[2] She studied modern dance with Merce Cunningham until 1969 when he recommended her for a job teaching at the Cuban National Schools of the Arts in Havana.

[5] Guillermoprieto was promoted to staff writer at the Post, where she worked for two years[4] before winning an Alicia Patterson Journalism Fellowship in 1985, funding research and writing about changes in rural life under the policies of the European Economic Community.

[7] Also in 1990, Guillermoprieto won a Maria Moors Cabot Prize, honoring her contributions to press freedom and inter-American understanding in the Western hemisphere.

[8] During the 1990s, she worked as a freelance writer, contributing long reported articles on Latin American culture and politics for The New Yorker,[9] and The New York Review of Books,[10] including on the Colombian civil war, the Shining Path during the Internal conflict in Peru, the aftermath of the "Dirty War" in Argentina, and post-Sandinista Nicaragua.

Thirteen of these pieces were bundled in the book The Heart That Bleeds (1994),[11] now considered a classic portrait of the politics and culture of Latin America during the "lost decade" (it was published in Spanish as Al pie de un volcán te escribo — Crónicas latinoamericanas in 1995).

[14] That year, she published a second anthology of articles, Looking for History: Latin America, collecting pieces on Cuba, Mexico and Colombia written for The New Yorker and The New York Review of Books.

In a review for The New York Times, Katha Pollitt praised the nuance Guillermoprieto brought to the book, as well as "sly humor, curiosity and knowledge.

In the fall of 2008, Guillermoprieto joined the faculty of the Center for Latin American Studies at the University of Chicago, as a Tinker Visiting professor.