“So many things I would have done, but clouds got in the way.” At 23, Joni Mitchell reflected on the essential unknowability of clouds and life and love and potentiality. It’s a song that aches with a lifetime of wisdom and longing. But the real genius of Both Sides Now is to reach both forward and back, connecting potentiality and regret. 

Look at Philippa York’s Twitter biog, and the line hits hard. “I’ve looked at clouds from both sides now.” Because York has mastered the unknowability of clouds and no longer lets them get in her way. Like her biog goes on to say: “And this view is better.”

“I was an exceptional person before I transitioned. And I can try and be an exceptional person now,” she says. “And my daughter said a really good thing. She said, ‘You know, you don't have to have to have a public profile. But it would be a good thing to do’. And that's why I do it.” 

York acknowledges that sometimes it's hard being visible again. “Because even though I have all those lessons I've learned as a writer and as a competitive person, it's still a lot more personal in the second half of my life.” We’re speaking via WhatsApp, and I’m still processing a combination of awe and respect. Fangirling the rider who lit up the earliest days of my long and complicated love affair with cycling, and admiring the woman who fights her corner with the effortless cool that was always part of the allure. 

I ask her if she thinks she’s an activist, albeit a reluctant one. “Do I want to argue with somebody that I don't exist? No. I’ve been on Pride marches, but does that make me an activist? No. I look at the people that are gonna come after me in a similar situation. And I think, what help did I get? What help can I give them?” She won’t be waving a placard, she says. “But I will use my profile to compete for stuff that matters to me.”

York draws a series of parallels from her racing days:  “So as a competitor,  you go through the crowds, and people shout abuse at you, and your colleagues abuse you, and you abuse them, and it's a competitive environment. So it's not nice. Nothing nice about it. It's nice to be a bike rider and race fast, and that looks beautiful. But the actual competition is, no, it's horrible. But the same kind of words and nastiness that you hear as a trans person is a lot more personal.”

“Because the competitive thing is kind of tribal. So you're racing somewhere, and you've beaten the local, and everybody abuses you. Fair enough, it’s part of what it is. And you learn to deal with that through the psychological processes you develop. To take that in, absorb it, and then use it against those people. But you can't really do that when it's your normal life. So you kind of use the same things that you've learned, that knowledge from competitive situations.”

I wonder how much of what she learned about herself in the feral competitiveness of the peloton has equipped her for this second half of her life, where the snarling doesn’t come in the heat of competition but from spiteful strangers on social media? 

“Being snarled at was an everyday race occurrence. Part of the mental gamesmanship. I’ve done it, I know I have, to intimidate people. Probably makes you feel better at the time.” She smiles and says that side of the sport didn’t affect her, that she’d sometimes take it as a compliment to still be thought of as competitive and relevant enough to be the target of someone’s mind games. “So I take those things from my previous life, and some of them apply to what happens to me now. There are people who say things to you to hurt you. And you can pretend that they don't hurt you. But you will never ever show that at all. You’d probably say I process it later. But to my face, it just doesn't affect me. You can't let it, not if you come from something as competitive as a peloton.”

Does she feel that she’s left the competitive side behind now? She laughs and tells me that these days she lives in a very nice house with nice neighbours. “But I’m not competing with them.” I remind her of an old quote from the racing days about doing anything to crush the opposition. “So that’s the competitive side,” she responds. “That person would exist up until about an hour, two hours after the bike race was finished. And then I turned her off because I had to let go of it. Because I can't be that person all the time. And then, when I got up in the morning, I’d go back into that person, I shut off all the emotions and the characteristics that I don't need in that environment. Because somebody will take advantage of them. The Robert Millar persona wasn’t who I wanted to be all day, every day. It was a shield from what was happening.”

She describes the peloton as a jungle and says she needed to assume a persona that let her survive in a hostile environment where “you either eat or get eaten. But I always thanked my teammates when they had to do something because I messed up. And not every team leader or directeur sportif comes and tells you you did a good job.” She says some riders never let go of their competitiveness, and that when they finally stop, it takes them years to come down from that level of aggression and self-protection.

While York has an incisive understanding of the coping mechanisms required in a competitive environment, she says she’s rejected some of them completely. “I don’t need them,” she says, then smiles knowingly before adding, “When you’re less successful, you can review and see what lessons you can carry forward into your normal everyday life.”

