Illustration by Antony Hare

The secret to failing upwards with Toby Young

When it comes to turning a seemingly bad situation into a resounding success the author of How to Lose Friends and Alienate People is something of a master

Toby Young needs to lose some weight. And before you start talking about pots calling kettles fat, let me say that this isn’t my analysis (I think he looks marvellous, really I do) but the judgement of his son, who’s challenged his old man to lose several kilos before the family depart for their summer holiday.

That’s why the writer is dressed head-to-toe in Nike activewear as he strolls across the sunny courtyard at Pomona’s to our table (his ensemble pairs beautifully with the California-lite intentions of the restaurant, actually, not to mention all these Notting Hill au pairs) and why we’re opting today to drink little test tubes of fragrant green detox juice as opposed to anything slightly more, well, journalistic.“I’ve just done an hour of HIIT workout in front of a Joe Wix YouTube video” he tells me as he sits down, which sounds just about millennial enough to do the trick.

There is another way to trim the fat. But, as Young discovered, it might come with a few unwanted side effects. At the start of the year, the Spectator columnist was subject to a social media witch hunt which soon ran amok in the mainstream press. After his appointment to the Office for Students, a pitchfork mob trawled through Young’s Twitter history in order to unearth some indiscretion with which to skewer him. Several risqué tweets, most of them poor jokes and tipsy asides dating back some seven years, were dug up and thrown across the front pages. Soon, the government caved to the hysteria and dismissed Young from the panel, despite his overwhelming expertise.

The secret to failing upwards with Toby Young

Still, in the nine days that the torchlights burned, the writer lost more than half a stone. “It’s fight or flight. Your body’s shedding weight so you can outrun the hoard” he laughs as we plough into a fresh, almost yoghurty pillow of buratta. It was a shock to the system. “There were moments when I thought: I’m glad my father isn’t here to see this.” Young says. “I did worry that sometimes it would spill over into the real world. I took to wearing a deerstalker on the way to work. And I also discovered online shopping during that period” he smiles “But I did at least slim down.”

Young has made a career from this mingling of optimism and self-destruction. His brilliant book, How to Lose Friends and Alienate People, chronicled his disastrous few years as an editor at Vanity Fair in New York. For all the gaffes and the excruciating self-flagellation, surely it was a brilliant time to be living out the dream of the Englishman in New York, I ask, as a skillet of plump Madagascan prawns, sat in a sultry garlic-and-chilli reduction, briefly distracts us both. “It was fun for about a year,” Young says, recalling the thrill every night of leaving a “Lincoln Continental idling at the curb” as he trotted through a milk run of Manhattan power parties.

But the life soon revealed itself to be shallow and inflected at every turn with bizarre pomposity.“I remember Graydon [Carter] bringing his personal architect, Basil, into the office and transforming the entire place into a giant cigar lounge” Young tells me. “This was not a sane place.” (Carter, for his own part, recalls Young’s time at the mag thus: “I basically forgot to fire Toby Young every day for two years.”) The book became a bestseller and was turned into a successful Hollywood film with Simon Pegg in the lead role.

“It was fun for about a year...”

This is victory tooth-picked from the jaws of defeat, or, as Young calls it, “failing upwards.” (There is some source material to draw on — in his 30-year career, he has been fired from the Observer, the Daily Telegraph, the Guardian, the Sunday Times, the Mail on Sunday, the Evening Standard, the Independent and Vanity Fair.)

The secret to failing upwards with Toby Young
The lovely setting of Pomona's terrace

As he settles into a gorgeous smoked duck and peach salad (an ingenious creation from new Executive Chef Mark Lloyd, it just about sneaks through the pre-holiday diet), I ask Young about the decline and fall of Modern Review, the magazine he co-founded with Julie Burchill in 1991 at the age of 28. Covering “low culture for high brows,” it was a raucous operation both on page and behind the scenes, and became a well-thumbed blueprint for all cultural coverage since — when you see academics eulogise over Love Island in the Sunday Times, that’s pure Modern Review. Eventually, Young and Burchill clashed in spectacular fashion, and Young decided to torch the publication in a bombastic final issue.

"I think it’s probably been my biggest challenge yet..."

“Everyone loves a feud” Toby tells me. For a brief period, the spat was splattered all over the broadsheet press. “That was when Matthew Freud [the PR Guru] told me what he tells all his clients: ‘don’t read your press coverage — weigh it.‘”

“But I don’t think that’s the case anymore.” Young says now, in the light of his own Twitter-mobbing. How does this test compare to his earlier stumbles? “I think it’s probably been my biggest challenge yet” he says with genuine feeling.

But the old game may well be afoot again. “I think I’ll have to turn the experience into something,” Young tells me, imagining a play or a novel based on this thoroughly modern ordeal. “It seems like such a representative story of the moment.” Then he leaves, and I eat a life-affirming chocolate fondant for one, because I am far beyond the help of Joe Wix. Whatever Young does next, it will likely be a huge success — the bigger the drop, the more spectacular the bounce.

Now find out what we learnt when we sat down for some lobster with Nick Grimshaw…

Further Reading