What I Learned From 'Failing' At My 20s

Designed by Serena Brown
The pressure to showcase your successful, #blessed life can be overwhelming in the Instagram age, with the gulf between what we see online and the disappointing, difficult reality of life a proven cause of mental ill health and unhappiness. So it's refreshing to hear someone championing the merits of failure and things not going right.
If you ever find yourself bemoaning the direction your life is taking, the upcoming book How To Fail: Everything I've Ever Learned From Things Going Wrong, by author, journalist and podcaster Elizabeth Day, published next month, will allay your fears and galvanise you to keep going – even when the urge to hibernate under your duvet is strong. Inspired by her hugely popular podcast, How To Fail – whose guests include Phoebe Waller-Bridge, Gina Miller, Mishal Husain, Lily Allen and author Kristen Roupenian – the book, described as "part memoir, part manifesto", contains chapters on dating, work, fitting in, romantic relationships, babies, friendship and more, plus nuggets of insight from Day's most memorable guests.
Fans of the podcast will be familiar with Day's trust in the premise "that understanding why we fail ultimately makes us stronger" and while a glossy, highly intelligent, award-winning journalist may not initially seem like a natural figurehead for the movement, fans will know she's not squeamish about sharing her own mistakes.
"I'm a naturally open person. I know some people find what I do horrifyingly exposing or they are kind enough to consider it brave. I don't feel it's either of those things," she tells Refinery29. "I think the most obvious and honest way to connect is to be open about the times when things aren't going right," adding that she's made "amazing connections" with people who've confided their own failures in her as a result of the podcast.
The pressure to succeed can feel particularly acute during one's 20s, when once-equal peers' lives start hurtling at different speeds and in different directions, but in reality it's a torrid decade for many. Day is open about her own failures during those formative years in How To Fail, particularly when it comes to romance. Having spent her 20s in a string of long-term relationships, with barely a few weeks of singledom between each one, she regrets giving so much of herself to others. "I took them so seriously because every single relationship, I was thinking, 'Well this will probably end up in marriage'. As a result, I forgot to find out who I was and I was constantly catering for the other person in the relationship," she admits.
"Have more flings, date more and worry less," she'd advise her twentysomething self, repeating the well-worn cliché with a laugh: "The best thing about getting older is you really know yourself and you acquire wisdom and experience. It's not just a good line, it's actually true and getting older is empowering."
To those currently wading through the decade's muddy waters, she says: "Getting through your 20s is the greatest achievement of that decade. It was a constant surprise to me that so many people I spoke to for the book and the podcast felt that their 20s have been times of chaos and difficulty and failure and sadness and this mishmash of emotions, and discovering that made me really look at my own 20s and write that particular chapter. I'm so glad I did because it seems to be the one that is resonating with people."
It's an unfair truth that while they're happening, people "don't really talk about how difficult your 20s" are, Day attests. "You only get that perspective in retrospect. So if you feel lost or that you're not doing as well as you should be, or you're comparing yourself to others who seem to be nailing their 20s, that is completely natural and it's a function of that decade. I promise you that when you turn 30 you're going to feel so liberated and so strong and your 30s are going to be your best decade yet."
Below is an extract from Day's chapter, "How to Fail at Your Twenties".
The longest I was single between the ages of nineteen and thirty-six was two months. In those two months, I came up with every excuse I could to keep in touch with my ex-boyfriend, and simultaneously tried to distract myself by saying yes to any man who crossed my path and expressed even the mildest interest (years later, when I told a male friend of mine about this period in my life, he replied with 'Fuck. I wish I’d known you had no standards back then,' which wasn’t exactly what I meant, but it wasn’t far off either).
During these eight weeks, I engineered the least spontaneous one-night stand in the history of random hook-ups, purely because I believed that having a one-night stand was exactly the sort of thing I should be experiencing in my twenties.
Photographed by Jenny Smith
The man in question was called Mike and lived in Paris but had come to London for the weekend. We spent an evening eating overly complicated Chinese food served on wooden platters and then we danced in a terrible basement club off Oxford Street that only played salsa music and had stains on the walls that looked like faecal matter. Mike was perfectly nice but had the unfortunate quality of becoming less attractive the more time I spent with him because he said things like 'Golly gosh' and 'Is that the time? Best be getting on then.' But so intent was I on having this much-lauded sexual experience of no-strings-attached, shirt-rippingly intense bodily contact with a near-stranger, that I insisted on going back to his hotel and falling into bed with him. It was, hands down, the worst sex of my life. At one point, I had to ask 'Are you in?' because amidst the fumbling-golly-gosh embarrassment of it all I honestly couldn’t tell.
As soon as it was over (he had, it turned out, been 'in') I gathered up my clothes, locked myself in the bathroom and got dressed.
'You’re not staying then?' he asked plaintively when I emerged.
'No ... erm ... deadlines ... so sorry ... lovely evening ...' I said, backing out of the door like a faithful retainer leaving an audience with the Queen. 'Speak soon!'
Outside, I took out my phone and called my ex-boyfriend. He answered and said he was missing me. We met the next day and got back together. We went out for another year.
As I walked to the tube in the early hours of that particular morning, I reflected that I had tried my best to live out the fantasy of my twenties, to experience the heady whirl of irresponsible youth and casual sex, and yet, when it came down to it, I’d rather be in a steady relationship and have a bath and an early night.
It felt like an extended metaphor for the whole decade: that shifting tension between where you wanted to be, where you thought you should be and where you were right now.
It was the same with work. The Londoner’s Diary was great training for spotting a story and writing it to deadline, but I was desperate to be getting on with the business of being a 'proper' journalist.
I was in a job in the area I most wanted to have a career – journalism – but it wasn’t the one I was really after, and it would take me several more years to get there.
I was in a long-term relationship that wasn’t serious enough to lead to marriage and wasn’t fun enough to be casual.
I was in a houseshare that, on paper, should have been a place of hedonistic excess but was mostly just a nice terrace inhabited by people who reminded each other of the need to buy toilet roll and made tray-bake brownies from Nigella’s latest cookbook when they had a spare couple of hours on a Sunday.
It didn’t help that there was so much cultural baggage around one's twenties. When this particular decade was represented on screen, it looked as if everyone else was having a fabulous time. The mood music of my twenties was provided by the Friends theme tune and the clatter of Sex and the City heels on New York sidewalks. But it never translated into real life. The rest of us who didn’t hang out with their closest pals in Central Perk coffee shop or drink Cosmopolitans and discuss the female orgasm were left labouring under the misapprehension that we were failing to make the most of it.
I remember my twenties being a decade in which no one talked – not really, not honestly – about the things they felt unhappy about or the stuff that was going wrong in their lives. It was, instead, ten years of trying to put on a good show – for yourself and for anyone else who might be watching. It was ten years of moving forwards while groping blindly for the point of it all; ten years of building a career but feeling impatient at the lack of pace; ten years of wondering who you were meant to be dating and how you would find the mythical right 'one'; ten years of casually assuming you had all the time in the world while knowing you were running out of it, to the extent that turning thirty seemed to me to be a giant cut-off after which I would never be truly young again.
One of the most interesting revelations that came from the How To Fail podcast was how many other people struggled with this period of their life. I’d assumed that my interviewees would have nightmare tales to tell of adolescence (I’d been preternaturally well behaved as a teenager, and I expected others to have misbehaved for me) but actually, it was their twenties that came up again and again as a time of immense transition and uncertainty. Unlike me, who had been lucky enough to know what I wanted to do professionally, many of those I spoke to had had little idea of what their future held, and that brought its own challenges.

More from Books & Art

R29 Original Series