She is an author of four books.[3] Her first book of poems, Radio Crackling, Radio Gone (Copper Canyon Press, 2006). She won the Hayden Carruth Award. Her second collection, Lost Alphabet (Copper Canyon Press, 2009) was named one of the best poetry books of the year by Library Journal. Shane McCrae selected her chapbook The Resemblance of the Enzymes of Grasses to Those of Whales Is a Family Resemblance for an Essay Press Chapbook Prize. Her most recent book of poetry, Late Empire (Copper Canyon Press, 2017) she explores the complexities - beautiful and brutal - of our present moment. Pain Studies, a book of creative non-fiction is forthcoming from Bellevue Literary Press in 2020.
Her poems have appeared in The Nation, Iowa Review, Denver Quarterly, LIT, and other journals.
Olstein has also worked with singer-songwriter Jeffrey Foucault in the band Cold Satellite.
She has been awarded a Guggenheim Fellowship, a Pushcart Prize, a Lannan Writing Residency, and poetry fellowships from the Massachusetts Cultural Council and the Sustainable Arts Foundation.