," replies his heart.  "But you have never been beyond it."

Then the Warrior realizes that these repeated experiences have but one aim:  to teach him what he does not want to learn.