Olstein grew up near Boston, Massachusetts. She received a BA from Barnard College and an MFA in creative writing from the University of Massachusetts Amherst. Her first book of poems, Radio Crackling, Radio Gone (2006), won the Copper Canyon Press Hayden Carruth Award. Olstein is also the author of the poetry collection Lost Alphabet (2009). Her poems have appeared in the Iowa Review, Denver Quarterly, LIT, and other journals. She has been awarded a Poetry Fellowship from the Massachusetts Cultural Council and a Pushcart Prize.
Of Radio Crackling, Radio Gone, reviewer Kendra L. Tanacea commented: “Olstein places the mystical next to the mundane, bees next to bricklayers, purple finches next to garage doors, reason next to faith, chance near fate.”
Olstein has been associate director of the MFA program at the University of Massachusetts Amherst, and directs the Juniper Initiative for Literary Arts and Action. She is a contributing editor of jubilat.