Manifesting authenticity - Looks Like Work, Season 1, Ep 24

A photo of Anna Przybylski. Looks Like Work by by Chedva Ludmir Kleinhandler. Season 1, Episode 24

What if the content that resonates most is also the content that’s saving you? In this raw and resonant episode, Chedva Ludmir sits down with Anna Przybylski—event director, content creator, and the wildly relatable voice behind @keepitupcutie—for a conversation about burnout, delegation guilt, and the surprising healing power of bathrobe honesty.

Originally sparked by a pandemic shutdown, Anna’s content creation journey grew from pure survival to a deeply personal platform where humor, sadness, and radical vulnerability coexist. Together, she and Chedva explore what it means to juggle two full-time identities, manage emotional labor, and resist the pressure to be productive when your body is begging for rest.

If you’ve ever felt guilty for slowing down, questioned your role as a leader, or just needed someone to say “you’re allowed to feel this,” this one’s for you.

What We Talk About:

  • The unexpected rise of @keepitupcutie during the chaos of 2020

  • Running an events business and a full-time content practice

  • How daily posting gave way to sustainable rhythms

  • Guilt and delegation: why we struggle to let go

  • Burnout as a full-body shutdown—not just a mindset

  • Sad girl content and its power (and limits)

  • The bathrobe as a uniform for radical truth

  • Learning to take a sick day before it’s urgent

  • Showing up online as a journal—not a performance

  • Anna’s Powerful Question:

    “What’s the truth behind this guilt—and is it actually helping anyone?”
    A question for leaders, creators, and anyone stuck in the cycle of "shoulds."

  • Key Lessons:

    • Burnout is not a productivity problem—it’s a nervous system message

    • Delegating isn’t failure; it’s a leadership skill

    • Your content can be a journal, even if no one gets it

    • You’re allowed to slow down, even if nothing is “wrong”

    • Sadness doesn’t need to be explained to be valid

    • Showing up online doesn’t require performance—just presence

    • Sometimes the best encouragement is simple: Keep it up, cutie

 

“Sometimes your brain and your body are having a disagreement—and you have to side with your body.”

 

Listen to this episode on Spotify | Apple | Wherever you get your podcasts

Resources & Mentions:

  1. Visit Anna’s Website

  2. Follow Anna on Instagram

  3. Follow Anna on TikTok

  4. Buy Anna’s Merch!

  5. Book recommendations from this season of LLW

  6. Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean

  7. Subscribe to the newsletter: chedva.substack.com

  8. Check out The Curiosity Lab and CuriosityGPT

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The Scrapy Way Up - Looks Like Work, Season 1, Ep 25

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Building & Maintaining the CEO Mindset - Looks Like Work, Season 1, Ep 26