How to Fail

How to Fail Plot Summary

Introduction

One of my earliest memories is of failure. I am three years old, and my sister is ill with chicken pox. My mother is upstairs trying to comfort her, placing a cool hand on her forehead. I desperately want to help, so I decide to make a hot-water bottle for my sister. I find my favorite one with a furry bear cover, take it to the bathroom, and fill it with water from the bathtub tap. Not understanding I need to wait for hot water, I use cold water instead. When I bring it to my sister, the cap loosens, spilling cold water all over her pajamas. She wails in distress, and I feel a swelling of acute shame in my chest. I had only wanted to help, but instead made things worse. This seemingly minor childhood failure might not appear significant, but it taught me something profound about life's unexpected twists. Failures aren't just setbacks – they're often our greatest teachers. Throughout life, we face countless moments where our best intentions go awry, where carefully crafted plans collapse, or where we simply don't measure up to our own expectations. Yet these detours aren't dead ends. They're pathways to deeper self-understanding, resilience, and authentic growth. The journey through failure isn't about becoming perfect – it's about embracing our imperfections and discovering that sometimes, our most meaningful growth happens precisely when things don't go according to plan.

Chapter 1: The Courage to Fail: Elizabeth Day's Personal Journey

On a crisp October day in 2017, my relationship ended abruptly. I was about to turn thirty-nine, just two years after getting divorced. This wasn't where I had expected to be at this stage of life. I had anticipated being married with children, not single and facing an uncertain personal future. I needed to heal, so I did what many do in times of emotional distress – I escaped. I went to Los Angeles, a city I regularly visit to recharge and write. While in LA, I had an epiphany. What if our failures actually teach us more than our successes? What if the moments when things go wrong contain the most profound life lessons? This thought sparked the idea for my podcast, where I would interview "successful" people about what they had learned from failure. The premise was simple: I would ask each guest to share three instances where they believed they had failed, and we would explore the lessons they'd gained from these experiences. When the first episode of the podcast went live, it attracted thousands of listeners overnight. By the end of eight episodes, I had accumulated 200,000 downloads and a book deal. But more importantly, I received dozens of messages every day from people going through difficult times who found comfort in these conversations about failure. A woman who had been told at fifteen she would never have children. An advertising executive signed off work with chronic fatigue. Someone whose mother was in intensive care, finding calm by listening to these discussions about failure and resilience. The podcast's success taught me something paradoxical: being honest about vulnerability is the root of real strength. When we share our failures openly, we create space for connection, understanding, and growth. Failure contains more meaningful lessons than straightforward success, and acknowledging this truth is perhaps the most liberating step we can take toward authentic living. As Arthur Russell so elegantly expressed in the chorus of "Love Comes Back," "being sad is not a crime" – and neither is failing.

Chapter 2: Identity and Belonging: When Fitting In Feels Impossible

When I was four, my family moved to Northern Ireland during the height of the Troubles. It was 1982, and bombs routinely exploded in shopping centers. My mother would be stopped at checkpoints by soldiers with machine guns on the school run. I spoke with a precise English accent and stood out from the first day of school. Born in suburban Surrey, I now found myself in a place where checkout ladies in supermarkets would suspiciously ask if we were "on holiday" when we did the weekly shop. To help us belong, my parents immersed us in local culture. My mother took me and my sister to Irish dancing lessons. When we moved deeper into the countryside around Claudy, my father bought a donkey, a painted cart, and four sheep to keep in what we called "The Rath." We named the sheep Lamborghini and Lambada. Each summer, my parents heroically attempted to shear them by hand, while my sister and I acted as sheepdogs. It was a peculiar existence – part rural idyll, part political conflict zone. My primary school was pleasant enough, but when I went to secondary school in Belfast, I became more aware of my difference. One weekend, walking to catch the bus home, my route took me through the aftermath of a bomb attack. Every window of the Europa Hotel had been blasted out, and glass crunched under my feet. At school, I learned that a boy in my year didn't fancy me "because she's English." Overnight, I started seeing myself through others' eyes: my fluorescent orange rucksack worn on both shoulders wasn't stylish; corduroy trousers had never been cool; my accent was foreign and off-putting. The girls I thought were my friends began talking about me rather than with me. They made plans without me to go to nightclubs with fake IDs. When I approached groups of them laughing, the laughter would mysteriously stop. I became used to not belonging. In response, I stopped talking as much at school. I no longer put my hand up to answer questions. If no one heard my Englishness, maybe they wouldn't notice my difference. During the days, I kept to myself, trudging long corridors with lever-arch files clasped to my chest. I developed two distinct personalities: a home self and a school self, taking great pains to ensure the two never coincided. Failure to fit in teaches us resilience and independence in ways nothing else can. It forces us to develop a rich interior life, to question received wisdom, and to cultivate empathy for others who stand outside the mainstream. Many of the most creative and successful people I've interviewed for my podcast shared similar experiences of alienation in their youth. The actress Christina Hendricks was bullied at school after her family moved from Idaho to Virginia. She found her tribe in the drama department, where acting provided an outlet for her feeling of impotent rage. She became a goth, dyeing her hair black and purple. "My parents would say, 'You're just alienating everyone,'" she recalled. "And I would say, 'I don't want those people to be my friends.'" Not fitting in taught me to observe human behavior, to listen more than I talked. It made me question conventional wisdom and develop my own perspective. These skills later proved invaluable for my writing career. Years later, when I returned to Ireland to promote my first novel, I was welcomed everywhere as a local novelist. After all those years of struggling to belong, it didn't matter to them how I spoke. It was the most amazing feeling. What did it feel like? It felt like coming home.

