Books about men who are their own worst enemy are a specific pleasure, and a slightly uncomfortable one. Not villains. Not tragic heroes brought down by fate or weather or the state. Just men standing next to a perfectly good life, explaining at length why they can't possibly have it, and then doing the one thing guaranteed to make sure they don't.
The trick, and most novels get it wrong, is that the self-sabotage has to be reasoned. It can't read as stupidity. He has to have an argument, and the argument has to be almost convincing — dignity, or principle, or standards, or a version of himself he refuses to let go of. The reader should be able to follow the logic right up to the point where it walks off the cliff.
Ten books. Four are funny. Four cost something. Two might just about get out of the way in time.
The funny ones, which are also the cruellest
Lucky Jim — Kingsley Amis
Jim Dixon is a junior lecturer in medieval history at a provincial university, and he has exactly one professional objective: keep the job. Everything he does for three hundred pages makes keeping the job less likely. He lies, badly. He drinks at the worst possible moment. He pulls faces at the back of the head of the professor who controls his future.
What makes it more than farce is that Jim is right about everything and it saves him from nothing. The department is a racket. Professor Welch's musical weekends are insufferable. His own lecture on Merrie England is genuine rubbish that he is required to pretend is scholarship. Amis lets him be correct and self-destructive at the same time, which is the actual condition — the men who wreck their own lives are very rarely the ones who misread the room.
Seventy-odd years on, the burned bedspread sequence is still the funniest set piece in English comic fiction. Read it for that. Stay for the sensation of watching a man argue himself out of a career one small, satisfying act of spite at a time.
Starter for Ten — David Nicholls
Brian Jackson arrives at university in 1985 with a head full of facts, a working-class Essex background he is quietly ashamed of, and a plan to become the sort of person who belongs there. He gets onto the University Challenge team. He falls for Alice Harbinger. He then spends the entire novel lying about books he hasn't read, music he doesn't like, and a father he can't talk about.
Nicholls is unusually precise about the mechanism here. Brian's problem is not that he is out of his depth — he isn't, he's cleverer than most of them — it's that he has decided in advance that the real version of himself is unacceptable, so every opportunity gets handed to a person who doesn't exist. Meanwhile Rebecca, who likes him as he actually is, stands about three feet to the left of the plot being ignored.
It is very funny and it hurts in a specific place. Anyone who has ever performed a self at a party will recognise the wince.
High Fidelity — Nick Hornby
Rob Fleming owns a failing record shop, ranks his life in top fives, and has just been left by Laura. His response is to go back through his all-time top five break-ups and interview the women involved, in order to establish, definitively, that none of it was his fault.
The novel's great move is to let Rob narrate. He is charming, he is funny about music, he is extremely good company — and the entire time, the reader can see the thing he cannot. Every relationship ended the same way, for the same reason, and the reason is standing in the shop arranging singles by chronology. Hornby never once steps in to tell you this. He just lets Rob keep talking.
Still the best novel ever written about mistaking taste for a personality. Which is, it turns out, a full-time job that pays nothing.
A Confederacy of Dunces — John Kennedy Toole
Ignatius J. Reilly is thirty, enormous, medievalist by self-appointment, and lives with his mother in New Orleans. He believes the modern world lacks theology and geometry. He judges every human being he meets against Boethius. He is forced, finally, to get a job, and each job he takes is destroyed within days by his own conviction that he is the only correct person alive.
This is the extreme end of the category — self-sabotage as a complete worldview rather than a habit. Ignatius doesn't fail because he's unlucky. He fails because succeeding would require him to accept that someone else might be right about something, and he would genuinely rather be destitute. The valve, the notebooks, the hot dog cart, Levy Pants: every disaster is downstream of a principle he refuses to drop.
It is one of the funniest books in American fiction and one of the most exasperating, and that's the same fact stated twice.
The ones where it costs something
The Twin Flame Game — Adam Eccles
Keith Myatt is a shareholder in his family's global hotel empire, employed under the invented title of comfort quality inspector, which is his brother Rory's polite way of keeping him moving and out of the business. He lives in suites. He keeps one phone for work and another for women. He is very funny about all of it, which is the first clue that something's wrong.
