How to Fail, and Failosophy: A Handbook for When Things Go Wrong

Elizabeth Day is an award-winning novelist and journalist. She graduated from Cambridge University in the U.K. with a double first-class degree in History, and worked as a feature writer for the British national newspaper the Observer from 2007 to 2016. Her writing has appeared regularly in a number of other newspapers and magazines. To date, she has written four novels, two of which have won notable literary awards. It's a glittering résumé.

In 2018, she launched a podcast called "How to Fail with Elizabeth Day." In it, she interviews a range of highly successful people, and encourages them to talk about their most notable failures. Ironically, it's been a huge success. Both books we're discussing in this podcast are based on the insights Day has gained from talking to successful people about failing.

But why would someone so outstandingly successful host a podcast and write books about failure? And why should the rest of us take any notice?

The point is that, for much of her life, Day has not regarded herself as a success. Her sense of who she really is has been submerged by a desire to be judged a success. But she can't bring herself to believe that she is a success. And this has led her to emphasize failure as a key element in her life.

It's only by finding new, positive ways of approaching failure that she's been able to understand what true success actually is. And, how important it is to connect with others, and share those insights.

So who are "How to Fail" and "Failosophy" for? Well, they're for pretty much anyone who fears failure but wants to change that. If you tend to give up when something doesn't work out, or you don't even start because you don't want to fail, these books can help.

Day writes from a feminist perspective. Both books contain thought-provoking ideas on the female experience of failure, in particular. And, while they aren't aimed solely at a female audience, many of the issues Day addresses will resonate more strongly with women than with men.

That said, Day champions the idea that we can all develop and grow from our failures. Failure becomes an opportunity to reflect, improve, or find new directions.

It's not a new idea. But Day has been highly successful in bringing her personal experiences to bear on this issue. That personalization has certainly struck a chord with many listeners and readers.

So, keep listening to hear more about what failure is, the Seven Principles of Failure, and why it's sometimes OK to be angry at the world.

"How to Fail" and "Failosophy" take very similar source material – the interviews from Day's popular podcast – but they use it in very different ways.

"How to Fail" interweaves material from the interviews with a series of reminiscences about Day's own failures, culled from every stage of her life so far. It's a kind of educational memoir.

The titles of its 13 chapters all begin with the words "How to Fail at… " followed by a particular topic. These include the ones you might expect, such as "Dating," "Relationships" and "Fitting In." But there are some more surprising ones, such as "Being Gwyneth Paltrow," and "Anger."

How, you might ask, does a person fail at anger? You might feel you've failed by being angry. Losing your temper when you shouldn't, for example. But failing at being angry? That's more intriguing.

Day says it's good to express your anger, particularly if you're a woman. Women tend to suppress expressions of anger, to avoid being seen as aggressive, or strident. That's not healthy. Instead, Day suggests, occasionally showing you're angry is not only liberating, it's essential. Suppressing it is by far the greater and more damaging failure.

And failing at being Gwyneth Paltrow? Well, that's OK too. This chapter is about how women, in particular, are so frequently made to feel bad about their bodies. Far better to come to terms with what you actually are, and stop beating yourself up for not being the "ideal."

One of the most pervasive themes in "How to Fail" is how we act out an idealized version of ourselves. This is especially true of people who have low self-esteem, and actively seek validation. This can lead them into a range of potentially destructive behaviors. For Day, this included seeking approval from others by overworking.

In the chapter "How to Fail at Work," she tells us how she failed to say no often enough. In her eight years at the Observer newspaper, she undertook every work assignment with complete commitment, and then volunteered for more. She never turned anything down, for fear of being thought unreliable or lazy, regardless of her workload.

This is the kind of fear that makes you want to please everyone, and it leads many people to exhaustion and career burnout.

In the end, her determination to be the model employee got her nowhere. The first time she asked for a concession in return, she was turned down. This led her to reflect on how unequal the relationship between employer and employee can be.

She identifies the same excessive willingness to please as the root of her relationship problems too. Her 20s passed with a series of long-term boyfriends. In each case, she subordinated her sense of self to the needs of her partner. None of these relationships worked out.

Reflecting on the reasons for these failures, the author takes positives from her experiences. She was trying to be a version of herself that wasn't authentic. This realization has helped her move on, finally, to a relationship in which she can really be herself.

There's a strong element of the confessional in "How to Fail." Although Day frequently refers to interviews from her podcast, the stories from her own life are the most striking. And her courage in sharing them can't be denied.

"Failosophy," by contrast, aims to be a much more practical guide. Its subtitle is "A Handbook for When Things Go Wrong." Both its approach and its structure are quite different from that of "How to Fail."

"Failosophy" seeks to analyze the nature of failure, and offers a program of ways to deal with it.

