What happens when extreme trauma, tech culture, and gender ideology collide? Sascha Bailey's journey from nearly transitioning in Tokyo to becoming a leading voice on male detransition reveals uncomfortable truths about control and identity. Diagnosed with "gender dysphoria" in 10 minutes, prescribed HRT on the spot, Bailey escaped Japan overnight—and slowly unraveled everything he thought he knew. Now expecting a child with his partner, he's decoded the "transmaxing" movement, exposed how tech rewards transition, and discovered why mice in utopia start acting like humans in crisis. His message: "I don't know what gender dysphoria means anymore." As society strips away male social roles, Bailey asks: What happens when you can't be anything, so you try to be someone else?
About Sascha Bailey
Sascha Bailey is a tech entrepreneur, marketer, and author who nearly transitioned at age 28 while living in Japan. Son of iconic photographer David Bailey, he brings a unique perspective on identity, social pressure, and the intersection of tech culture with gender ideology. After escaping an abusive relationship and leaving Japan overnight, he gradually stepped back from transition. A childhood sexual abuse survivor, Bailey now frames his three "gender episodes" as attempts to gain control when he had none. His book "Try to Hit the Pool: Modern Man and Behavioral Sink" explores why affluent societies produce identity crises. He lives in the UK with his partner and is expecting his first child.
"I Don't Know What Gender Dysphoria Means Anymore"
Tokyo clinic, 10 minutes: diagnosed, prescribed HRT. Bailey's decade-long "living hell" relationship weaponized his childhood trauma daily. His response? Complete dissociation. "I think they were just episodes of not wanting to be me." Three distinct moments emerge—at 7 after abuse, at 18 discovering trans forums, at 28 in crisis. The pattern: lack of control, no options, then transition as escape. "It was one of the very few things that I could do...no matter what." His evolution from believing in gender dysphoria to recognizing "I don't want to be me distress" reveals how trauma gets reframed through gender when that's the only lens offered.
The Spreadsheet Approach to Changing Sex
Enter transmaxing—not what Channel 4 told you. "It's transitioning viewed through an autistic lens." No feelings, just data: height stats, passing rates, benefit analyses. Meanwhile, tech culture rewards transition. "If you transition, you're one of the first trans people, you are guaranteed extra press." The uncomfortable truth: in Silicon Valley, being trans makes you "different and interesting." Some calculate beforehand, others justify retroactively. Bailey sees both sides—the conscious game theory and the post-hoc rationalization. But beneath the spreadsheets lies desperation: "Every route I tried to take I was blocked from...then this one thing."
Escape, Environment, and Evolution
Bailey fled Japan overnight, waiting 12 hours at the airport. Back in the UK, everything changed. Meeting his now-partner, gaining distance from trauma, having "control and options." The unraveling was slow but certain. Someone mirroring his words back—"What will happen after your transition?"—broke the spell. His insight: environment matters more than identity. "I removed myself from the situation which left me with no options...ended up in a situation where I had control." Unlike dramatic moments, his recovery was gradual: new people, new possibilities, a future as himself.
Why Men Don't Detransition
"Men do tend to make more final decisions. There's a lot of shame in going back." Young men are told their sexuality is "pathological," that masculinity itself is toxic. "You grow up thinking all that stuff is bad because you're told it's bad." Meanwhile, women hear "celebrate sexuality," "you go girl." The double bind: "Come here, see me sexually. Don't you dare see me sexually." Bailey's theory: sensitive boys need their spaces celebrated, not colonized. "Gaming is just chess...some men like to be competitive with their minds." But these spaces—coding, gaming, tech—are under assault. The message to awkward boys: you're the problem.
The Behavioral Sink
Why do famous people's kids keep transitioning? Bailey connects mice experiments to modern malaise. John Calhoun's 1970s studies: unlimited food, limited space. Result? Male mice split into three groups—obsessive groomers who won't mate, random violence in the center, aggressive harems. Sound familiar? "In societies that have low survival pressures and high affluence...a lack of social roles." From Robert De Niro's child to Elon Musk's—the pattern holds. Rich or poor, the behavioral sink catches all: "You can't really be a whole lot, but if you change your entire identity, then you can." Ancient Rome knew it: "We are now suffering the calamities of long peace."
"There's Another Universe Next Door"
Bailey's book explores the internet as a crowded city where you can never leave, where mistakes stick forever, where identity calcifies. His prescription: create social roles, celebrate what boys naturally gravitate toward, stop the colonization of male spaces. "The Internet probably shouldn't be allowed for under eighteens." Bold? Yes. But when six-year-olds discuss sexuality while sensitive boys have nowhere to belong, something's broken. Bailey escaped by changing everything—environment, people, possibilities. His message to those still trapped: control isn't found in changing your body. It's found in changing your life.
If you've ever felt like something bigger is happening but struggled to make sense of it, Beyond Gender is for you. This podcast cuts through the noise with honest, thoughtful discussions about one of the most pressing topics of our time.
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