Chapter 3: Relationships and Heartbreak: Finding Strength in Vulnerability

When my marriage ended at age thirty-six, I found myself single and clueless, having never really dated. For the next seventeen years, I'd been in long-term relationships, constantly schlepping across London with hair-straighteners and clean underwear stuffed in my handbag. Now, I was entering a completely transformed dating landscape. Meeting someone online was no longer considered weird or desperate. Swiping left on Tinder was the new normal. The idea terrified me. "What if I meet an axe-murderer?" I asked my friend Francesca. "Well, you'd be more likely to end up with an axe-murderer if you randomly met someone on the street," she reasoned. "At least online you can read their profile first." It was a good point. So I signed up to Bumble, the app meant to give women control over dating. Once matched, women must initiate first contact. You might think this sounds empowering, but in reality, it meant I had to come up with witty opening lines and then feel personally rejected when men didn't respond. My first Bumble date was with Kenny, who had just completed the Hoffman Process, a psychological detox course. He stared at me with dilated pupils, spoke with the zeal of a born-again Christian, and followed me to the bathroom when I excused myself. Then there was Alec, who sent hand-drawn pictures of flowers before we'd even met, then wrote a song about me after our first date. There was the lawyer who quoted Deepak Chopra excessively, and the man whose profile photo showed him posing in front of the Auschwitz gate. One experience taught me more about navigating modern romance than any other. I met Jonathan through a friend, and on paper, he seemed perfect: my age, bright, financially solvent, with no emotional baggage. Over email before meeting, he was funny and engaging. In person, I liked him, though without feeling overwhelmed by passion. He had quirks – making too many puns, wearing bow-ties with casual shirts, and stopping to smell every flower we passed. We had drinks, then dinner, then I took him back to my flat. By our fourth meeting, warning signs were flashing. He buzzed my door and asked me to come downstairs for a "surprise." I found myself cycling through two possible scenarios: either this was a winningly romantic gesture like the final scene in Pretty Woman, or he was about to bundle me into a white transit van. When I went downstairs in my slippers, he opened his car door and pulled out a hefty rolled-up bundle – a camp bed. "I've been thinking," he explained, "part of the reason things are going awry between us is because I've been sleeping so badly on your bed." That night, after we'd been intimate, he rolled off and into his camp bed without discussion. The next morning, I knew I had to end things. "As long as you don't change your mind in six months and come running back," he said. "Because by then your ovaries will have dried up and I won't be interested anymore." It was cruel, but it confirmed my instinct that he wasn't right for me. Dating taught me that true strength comes from owning your vulnerability. It's not weakness to have feelings and explore them honestly. The stronger you are, the more you can afford to be vulnerable and still retain your dignity. As Tara Westover writes in her memoir Educated: "To admit uncertainty is to admit to weakness, to powerlessness, and to believe in yourself despite both. It is a frailty, but in this frailty there is a strength: the conviction to live in your own mind, and not in someone else's." Once I started applying that to my own life – being honest about who I was and what I wanted – everything changed. I realized I was fine on my own, empowered by self-knowledge rather than defined by relationship status. And ironically, that's precisely when I met J, who is now my boyfriend.

