I’m fond of a certain type of usually-humour writing which I catagorise as ‘gimmick non-fiction’, or maybe a little more generously, ‘quest memoirs’ — where someone, usually a young(ish) man, sets out on some oddball undertaking often involving physical discomfort, some travel, and/or embarrassment and other social difficulties, and often for a period of a year.
The undisputed master of this type of thing (he calls them ‘boy projects’, or at least his ex-girlfriend does) in my world is Danny Wallace, who has so far started a cult (a nice cult) in Join Me, said yes to everything for a year (Yes Man, the book on which the Jim Carrey movie was based) and tracked down old schoolfriends (in person, not Facebook) to see what they’re up to now (Friends Like These). He’s very funny, charming and has a nice touch with the occasionally sweet — the end of Yes Man for example is a beautiful moment plus a narrative touch worthy of fiction.
In fact, young male UK writers seem to have a bit of a stranglehold on this genre. There’s Danny’s mate, stand-up comedian Dave Gorman, who has gone on a Googlewhack Adventure in which he tracked down people who had created googlewhacks to see how they felt about it. Before that, he asked a bunch of people Are You Dave Gorman? in an effort to find over 50 people with the same name as him. Tony Hawkes, once the man responsible for inflicting Stutter Rap on us, has hitchhiked Round Ireland with a Fridge (now being made into a movie), taken on a bet about natural talent vs practice by Playing the Moldovans at Tennis, and attempted to become more than a One Hit Wonderland by getting another Top Ten hit, among other adventures. And I’m just about to read Word Watching in which Alex Horne attempts to force those sticklers at the OED to accept one of his made-up words into the dictionary.
Over in the US, my favourite practitioner is AJ Jacobs, though he dignifies his efforts with the phrase ‘participatory journalism’, which is probably fair; his efforts are perhaps less outright funny (though still very funny in that self-deprecating way) than the UK boy projects, but deeper. He’s read the Encyclopedia from A to Z in The Know-It-All in an effort to arrest his declining intelligence, taken things a little too literally in My Year of Living Biblically and has just released a collection of essays detailing his various experiments to improve his lifestyle, relationships and work life, My Life as An Experiment or My Experimental Life (the title on the version I’m reading and enjoying greatly right now).
Kyle MacDonald, meanwhile, used One Red Paperclip to trade up to a house. It tries a little too hard to be funny and has some painful self-help cliches in an effort to inject depth, but it’s a fun and feel-good read. Going up a level or two or three in seriousness, we have David Denby’s Great Books in which he returns to his old alma mater to re-take the core courses which examine the great books of Western civilisation and record his own experiences with them while seeing how the younger students handle them. This is quite an old book now, but I still remember the King Lear chapter.
Up here at the serious end is also where you finally find a few women engaging on quests. My favourite is Barbara Ehrenreich, whose ‘boy project’ Nickel and Dimed, involving her working different sorts of minimum wage jobs for a year, is actually a piece of weighty investigative journalism and exposes the daily struggle to make the rent and feed yourself and maintain dignity when it comes to these types of jobs. In Bait and Switch, she looks at the effects of redundancy on middle-class Americans, but despite taking part in the job hunt process to see what it’s like for them (depressing), it’s not as immersive as actually living a minimal wage life (and she still got to go home to her nice house even then). Another woman undertaking a quest was Norah Vincent in Self-Made Man, in which she lived as a man in various situations to try to capture something of what men are like when women aren’t around. I found it an interesting read but quite superficial.
It’s a booming genre: there’s hundreds of other examples. Do you have any favourites?

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