Rupi Kaur on creative freedom, imposter syndrome, and empowering others through poetry

Executive overview

Success can trap artists in a cycle of performance, promotion, and output that crowds out the work itself. Rupi Kaur and Ryan Holiday reflect on ten years since their breakout books — and the hard-won realisation that freedom to create requires actively choosing it over security.

The conversation centres on writing without judgment, the "catastrophe of success," and why helping others succeed is more meaningful than any bestseller list.

Real success is having enough freedom to do the work — and using what you've built to bring others with you.

The trap of success and the cost of saying yes

• The reward for succeeding at your craft should not be that you lose time to do the craft.
• Opportunity costs of skipped creative work are invisible; the number on a declined gig is not.
• Saying yes to everything is often a scarcity mindset — fear that the offers won't keep coming.
• If you can't stop without it all falling apart, the thing owns you — not the other way around.
• A deliberate break requires confidence: believing you can earn an audience back, not that one will wait forever.

Writing without judgment — and what kills creative flow

• Milk and Honey was written in a state of total presence, without focus on outcome or result.
• The freedom came partly from having nothing to lose: no audience, no expectations, just passion.
• Books two and three were harder — the algorithm-awareness crept in and the self-doubt followed.
• Writer's block arrives when you write for outcome rather than honesty.
• Writing about depression and anxiety felt risky; publishing it anyway and having it land rebuilt trust in the instinct.
• Ten years on, Kaur is back to writing without judgment — the same place she started.

The catastrophe of success

• Overnight success is genuinely destabilising — Kaur describes it as boarding a train that never stopped and only accelerated.
• Many people don't survive it: the 27 Club, the absence of second-act success stories.
• Distractions, complacency, and feelings of unworthiness make it hard to sit down and create from an authentic place.
• Holiday's slower build shielded him from both the downside and the upside — his process developed independently of commercial results.
• The real measure is staying power: is the work still here in 10 or 20 years?

Imposter syndrome and mystification of craft

• Kaur sold millions of copies and was still trying to enrol in a master's programme to feel "official."
• Imposter syndrome is almost universal — and actual imposters with credentials exist and get away with it.
• Mystifying craft (the right pen, the MFA, the list) is intimidating to outsiders and makes practitioners self-important.
• The New York Times bestseller list is gameable; a PAC bulk-buying copies can manufacture number one.
• None of the external markers matter much. What matters is whether the work feeds you and holds up.

Writing process and constraints

• Kaur writes hundreds of drafts per poem, saving each version so she can track evolution and revert.
• A short poem with simple diction is harder to write than a long prose piece — brevity demands precision.
• Her rule: one thesis statement per poem; every word must prove it.
• Constraints — like the formal limits of poetry — force creativity the way a flute's structure creates music.
• Holiday structures long books as 30 separate documents, each of which must stand on its own, then edits as a whole at the end.
• Diversity of sources (geography, era, background) is a craft rule: if all examples come from the same world, you lose readers.

Impact, readers, and paying it forward

• A woman in Brazil credited Milk and Honey with triggering her own publishing deal — the audience confirmed the book's thesis live on stage.
• Readers use the work in ways far exceeding the circumstances under which it was written; the emotional universality carries it.
• The right response when someone credits your work: remind them they did the work — the book just sat there.
• Relevance follows genuine interest, not audience calculation; the moment you write for them, you stop being relevant.
• Hosting open mics, giving opening acts to local poets, and lifting other writers onto the same stage: this kind of impact outlasts any bestseller position.
• The Milk and Honey poem itself: success is not for its own sake — it's gaining enough to help those around you succeed.