After the September 11 attacks in 2001, he served as the president of the Lower Manhattan Cultural Council (LMCC), where he led rebuilding efforts for the downtown arts community.
He lives in New York City and Miami with his long-time partner Fred Hochberg, former chairman of the Export-Import Bank of the United States.
In his mid-twenties, Healy founded a consulting business offering public relations and sponsorship services to museums, film festivals and other not-for-profit institutions.
His gallery showed numerous young artists who later rose to prominence, including Tom Sachs, Janet Cardiff, Kara Walker, and Karen Finley.
After 9/11, Healy was named president of the Lower Manhattan Cultural Council, where he led rebuilding efforts for the downtown arts community.
As Chairman, Healy traveled extensively for the State Department, visiting more than thirty countries on six continents to advocate for peace and understanding through the exchange of ideas.
After his tenure at Fulbright, Healy joined the board University of the People, helping to establish the world's first non-profit, tuition-free, online academic institution that seeks to revolutionize higher education by making college-level studies accessible to students worldwide.
In 2018, he created the Curator Culture series at The Bass Museum where he interviewed prominent artists, writers, journalists, activists, educators and entrepreneurs.
Healy, who is HIV+, has long been active in various HIV/AIDS causes and anti-poverty efforts and has traveled extensively around the world for microfinance projects and AIDS-prevention organizations.
His first collection, What the Right Hand Knows, with an introduction by poet Richard Howard and a cover by the late John Ashbery, was a 2009 finalist for both the Los Angeles Times Book Prize and the Lambda Literary Award in poetry.
In the Huffington Post, poet Carol Muske-Dukes wrote, "From the near-cheerful merciless poems about childhood on a farm and the brutal lives of animals to big city glamour with new possibilities of flight from a flawed paradise—there is the sharp edge of art."