How To Lose Friends & Alienate People

In 1995, British journalist Toby Young got the phone call every Fleet Street hack dreams of — an offer from Graydon Carter, the renowned editor of Vanity Fair, to fly to New York and work for the magazine. Toby, in spectacular fashion, then proceeded to stuff up every opportunity that came his way, starting , most comically, with his interpretation of the ‘casual’ dress code, as a pair of vintage 501s and a T-shirt ‘featuring a bare-chested Keanu Reeves and the strapline: “Young, Dumb and Full of Come”’.

I first read How To Lose Friends & Alienate People in 2010 as I commuted to my first internship at Coty Int. a multi national I came to refer to as The Ministry of The Dark Arts. It was all I could do not to burst into horrified laughter right there on the Metro in central Paris. Three years short of a decade later, Toby Young’s ghastly faux pas, complete lack of judgement, and drunken antics continue to appal, appeal, and seem more than relatable.

I re-read How To Lose Friends & Alienate People more recently, shortly after My Salinger Year another memoir set in the New York publishing industry. Poignant, keenly observed, and irresistibly funny: a memoir about literary New York in the late nineties, a pre-digital world on the cusp of vanishing, where a young woman finds herself entangled with one of the last great figures of the century.



At twenty-three, after leaving graduate school to pursue her dreams of becoming a poet, Joanna Rakoff moves to New York City and takes a job as assistant to the storied literary agent for J. D. Salinger. She spends her days in a plush, wood-paneled office, where Dictaphones and Typewriters still reign and old-time agents doze at their desks after martini lunches. At night she goes home to the tiny, threadbare Williamsburg apartment she shares with her socialist boyfriend; a detail I found deliciously amusing.

Precariously balanced between glamour and poverty, surrounded by titanic personalities, and struggling to trust her own artistic instinct, Rakoff is tasked with answering Salinger’s voluminous fan mail. But as she reads the candid, heart-wrenching letters from his readers around the world, she finds herself unable to type out the agency’s decades-old form response. Instead, drawn inexorably into the emotional world of Salinger’s devotees, she abandons the template and begins writing back. Over the course of the year, she finds her own voice by acting as Salinger’s, on her own dangerous and liberating terms. 

Rakoff paints a vibrant portrait of a bright, hungry young woman navigating a heady and longed-for world, trying to square romantic aspirations with burgeoning self-awareness, the idea of a life with life itself. Charming and deeply moving, filled with electrifying glimpses of an American literary icon, My Salinger Year is the coming-of-age story of a talented writer (my time will come). Above all, it is a testament to the universal power of books to shape our lives and awaken our true selves. 


While the latter could be a career guide for young hopefuls (do what you’re asked but be prepared to take on more challenging work, be discreet at all times, and be aware of the impression you’re making), Toby Young’s book is a how-not-to guide (don’t smuggle a strippergram into the office on Take Our Daughters to Work Day, don’t slide smart-ass remarks under your boss’s door, and try to avoid being photographed doing lines of coke at work).

Between his truly outrageous tales, Toby Young offers up interesting digressions on celebrity culture and academia in the late 1980s, and the importance of the New York media in determining the zeitgeist:

‘If Vanity Fair announces that London is on fire, then, to all intents and purposes, it’s on fire. On the other hand, if London’s so-called cultural renaissance goes completely unnoticed by anyone outside the city, then the whole thing is a bit of a non-event… In the global kingdom, New York is the home of international court society.’

He also muses on exactly what it takes to be successful at a magazine like Vanity Fair:

‘I often wondered how it was that a group of such apparently sophisticated people were able to devote so much energy to producing an upscale supermarket tabloid. How did they preserve their sanity while thinking up cover lines like “Jemima and Imran: The High-Stakes Marriage of Pakistan’s Camelot Couple?” Were they all on Prozac?’

Toby answers this question in a footnote: ‘The answer is probably yes.’

How To Lose Friends & Alienate People is much more than gossipy recollections of Toby’s time among the glitterati. He shows enough insight, self-awareness and wit to keep the reader on his side, despite his unspeakable behaviour. In the last chapter, he recounts some of the ‘spectacularly idiotic’ things he did, then ponders:

‘Up to a point, these episodes were simply the result of blind ignorance; of not knowing, and not bothering to find out, the appropriate way to behave. But some of my more destructive acts seemed to be the result of the anarchic side of my character tripping the other side up, doing whatever it could to ensure I’d never end up achieving the things I’d set my heart on…
I can’t help feeling that the terrorist inside of me was the British part sabotaging the American part. The longer I spent in the States, the more British I felt. Like so many others, I thought that by moving to New York, I could re-invent myself; I could become an American. It seemed entirely possible, too — for about six months. Then my Britishness started to reassert itself. It was if I took a flight across the Atlantic and my nationality came by boat.’

But perhaps the last word should go to the Director of Public Relations at Vanity Fair, quoted in the reviews at the front of the book:

‘We’ve been looking through our files, and we can’t seem to find any record of a Toby Young ever having worked here.’

Brilliant isn’t it?