On X/Twitter, York is subject to the same microaggressions that anyone speaking out on trans issues encounters. I ask her if she doesn’t sometimes want to type, “Do you know who I am?” She laughs - we laugh a lot - and then replies, “I’ve never said, ‘Do you know how good I am?’ Or, in my case now, how good I was. I’m reasonably satisfied with how my career went. But I never said ‘do you know who I am’ when I was doing it, so why would I do it now?”

But how does she cope with the endless pushback against her right to exist? The toxic “debate” that has come to dominate the culture wars? York adopts the twee, venomous tones of a certain type of middle-class lady who ‘has concerns’: “They say ‘I think we need to have this debate.’ And you say, just do one, go back to suburbia or whatever.” 

The Gender Critical movement embraces everything from trans-exclusionary radical feminists (terfs) to Matt Walsh, a self-identified theocratic fascist and presenter of the online film “What is a Woman?” It’s a set of malleable beliefs that attract men and women from across the political spectrum who have developed ‘concerns’ about the rights of trans people to do anything from play sport to exist in public spaces. It’s best understood as part of a wider far-right project that seeks to centre cis white women as feminism’s “good actors” with the ultimate goal of legislating against women’s bodily autonomy and for a return to traditional sex-based roles. And it’s a fundamental part of the populism currently sweeping the anglophone world. 

Intellectually, it fits into a post fascist movement that uses extreme fear mongering as control, pitting “natural” biological women against their “perverted” trans counterparts. In reality, the flashpoint for assaults on the rights of trans people has focused on women’s toilets. These single-sex spaces are central to gender essentialism and the heteronormative discourse. And public toilets are where women are most at risk of predatory men posing as trans women to rape and assault them - at least according to gender critical ‘feminists’ and the UK press. The Daily Mail alone published an astonishing 115 articles on trans people in January 2023. And this despite overwhelming evidence that the majority of perpetrators are cis heterosexual men, known to the victim. Despite this, the women’s toilet has become the frontline in the terf war.

“When it’s your real life, and you want to use the toilet somewhere. Are we going to start with the whole ‘biological woman’ thing? I’ve got to have a badge or something, like the Nazis?” York asks. We’re talking about the unrelenting tsunami of anti-trans articles in the media and the single-sex spaces wars that rage on social media. “Once a month, you’ll get something supportive, and then there’ll be four of five things saying, ‘I saw someone’s penis in the toilet.’ 

She recounts an anecdote widely reported without verification by the right-wing commentariat: “There was a really stupid thing the other day about somebody accusing this trans woman of flashing her genitalia. And it turns out they've already had their operation, so they’re post-op. So they just made that up.” She says when she talks about her own transition, women are okay with it. “But when men are present most of them are really uncomfortable with it because they don't imagine…(the pause for comic effect is immaculate) You know, they're quite attached to their genitals.” Obviously, we both hoot with laughter.

In July 2022, Maya Forstater successfully appealed a decision that holding absolutist gender critical beliefs was “not worthy of respect in a democratic society”. The appeal upheld the right to hold a ‘philosophical belief’ under section 10 of the Equality Act 2010, ruling that “The Claimant’s gender-critical beliefs, which were widely shared, and which did not seek to destroy the rights of trans persons, clearly did not fall into that category (Nazism or Totalitarianism)”. 

As York is quick to point out, Gender Critical views are only a “protected belief” in the same way that humanism and veganism are viewed as genuinely held beliefs. “You can believe whatever you like,” she continues, “You can believe that Hitler was right. That Attila the Hun was the best person ever. That Elvis is alive and living on the moon. In your head. But as soon as it comes out, it's an offence if you express it in a way that breaks the law. So there are consequences.” As the Forstater appeal judgement explicitly points out, “This judgement does not mean that those with gender-critical beliefs can ‘misgender’ trans persons with impunity” and “This judgement does not mean that trans persons do not have the protections against discrimination and harassment conferred by the Equality Act”.

Reflecting on what has been published and posted and tweeted since her own reemergence as a trans woman, she’s remarkably sanguine. “We can all be horrible people.  But it doesn't make you feel good,” she says. “It goes back to when I competed, and you were expected to cheat, and you’re told ‘if we don't cheat, the others are going to’. And you go through that, and you come out of that system. And you just feel crap about yourself. Even though you know that everybody cheated.”

She says she looks at the noxious online climate and thinks, “How crap must you feel at the end of this? You’re just finding an outlet because there’s something about yourself that you hate and don’t want to deal with it. And you think if you pass the hatred onto somebody else, that's going to make it better. But it doesn't. Whatever your issue is, it doesn't go away. It's not going to go away by taking it out on me. Because I can just turn it off. I just leave.” York says she’s only recently started watching BBC News again: “I felt so much better not being terrorised by everything anymore.”

