The title does a good deal of work before the first line begins. "Pilgrim's Regress" turns the familiar phrase "pilgrim's progress" on its head (Bunyan's allegory is the obvious echo), promising a traveler who moves backward, or at least downward. The four lines that follow bear that out. They give us a speaker who cannot work out how to stop losing, and who has somehow been welcomed by the dark in the process.
The opening line is a paradox disguised as a question: "how do I continue to lose it all". If you have lost everything, what is left to lose? The word "continue" belongs to the vocabulary of journeys and perseverance, the word a pilgrim would use of the road, yet here it is attached to loss. "It all" is deliberately empty. The poem never says whether it means faith, memory, a person, or simply the light of day, and that vagueness lets nearly any reader pour their own loss into it. There is a quiet colloquial pun too, since "to lose it" can mean to lose one's composure. The line has no question mark and no capital letter, so it sounds less like a formal enquiry than a thought half-overheard, a sentence picked up in the middle.
The construction is spare. There is no rhyme and no punctuation, and the lines shrink as they go: roughly ten syllables, then six, then four, then four. The poem seems to narrow as it descends, the way a speaker's voice drops when they stop asking and start noticing. Sound does the work that rhyme usually does. Look at how many of the closing words carry an "r": "received," "strange," "ear," "from," "ground." The repetition gives the second half a low, murmuring texture, like something heard through a wall or through earth.
The imagery turns on that word "received." Night receives the speaker in the sense of a host welcoming a guest, but "received" also belongs to listening and signals, as a radio or an ear receives. The simile that follows, "like a strange ear", is startling because we expect night to be compared to a blanket or a cloak, something that covers. Instead it becomes an organ of attention. The simile is also slightly ambiguous. Night might be the ear, taking in the speaker like a confession. Or the speaker might be received the way a stranger's ear receives a stranger's words. "Strange" cuts both ways, unfamiliar and a little unsettling, so the welcome is neither warm nor cold. It is simply attentive.
The last line, "from the ground up", is the most layered. As an idiom it means thoroughly, as in rebuilding something from the ground up, and that sets the language of starting over against the language of loss. Literally, it describes a direction. Darkness does seem to rise from the earth at dusk, pooling first in low places, and an ear pressed to the ground listens to what is underneath. Burial is faintly present too. The motion is upward, which is the opposite of regress, though it begins in the soil. The poem doesn't choose between these readings, and the line is richer for it.
Taken together, the lines suggest that loss and welcome are not opposites. Read as a sentence, the poem implies that the losing goes on *after* night receives the speaker, so being taken in and being stripped bare may be the same event. Being listened to by something vast and unfamiliar can feel like consolation and dispossession at once. The poem doesn't resolve the question it opens with. It leaves the speaker in that dark, attentive space, still asking.
That restraint is what makes the poem worth studying. In about twenty words it uses a borrowed title, an unanswerable question, a surprising simile and an idiom that points two ways to create a mood larger than its statement. It also gives the reader a share of the work, since "it all" means whatever you most fear to lose. Small poems can be this open only if every word is chosen with care, and here "continue," "received" and "strange" each carry more than one meaning.