How Not To Be A Boy by Robert Webb

At the moment I’m writing a novel. The protagonist is a teenage boy. His name is Anthony and he’s dealing with a lot of things in his life, one of which is the underlying current of societal expectations of masculinity. This isn’t exactly a huge theme in the book, but I think it’s probably an important part of any boy’s upbringing, so I want to get it right. I decided therefore to read some things about what it’s like to grow up male.

I am not, and nor have I ever been, male. However I have always empathised with expectations of masculinity. I’ve been the breadwinner in every household I’ve lived in since a young age, and I’ve been surrounded by people and situations that made showing any kind of emotion discouraged. Growing up, I felt pressured to swallow whatever I might have been feeling and essentially ‘man up and get on with it.’ Despite not knowing what it’s like to be a boy, therefore, I have perhaps an above-average level of empathy for the challenges brought on by society’s expectations of masculinity.

Enter Webb’s autobiography.

I was vaguely aware of Robert Webb before reading this book, but I didn’t really know anything about him, and I hadn’t come across any of his work. I knew Peep Show was a thing, but for most of my life I haven’t owned a television so I’d never seen it. These days I binge-watch panel shows on YouTube with reasonable regularity, but he hasn’t appeared on a lot of the ones I’ve seen. All I knew about him was that he’s a comedian from a popular show.

By the time I hit page 167, I was head over heels for Webb’s brutal honesty about himself:

I’ll finish the essay, I think. I’ll show them… I’m fascinated by the idea of what a hero I’m going to be.

I do nothing.

Without a doubt my favourite thing throughout the book is how Webb manages to be hilariously self-deprecating yet sympathetic towards his younger self. He is searingly honest about his own thoughts and beliefs, even when being so doesn’t paint him in the best light. We are all assholes at times, as I mentioned in yesterday’s post, and one of the most important elements of an autobiography is honesty.

There are several points in the book where Webb converses with his younger self. There are also extracts from his teenage diaries (I do like a good teen journal extract), interspersed with his thoughts when looking back. The balance of tenderness and amusement he shows towards himself as a teenager is frankly beautiful. I nearly cried. Here is a person who knows when to rib someone for being a bit of a twat, and when to quietly tell them that it’s OK, they’ll get through this.

He talks about things he’s not ‘supposed’ to like as a teenage boy – the poetry of Wordsworth; the beauty of nature; after his mother dies, the way “people keep squeezing my hand and I like it.” It’s the little details like this that help to make this book such an important read.

Webb also doesn’t shy away from playing with the reader. Occasionally he addresses us directly, like when he suggests a game in which the reader should take a drink every time they notice a man using anger to conceal another less ‘masculine’ emotion.

He has a real way with words, too. Not only in that the story is well told, but also in his turn of phrase. The book was a joy to read. Often autobiographies are good in terms of storyline but not particularly well written. Not the case here. Also, he coins the word ‘encardiganned’ (to mean ‘wearing a cardigan’, like ‘bespectacled’), which I love.

How Not To Be A Boy also deals with the f-word. No, not that. Well, that too. But I’m talking about feminism. And as it turns out, Webb has a very similar view to my own about people who call themselves feminists:

A young man may call himself a feminist, but to do so is hardly a test of character. It isn’t even a test of feminism. He’ll find out how firmly he believes that women have minds of their own when one of them breaks his heart.

And when it comes to the way many of us feel we need to act like bolshy overconfident people in order to get ahead at work:

We’re not talking about women trying to be men. We’re talking about women and men trying to be arseholes. Because that’s what you think you’re supposed to be like at work.

It’s not just about masculinity, though. It’s also about moving from a working-class northern town to Cambridge university and beyond. I was particularly interested in this bit, as someone who’s made a similar move. It feels so weird to be plucked out of your background – even if you’re the one doing the plucking – and plunked into a place where people just don’t get it. You bring your own expectations to the table, of course, and they bring theirs. We all see things through our own glasses. (I originally typoed that as ‘We all see things through our own classes’, which would also work.)

And there are some notes on the popular opinion that ‘someone else has it worse than me, so I shouldn’t complain’:

Yes, of course there is always someone worse off than you. But imagine you’re in a doctor’s surgery with a broken arm. The person next to you has two broken arms… the point is that you have a broken arm and it hurts.

I like the physical-for-mental metaphor in general when talking about subjects like these, but I thought this put it particularly cleverly. No one would dream of telling someone who has a broken arm not to bother getting it fixed because there’s someone else with two of them. Sure, they might have to wait a little longer than the person who’s just been crushed in a car wreck. But they still can (and should) expect to be able to access the help they need to get it fixed.

Honestly, I could go on about this book all day. Other books could be written about it.

But I won’t. I’ll just conclude by saying that Robert Webb in his autobiography demonstrates all the qualities of the best possible kind of man, ironically largely because he demonstrates some bad ones too.


  1. Scar, your page got a makeover ( or am I crazy?) I like it!
    I have so many feelings about this post. We are similar, aren’t we? I have simultaneously a girly-girl and the man of the house lol. I am ambitious and direct and not sentimental and have been bringing home the most bacon since I was 15 haha! This book you are writing, how is it going so far?

    Liked by 1 person

    1. It got a teeny makeover yes, I added featured images so they’d show up at the top of each post 🙂

      We definitely seem to be similar! I’m a girly-girl in some ways (mainly involving wine, bubble baths, nail polish and chick flicks) and the man of the house in most other ways. Lots of people seem to find this impossible to understand.

      The novel’s going quite well, early stages at the moment but the whole thing’s planned which is the first hurdle! Chapter one is done, just another 47 to go!

      Liked by 1 person

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