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You Are More Like Grammy-Winner Jacob Collier Than You Think | A Bit of Optimism Podcast

To create something truly original, do we build something new or break what came before? Perhaps the answer is both—simultaneously. Jacob Collier does exactly that. A brilliant songwriter and musician, he’s known for transforming his live audiences into massive three-part choirs, making music with the very people who attend his concerts. His album "Djesse Volume 4" was nominated for Album of the Year at the 2025 Grammy Awards, alongside icons like Beyoncé, Billie Eilish, and Taylor Swift. Although Beyoncé's "Cowboy Carter" won, Jacob snagged his seventh Grammy for his rendition of "Bridge Over Troubled Water." I sat down with him in a music studio a few days before the Grammys, surrounded by multiple pianos, and it was a joy to hear him play. Jacob’s approach to music—blending structure with spontaneity—offers inspiring insights into creativity that are as inspiring as his sound. This…is A Bit of Optimism. For more on Jacob, check out: http://jacobcollier.com/ @jacobcollier ⏰ Timestamps 0:00 An intro to Jacob Collier 2:19 Album of the Year, and how it feels to be nominated 3:26 Jacob's creative mind as a kid 6:59 Practice versus play 9:39 Simon loves lists 10:19 Simon reads Shel Silverstein's "Twistable Turnable Man" 13:25 The job versus the joy of music 15:31 How Jacob learned to make music with his audiences 20:39 Everyone instinctively understands music 21:30 Jacob plays the piano (arrival and departure) 24:30 What anger sounds like on the piano 28:16 Jacob asks Simon how he keeps old ideas fresh 31:00 Are there any ideas Simon would disavow? 32:15 Jacob's WHY 34:06 The irrational mind and creativity 38:36- What AI taught Jacob about creativity 40:03 Creative mastery versus creative stagnation 44:40 Jacob talks about making two albums (In My Room and Djesse Vol. 4) 49:49 To be a container for creativity 51:58 Catching ideas is like surfing 54:13 Jacob plays Simon a Bartok Bagatelle + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek Simon’s books: The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Start With Why: https://simonsinek.com/books/start-with-why/ Find Your Why: https://simonsinek.com/books/find-your-why/ Leaders Eat Last: https://simonsinek.com/books/leaders-eat-last/ Together is Better: https://simonsinek.com/books/together-is-better/ + + + #SimonSinek

Jacob CollierguestSimon Sinekhost
Feb 4, 202558mWatch on YouTube ↗

CHAPTERS

  1. Why Jacob Collier embodies “build and break” creativity

    Simon frames creativity as a paradox—simultaneously constructing and dismantling—and introduces Jacob Collier as a rare example of that duality in action. The setup positions Jacob’s genius as accessible: the point isn’t to admire from afar, but to recognize similar creative instincts in ourselves.

  2. Grammy nomination perspective: honor without over-identifying

    Jacob reflects on his Album of the Year nomination with humility and a sense of play. He shares an unusual stat—being nominated without charting—and downplays awards as constructs while still appreciating the recognition.

  3. Childhood environment: feelings welcomed, curiosity nurtured

    Jacob describes growing up in an artistic, introverted household with candlelit family dinners and a strong emphasis on nonjudgmental emotional expression. He credits that upbringing with shaping music as a tool for self-understanding rather than a product of suffering.

  4. Practice vs play: learning by following what lights you up

    Jacob distinguishes structured practice from exploratory play, arguing that much of his growth came from chasing fascination rather than rigid routines. He also connects his early love of language to musical thinking—both rely on surprising combinations that spark new meaning.

  5. The poetry of lists: how language creates mini-explosions in the brain

    Simon shares his love of poetic lists and reads Shel Silverstein’s “Twistable Turnable Man.” Jacob relates this to creativity: rapid-fire combinations create a chain reaction of attention, delight, and discovery that’s universally accessible.

  6. Music as emotional modulation: listening and making are mirror processes

    Jacob argues that making music is like listening in reverse—both involve finding what matches your current emotional state and then shifting it. Simon reframes it as “playing how you feel” versus making playlists, highlighting music as an emotional technology anyone uses.

  7. When music becomes a job: designing performances that stay alive

    Simon asks how Jacob protects joy when music is also a career with expectations. Jacob explains his shows are built to avoid repetition; preparation is less finger-practice and more readiness to sense the room and articulate what’s present through improvisation.

  8. Turning audiences into choirs: learning the ‘container’ from his mother’s conducting

    Jacob traces audience participation back to childhood memories of watching his mother conduct—hands transforming a room and uplifting people. He then describes the pivotal 2019 moment when his audience work evolved from call-and-response into real-time multi-part harmony without rehearsal.

  9. Everyone instinctively understands music: simple axes and the ‘arrival/departure’ lesson

    Jacob explains that audience choirs work because musical understanding is innate: people grasp high/low, loud/quiet, thick/thin, and harmonic “home.” At the piano he demonstrates key centers as emotional locations—tension, movement, and the satisfaction of returning home.

  10. What anger sounds like: music as therapy, improvisation vs composition

    Simon explores whether Jacob uses the piano like therapy to express complex emotions such as anger. Jacob describes the catharsis of starting from a feeling and untangling it in sound, then contrasts improvisation with songwriting—composition as “stop-time” improvisation that risks losing raw energy during distillation.

  11. Keeping old ideas fresh: novelty-seeking, evolution, and what to disavow

    Jacob asks Simon how he relates to older ideas and avoids stagnation. Simon explains he’s driven to move toward what he doesn’t yet understand; he won’t give talks rehashing old frameworks, though he still stands by them and builds upon them—while sometimes regretting specific language choices.

  12. Jacob’s WHY and the irrational mind: resisting being defined

    Jacob shares that audience analysis pushed him to articulate what he stands for—his WHY—while part of him resists definition because creativity lives at the edge of the undefinable. The conversation opens into the tension between rational explanation and the “animal” creative self that won’t obey data or boxes.

  13. AI, mastery, and stagnation: creativity between chaos and order

    Jacob and Simon use AI and musical learning to explore why creativity often peaks before complete mastery. Early AI’s ‘imperfect’ outputs captured feeling; similarly, artists can ossify after mastery—so real creativity requires cycling between breaking order and rebuilding structure, and learning to craft containers that keep chaos usable.

  14. Two albums as opposite poles of the same ‘thing’: voice, vessel, and 100,000 people

    Jacob identifies two defining projects: ‘In My Room’ (solo exploration) and ‘Djesse Vol. 4’ (mass collaboration). He describes recording audiences worldwide to build a track with over 100,000 voices, framing both albums as expressions of the same pursuit—finding self through voice and finding self through others.

  15. Catching ideas like surfing—and closing with Bartók

    Jacob and Simon compare creativity to surfing: long waits punctuated by waves of brilliance, and the real skill is knowing how to ride and capture them. Simon shares his habit of relentless note-taking, then ends with a playful request—Jacob performs a Bartók Bagatelle, closing the episode with live music and mutual admiration.

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