How to Fail summary

Day’s older sister was so good at driving and marksmanship that she earned the nickname Jane Bond. So, when Day could finally take her own driving test, she was crushed when her small mistake in shifting into gear on a steep hill resulted in a fail.

Ultimately though, the failed test was a benefit in disguise since it allowed Day to approach the second test with more confidence and feeling she had nothing to lose. As a result, she not only aced the test, she also learned that test scores are often arbitrary. With so little separating the two tests, she could see that it was all up to the instructor and what they felt was good enough on any given day.

Between her twenties and early thirties, Day moved directly from a few long-term relationships into a marriage. And despite the strides women had made over the previous few decades, all her relationships could have existed in the 1970s, since she was doing the shopping, cooking and cleaning – all the while holding down a full-time job.

Essentially, Day was failing at her relationships. While she was telling herself that working and doing all the chores made her a strong woman, she now knows that she was really treating the men in her life better than she was treating herself. And during this time, her own sense of self-worth was circling the drain.

It’s difficult for any woman to live in a culture where the impossibly flawless and thin bodies of female celebrities are worshipped non-stop in all media. But Day knows first hand that it’s impossible for anyone with a normal life to look like these celebrities.

This comforting knowledge was gained after she took on a commissioned job with the Sunday Times to spend a week living like Gwyneth Paltrow, whose online Goop empire suggests that you too can be as happy and pretty as she is, with the right hundred-dollar face cream, yoga pants and recipe book.

When Day was in primary school, she had a close friend named Susan. They did everything together, whether it was acting in school plays, going bowling or creating dance routines to their favorite ABBA songs. Susan was not only fun; she was also excellent at math and art – two things Day could never claim as strengths.

But then, one day, Rachel arrived. Rachel was also great at math, art and just about everything else. Soon, Day was only able to look on in despair as Susan started spending more time with Rachel and less time with her.

Day had always imagined having kids of her own. As a teen, she remembers having fun with her sister as they picked out possible baby names. So it’s safe to say that one of the most difficult ordeals in Day’s life has been “failing” at babies, and coping with the fact that she might never be able to get pregnant.

In the “Life Skills” class she took at boarding school, Day and her fellow female classmates learned about birth control and the dangers of sexually transmitted diseases. Yet they never learned about what really goes on in a woman’s body when it comes to fertility.

Along with more women choosing not to have kids, there’s also been a change in the way women are dealing with their anger.

For a long time, whenever a woman displayed anger, it was taken as some sort of character defect on their part. They were treated as irrational, laughable or even dangerous. At one point in history, angry women were even burned at the stake as witches. At another point, an angry woman by the name of Rosa Parks was recast in the history books as being a demure lady who simply refused to give up her seat in a bus to a white man – even though Parks described herself as angry, and rightfully so.

When people hear that a “successful” person is unhappy, often some serious eye-rolling takes place. How can someone with adoring fans or millions of dollars complain about anything? Obviously, they must be completely ungrateful to think they have the right to be unhappy.

However, this response misses out on a major issue. Namely, if people aren’t happy with fame and money, maybe we’re putting too much value on such things?