It is a disquieting fact that it is more difficult to gain knowledge of the Divine through ordinary, positive living, than through negative or tragic experience.
The negative seems to have much more power to break down one's resistance; the positive tends to reinforce one's smugness.
Of course, sadness can also drag a person into depths beyond sensitivity, but, here too, the direction is important.
And when one is aware of one's degradation, the sense of shame or of self-pity can function to restore the balance.
Because it is sometimes necessary for a person to come to the conclusion that his life is not worth anything.
Only when a person is burned so badly that his skin begins to peel, will he begin to feel himself.
A Kabbalistic insight claims: "It is Jacob who redeems Abraham."
Abraham is Chesed, or love, and Jacob is Tiferet (mercy and beauty).
One may discover in life that grace is absent and that one cannot awaken love in one's heart.
Upon such discovery, one falls back on pity, and this stimulates the love and the grace which had been absent.
This stirring of compassion in the heart awakens great love, even the love of God.
Here too, the essential confrontation is with Truth, the truth of oneself, and the need to break down the partition or veil that separates one from the Divine.
The Psalmist expressed it: "A broken and contrite heart, O. God, thou wilt not despise" (Psalms 51:19).
Just as a ladder cannot be useful unless it has something to lean against, so too, is there nothing more whole than a broken heart.
Even though, to be sure, God prefers vessels that are without blemishes or cracks, and it is written in the Zohar that the Shechinah does not lodge itself anywhere except in a whole vessel.
Nevertheless, this does not include a broken heart.
As Rabbi Schneur Zalman of Liadi mentions elsewhere: If one does not have a broken and contrite heart, one cannot be said to have a heart at all.
–Rabbi Adin Steinsaltz
From The Long Shorter Way by Rabbi Adin Steinsaltz