How To Overcome Imposter Syndrome | Rupi Kaur

Here are the top 10 key takeaways from Rupi Kaur's conversation with Ryan Holiday on the "Daily Stoic" podcast about creative success, imposter syndrome, and finding balance as an artist.

1. The craft comes first

The conversation reveals how both speakers prioritize their creative work above all else. Rupi Kaur shares how she finds it challenging that other responsibilities now take up more time than writing poetry, which is what she loves most. She struggles with the balance between promotional activities and actual writing.

This dilemma is common for successful artists - the reward for succeeding at your craft often means having less time to practice it. Both discuss how hard it is to turn down paying gigs to dedicate time to creative work, especially when the financial opportunity cost is clear but the creative opportunity cost remains invisible.

2. Success brings unique challenges

Kaur discusses the "catastrophe of success" - how unexpected fame from her first poetry collection created pressures she wasn't prepared for. She describes feeling like she got on a train that kept accelerating with no opportunity to get off, pulling the ground from beneath her feet.

Unlike writers who experience gradual growth, Kaur went from self-publishing as a college student to massive international success almost overnight. This rapid success meant she didn't have the safety or obscurity to develop normally as a writer. The conversation acknowledges that while these are fortunate problems, they're real challenges that many successful artists face.

3. Finding freedom from judgment

Kaur explains that her first collection came from a place of pure creative expression without self-judgment. As her audience grew, she began thinking about outcomes and results while writing, which led to writer's block and creative challenges with her subsequent books.

She describes how poetry for her is a spiritual and personal experience, with the magic coming from honest expression. Ten years after her initial success, she's finally returning to a place where she can write without judgment. The conversation emphasizes that audience awareness can be creatively paralyzing.

4. The power of constraints

The discussion highlights how constraints in poetry create opportunities for creativity. Kaur explains that her shorter poems are actually more difficult to write than longer pieces. Each word must do significant work to support the poem's central thesis.

This echoes the Stoic philosopher Cleanthes' idea that poetry's constraining nature creates music, similar to how air pushed through a flute creates sound. In Kaur's writing process, each poem must justify its space in the book by working hard to convey its message. The limited format forces creative solutions that unlimited space might not inspire.

5. The meticulous craft behind simple words

Despite the apparent simplicity of her poetry, Kaur reveals the intensive process behind her work. She saves every version of her poems during editing, often creating hundreds of drafts for even short pieces. This allows her to track the evolution of each poem and return to earlier versions if needed.

Kaur intentionally uses simple language to make the emotional work more accessible. Her aim is for readers to focus on processing feelings rather than deciphering complex language. The conversation references Mark Twain's observation about the difference between the right word and the almost right word being like "lightning and lightning bug."

6. The unexpected impact of creative work

Both speakers express amazement at how their work affects readers in ways they never anticipated. Kaur shares stories of people finding comfort in her poetry during serious illness, despite her never explicitly writing about disease or sickness. The human emotions in her work resonated with readers in unexpected contexts.

This unpredictability of impact is part of what makes creative work meaningful. Kaur recalls a particularly moving moment when a woman in Brazil told her that publishers discovered her work because they were seeking writers similar to Kaur, leading to her becoming a bestselling author. These stories affirm that the challenges of creating are worthwhile when the work connects so deeply with others.

7. The illusion of expertise

The conversation touches on how success can be mistaken for expertise. Despite selling millions of books, Kaur still felt she needed formal credentials like a master's degree to legitimately call herself a writer. They discuss how creative fields are often unnecessarily mystified, making them seem more complex than they are.

Both speakers suggest that when people present themselves as having all the answers about creative work, it's a reason for suspicion. The reality is that creative work involves uncertainty and personal discovery. They agree that focusing on superficial aspects like what pen to use misses the point - what matters is simply doing the work.

8. The value of stepping away

Kaur discusses her desire to take a meaningful break after ten years of continuous work and promotion. She recognizes that consistently applying the same solution - taking on more work out of fear of scarcity - hasn't led to greater happiness. Instead, she feels ready to prioritize her personal life and relationships.

The conversation explores the tension between ambition and balance. While Kaur loves her work and considers herself highly ambitious, she acknowledges that work success doesn't satisfy the human need for connection. Taking time to live rather than constantly produce is both necessary and frightening for someone dedicated to their craft.

9. The double-edged sword of algorithms

The discussion touches on how social media algorithms can influence creative decisions. Kaur adopted different writing styles for performance versus social media platforms like Tumblr and Instagram, recognizing that what works in live performance doesn't necessarily translate to online formats.

There's an acknowledged challenge in maintaining creative integrity while being aware of how content performs online. They discuss the difficulty of tuning out the metrics and avoiding the twisted thinking of "how will this do?" when creating. This external validation system can pull artists away from their authentic voice.

10. The connection between creator and audience

The transcript reveals the profound relationship between creators and their audience. Kaur shares how her readers have been grounding forces during difficult times, often telling her she should take time off rather than rushing to produce more content.

This contradicts the narrative artists sometimes tell themselves about audience demands. In reality, genuine fans often care about the person behind the work and want them to thrive. Both speakers reflect on how connecting with individuals affected by their work provides perspective on success that transcends metrics like sales figures or follower counts.