Tell him of your life
From Fallen London Wiki
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From: The Shepherd's Wash
Perhaps there is instruction in all the choices that led you to sit on a ledge, far, far above, overlooking London far, far away.
Unlocked with 
An Invitation to Sing in the High Places exactly 2
Success
It takes a city
The Forlorn Shepherd says nothing [...] From the first dirigible [...] the places and people in between. Those who remain, and those to whom you cannot or will not return.
"We are what we have done," the Shepherd says, [...] "And all that we could have done, and did not."
[...]
The Shepherd has a request. (Sets 
An Invitation to Sing in the High Places to 5 - A moment with the Forlorn Shepherd)
