Doug welcomes freelance journalist Alyson Krueger, whose bylines include The New York Times and who recently launched the widely read Substack newsletter The Great Conversation. They open by mapping out what modern freelance journalism actually looks like day to day — from pitching ideas to editors, to landing assignments, to the patience required to build a career one byline at a time.
The conversation turns to voice: how a writer's tone and sense of objectivity shift depending on the outlet, and how that compares to the unfiltered, direct-to-reader relationship Substack allows. Alyson explains why she stepped outside the pitch-and-wait cycle of traditional freelancing to build an audience of her own, and what she's learned about writing for readers instead of for an editor's inbox.
Alyson also traces her own path into journalism — from studying international relations and working events in London to attending NYU's journalism school — and credits networking, coachability, and charisma as much as writing talent for how she landed her first bylines at the Times.