I Almost Transitioned - Here’s Why I Didn’t - Sascha Bailey (#26)
Sascha Bailey, British tech entrepreneur and son of photographer David Bailey, nearly transitioned at twenty-eight after a ten-minute diagnosis in Tokyo. Now living in the UK and expecting his first child, he unpacks how trauma, Silicon Valley culture and social-role collapse drove him to the edge of transition — and what his story reveals about the NHS, the Cass Review's findings, and the thousands of British boys navigating identity without adequate support.
Sascha Bailey is a British tech entrepreneur and author — and the son of photographer David Bailey. He is also a man who came within a breath of medically transitioning. At twenty-eight, living in Tokyo and emerging from an abusive relationship, he walked into a clinic and received a diagnosis of gender dysphoria in ten minutes, followed immediately by a prescription for hormone replacement therapy. He left Japan overnight. Over the months that followed, he stepped back from transition entirely. This episode traces that journey and the ideas he has built from it. The ten-minute diagnosis deserves attention from British listeners. The Cass Review, published in April 2024, found that gender clinics too often affirmed patients rapidly, without adequately exploring co-occurring mental health conditions, trauma or neurodevelopmental factors. Bailey's experience in Japan reflects the same failure in adult medicine. He describes his three gender episodes across his life as attempts to regain control after periods of profound powerlessness. Childhood sexual abuse, dissociation and unprocessed PTSD were, he argues, the actual drivers — not some settled sense of a different gender identity. He reached the point where he could no longer define what gender dysphoria actually meant. Bailey brings a marketer's precision to what he calls the transmaxxing movement — online communities that treat transition as a rational, data-driven life upgrade, particularly for autistic men in tech. Silicon Valley culture, with its preference for optimisation and self-reinvention, creates a distinctive vulnerability. Algorithms reward transition content; identity becomes a product to refine. His book, Try to Hit the Pool: Modern Man and Behavioral Sink, draws on the mouse-utopia experiments to argue that affluent societies, by stripping away meaningful social roles, produce the very identity crises that gender ideology then rushes to fill. That argument has clear implications for Britain's own culture of aspiration without belonging. The conversation is particularly sharp on what is happening to boys. Bailey contends that sensitive and neurodivergent young men receive contradictory signals about masculinity, ambition and what they are permitted to want — and that this leaves them exposed. He is not calling for a return to rigid gender expectations, but he insists that the absence of recognised social purpose for young men creates a vacuum, and that transition is one way of stepping into it. The discussion of gaming, information overload and why children of the affluent are disproportionately represented among those who transition will resonate with teachers, parents and clinicians across Britain. Bailey's account arrives at a significant moment for the United Kingdom. Tavistock has closed, NHS England has paused puberty blockers for gender dysphoria outside clinical trials, and the Cass Review has redrawn the clinical landscape. Yet male detransitioners remain largely invisible in public debate — the necessary focus on girls and young women has left men like Bailey without much of a framework or a platform. He is now living in Britain and expecting his first child, and that gives his reflections an urgency that goes beyond ideology. The question he is really asking is what kind of society, and what kind of support, awaits the next generation.