Chapter 4: Career Setbacks: Redefining Success on Your Own Terms

I once found myself in an isolated farmhouse on Bodmin Moor in Cornwall being fed badger by a stranger. As a journalist, my work has taken me to unexpected places. I've interviewed murderers and fraudsters, cooked with Michelin-starred chefs, and gone undercover as a contestant on a dating show. But the badger incident was among the strangest assignments. I was sent to interview a "roadkill chef" who scoured nearby roads for animals that had been run over, then skinned and cooked them. The man seemed eccentric but harmless. His house was filled with animal skulls, and he showed me his barn where badger and sheep carcasses hung. We drove around looking for fresh roadkill, eventually finding a pheasant which he scooped into a plastic Laura Ashley bag. Back at his house, he prepared a pheasant stew and defrosted a badger casserole he'd made previously. "Taste it," he insisted, and in the name of journalistic integrity, I forked a cube of cooked badger into my mouth. It smelled of damp wool and tasted like a cross between lamb and corned beef. I stayed overnight at his bed and breakfast, in an outbuilding at the bottom of his garden. At one point, he knocked on my door in the middle of the night, standing there with three rolls of toilet paper. "I thought you might need this," he said, peering past my shoulder. I made it through the night dreaming of murderous badgers, skipped breakfast, and got the earliest possible taxi back to civilization. For years I recounted this as an entertaining anecdote. But eventually, it made me question my job and how happy I was. I'd dreamed of being a writer since childhood, and by my mid-twenties had secured a staff position on a national newspaper. But journalism wasn't quite what I'd anticipated. I'd nurtured ambitions of being a political correspondent holding elected representatives accountable. Instead, I was eating badger casserole and putting myself in uncomfortable situations. At the Observer, where I worked for eight years, I became known as the writer who could turn her hand to anything. I'd write about the discovery of Buddha's birthplace one week and the resurgence of female rock stars the next. I covered for the television critic and the high-profile columnist when they were on holiday. But I never got a regular gig of my own, despite repeatedly suggesting ideas. I said yes to everything, including the dreaded Q&As that everyone else avoided – short verbatim interviews that required just as much work as full-length pieces but carried none of the glory. According to research published in the Harvard Business Review in 2018, female employees are far more likely to say yes to thankless office tasks than their male counterparts. They're also 44 percent more likely to be asked. The economics professors who authored the report concluded that taking on "office housework" (non-revenue-generating work) could actually harm career prospects. "This can have serious consequences for women," the report stated. "If they are disproportionately saddled with work that has little visibility or impact, it will take them much longer to advance." My frustration grew as I watched contemporaries on other papers get regular columns and coveted interviewing slots while my salary and position remained static. I began writing novels in my lunch breaks, on train journeys, and at weekends. My third novel, Paradise City, featured a bombastic millionaire businessman named Howard Pink – a hybrid character loosely based on powerful men I'd met. I loved writing Howard because for the duration of each sentence, I could suspend all my internal self-doubt and inject myself with the narcotic high of imagined male confidence. Howard rubbed off on me. At work, whenever approached to take on an assignment I didn't want, I'd ask myself: What Would Howard Do? It became easier to shed those mitigating words and phrases I'd previously littered my emails with – no more "justs," "mights," "would you mind ifs...?" Howard didn't apologize when he didn't need to. Howard never put kisses at the bottom of a work email. I had found a specific way to be more assertive by creating an alter ego who knew himself. Eventually, I realized the only way to be the writer I wanted to be was to create my own opportunities. After eight years at the Observer, I left without a backup plan. It was terrifying but liberating. Within a year, I was accepting freelance commissions, pitching story ideas with fervour, and writing more productively than ever. Working for myself meant seeing direct results in my bank balance with every article filed. I quickly sorted out which jobs I needed to pay rent, which jobs I wanted to do, and which were "prestige" commissions good for my reputation. The experience taught me that when your career feels stagnant, it might be leading you unexpectedly to where you most want to be. What feels like professional failure can become a great opportunity, but often you need time to recognize that and courage to make the leap. As my friend Viv said: "If you want to be Elizabeth Day, novelist, you have to see yourself as Elizabeth Day, novelist. You need to play big." Sometimes, the bravest professional decision is betting on yourself.

