Olivia: We're told to 'fail fast, fail often.' But what if our deepest fear isn't failing, but succeeding at the wrong things? What if the real failure is getting everything you ever wanted? Jackson: Whoa, that’s a heavy opener. It flips the whole Silicon Valley mantra on its head. The goal is supposed to be learning from failure to eventually win, not realizing the win itself was the mistake. Olivia: Exactly. And that's the provocative heart of How to Fail by Elizabeth Day. It's this brilliant blend of memoir and manifesto that flips our whole script on what it means to mess up. Jackson: And it's so authentic because it came from her own life hitting a wall, right? I read that she started the podcast that led to this book after a painful divorce and other setbacks, feeling like she'd failed at her own life plan. It’s not theoretical. Olivia: Absolutely. She argues that this misunderstanding of failure starts incredibly young. She shares her very first memory of it, and it’s a perfect example of how we learn to equate good intentions with a perfect outcome, and anything less is a catastrophe.

Jackson: I’m curious, what could a three-year-old possibly fail at that would stick with them for life? Olivia: It's called the "Hot-Water Bottle Incident." Picture this: Elizabeth is three, and her older sister is sick with chickenpox, miserable and crying in bed. Her sister asks for a hot-water bottle. Little Elizabeth, wanting to be the hero, decides she'll do it herself. Jackson: Oh, I can already see where this is going. A three-year-old and hot water is a recipe for disaster. Olivia: Well, almost. She’s smart enough to know not to use the kettle. She goes to the bathroom, finds a bottle shaped like a bear, and tries to fill it from the bathtub tap. But she doesn't know you have to wait for the water to heat up, so she fills it with cold water. Then, she struggles to screw the cap on tightly. Jackson: Okay, so it’s a lukewarm, leaky bear. Not ideal, but not a total disaster. Olivia: But to her sick sister, it was. She rushes into the room, so proud, and presents the bottle. But it leaks cold water all over her sister's pyjamas, making her even more cold, miserable, and causing her to cry even harder. And in that moment, Day says she felt this profound, crushing sense of shame. Her good intentions meant nothing. She had failed. Jackson: Oh, that's just devastating for a little kid! You want to help so badly, and you just make everything worse. It’s that feeling of total helplessness. Olivia: Exactly. And that feeling becomes the blueprint for how we view failure for the rest of our lives: as a personal indictment. But Day’s whole argument is that this is wrong. She quotes the author Sebastian Faulks, who she interviewed for her podcast. He playfully listed his "failures" as things like losing the over-40s tennis doubles final or having a soufflé not rise perfectly. Jackson: That sounds a bit like a humblebrag. "Oh no, my soufflé was merely excellent, not transcendent." Olivia: Right, but his point was that failure is entirely subjective. What he considered a failure—being shortlisted for a prize but not winning—was also a huge success, because he was being celebrated for his work in a foreign country. It’s all about perspective. Day’s core message is that failure isn't the opposite of success; it's a component of it. It’s a teacher. As she writes, "failure has taught me lessons I would never otherwise have understood." Jackson: That makes sense. We're so focused on the binary of pass/fail that we miss the lesson in the attempt. It’s like the civil rights lawyer she mentions, Jim, who was dismayed that young lawyers wouldn't take on cases they weren't guaranteed to win. They were terrified of the public failure. Olivia: And in being terrified, they failed to do what was morally right. They failed to learn, to grow, to push boundaries. That fear of failure is what actually holds us back, not the failure itself.

Jackson: That idea of childhood shame is so powerful. It makes me think of that other failure she talks about, which feels even more universal: the failure to fit in. Olivia: Oh, it's one of the most poignant parts of the book. She moves from England to Northern Ireland during the Troubles. Her English accent immediately marks her as an outsider, an "other." Her family tries to assimilate in these almost comically absurd ways, like taking up Irish dancing and raising sheep. But nothing works. Jackson: It’s that desperate feeling of wanting to belong, but every attempt just highlights how different you are. Olivia: And it gets so much worse when she goes to secondary school in Belfast. She’s a bit nerdy, her clothes are wrong, and her accent is a constant target. This culminates in what she calls "The School Photograph Incident." Jackson: I’m almost afraid to ask. Olivia: It’s as brutal as it sounds. School picture day. She feels awkward and self-conscious. Later, she sees Siobhan, the most popular girl in her year, laughing with her friends while looking at the photos. Siobhan holds up Elizabeth’s picture and says sarcastically, "God, you look so pretty." And in that moment, Day has this devastating realization: "I was the school joke." Jackson: Wow. That’s a core memory you don't just shake off. It’s the kind of thing that can define your entire adolescence. Olivia: It did. And it led to what she calls an "internal dislocation." She developed two personalities: a "home" self and a "school" self. At school, she suppressed her real interests and became a people-pleaser, desperate for acceptance. She was performing an identity, not living one. Jackson: It's like creating an avatar for school versus your real self at home. Today, it's our social media profile versus our messy reality. But does Day see this as a permanent weakness? Olivia: Not at all. This is the beautiful turn in her thinking. While that coping mechanism caused her a lot of heartache, the experience of being an outsider also forged her greatest strengths: empathy, independence, and a keen observational eye. It's what made her a great writer. She cites people like Clint Eastwood, whose itinerant childhood made him feel lonely but also fiercely independent. Jackson: So the failure to fit in is what gives you the tools to build your own world, on your own terms. Olivia: Precisely. And she has this beautiful full-circle moment. Years later, as a successful novelist, she returns to Northern Ireland for a book festival. She’s terrified they’ll still see her as the weird English girl. But instead, she gets this incredibly warm reception. And she writes, "After all those years, 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." Jackson: That gives me chills. It’s like the failure was the long, painful path back to a sense of belonging she couldn't have achieved any other way.