At this very instance, I find myself entangled in a moment somewhere in between a Toby and a Joanna. Caught on the way down of what feels like a lengthy descent into something I call, The Belly of The Beast; at the same time enamoured with the brevity of romance in the time of ‘Men Are Trash’.

I too moved to New York in my early twenties; glassy eyed and green, the city raised me. Grad school became an escape; I was completely unknown and foreign; a commodity in certain circles. It felt like I had successfully struck a balance between the visibility of my affluent upbringing, and the freedom to ‘figure it out’. I wrote, and I partied, and I networked, and I graduated spectacularly with an impressive body of work to my name, if I do say so myself. Folks back home found me aspirational, interesting, almost inhuman; I was after all, living the dream. I revelled in it, got sucked into it, let the lights seduce me like a sea nymph or the last Rolo. The darkness fell however, when I came back.

I am now smack bang in the eye of the ‘visibility’ storm. I’m not famous, nor in anyway a celebrity, but the hyper visibility of social media and the space I occupy within it, have begun to come crashing down around me. I think now is an important place to remind you all that I am a writer. I absorb my world and spew it back out in Times New Roman and Helvetica Neue. Everything and everyone in and around my life are fair game. Is this really fair? Probably not. But wasn’t it Picasso who said that ‘all artists steal.’ I have stolen character traits, experiences, phrases and even physical features, from the people around me, to not only fuel the creative engine producing this work, but to populate it with tidbits of hyper reality.

I have come to terms with the nature of my beast. Opening up about intimate details of my life and experiences to people, often times total strangers, puts a neon target on my back, conspicuous; worthy of Times Square. But what my naivité graciously shielded me from, was the ripple effect of every shot that landed.

I recently signed up for Curious Cat on Twitter, an app that allows your Twitter followers to ask you questions anonymously, and publishes your responses to your Twitter timeline. I’ve seen it play out before, where some of the people I follow are asked intimate, personal questions. There is a brief uproar and then it all dies down pretty quickly, as is the news cycle of 140 characters.

Nasty things are said, or rather asked, but the little troll that lives in a dusty corner of my chest, rationalised that my audience is genuinely more concerned with the way I answer a question than the answer itself, so I would be spared, or at least could dance my way out of a trciky conversation. And for the most part I did. The simple questions came first, ‘where do you see yourself in 5 years’, and then the trickier ones, ‘are you still biting Duey’ [my ex boyfriend]. ‘Running my own company’ I replied first, and then ‘no’ to the latter. I screenshot the question and my response and sent it to him as a heads up. I’m careful to not talk about people online directly, without letting them know. ‘Thanks for letting me know,’ he said, ‘but I’ve got nothing to worry about, so you’re fine.’

Great, I thought. He gets it.

The real test came when things got ugly.

‘Do you wear black because of the weight gain,’ will you ever return to bulimia?’

Now…I’m no stranger to openess, to transparency, but I can’t deny I was blown away. It felt malicious, spiteful, and dark, in a way I hadn’t experienced since I was bullied at school. I have openly discussed my Bulimia online, in fact, if I hadn’t written about it myself, no one would know. So for someone to use the façade of this very convenient anonymous app, felt redundant and that extra bit ugly.

‘I always wear black,’ I responded, and ‘you don’t just get over Bulimia.’ I was hurt.

The next series of questions asked quite explicitly if I was engaged in a sexual relationship with one or both of two of my closest friends. Deflecting the questions with semantics, I avoided answering anything directly, but still made a point to engage because hey, I am a writer, and I volunteered to play. I want to control my narrative, I want to be in charge of my story, get in front of it all before someone else decides. Again I sent screenshots to all in question, but the response this time was less than favourable. Actually, it was awful. In fact, it’s still stings.

He felt betrayed, like I had tarnished his image simply by engaging. Like his name being associated with that kind of chatter was a stain on his reputation, like I had lost my mind. He cut me off. ‘I didn’t sign up for this.’

 My visibility and engagement with that space had suddenly filtered over into my personal relationships in a way I had never thought about before. ‘Collateral damage’ an Ad Man I know personally commented.

But he was, is, right. He didn’t sign up for that and neither did anyone else in my life. My parents for example, who may one day have to read all of this; my friends, who are with me (I hope so at least) for everything other than the spaces I occupy (or am trying to at least), and of course my intimate partners, whose lives suddenly become of public interest when attached to mine. I was however, a little concerned at the severity of his reaction, how easy it was to shut me out. Had I underestimated the real impact of that conversation online [though I deleted the offending tweets immediately]? Have I become an entity outside of myself that is now threatening to people around me? Will he ever forgive me?

I had hoped that the conditions of ‘fame’ did not apply to me, because I was known for something very particular, very niche, away from the standard of entertainment. I thought I was well liked because I made a conscious effort to be warm, engaging, present and reliable. I thought that because the trade I peddled was relatability, people would go easy on me, that I would be safe. It turns out I’m not. I’m not sure how to move past this in a way that is both constructive and productive, without having to compromise on transparency, a cornerstone of my personal brand.

I’m not sure if he will ever forgive me, and I can’t promise I will get it right every time, but I am learning these lessons, out loud, online, so maybe you don’t have to.


Photography by Anthony Bila