Chapter 5: Body Image: Breaking Free from Cultural Expectations

When my boyfriend J and I had been dating a few months, we went for a drink in a hidden London pub. We sat in a corner discussing our days, which led to talking about bodies and insecurities. J outlined his exercise regime and need for control over his physique. I related to that sense of uncertainty over how my body appeared to others, and how difficult it was to get a clear idea of who I really was when internally I felt filled with self-loathing. "Yes," J agreed. "I think it's hard for people like you and me who are, you know, big." "What?" I said icily. "Did you just call me... big?" His eyes widened. "No, no, I meant tall," he insisted, putting his hand over mine. But that tiny three-letter monosyllable occupied an ever-larger space in my mind. I couldn't shake it off. I'm 5ft 11 and a size 10, sometimes a 12 in fitted trousers, sometimes an 8 in different shops. I've been almost exactly the same size all my life, no matter how much exercise I do or how much I eat. I was once scouted as a teenager and had a brief stint as a model at university. In many respects, I'm pretty well balanced. I exercise to feel strong and look toned, not to appear thin. I eat healthily but don't exclude food groups or calorie-count. Yet despite being clear about this intellectually, when it comes to how I truly feel, I always want to be thinner than I am. I have positive phases when I think I look good, and bluer phases when I don't. Not a day goes by when I don't feel a bit guilty for something I have or haven't eaten. According to the 2014 British Social Attitudes Survey, around one in ten women reports being dissatisfied with their appearance. Men were more likely to feel confident, with the gender disparity most marked in the 35-49-year-old cohort. Almost one-third of 18-34-year-olds agreed with the statement "Your value as a person depends on how you look." Centuries of conditioning society to assess women by their looks means we're especially prone to giving ourselves a hard time over appearance. We fear our looks will be judged by those in power and found wanting. Social media has intensified these pressures. Instagram enables us to follow celebrities directly, creating an illusion of intimacy. We begin to feel closer to these famous people, as if for all their wealth and success, they are "just one of us." And if they are "just one of us," it makes a twisted kind of sense to compare ourselves to them. Yet we're comparing ourselves not just to our peer group but to people whose career is constructed at least partially on maintaining and projecting beauty – people with money for personal trainers, plastic surgeons, and vegan chefs. In 2017, I was commissioned to spend a week living as Gwyneth Paltrow. I started with a vegan meal at Cafe Gratitude, where every menu item is named after an inspiring noun. I had an infra-red sauna, a laser facial, and a vagina steam (yes, really). I attended a master-class with Tracy Anderson, the trainer Paltrow credits with giving her "the butt of a 22-year-old stripper." The class was filled with compact, lean women sporting high ponytails and crop-tops. I stood at the back in a saggy T-shirt while Anderson led us through complicated dance routines without explanation. That week taught me that the celebrity lifestyle takes enormous work and is only available to the wealthy with ample time. It was a relief to discover this. It brought home the hopeless stupidity of trying to look like a Hollywood A-lister. Just imagine all the other things I could have been doing with that time. The older I get, the more I realize that youth (particularly female youth) is fetishized and celebrated, while paedophilia is rightly viewed with outright horror. But in mainstream media, there seems a worryingly thin line between admiration of youth and something altogether more problematic. To be comfortable with our bodies, we should honor their realness rather than seeking to exist in a freakish state of cryogenic youth. We should celebrate our bodies for what they can do rather than how they look to others. My late thirties have given me new respect for my body's strength. I'm more interested in that now rather than its relationship to thinness. As Phoebe Waller-Bridge told me: "Women can be so haunted by or hunted by [these things] as they get older... It's the gloom of self-loathing that we're supposed to grow around us as we get older and start fearing that our value is diminishing... I feel like there's a message from society teaching us to hate ourselves. And I always felt like that was a way of controlling us."