Olivia: And that idea of forging your own path, even if it feels like a failure to others, leads to the book's most counter-intuitive point: failing at success. Jackson: This is the one I’m most skeptical about. It’s easy to romanticize failure when you’ve ultimately succeeded. What does "failing at success" even mean? Olivia: It means achieving the external markers of success—the job, the relationship, the award—but feeling empty inside because it’s not aligned with who you truly are. Day’s own story is a perfect example. She landed a prestigious staff job at the Observer newspaper, a dream for any young journalist. Jackson: Sounds like success to me. Olivia: Externally, yes. But internally, her people-pleasing tendencies took over. She said yes to every thankless assignment, especially the Q&A interviews nobody else wanted. She became the go-to person for the grunt work. After eight years, she looked up and realized her career hadn't progressed. She was stuck, underpaid, and unfulfilled. Jackson: So she was succeeding at being a "good employee" but failing at being a fulfilled writer. Olivia: Exactly. So she took a huge risk. She quit her stable job to go freelance and focus on writing novels. To many, leaving a staff job at a top paper would look like a career failure. But for her, it was the first step toward authentic success. Jackson: Okay, but leaving a job to become a bestselling novelist doesn't sound like a failure. What about people who achieve massive, undeniable success and still feel empty? Olivia: That’s the deeper layer of it. And she uses these incredible high-profile examples. She talks about Nicole Kidman, who, on the night she won the Best Actress Oscar for The Hours—the absolute pinnacle of her profession—went back to her hotel room and felt completely, utterly alone. She realized the award meant nothing without a life to share it with. That moment of "success" was what made her realize she needed to redefine her life around personal happiness, not just professional achievement. Jackson: Wow. So the ultimate prize just highlighted what was missing. Olivia: And it’s the same with her interview with Robert Pattinson. At the height of his Twilight fame, he was one of the most famous people on the planet, but he was riddled with anxiety and had to create these elaborate, paranoid schemes just to leave his house. He told her, "If the control of your life has been taken away from you, that’s when you go a little crazy." He was a massive success, but he was failing at having a life. Jackson: It’s a powerful reminder that the metrics we use for success—fame, money, awards—are often completely disconnected from our actual well-being. Olivia: That’s the whole point. True success is internal. It's about self-worth, connection, and living a life that feels true to you, not one that looks good on paper.

Olivia: So when you put it all together, the book tells a kind of three-act story about our relationship with failure. First, we misunderstand it in childhood, seeing it as a final, shameful verdict. Jackson: Right, the hot-water bottle. Olivia: Then, in adolescence and early adulthood, we do everything we can to avoid it. We perform, we people-please, we try to fit into a mold that isn’t ours, and we lose ourselves in the process. Jackson: The school photograph. The thankless job. Olivia: And finally, even if we manage to achieve what society calls "success," we often find it’s a hollow victory if it’s not built on a foundation of our own values. We can fail at success itself. Jackson: It seems the real success Day is talking about is the courage to be honest with yourself about what's not working. The book is really a permission slip to stop performing, to stop chasing someone else's definition of a good life. Olivia: It absolutely is. It’s about accepting that things go wrong, that life is messy, and that our cracks are what make us interesting, and ultimately, what make us strong. Jackson: It makes you wonder, what's one 'failure' in your life that actually taught you something vital? Something you wouldn't trade, even though it was painful at the time. Olivia: That’s a powerful question. And we'd love to hear your stories. Share them with us on our social channels. It’s clear from the incredible reception to Day's work that these conversations are what help us all feel less alone in our struggles. Jackson: Because if there's one thing this book teaches us, it's that failure is one of the most universal, and human, experiences we have. Olivia: This is Aibrary, signing off.