“Why learning how to fail is the key to our liberation”

Journalist, author and podcast host Elizabeth Day reveals how to own your failures, and why doing so is the key to success.

Four out of the six universities I applied to rejected me. Decades have passed since then, but  I can still recall the cold feeling in my stomach and the heaviness behind my eyes that eventually led to me bursting into tears in front of a (very kind) teacher. It’s been a little less time since my fourth shorthand exam, which went so badly that I sobbed – crying hysterically is a big theme when it comes to the aftermath of my failures – as I transcribed my notes in the exam room. At that moment, I felt devastated.

Those feelings come back whenever I remember my failures, which is why I don’t like to think about them. But thinking about our failures is exactly what Elizabeth Day thinks we should be doing.

The journalist and author is the host of the podcast How to Fail, where she interviews people about the moments in their lives where they’ve not succeeded, and she’s now written book of the same name that is part-memoir, part-guide to confronting your failures.

Remarkably honest, and at times emotional reading, How to Fail covers topics such as sports, relationships, having children and being Gwyneth Paltrow (Day had to spend a week living like Paltrow for a feature). 

Elizabeth Day addresses failure in her podcast and book.

The original idea for the podcast began after Day “got dumped” in 2017.

“It was the end of a two-year relationship and it was really out of the blue and it was quite brutal,” she tells Stylist. She went to Los Angeles for a break, and three things happened that led her to start thinking deeply about failure.

“I was ghosting a memoir for Gina Miller, and I was having to assume the voice of an incredibly strong, amazing, aspirational woman at a time when I felt extremely emotionally vulnerable myself,” says Day. “The exercise of doing that was extremely helpful for me because I was having to pretend to be strong on the page.”

She also stopped listening to pop music, turning instead to podcasts including Where Should We Begin?, in which counsellor Esther Perel opens the door to her therapy room and talks about relationships.

“I was also having these great in-depth conversations with a lot of my female friends about break ups and what they teach us,” says Day. “Because I was having these honest conversations and because I was thinking about my own life, I started looking back at my 30s, a decade where an enormous amount of stuff happened.

You may also like

Alexandria Ocasio-Cortez has an important message about feeling like a failure

“I’d published four novels, I’d got married, I’d got divorced, I’d had IVF, I’d had a miscarriage, I’d failed to have children. I realised that I was approaching my 40th birthday and that all my biggest life lessons had come in the guise of failure, in the guise of endings of relationships or in the guise of things not happening that I thought would. I thought, how great would it be if we could have more honest conversations about vulnerability? I believe being open and honest about one’s vulnerability is the source of true strength and self awareness.”

After letting the idea percolate, Day drew her own logo with felt tip pens, found a producer through Google, sold her wedding dress on eBay to fund the podcast and asked eight people she knew to take part. Although she knew it was something she wanted to talk about and hear, she was unsure if others felt the same – they did and the podcast was a hit.

Process your grief

Writing a book has been a slightly different prospect, with Day turning the focus properly onto herself. There is humour within How to Fail (the aforementioned Paltrow chapter is very funny), but it’s also sad at times, particularly when Day addresses her desire to have children – she went through two rounds of IVF, had a miscarriage at three months, and froze her eggs.

Day describes the chapter as both the “easiest and most emotional to write”.

“Writing that chapter was really wonderful in so many respects because it felt very liberating to put it down in its granular detail, and I was determined to do that because women’s narratives have historically been marginalised,” says Day. “When I did IVF there was no literature out there. There were so many mother and baby books, and there was nothing that was just a cool, calm, informative response to what I was going through. So I wanted it to exist for other women like me.

How to Fail by Elizabeth Day

“At the same time I was talking about stuff that is very painful to me still, personally. It has been a slow motion process of grief for me coming to terms with the fact that it is highly unlikely I will have my own biological child.

“That’s been very, very sad and I don’t want to give the impression that I am Pollyanna-ish about failure, and that I think everything is unrelentingly positive. I think life is texture, I think you’re able to be sad and ok with something at the same time. But writing that chapter was enormously important for me in terms of processing that grief. Once I had finished it, I felt relief and a sense of liberation, and a sense of empowerment that I had got my experience down on the page.”

The story of Day’s desire to have a child also reveals the gendered way in which failure is spoken about, particularly in regards to fertility.

Day was treated by male doctors, who told her “time and again that I, personally, was failing to respond to the drugs rather than it being the drugs that were not giving me what I needed”. The language the doctors used, says Day, was the language of “my failure as a woman”.

“It’s difficult to think of another condition where the same sort of language would be applied,” she says. “A friend of mine was told that her womb was an ‘inhospitable environment’. You’re told that you have an ‘incompetent cervix’.

“Language holds power and when you’re going through something so emotionally draining as fertility treatment, to be told all of these things is really hard to take. You feel like you’re not good enough.

“Then there is a broader sense that society still makes one feel, as a woman, that one has failed for not having a child.”