The book falls into five parts. The Introduction sets out the terms of the book and outlines Day's attitude to failure. In short, she says, it makes us human. Failure doesn't have to be demoralizing. Nor should it isolate us, or make us turn inward. Indeed, one of the most consistent themes of both books is the need to connect with others, and to share our experiences.

The book goes on to discuss what failure really means. Day defines it as what happens when something doesn't go according to plan. However, she immediately qualifies this by questioning the value of planning. Should we invest so much in our plans for the future? Might we not all fail more profitably, and less hurtfully, if we didn't have so many preconceived ideas of what we ought to be in five or 10 years? We'll come back to this in a minute.

Day acknowledges that sometimes we fail because of circumstances beyond our control. For example, her infertility is a recurring theme. So is her battle not to blame herself for it.

The main substance of "Failosophy" is what Day calls "The Seven Failure Principles." These are a thematic analysis of failure, and how to address it. Each principle is titled with a statement, beginning with "Failure just is," and ending with "Being open about your vulnerabilities is the ultimate act of strength."

These principles make up a manifesto for resilience in the face of failure. Day suggests that the reader can dip in and out of the sections in the manner of a handbook. But she hasn't written "Failosophy" quite like that. There are no handy summaries or subsections under each principle. You really need to read the whole thing. Or at least, read each principle in full, when you think you might need to.

The principles will seem familiar to readers with experience of positive psychology. For example, the second principle is "You are not your worst thoughts." It addresses our tendency to succumb to negative thinking and self-criticism. In the same way, "Failure is data acquisition" underlines the importance of making every failure a learning experience.

Perhaps the most interesting of the seven principles are the last two. "There is no such thing as a future you" casts a skeptical eye over the need for a detailed life plan. You may have a clear idea of where you want to be in your life and career in five years' time. Job interviewers often ask you about it. Such apparent self-knowledge can make you seem organized, and in control.

But what if things don't quite pan out as you'd hoped or intended? Are you not setting yourself up for another self-perceived failure?

Day believes so. She doesn't say you should live your life chaotically, with no thought for the future. But she does believe that none of us have such a thing as a fully realized future self. And such a self is certainly not something that we should try to live up to, all the time.

The final principle, "Being open about your vulnerabilities is the ultimate act of strength," is one of the overarching themes of Day's writing. It's also one of the things people find hardest to do. We're conditioned to see vulnerability as a weakness. Day skillfully turns this idea on its head.

In her view, sharing vulnerability is a way of forging connections between people. It allows them to be completely themselves with one another. By doing so, they can draw strength from the moment of sharing.

And sharing is the crucial thing, because Day sees herself and others as fundamentally connected. And anything that builds that sense of emotional community must be a good thing.

So what do we make of "How to Fail" and "Failosophy"? Well, both books contain a wealth of good advice from highly successful people. The fact that they are highly successful stimulates the reader's curiosity. For instance, the section of "Failosophy" where podcast interviewees list their selected personal failures makes for compulsive reading.

Both books are very moving too, especially where Day describes her experience of infertility, or her best friend's recovery from a stroke. And they're provocative, like when Day expresses anger at a world where the political and social agenda continues to be dominated by men.

But these books are also very funny. This needs to be emphasized. Two books about failure could so easily be grim reading. But Day's talent for self-deprecation means there are some real laugh-out-loud moments. And the general tone is always upbeat, even at its most reflective.

Are there any downsides to these books?

Well, by any measure, Elizabeth Day is a highly successful person. She's an acclaimed novelist, journalist and podcaster. A genuine media phenomenon.

So her focus on the value of failure may seem perverse. She has a top-rated degree from one of the finest universities in the world. And yet she glosses over this and other achievements – successes that most of us can only dream of. Instead, she shares with us the pain and anxiety she felt on failing her driver's test at the first attempt.

She has a list of contacts that would be the envy of any A-list celebrity. She also has many close friends whom she clearly treasures. Yet, as an example of failure, she chooses to highlight the episode when a childhood friend transferred her affection to another girl.

Something about that doesn't quite ring true. Highly successful people may well find it easy to talk about their failures. After all, those missteps haven't had a lasting negative effect on their lives. That isn't the story either the books or the podcast want to tell.

Quite the opposite. The podcast guests were invited to interview precisely because they have the resilience and positive outlook necessary to learn the lessons failure brings and become hugely successful.

Not everyone does. Many people keep failing, because they don't quite have the talent, the drive, or the opportunity to turn things around. Or the carefully cultivated networks. It's hard to see what these two books have to offer them, apart from the injunction not to give up.

"How to Fail" and "Failosophy," by Elizabeth Day, are published by 4th Estate, an imprint of HarperCollins.

That's the end of this episode of Mind Tools Book Insights, from Emerald Works. Thanks for listening.