The Questlove Show

Malcolm Gladwell

Dec 3, 2025
In a lively discussion, bestselling author Malcolm Gladwell shares his insights on creativity and genius, drawing from his multicultural upbringing and belief in the power of failure. He recounts how enforced boredom fostered his early creativity and highlights the importance of serendipity in discovering stories. Gladwell emphasizes learning from criticism and the necessity of collaborative feedback in the creative process. He also discusses his new book, touching on how COVID reshaped our understanding of social dynamics and the role of AI in storytelling.
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ANECDOTE

Formative Record Choice

  • Malcolm Gladwell's first concentrated exposure to pop music was Simon & Garfunkel's Bridge Over Troubled Water after his family moved to Canada in 1969.
  • That album taught him about joy in popular music and resonated with his mixed cultural upbringing.
ANECDOTE

Playful, Strategic Rebellion

  • As a kid Malcolm and his friend Terry gamed school metrics by maximizing grade average times absences, treating rebellion as a constrained competition.
  • He later skipped a high school year without anyone noticing and relied on his mathematician father for help.
ADVICE

Iterate Ideas Publicly

  • Talk obsessively about nascent ideas and iterate them in conversation to reveal clearer forms and timing, like a stand-up comic's practice runs.
  • Use honest listeners to detect pacing and holes before finalizing work.
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