How to fail in the media and how I’ve failed...

A story of bad choices, bad takes, and bad people.

“Failure is the real f-word,” is the kind of lede that should get red penned out of existence. So, I’m not writing that. Instead, I’m writing this meta-lede about what the lede should be, which is also a cheap trick, but I’m so fond of a cheap trick, I could sell out the Budokan eight nights on the bounce. It’s cultural references that fresh that have me on track to become the king of TikTok.

There’s a good reason for me harping on about failure however. I’m currently reading Elizabeth Day’s new book Failosophy: Handbook For When Things Go Wrong, a printed extension of her unmissable podcast How To Fail… with Elizabeth Day. (Incidentally, she recounts early in the book the amusing tale of how she failed to Google the title and therefore ended up adding the “…with” suffix because another podcaster had already grabbed How To Fail for their programme.)

In the succession of bridge burnings that I laughably call my career, I have become intimately familiar with failure. I have taken failure on expensive dates, had fun but ultimately regrettable sex with failure, and woken up in failure’s bed, uncertain how I got there, but sure that the process that led me there included hanging around with the wrong people, talking about the wrong things and making the wrong decisions with the wild abandon of Jay Gatsby behind the wheel of an expensive motorcar.

My first media failure story comes from before I was even really a professional writer. I was in my first year of university, and had managed to get a piece of poetry selected for the (it says here) prestigious May Anthologies, an annual collection of prose, poetry and non-fiction by the most precocious monsters at Oxford and Cambridge. Having succeeded in rocking up to Cambridge despite ending my admissions interview with the dread phrase, “Well, thanks for that. You’re probably not going to let me in…”, I had set about treating the university as an all-you-can-eat buffet of lectures, drinking, sex, stand-up comedy, and student journalism.

I ended up as the only person to get writing in the book that had been written while still a snot nosed fresher. I was obviously delighted and even more so when it transpired that I had also got an invite to a bash for contributors being held by an important literary agent.

Accompanied by my wonderful friend, Abi, the nicest woman to ever emerge from Aberdare, I schlepped down to London, not in my finery, but my usual combination of near-dead trainers, secondhand leather jacket and a t-shirt that might have been described as “distressed” had I got a handle on the vocabulary of fashion fuckistas by that point. There was copious booze. Abi and I drank it and I, fully intending to wow an agent, stood in the corner with her for the entirety, too scared to talk to anyone. Some wunderkind.


I signed with a literary agent in 2019, a full 17 years after I attended the agent’s party. I found my representation through Twitter, where he was taken by a thread I wrote about McDonalds. I have yet to sign a book deal, though little hopeful shoots can be witnessed, awaiting a fucking by the first frost of commercial reality.

Other failures include 9 months at my dream job as an editor at Q magazine, which ended with me resigning as a broken man, retreating to the North for two months to scheme a return, before getting freelance gigs with Wired, and then being rehired by Stuff — where I had edited part of the print magazine — as deputy editor of the website, only to be suspended for the cardinal error of having freelanced for Wired when not employed by Stuff. I was marched off the premises by a goon squad (thanks for that publisher Mark Payton, I’ve not forgotten or forgiven). I resigned the same day preventing them from convening a kangaroo court investigation.

I then went on to fail too as a contract writer at The Daily Telegraph, where I was treated as you might a dog that can dance on its hind legs/ write compelling copy about Ed Miliband. Further failures as a wannabe publication founder, tech startup creator, and agency boss followed, the latter assisted by a partner who stole £1,000 of client cash in the second month and contributed to me having a breakdown.

Other failures include getting myself asked to leave at tech site The Next Web by writing a publishing a post called Why I’m Quitting Tech Journalism — funnily enough, they weren’t very happy about that one — and being made redundant as Head of Comms for a software firm after 9 months because my boss had spunked away thousands on ill-fated projects before he’d hired me. The CEO of that company, a gangly man child who wore Wedding Present t-shirts to the office, remains one of the most odious bastards I’ve ever worked with and, as previously mentioned, I was once contracted to attend The Daily Telegraph’s offices on a regular basis.

What’s the great life lesson I have to impart? Beyond, don’t spit in the wind, and resign before they can sack you, it’s simply this : Failures and fuck-ups happen and every relationship with a publication will likely end in some kind of failure, because the media industry is lousy with managers who struggle to manage not pissing on their shoes, let alone managing teams of volatile journalists.

Something that isn’t a failure is Elizabeth’s book, which I recommend without hesitation but also, crucially without having been paid to say so. In fact, while we are mutuals on Twitter, we’ve never met and I am merely a fan of her work. But look, I couldn’t fail to make the recommendation…