It’s not just around fertility that failure is gendered – the way men and women react to failure is different, Day has found. When asking men to appear on her podcast, she discovered they had “a very positive spin on the topic of failure, and would say ‘I don’t think I have really failed’”.

Elizabeth Day
Elizabeth Day is the host of the chart-topping How To Fail podcast.

“For me as a woman, that blew my mind because I’m constantly obsessing over my imperfections,” Day continues. “It’s taught me a lot about being born into privilege. I’m a very privileged person and I completely acknowledge that, but a white man is the most privileged of all.

“They had a mindset that hadn’t been taught by millennia of social conditioning that they weren’t good enough. They were born, many of them, with the idea that they were good enough. So that if something failed to go their way, they would have a way of processing it that would speak to a profound self-belief. It’s not all men, but it was something I noticed.”

Among the guests on the first season of How to Fail was the author Sebastian Faulks, who said something that has stuck with Day: “He said failure is how you see it. He gave the example that he could be really sad he failed to win an Italian literary prize, or he could be happy he got a trip to Italy out of it, and got to eat some nice food and meet some nice people.”

Remember that everyone fails

Faulks’ outlook is a good way to put a positive spin on failure, but it’s still a subject many of us find difficult to confront. Day’s advice is to remember that we all fail, which seems obvious but is actually a huge comfort.

“We are all going to fail in our life, that’s a fact. You might as well build up emotional resilience and you might as well confront failure so that the next time it happens, because it will happen, you feel better equipped, stronger and you can learn more from it.

You may also like

Millennial burnout: 3 women share their experiences of overcoming career exhaustion and paralysis

Remembering that even the most successful people fail is “very democratising”, especially in a world where we have standards for perfection, partly because of the impression of perfection given through Instagram and partly because we live in a world which is very competitive.

We’re often taught that failure is something to be ashamed of, says Day, and that certainly rings true – there was a healthy dose of shame that caused me to react the way I did when I was rejected from universities I really, really wanted to go to.

Control your response to failure

But, says Day, failure is just a fact and it’s up to us how to respond to it: “How you respond to failure is within your control and it’s predicated on the emotion you choose to respond to it with. Ultimately, I know it’s going to make me stronger.

“Failure is data acquisition. Instead of thinking, ‘oh, this relationship has ended, I’m devastated’, allow yourself time to think that but also think, ‘this relationship ended for a reason, because this relationship wasn’t for me, and by it ending it has freed up space that I can use to find the thing that is for me.”

Failures can have long term effects on us, says Day, and it’s important to think about them so we can figure out what these effects are. 

Understanding = liberation

“I am someone who has been in therapy, and I am still in therapy and I am a massive advocate of therapy,” says Day.

“Therapy has helped me understand what triggers my reactions in certain situations often has a very deep route, and it will often come from something that seems so insignificant or small at the time.”

In How to Fail, Day recounts moving to Northern Ireland at the age of four. Her English accent made her an outsider at secondary school, as did the fact that she was “deeply uncool, deeply nerdy, and wore courdoroy trousers”.

“There was a girl who was slightly mean about how I looked and that stayed with me for decades,” says Day. “It’s still with me, the sense that I am not good enough and I need to be reassured that I look okay or I’m accepted, that I belong.”

The failures of the past “can have huge knock on effects”, says Day.

Looking back now, I can see the impact of being rejected by UCL, Warwick, York and Cambridge had on me – they made me feel like I wasn’t clever enough or good enough, so I’ve worked triply hard in my career to prove I am. I can see, having read How to Fail, that I shouldn’t let the failure of decades past own me now, but at the same time I should acknowledge the role it played in my current life.

Rejections and failures in the past “can have huge knock on effects, and to understand that is to give yourself the key to your own liberation” says Day.

“But, that’s not to say we should obsess over the past, that’s not to say we should hanker after a need to change it, because the past is done, the future is unknown and all we have is the present and we need to value that,” she continues. “It is a question of understanding the lessons of the past and I think that makes you into a more self-aware person.”

How to Fail is out on 4 April (4th Estate, £12.99).

Images: Jenny Smith Photography


Share this article

Recommended by Sarah Shaffi


These 3 women came face to face with career burnout. Here’s how they overcame it

“I ended up with a medical device that helps my brain function.”

Posted by
Susan Devaney

Why failure is good for you

(Even you, Supergirl)

Posted by
Stylist Team

Lili Reinhart powerfully reminds us there is no ‘shame’ in attending therapy

“Today I started therapy again. And so the journey of self-love begins for me...”

Posted by
Kayleigh Dray

Kristen Bell doesn’t have her “s**t together” – and this is how it’s impacting her career

The Good Place actress is just like us, okay?

Posted by
Susan Devaney

Alexandria Ocasio-Cortez has an important message about feeling like a failure

Anxiety is normal – but as long as you’re trying, you’re the boss.

Posted by
Sarah Shaffi