Jesus did not choose the life of the householder. Jesus was probably not married. (What kind of husband and father leaves his family to live the life that Jesus lived? What kind of husband and father willingly sets off on a course of certain death?)
Jesus operated on the margins. He did not choose a "normal" life by any stretch of the imagination. Why such an extreme position?
Perhaps he recognized a larger reality than our little world of self-imposed worry and woe.
Maybe he chose his fringe style of living not to escape, but to be in an enlightened state of contemplation and passion.
I think he made the choice out of sheer practicality - so we would pay attention. (From the edges, there is a different view. We listen to people who live there.)
Jesus did not mince words. He gave us a stark choice: either I am who I say I am, or I am a raving lunatic. Let my words, and my actions be your guide. But I am not just a really smart, really nice guy wandering around performing cute tricks. (Reconciling oneself to this distinction is the sine qua non of being a Christian.)
Listen to Father Jonathan's sermon here.