S2 E16: It’s Not Funny to Get Punched in the Face, but I Do It Anyway with Kaytlin Bailey

Kaytlin Bailey discusses her show “Whore’s Eye View,” which combines comedy with a historical perspective on sex work, blending stand-up comedy with a real history lecture. She shares how her father’s military background and her experiences as a sex worker influenced her writing, exploring themes of exploitation and violence across different professions. Through her show, Kaytlin aims to provide a nuanced understanding of sex work by juxtaposing it with other forms of labor and highlighting the boundaries and consent involved in both.

Kaytlin also talks about her passion for boxing, which started as a way to channel her aggression and has become a recreational hobby. She explains how boxing has helped her process emotions, overcome trauma, and stay connected to her body. Jessie and Kaitlyn discuss the parallels between their experiences in sex work and boxing, emphasizing the importance of boundaries, consent, and self-discovery in both fields.

Kaytlin also shares insights from her travels and experiences boxing in different countries, noting cultural differences and similarities in boxing gyms worldwide. The episode concludes with Kaitlyn discussing her upcoming projects, including future performances of “Whore’s Eye View,” and sharing resources for listeners interested in sex worker rights advocacy.

In This Episode: 

00:01: Introduction to When We’re Not Hustling podcast

01:23: Podcast host introduction & mission

02:44: Upcoming live event & nonprofit status

05:07: Kaytlin Bailey’s show & background

08:02: Kaytlin introduces herself & her work

10:47: Juxtaposing military & sex work experiences

13:56: Boxing as a hobby & its impact

22:26: Lessons from sparring & personal growth

35:52: Wrap-up and book recommendations

Guest:

Sex worker rights advocate, comedian, and writer, Kaytlin Bailey is the Founder & Executive Director of Old Pros, a non-profit media organization creating conditions to change the status of sex workers in society. Host of The Oldest Profession Podcast, she is also the creator of Whore’s Eye View, a mad dash through 10,000 years of sex worker history.

You can find Kaytlin: 

Website: kaytlinbailey.com

X: @kaytlinbailey

Instagram: @kaytlinbailey

Recommendations:

Candida Royalle and the Sexual Revolution: A History from Below by Jane Kamensky

Normal Women: 900 Years of Making History by Philippa Gregory

Florence and the Machine 

The Rest: 

RSVP to The Holy Hour Book Launch Event in Pittsburgh on Oct 16: HERE.

Host: Jessie Sage

Producer: Emily Foster

Music: Benjamin J Benamati

Sponsor: Assembly Four

Powered by Black Venom Digital

When We’re Not Hustling is a 501(c)(3) non-profit project of the Social Good Fund.

You can support our show with your tax-deductive donation HERE.

 

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