How To Fail’s Elizabeth Day On The Inevitability of Failure and Why Vulnerability Is The Source Of Our Connection

You may not expect someone who’s an award-winning author, journalist and broadcaster to understand the loneliness and trauma of failure, but UK podcaster Elizabeth Day has managed to capture that journey perfectly in her wonderful podcast How To Fail With Elizabeth Day. Emma Clifton was lucky enough to have a phone chat with Elizabeth to talk about her new book, Failosophy: A Handbook For When Things Go Wrong, and why personal chats make for universal catharsis.

If you had a dollar for every time a Capsule member frothed at the mouth about some podcast they were obsessed with, you’d be a rich woman. But one of our total and utter favourites is the extraordinary How To Fail With Elizabeth Day, a series hosted by the award-winning journalist and author Elizabeth Day that ‘celebrates the things that haven’t gone right’. (I’m not the only Kiwi to feel this way, it turns out – one of the first things Elizabeth says in our interview is that New Zealand was her second largest audience for a long time.) It’s been a must-listen to of ours since it launched in 2018 and has become exceedingly popular in the years that have followed, with Elizabeth deftly getting honest and vulnerable admissions of failure from some of the biggest names out there: Phoebe Waller-Bridge, Glennon Doyle, Jamie Dornan, Gloria Steinem, Alain De Botton, Bernardine Evaristo… an absolute plethora of stars who walk us through their biggest failings and the lessons they’ve learned from them. With so much wisdom at her fingertips, Elizabeth has just released her second ‘How to Fail’ companion book: Failosophy: A Handbook For When Things Go Wrong. Considering that 2020 could very much be referred to as ‘The Year When Things Went Wrong,’ it is darkly humorous that the idea for the book actually pre-dated the pandemic entirely.

All photos taken from Instagram

“I started writing Failosophy before I’d even heard the words ‘Covid-19,’” Elizabeth says dryly down the phone from her London flat. “It’s so strange when I think back to that time – I had so much material from doing the podcast for two years. When I wrote the first podcast book – How To Fail – the podcast had only been going for two seasons… I realised I had this wealth of research and all these incredibly wise, interesting people who I got to ask nosy questions of, week after week.”

The first book, described by Elizabeth as “part memoir, part manifesto”, talked the reader through Elizabeth’s own failings and how that had led to the super successful podcast. While this new book briefly covers that backstory (my personal favourite detail is that Elizabeth sold the wedding dress from her failed marriage in order to fund the podcast), it’s designed to be a handbook for people to “pick up if and when they need it,” Elizabeth says.

“The whole idea was to make the idea of failure accessible and less scary… and then the pandemic happened! So it became even more relevant as we were all dealing with the fact that 2020 failed to be the year that we anticipated.”

So much of the kaupapa for How to Fail is the idea of vulnerability – of learning from our failures, rather than being defined by them. This means that the conversations are often very mental health focused, and Elizabeth is positive that the one sliver of a silver lining from the pandemic is that we’ve all become far more accustomed to talking about our mental state. “I’m optimistic about what it’s taught us, moving forward, about being more open and understanding that vulnerability is the source of our connection – and that no-one can be operating at their perfect level, all the time.”

Elizabeth has worked in print media for two decades, including as a current columnist for UK magazine You

As well as being a podcast host and best-selling author, Elizabeth is also a print journalist – both in newspapers and magazines, where she was regularly profiling big-name celebrities and often found that the tight word counts required for print stories meant that some of the most interesting details ended up on the cutting room floor. The How To Fail podcast allows for a meandering and personal conversation between Elizabeth and her chosen subject and follows a simple and powerful structure; before the interview, Elizabeth asks the guest to email her with their three biggest failures.

“I knew that I wanted to talk about failure; that had come out of a series of personal failures in my own life,” Elizabeth says. “And the best interviews, I knew from being a print journalist, have a structure to them – so I wanted the same thing for the podcast.” The inspiration for having the idea to have the podcast follow that list of three came partly from Desert Island Discs – a podcast where well-known people discuss the seven pieces of music that mean the most to them – and also from the print media rule about the power of three.

