How do we get to a genuine personal wisdom?

Sometimes the adult in me rationalizes that loss is simply a part of life. Yet when we do face significant losses, such words of comfort and acts of support often fail to hit the mark. Grief overwhelms the senses, making it difficult to see beyond despair. 

I am a hospital chaplain. One evening, just before going home for the day, I noticed a stooped, elderly Hispanic gentleman wandering up and down a deserted hall of the hospital as if he was lost. I asked if I could help him.

"I am open and I am willing.
To be hopeless would seem so strange.
It dishonors those who go before us.
So lift me up to the light of change."
(Holly Near, “I Am Willing”)

1
Oh, when will dawn for me that day of blessedness
When He who is all Good, all Beauty, and all Truth,
Will light the inmost shrine of my heart?