Then a woman in London tells him, quite matter-of-factly, that he is not her twin flame — and Keith goes and reads about the whole subculture, the belief that one soul gets split into two bodies and destiny does the rest. His conclusion is not what if that were true. His conclusion is this is exploitable. He starts mining forums and social profiles for favourite songs and books, then engineering coincidences, manufacturing fate to order. His first attempt goes catastrophically, and deservedly, wrong.
What makes Keith belong on this list rather than a list of charming rogues is that he knows. He is entirely aware that he has money, access, freedom and nothing else, and his response to that awareness is to build a more sophisticated method of not being known by anybody. The comedy is genuine and the lad-lit swagger is real, but underneath it Eccles is writing about a man whose defences are so good they've become the problem. When the book finally takes something away from him, it lands, because he built the conditions himself.
The Remains of the Day — Kazuo Ishiguro
Stevens, butler at Darlington Hall, takes a motoring trip across the West Country in 1956 and narrates his own professional life along the way: the dinners, the standards, the question of what constitutes a great butler. He is not aware that he is telling you anything else. He absolutely is.
This is the quietest and most devastating book here. Stevens never does a single dramatic thing wrong. He simply chooses dignity over every human opportunity presented to him, one at a time, over decades, and defends each choice so thoroughly that by the time the bill arrives he cannot even name what he's paying for. Miss Kenton stands in the corridor. Stevens stays professional. That's the whole disaster, repeated until it's permanent.
Ishiguro's control is absurd — the prose is so composed that you feel the loss through the gaps in it rather than the words. The self-sabotage novel raised to something close to perfect.
Revolutionary Road — Richard Yates
Frank and April Wheeler live in suburban Connecticut in the 1950s and consider themselves superior to it. They have a plan to move to Paris, where April will work and Frank will finally find out what he was meant to be doing. The plan is real. It is affordable. It is, for a while, actually happening.
Frank Wheeler is the most frightening man on this list because his self-sabotage is dressed as maturity. Every time the escape gets close he finds a sensible-sounding reason to stall, and every reason is really the same reason: as long as Paris stays in the future, he never has to discover that there is nothing exceptional underneath the talk. Being a man of unrealised promise is a comfortable job. Yates writes the interior justifications with a coldness that borders on cruelty.
Not a fun read. A true one. If you have ever talked yourself out of the thing you said you wanted, this book knows exactly how you did it.
Espedair Street — Iain Banks
Daniel Weir was the songwriter behind Frozen Gold, one of the biggest rock bands of the seventies. He is now living in a converted church in Glasgow under a false name, enormous and unrecognisable, drinking in a pub where nobody has any idea who he is, telling you how he got here.
Banks does two things brilliantly. First, he makes the rise genuinely thrilling — the band, the songs, the ludicrous scale of it, rendered by someone who clearly loves music rather than the idea of music. Second, he makes Danny's hiding entirely comprehensible. This is not a man brought low by the industry. This is a man who decided he was the problem, filed himself away, and has been maintaining the filing system ever since with real diligence.
Banks outside science fiction is an underrated proposition, and this is the best argument for it. Funny, Scottish, enormous-hearted, and unsentimental about the cost of deciding you don't deserve the life you built.
The ones who might still get out of the way
Cold Heart October — Adam Eccles
In June 1994, a nineteen-year-old Mick Grady stepped in for a cancelled support act at Whelan's in Dublin and opened his mouth, and the room changed. Not metaphorically. Grady's voice does something to people that nobody has ever been able to explain — euphoria, release, the sort of thing a Rolling Stone writer went away and called a spiritual experience. His band, Cold Heart October, accidentally rewrote a decade of Irish rock on the strength of it.
