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157 - Is Our Culture Incentivizing Men to Transition? with Sascha Bailey


Sasha and Stella welcome Sascha Bailey this week to the show. And what an incredibly fascinating conversation stretching the podcast host duo far outside their familiar gender-centric framework.

Guest, Sascha, reflects on his journey as a model, art curator, and pioneer in the NFT (Non-Fungible Tokens) art scene. A captivating account of the intersection where art, tech, and culture collide with personal identity. Sascha differentiates between emotional and functional motives for transitioning, discussing transmaxxing, incentives, and societal trends. A conversation sure to offering listeners an intriguing blend of unexpected insights!

Sascha Bailey, who at one point was convinced that 'transitioning' was a way out of his intense feelings of despair, started his professional life at the age of 16 when he made a mark in the fashion industry as a model, being featured in the editorials of many major fashion magazines and working for renowned brands such as Valentino, ID, Dazed and Confused, and walking for Dolce and Gabbana. During his time as a model, Sascha spent two months in Tokyo for work where he fell in love with the country and made connections that would later play a role in his art curation there.

During his early 20s, Sascha began his career as an art curator. He has curated over 28 art shows in major cultural hubs such as Tokyo and London, collaborating with esteemed names including Paul Smith and Damien Hirst, as well as working with over 150 young, emerging talents.

One of Sascha's groundbreaking achievements was the conception and execution of the first-ever NFT art show in Asia in 2021, featured on mainstream Japanese news, CryptoTokyo. This groundbreaking event showcased digital artworks tied to non-fungible tokens, with notable artists like Beeple featured prominently. Beeple's artwork, displayed at CryptoTokyo, later made headlines when it sold for a staggering $69 million, solidifying Sascha's position at the forefront of the intersection between art and technology.

In addition to his curatorial work, Sascha is a contributor of FOMA Magazine (@fomamag), which he has been working with since 2020, standing for 'Fear of Missing Art.' FOMA is a publication dedicated to pushing the boundaries of artistic expression and engagement in the digital age, as well as conducting deep investigations into online subcultures. Through FOMA, Sascha continues to bring light to the digital renaissance currently taking place.

The conversation exposes Sascha's personal experience with gender identity and his decision not to transition. He reflects on the societal pressures and personal realizations that shaped his understanding of gender and identity, as well as his own anecdotal account of the impact of online forums and communities focused on transgender-related topics. 

Sascha thoughtfully discusses the evolving societal landscape surrounding transitioning and highlights potential incentives influencing an individual’s decision to undergo the process. He acknowledges that transitioning has become a trend in contemporary society, and as transition gains more recognition and societal validation, Sascha suggests that some individuals may be influenced and even incentivized by external factors rather than from genuine personal reasons.

An episode packed full with insights illuminating the intricate dynamics at play, weaving together personal identity, societal influences, cultural incentives and individual aspirations in the journey towards transition.

Resources & Links

@saschabailey on X(Twitter)

@baileysascha on Instagram

@fomamag on X(Twitter) and Instagram

Sascha Bailey - son of iconic photographer David - describes how close he came to becoming a woman and fears for other young people like him: 'Society has a gun to its head. You're either for children changing their gender, or you are transphobic', by Kathryn Knight

FAKE ISSUE 1, “How to be a Man”, from FOMA - Fear of Missing Art || Online international mag for immutable culture. Insights into the digital art movement & internet subcultures

Sascha mentions reading “The Culture”, referring to a sci-fi book series by Scottish author Iain M. Banks, which explores futuristic concepts including extreme body modification and transhumanism. The series delves into the idea of individuals modifying their bodies to such an extent that humanity itself is transformed. Sascha draws parallels between the themes in "The Culture" and the ongoing discussions surrounding gender identity and bodily autonomy.

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Therapy First

If you liked this episode, more episodes you might find interesting include:

Gender: A Wider Lens
Gender: A Wider Lens
In this podcast, now in its fourth year, therapists Stella O'Malley and Sasha Ayad take a deep dive into the psychological and cultural forces impacting the social changes around "gender." Through interviews with researchers, doctors, therapists, parents, detransitioners, and others, Sasha and Stella's podcast is a "must listen" for anyone trying to navigate the current gender landscape. With their sharp analytical minds and deep compassionate hearts, Stella and Sasha have also become known throughout many parent networks as lighthouses in the midst of some very stormy seas. Previous guests include Helen Joyce, Jesse Singal, Leor Sapir, Kathleen Stock, Jamie Reed, Peter Boghossian and more.