After university, Gladwell pursued advertising, but wound up in journalism instead. He worked for the Washington Post for almost 10 years before taking up at The New Yorker, where he has been a staff writer for the past 25 years.

Gladwell is the co-founder of audio-content company Pushkin Industries, where he hosts a podcast called Revisionist History, which examines "things both overlooked and misunderstood". This pursuit typifies Gladwell; in the words of the Washintonian, his modus operandi is "cutting through conventional wisdom to define a new way of understanding how something works." He also co-hosts Broken Record, a podcast wherein he and his co-hosts interview a wide variety of musicians.

Gladwell has published seven non-fiction titles. His first, The Tipping Point, was released in 2000 and became a New York Times bestseller. Since then, 4 more of his books have also achieved that distinction. His most recent books, Talking to Strangers (2019) and The Bomber Mafia (2021) were released in print, but also in a unique audiobook format that listens more like a podcast than a book on tape, with snippets of interviews, historical recordings, and music accompanying the text read by Gladwell himself.

Gladwell was appointed to the Order of Canada in 2011. He has also been named one of TIME's 100 Most Influential People and one of Foreign Policy's Top Global Thinkers. He currently resides in New York, where he continues to write and to run very fast indeed.