Chapter 6: Family Dynamics: Navigating Childhood Roles and Adult Choices

I once appeared at a literary festival in Ireland alongside another novelist. The day before our event, an interview she'd given appeared in a newspaper where she claimed she was "more interested in the panorama of life, and what shapes people, than in small, domestic nuances between husbands and wives." I had just written my second novel, which was almost entirely a sequence of domestic nuances between a husband and a wife whose son had been killed. Well, I thought as I took to the stage, this should be interesting. Families have always fascinated me. It's partly why I ask every celebrity interviewee about their upbringing. Those formative years have lasting influence. As a journalist, I went through a phase where every female starlet I met had an absent father, and many attributed their ambition to a desire to make this unknown figure proud. I think it's easy to feel you've failed at families, even when it's no one's fault; even when everyone is trying their best. I am the youngest sister of two, and as a child was desperate to be as brilliant as my older sibling. I adored her and wanted to be almost exactly like her. But where she was sociable and easy to like, I was solitary and stubborn. She loved younger children; I hated babies. She was good across the board at school; I had distinct pockets of academia I liked and was terrible at anything involving numbers. She was a gifted artist while I just managed to draw a cartoon cat that reappeared on every birthday card for decades. Being the youngest meant I was excluded from certain things. My bedtime was earlier, and my bedroom was directly above the kitchen, so I could hear my family talking and laughing as I tried to fall asleep. I felt I was missing out and let my imagination run wild, writing notes claiming to have been taken prisoner and hiding them under loose floorboards. Once, my father found one detailing how he had kidnapped me and left me in the attic. To his credit, he simply re-folded it and put it back without comment. When I was thirteen, my parents sent me to live in Russia for a month. It was 1992, just after the collapse of the Soviet Union. My sister, who was also learning Russian, went on a two-week exchange with her class, while I stayed for a full month with a retired teacher in Novgorod. Everything was startlingly different from home. There was no hot water in my host's apartment. The streets were nearly empty of cars. There was an omnipresent smell of sewage. At school, there was a black-market exchange in Soviet-era badges. During my second week, I noticed my host Vera had special nighttime "cousins" who visited – always men. I could hear sounds of intimacy through the thin walls. On another occasion, she sat me down and described in detail the contents of my suitcase, revealing she had been inventorying my possessions. Despite these uncomfortable moments, there were many acts of kindness. The thoughtful generosity shown by people who had very little was deeply affecting. I spoke no Russian when I arrived but was fluent by the time I left. For years afterward, I didn't talk much about this experience. It wasn't until recently, when my friend Olivia expressed disbelief at my story, that I realized how challenging it had been. When I asked my parents about it, my mother said the experience gave me self-sufficiency and empathy for how others lived. My father said: "Adventures do by definition involve risk, but not having an adventure means missing out on life, a far greater risk." This experience made me intensely independent but also created a tendency to overwork, to do as much as possible without complaint. My friend Ross calls me "Blitzkrieg Betty" because of my blinkered focus on getting things done regardless of personal cost. In the last two years, I've had bouts of pneumonia that both Ross and my mother attribute to my strange addiction to keeping going until I burn out. Only recently have I understood that, independent-spirited as I am, I didn't have to keep trying quite so hard; that perhaps my parents might occasionally like to help out, to be confided in. It taught me that even in loving families, where everyone acts with the best intentions, the impact can be far-reaching. Family roles we're born into don't have to shape our adult lives – we can choose to be different. And it left me with the belief that the most brilliant, unexpected, insightful stories about who we are and why we act the way we do start with family, in whatever form it exists.

