“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.”