Caldwell moved to
New York City after graduating and became a freelance journalist. She won an investigative journalism award from the Independent Press Association for her coverage of the rebuilding of New York City after the
September 11 attacks. In April 2022, she announced that she was joining
The Washington Post to write a morning newsletter and host live events.
Career Timeline • Free Speech Radio News (2006–2011) • C-SPAN (2011) • CBS News (2012–2013) • CNN (2013–2014) • NBC News (2014–2022) • Washington Post (2022–2025) • Puck News (2025–present) ==Personal life==