The list of failures was extraordinary in both honesty and accessibility – Nigel Slater’s failure to become a chef, Marian Keyes’ failure to have children, a phenomenal typo from Malcolm Gladwell that is any journalist’s worse nightmare… there are divorces and breakdowns and failed businesses and never-finished degrees and everything you can imagine, all from people we view as being total success stories. The funny, heartfelt and moving conversations that come out of these failures is one of the reasons How To Fail has become a chart-topper, the poetry of which is not lost on Elizabeth. “It is ironic – and I say this in Failosophy – that a podcast about failure has become, without a doubt, the most successful thing I’ve ever done. Not just in terms of numbers and reach but in terms of how understood I feel and how honoured I am when people share their stories with me. It feels very, very special.”

In Failosophy, Elizabeth includes the famous Carl R Rogers quote “What is most personal is most universal”, and it’s a lesson she’s learned during the slow merging of her personal and professional life that formed the bedrock of How to Fail. At the beginning of the series, she says her years in print journalism made her reticent to put herself into the conversation as much – wanting to keep the guest on the show very much the focus, as you would when writing a story about them. “I didn’t feel that anybody would be listening because they wanted to hear my story, but I’d half thought of being interviewed myself [for the show] but then I thought ‘Is that too egomaniacal?’” she laughs.

Podcast Pals – Elizabeth with Dolly Alderton

It was when her good friend – and fellow podcaster/journalist – Dolly Alderton suggested it, and volunteered to do the interview, that Elizabeth relented. While she says editing the episode was torturous – “hearing your own voice in your head being open about the things that have gone wrong in your life is WAY too much” – she ended up being proud of the final result, where one of the failures she discussed was her failure to conceive. It is, heartbreakingly, a thread that has continued along a lot of Elizabeth’s recent years. “As women, I think we have been done a tremendous disservice, historically, by being told our stories are not important, that we mustn’t talk about things that are internal to our bodies, that by miscarrying we, in some way, fail to fulfil our biological imperative as women. These are all things that are incorrect but carry an enormous weight for us, still. And I can speak very personally to that, having had three miscarriages now, unsuccessful IVF… the whole gamut of fertility treatment.”

Last year saw high profile women like Chrissy Teigen and Megan Markle write, in full, unflinching detail about the pain and trauma of pregnancy loss, kick-starting a global conversation about how common it is – and how hard it is. “When somebody of that profile and stature, who is still a member of the royal family, talks about miscarriage, it does something fundamentally important in that it changes the landscape for any woman who has ever felt misplaced or shamed about talking openly or sharing her story,” Elizabeth says. “When I first spoke about my miscarriage, I felt so held by other women but I was also so surprised by how many of them had experienced something similar but never spoken about it before. I do think that’s because there’s still this sense that we should all be doing it behind closed doors and that’s really changing and I’m extremely proud to be a tiny part of it. I am super passionate about it, because I didn’t know what a miscarriage entailed until I experienced one. And I don’t want other women to go through that sense of isolation.”

The crux of Failosophy is the Seven Failure Principles, the boiled-down, little gems of concepts that Elizabeth has learned along the way from her many guests – taking the big, complex, personal experiences of failure and turning them into teachable moments for anyone going through crisis. At the tail end of the book, Elizabeth writes movingly about having to put them into practice, again, after experiencing another miscarriage just before Christmas in 2019. “I don’t write for catharsis but sometimes it’s a really welcome by-product,” she chuckles. “I knew that in Failosophy, for my words to carry any weight, I would also have to be vulnerable. That’s not to say it’s a personal book – because it isn’t, it’s very much focused on what other people have taught me – but I wanted to show that following that set of failure rules had actually worked in my own life.”

In an extra cruel bit of timing, Elizabeth then got pregnant again in 2020 , only to then experience another miscarriage – all while still in lockdown. “It was isolation heaped on isolation,” she says. “Having said that, one of the positives was that I was with my partner and he was working from home, so we were able to process it together so much more powerfully than we had been able to do before that.”

All the while, she was releasing this book and releasing lockdown specials of How to Fail. The work, she says, is enormously helpful in helping her own mental state. “These are things that have cost me an enormous amount, have caused me a lot of grief and still do make me sad,” she says of her miscarriages. “However, I have realised that I can live with that sadness, but I don’t have to live IN it. And that really goes to the core of what are some of the most profound concepts I’ve learned through the podcast, which is that pain is inevitable but suffering is optional. Failure, also, is inevitable but we don’t have to be defined by it. Just because we fail does not make us a failure forever and actually, we can choose how to respond to it.”

Failosophy: A Handbook For When Things Go Wrong is available now in all good bookstores. For more information on How To Fail With Elizabeth Day, visit here, and for some of our favourite episodes, visit here.

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