He held an assortment of jobs, which included working on a painting crew and on a commercial fishing pier.

[3] Drury began his writing career after hearing about a publication opportunity while playing for the Cape Cod Basketball League.

Drury eventually took his advice and joined Sports Magazine and worked on freelance crime stories for Daily News.

[5][6] He has written for many publications including, The New York Times, Vanity Fair, Men's Journal, and GQ.

[4][5] Throughout his writing career, Drury has reported from Iraq, Darfur, Afghanistan, Liberia, Belfast, Haiti, and Sarajevo.