Chapter 7: The Power of Friendship: Finding Your Tribe Through Difficulties

There are few more defining moments in a young girl's life than when her best friend is taken away from her. When I was nine, a new girl named Rachel joined our class. Suddenly, the friendship dynamics were thrown completely out of balance. Rachel was self-composed, quietly confident, and brilliantly clever. She aced every test and could dash off superb drawings. Worse, my best friend Susan was drawn to her as an unmanned canoe is drawn toward Niagara Falls. I looked on helplessly as the two of them started playing together during breaks. They would wander off to gather catkins while I attempted to Have Fun on my own. "We were just looking at your photo," Susan's new friend sniggered one day. "You look... really... pretty." There was an outburst of laughter. Even I knew I didn't look pretty. My eyes prickled with tears as I realized I was the school joke. I didn't fit in and never had. From this formative episode, I learned two things. First, the unforgettable feeling of being left out in a group of three. The knock to my confidence was so great that I wouldn't have a best friend again until university. Second, the realization that friendships can change and evolve. They aren't fixed anchors but plants that need watering and specific conditions to flourish. The challenge is taking friendship personally enough to invest your time and affection, but not so personally that you feel devastated when a friend goes through a different phase. When my marriage imploded years later, it was my friends who rallied around and picked me up. It was a friend who dropped everything to come to the hospital after I'd had a miscarriage. It was Roya who gave me somewhere to stay, refusing to take proper rent. It was Emma who gave me a T-shirt emblazoned with "Rock Solid" because, she explained, "I'm rock solid for your future and I know you're going to be OK." My friends helped me survive. Without them, I honestly don't know where I'd be now. For a long time, I felt I had failed to be a wife and failed to be a mother, and these things spoke badly of me as a person. But my friends made me realize this was nonsense. They preferred me as someone who made mistakes, as long as I was honest about them. "It's more real to fuck up," Emma told me. "You don't have to try to be better than you are, because who you are already is why I love you." Unlike my romantic partners, my closest friends had never once let me down. My friends are the people to whom I never have to explain or make excuses. They accept me for who I am. And if I were to think back and pinpoint one of the most successful and joyous weekend minibreaks of my life, it would not be with a romantic partner but one I had with my friend Clemmie. We met at a wedding in Brooklyn where neither of us knew anyone else, spent the evening talking about everything from the sublime to the ridiculous, and fell deeply, platonically in love against the backdrop of New York in the fall. Why don't we accord our platonic friendships the same importance as our romantic relationships? Until recently, all the greatest love stories in popular culture were played out through conventional man-woman pairings, as if real love could only exist in heteronormative form. That is, thankfully, changing. When Bridesmaids was released in 2011, I was blown away by seeing the first accurate representation of female friendship as I knew it. Similarly, Elena Ferrante's Neapolitan Quartet of novels offered a blistering account of a fifty-year female friendship in all its tortuous complexity. Phoebe Waller-Bridge spoke to me about her best friend, Vicky Jones: "I met somebody who changed my life and gave me a sense of confidence and fearlessness, because I was like, 'If I've got her and I fail, she'll be there with me and she'll laugh it out.'" When I asked if their friendship was like a romantic partnership, she said: "We joke about that with each other: that we're the loves of each other's lives. We're each other's wives and the men in our lives are our mistresses. It really is the most romantic story." Sometimes, even the closest friendships outgrow themselves. People you considered loyal allies drift away, and quite often, you won't know why. In my thirties, this happened to me, causing as much grief as a romantic breakup. I agonized over it, examining past actions to see if I'd done something unforgivable. I tried keeping in touch with gentle emails and texts, but the answers became fewer until they stopped completely. I miss her, but I respect that she has chosen to move on. The best friends are those who accept your failures and imperfections and love you because of them. There's a not-very-good rap song about people dying twice: once when they're buried and once when the last person alive mentions their name. I like this sentiment – that we never fully die while we remain alive in someone's memory. That is what friendship offers: the chance to be truly known, seen, and remembered. It's the longest love affair of my life, and I'm grateful for it every day.

Summary

Throughout this journey into imperfection, we've explored how our greatest failures often become our most profound teachers. From Elizabeth Day's personal heartbreaks and professional setbacks to her struggles with identity and belonging, we've seen how embracing vulnerability transforms our relationship with failure. Rather than viewing our missteps as catastrophes from which we cannot recover, we can reframe them as necessary stepping stones toward authentic growth and deeper self-understanding. The most powerful lesson here is that we don't need to hide our failures or pretend they never happened. Instead, we can own them, learn from them, and use them as fuel for connection and compassion. When we share our struggles openly, we create space for others to do the same, breaking down the isolating walls of perfectionism that separate us from genuine human connection. As Day discovered through her podcast conversations, there's incredible strength in admitting "I don't know" or "I got it wrong." This vulnerability isn't weakness – it's the foundation of resilience. By accepting our limitations and failures with grace, we free ourselves from the exhausting performance of perfectionism and step into a more authentic, connected way of being. The path to success isn't a straight line but a series of detours, each offering its own unique wisdom if we're brave enough to embrace the journey.

About Author

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Elizabeth Day

Elizabeth Day is an English journalist, broadcaster and novelist. She was a feature writer for The Observer from 2007 to 2016 and has written four novels.

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