Simone de Beauvoir famously wrote in The Second Sex: “One is not born, but rather becomes, a woman.” It’s the foundational statement for examinations of sex and gender. So how does it feel to become a woman during a culture war? York takes a beat, then asks: “What is gender ideology?” Another beat. “Apparently, I’ve been through it.” She laughs at the absurdity of it all.

York was recently photographed at the Robert Millar mural on the Crow Road in her native Glasgow. It’s a defining snapshot of the mutability of the body and spirit, the then and the now, the will to live a complete life. Time and hormones have softened her body, but her mind is as sharp as those era-defining cheekbones. Always slight and bird-like, Millar was the perfect physical manifestation of a mountain climber, with the heron-like profile of Coppi, the panache of Pantani, and Gaul’s urge to escape the very confines of the sport in the solitude of the highest peaks.

In Mountains of the Mind, Robert McFarlane writes, “This is the human paradox of altitude: that it both exalts the individual mind and erases it. Those who travel to mountain tops are half in love with themselves, and half in love with oblivion.” To fall in love with climbing to those oxygen-starved heights requires physical gifts and mental toughness. York has described the art of winning at altitude:

"One brutal acceleration might be enough, or it might take five or six, but when the elastic snaps and no one can follow any longer you’ll be on your own – and believe me, there’s nothing more a climber can ask for than dancing away at the head of the race alone. Alone against nature, no numbers involved."

York says that when she first arrived at the pro level, “everyone's a champion of something.” She says you have to work out how you’re going to deal with that level of competition, your place in the hierarchy. How you’re going to deal with your ego, and how to learn what makes you tick. “So your talent takes you so far, and you kind of learn where you might end up in terms of your physical performances, but mentally, you haven't really been tested to your limits yet.”

It’s a balancing act, she says, controlling your weaknesses without letting your strengths become dominant. “Because you're being aggressive, but you need a certain level of aggression and competition, otherwise you just get eaten. But you can be overly aggressive, so you have to control that. You have to learn to control all the parts of your emotions, the kind of mental capacities that you have and work on your weaknesses as well. And some of those weaknesses, you will never get right. And you have to accept that you will never get them right and learn how to control the emotions and the other kind of feelings that come with that.”

Normal people, York says, aren’t generally taken to their absolute limits. “Unless it’s an emergency, a life or death situation, people are rarely taken to the physical limits, almost never taken to the mental limits. Whereas when you do pro bike racing, you're taken to it most days. Quite often, you go beyond. That’s part of the deal. And the people that sit at the top, they deal with that, and it doesn’t eat them.”

She espouses the Eastern way of thinking about energy, of only having so much for each activity and running into trouble when the qi runs out (York is a second dan black belt in Taekwondo). She says it explains “why I’m kind of lazy now. It’s a consequence. It’s being a bike rider for fifteen years as a pro. You’re going to have a sore back and physical problems.” She pauses, and then adds “It’s part of the deal. If you want an easy life you go and work in a shoe shop.”

I ask if being a trans woman gave her a greater insight into the hyper-masculine world of professional cycling, but she simply shrugs and says no, that’s just her character. “So the things that I like to do are probably overanalyzed, and I’d be really meticulous, right? And things that I'm not interested in and are probably very important to most people, I’ll just go whatever, I don't care.” She laughs and breaks the mood.

It’s one of the criteria for getting to the top of the sport, York says. Not to be intimidated by criticism or the things people snarl at you. She cites the example of Thibaut Pinot’s exchange with Jonathan Vaughters after the Frenchman had blown a chance for success in the Giro. “It was beautiful, just classic,” she laughs, “A perfect response because he knows perfectly well who he is.”

York knows all about perfect responses and landing a pithy truth bomb. In tandem with her cycling career, she’s worked as a journalist since the 1990s, penning funny and insightful columns for a range of cycling publications. She says she tries to give observations that embrace the positives, not the negatives. And she has a keen eye on how the racing cyclists brain works - for example, this on the French hero Pinot:

“It’s clear that the parts that are damaging him as a person are not worth the pain. What he's getting out of that life is not worth putting up with the pain. Because he can step outside of that cycling world and back into the real world. Because he’s observing the suffering and cruelty during the race, and afterwards he gets to reflect.”