O'Brien grew up playing lacrosse and field hockey. Her first experience sailing was during Plebe summer and was a jib and spinnaker trimmer in the fall of Plebe year. Participated in Annapolis to Bermuda Race, Southern Bay Race week and NASS Spring Regatta on NA 24 Gallant as pit and co-navigator in 2016. Served as a Colgate skipper in the fall of youngster year. Summer 2017 was the spinnaker trimmer on NA 22 Integrity as well as assistant navigator for the Annapolis - Newport Race and the Marion to Bermuda Race. Currently serves as the spinnaker trimmer aboard NA 22 Integrity. Majoring in aerospace engineering.