Thirty years on he is nearly fifty and living in his late mother's cottage in a village in County Clare, doing nothing. He has not written anything worth keeping since Donal Lynch — his best friend, the band's songwriter — died in 2012, and he holds himself responsible. His marriage ended once it became clear it had always been about the voice rather than the man. His manager keeps arriving with comeback plans and keeps being refused. The gift is still there. He simply won't use it, and he has a decade of well-rehearsed reasons why not.
What makes this belong here rather than on a grief list is the shape of Mick's refusal. Nothing is stopping him. The village would have him, the band would have him, the world plainly would. Grief has calcified into something more like a policy, and the arrival of Siofra Wilde — a Belfast paranormal investigator with a YouTube channel and a career crisis of her own, who wants to document the voice as a genuine unexplained phenomenon — works precisely because she has no interest whatsoever in respecting the policy.
Eccles keeps exactly one impossible thing in the book and makes everything else brutally ordinary: the pub, the rain, the manager, the men who won't say the difficult sentence. It is a novel about an Irishman who has spent ten years being extremely busy doing nothing, and about how much of that he chose.
Nobody's Fool — Richard Russo
Donald "Sully" Sullivan is sixty, works construction he shouldn't with a knee that won't hold, rents a room from his old schoolteacher, and has spent his entire adult life in North Bath, a dying town in upstate New York, declining to become a person anyone could depend on. His son turns up. So does the son's son. Sully responds the way he responds to everything, which is to keep things light and keep moving.
Russo's gift is patience. Over six hundred pages of bar talk, small feuds, a stolen snowblower and a running war with a man named Carl, he assembles a complete portrait of a man whose charm has been load-bearing for forty years and is now starting to crack. Sully isn't tortured. He's just permanently, cheerfully unavailable, and Russo lets you see exactly what that has cost the people who kept waiting for him anyway.
The warmest book on this list, and the only one where you get the real sense of a man noticing, late and reluctantly, that the thing he's been avoiding might have been worth having. Comic, humane, and quietly enormous.
Why this list exists
The reason these novels work — and the reason there are so many of them — is that self-sabotage is the only kind of disaster the reader is guaranteed to have first-hand experience of. Very few of us have been betrayed by a hotel-empire brother or hunted through a dying mill town. All of us have talked ourselves out of something.
What separates the ten here from the hundreds that fail is that none of them treats the man as an idiot. Jim Dixon is right about the department. Stevens is right about standards. Mick Grady is right that the voice took more from him than it gave. The novel's job is to hold that up, agree with it, and then show you the cost anyway.
That's the difficult bit. Anyone can write a man making a bad decision. Writing one making a defensible decision, over and over, until there's nothing left to defend — that takes some doing.
FAQ
What is the best novel about a man who is his own worst enemy?
For the comic version, Lucky Jim by Kingsley Amis is still the template seventy years on. For the version that actually costs a life, The Remains of the Day. For the one where the damage is a decade of silence in a cottage in County Clare, Cold Heart October by Adam Eccles.
Are these depressing?
Four of them are extremely funny and two of those are cruel about it. Starter for Ten and A Confederacy of Dunces are comedies first. The Twin Flame Game by Adam Eccles is a comedy that quietly stops being one. Revolutionary Road is the one to skip if you want to stay cheerful.
What is the difference between a flawed protagonist and a man who is his own worst enemy?
A flawed protagonist hurts other people. A man who is his own worst enemy builds the trap, tests it, and then steps into it while explaining to you why it was the only reasonable option. The novels here are about self-inflicted damage specifically — the good thing that was sitting right there, and what he did instead.
Which one should I give to a man who would never buy this sort of book for himself?
High Fidelity, because it is disguised as a book about records. Nobody's Fool if he likes a small town and a bad knee. Espedair Street if he has ever owned a guitar he no longer plays.
Is there one where the self-sabotage is entirely internal?
The Soul Bank by Adam Eccles. Andy Clarke spends one forgettable night in a business hotel and comes home with a tune he cannot place and dreams he would rather be having than his actual life. Nobody does anything to him. He simply starts preferring the inside of his own head, and lets everything real drift out of reach while he does it.