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How to Fail

10 min

Everything I've Ever Learned From Things Going Wrong

Introduction

Narrator: At three years old, a little girl watches her older sister suffer from chickenpox. Wanting to help, she decides to fetch a hot-water bottle. She finds one shaped like a bear, fills it with cold water from the tap, and struggles to screw the cap on tightly. Rushing back to her sister’s room, she presents her offering, only for the cold water to leak all over her sister’s pyjamas, making her cry even more. That feeling—a deep, searing shame for a well-intentioned act gone wrong—was author Elizabeth Day's first memory of failure. It’s a feeling we all know, a moment where our efforts fall short and leave us feeling exposed.

In her book, How to Fail: Everything I've Ever Learned From Things Going Wrong, Elizabeth Day argues that these moments are not aberrations to be hidden away, but the most formative and instructive experiences of our lives. The book is a profound exploration of how our setbacks, from minor childhood mishaps to life-altering crises, are the very things that teach us, shape us, and ultimately lead us toward a more authentic and resilient self.

Failure is a Matter of Perception

Key Insight 1

Narrator: At its core, the book challenges the very definition of failure. Day posits that failure is not an objective event but a subjective interpretation. What one person considers a catastrophic loss, another might see as a valuable lesson or even a success. The label of "failure" is entirely dependent on the story we choose to tell ourselves about it.

Day illustrates this with a story from the author Sebastian Faulks. When asked about his failures, Faulks humorously listed things like losing the final of an over-40s doubles tennis match or having a soufflé rise slightly less than desired. But he also mentioned a time his book was shortlisted for a prestigious prize but didn't win. From one perspective, this was a failure. Yet, Faulks reframed it. The shortlisting led to him being celebrated in a foreign country, an experience he considered a profound success. This shift in perspective is crucial. It suggests that success and failure are not opposites, but two sides of the same coin, and we have the power to decide which side we focus on.

The Pressure to Conform Breeds Inauthenticity

Key Insight 2

Narrator: From a young age, we are conditioned to succeed according to external metrics. Whether it's fitting in socially or excelling academically, we learn to build our identity on a foundation of outside approval. Day argues this is a precarious way to live. Her own childhood, spent as an English girl in Northern Ireland during the Troubles, was a masterclass in failing to fit in. This experience led her to develop people-pleasing tendencies as a coping mechanism, a habit of suppressing her true self to gain acceptance.

This pattern continued into her academic life. Having always succeeded in school, Day built her self-worth on getting good grades. This created a sense of entitlement, a belief that hard work and intelligence would always guarantee success. The illusion shattered when she took her driving test. Despite her confidence and preparation, she made a small error on a hill start and failed instantly. The failure was devastating, not because of the test itself, but because it attacked the core of her identity. It revealed an arrogance she didn't know she had and taught her a vital lesson: life doesn't grade on a curve, and no amount of privilege or effort can protect you from its random, often humbling, setbacks.

Romantic Endings Are Not Personal Failures

Key Insight 3

Narrator: Nowhere is the feeling of failure more acute than in our relationships. A breakup or divorce is often seen as a public declaration of personal inadequacy. Day pushes back against this narrative, suggesting that we must redefine what a "successful" relationship looks like.

After her own marriage ended, Day was forced to confront this societal script. She realized that for years, she had suppressed her own needs to be a "good" wife, losing her sense of self in the process. The end of the marriage felt like a colossal failure. However, with time and reflection, she began to see it differently. She quotes a line from Andrew Sean Greer's novel Less: "Twenty years of joy and support and friendship, that’s a success... Is the sun a failure because it’s going to end in a billion years? No, it’s the fucking sun." This perspective reframes a relationship's value not by its longevity, but by the love, growth, and joy it contained. The end of a relationship doesn't erase its success; it simply marks the conclusion of a chapter.

Professional Setbacks Pave the Way for True Vocation

Key Insight 4

Narrator: In the professional world, the fear of failure can be paralyzing. It can lead us to play it safe, to say "yes" to every task for fear of being seen as difficult, and to never ask for what we're worth. For years, Day followed this path as a journalist at The Observer. She became the go-to person for thankless assignments, never carved out a specialty, and never asked for a raise. Her career stagnated because she was too afraid to fail by saying "no."

The turning point came when she finally decided to bet on herself. She left her stable job to pursue a freelance career and focus on writing novels. It was a terrifying leap, but it was born from the realization that her current path was a slow-motion failure. The book is filled with similar stories, from actors like Jessie Burton and David Nicholls who "failed" at acting only to become bestselling novelists, to broadcaster Mishal Husain, whose rejection from the BBC led her to a different job where she gained the exact experience she needed to be hired by the BBC two years later. These stories reveal a powerful truth: sometimes, the job you get fired from, the career path that closes, or the risk you take is the necessary catalyst to push you toward the work you were truly meant to do.

Anger is a Catalyst, Not a Character Flaw

Key Insight 5

Narrator: Society, Day argues, is particularly uncomfortable with female anger. Women are often socialized to suppress anger, transmuting it into more "acceptable" emotions like sadness or anxiety. But this suppression is toxic. Unacknowledged anger doesn't disappear; it festers.

Day shares a deeply personal story of a painful breakup with a younger man who, after nearly two years, admitted he wasn't ready for the commitment she desired. Her initial reaction was profound sadness. But as she processed the grief, another emotion emerged: anger. She was angry at him for his lack of honesty and angry at herself for ignoring the red flags. Acknowledging this anger was transformative. It wasn't a destructive force but a clarifying one. It was a signal that a boundary had been crossed and that her own needs had been devalued. This righteous anger became the fuel for her to move forward, not with bitterness, but with a stronger sense of self-worth and a refusal to ever let herself be that powerless again.

True Success is an Inside Job

Key Insight 6

Narrator: If failure is an internal state of mind, then so is success. The book's final and most profound lesson is that external markers of achievement—fame, awards, wealth—do not guarantee happiness. In fact, they can often lead to a unique kind of failure: the failure to feel fulfilled despite having "made it."

Day shares the story of actress Nicole Kidman, who, on the night she won her Oscar, sat alone in her hotel room feeling completely empty. At the peak of her professional life, she realized what she truly wanted was a loving partner and a family. Similarly, actor Simon Pegg found himself miserable and depressed in Hollywood, surrounded by the fame and fortune he had always dreamed of. Both eventually found happiness not by chasing more accolades, but by cultivating their inner lives and personal relationships. True success, the book concludes, is not about what you achieve, but about how you feel. It is an inside job, measured by a quiet, internal sense of peace and contentment that no external validation can provide.

Conclusion

Narrator: The single most important takeaway from How to Fail is that failure is not an indictment of our worth, but an essential part of our humanity. It is the raw data of a life being lived to its fullest, providing the lessons we could never learn from success alone. By embracing vulnerability and sharing our stories of things going wrong, we find our deepest connections to others and to ourselves.

Elizabeth Day’s work offers more than just comfort; it offers a radical re-evaluation of what it means to live a good life. It challenges us to look back at our own histories of failure—the rejections, the heartbreaks, the missteps—and to see them not as sources of shame, but as moments of profound learning and strength. The book leaves us with an empowering question: What if your greatest failures are actually your most valuable assets?

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