The speaker opens with a question that sounds half like a complaint and half like wonder: how do I keep on losing everything? The word "continue" suggests this isn't a single loss but something ongoing, a habit of letting go. The title, "Pilgrim's Regress," points the same way. A pilgrim is supposed to move forward toward something, but here the journey seems to run backward or fall away.
The strange image comes next. Night "received" the speaker, as if welcoming a guest, but it does so "like a strange ear / from the ground up." Night becomes a listening thing, an ear that rises out of the earth and takes the speaker in. That makes the dark feel intimate and a little eerie at once, attentive rather than empty.
The mood is hushed, uneasy, and oddly calm. The loss doesn't read as violent. It feels more like being absorbed, quietly heard by something much larger than oneself.