At a September 1, 2008, concert at The Gravity Lounge in Charlottesville, Virginia, McKeown told the audience that they wrote this album "in an attempt to write myself out of the worst heartache I'd experienced up to that point."

McKeown performs regularly, spending much of their time touring throughout the world with artists such as Ani DiFranco, Josh Ritter, the Indigo Girls, Martin Sexton, Andrew Bird, Thea Gilmore, Melissa Ferrick, Allison Miller, Welcome to Night Vale, and others.

[5] McKeown is noted for their energetic stage presence and their habit of wearing tailored suits, often with ties and Fluevog shoes, to performances.

There, they will "work to connect the worlds of policy, art, and technology while considering questions about how to make a creative life a viable vocation.

"[7] In October 2016, a new musical McKeown wrote with the playwright Quiara Alegría Hudes titled Miss You Like Hell opened at the La Jolla Playhouse directed by Lear deBessonet and starring Daphne Rubin-Vega.