This piece is part of an occasional series on succeeding as a writer.
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After my third novel came out in 2018, I began to get requests to write “a guide for writers”. Note: not a guide to being a better writer. A guide to “making it” as a writer.
2018 is four + years ago. I have been ignoring those requests for some time. I did so because I thought my path to success—I have a comfortable upper-middle-class life and was able to retire from full-time legal practice in mid-2016—was too idiosyncratic to be useful to anyone else.
Relatedly—given how publishing is crawling with the worst sort of idiotic wokery—I did wonder at the wisdom of advising people to persist with writing. I mean, even Roald Dahl isn’t safe from sensitivity readers these days.
I’m also in a private chat group with other “substackers”. Between them, they persuaded me to change my mind. Writing any sort of guide, however, means acknowledging those career quirks. What I say here may have no direct relevance to my readers’ lives or literary aspirations.
In the background to my observations is this piece by
, The Creative Underclass is Still Raging. The guts of his argument is that a significant amount of online nastiness stems from the experience of artistic failure.I’m talking about people, almost always college-educated, most gainfully employed, who have unrealised dreams in creative industries like movies, novels, journalism, music, essays, TV, podcasts. They have positions in the world that are, by international or historical comparison, quite comfortable. And yet they’re angry all the time, angry because of thwarted ambition and the sense that they were meant for more than comfort. Sometimes these people have actually tried and failed in various creative endeavours—gone to film school, sent their manuscript out to agents, bought an expensive microphone and ring light for their YouTube channel, spent a year begging people to like, share, and subscribe to their podcast.
Freddie deBoer is not making this up. These people exist in large numbers. Some of them may be reading this piece. Many of them no doubt read his piece. I’ve been on the receiving end of their vitriol, made worse in my case because I’m not of the same political colour as most people who aspire to write novels or essays and live on the proceeds.
I also think his argument applies to what is often called “the precariat” but could just as easily be called “the academic underclass”. These people are perennial sessionals or adjuncts or post-docs who will struggle to get proper jobs because the academy is a Ponzi scheme. Universities, by their very nature, are almost doomed to be institutions full of thwarted ambition.
There are false and romantic notions out there of what both literary and academic jobs entail, too. I spent a year as an Oxford tutor, and while it was a nice job to have in the middle of a gorgeous medieval town, it was also bloody hard work if it were to be done properly.
Unfortunately, many people desire that sort of job because they want lie-ins, because they want plushy lives where they don’t have to punch the clock. Few people achieve this. And if they do, there’s often a perverse form of luck involved. My first novel was an enormous bestseller. It opened doors and made it much easier to get more novels published, as well as other, shorter-form writing elsewhere. However, it became a bestseller because it was immensely controversial. I was on the receiving end of a determined—but nonetheless failed—cancellation attempt. This was unpleasant in the extreme. “Perverse luck” captures the situation well.
It also forgets that too many lie-ins and too much booze tend to mean very little writing gets done (and no money to speak of is earned).
Sometimes, you must take your licks. You don’t have a right to be a writer, artist, or member of the commentariat. Literature has always been close to a “winner-takes-all” market, subject to the harshest of mathematical power-laws: ten per cent of those in it make 90 per cent of the money. This may be your lot. It was very nearly mine. I was a whisker away from spending life as a country lawyer who drafted unusually lucid pleadings and advices (because that’s where a flair for turning phrases goes to work among the legal fraternity).

Mention of my day job—a day job I no longer need to do, because writing worked out for me—leads me to echo another bit from deBoer. He points out that “a big part of my advice is to have a day job. People really, really don’t want to hear that; they want to write, as a profession, and have it support their lifestyle, which is eminently understandable. But it’s just really hard, especially when you’re starting out.”
Like all standard book contracts, that for my first novel included an “option” clause, which gives a publisher right of first refusal on one’s next book. Because the first one had done so well, there was considerable pressure on me to produce a followup. And in time, it became clear I was “writing to a contract”.
One afternoon, it occurred to me that I was going to have to dispose of roughly 40,000 words of second novel that were, not to put too fine a point on it, shite. I taped up my notes, printouts and research in a box and left it on the footpath for the council to take away on one of its hard waste collection days. I can’t even remember the plot.
This left me in loose end territory. I still had a decent amount of money in the bank, but not enough to retire. At that moment, I had to accept it was time to pull my finger out and get a job.
Back when I finished high school, I’d originally started a dual qualification in liberal arts and law, a common Australian practice, expressed thusly: “I’m studying arts/law”. This lengthens a standard law course to five or six years, but at no point pretends the people who pursue classics or literature or history at the same time as learning how to draft a commercial lease or incorporate a company will get work as classicists or novelists or historians. The rationale—given at the time such dual degrees were introduced—was to ensure members of an important profession were not “dreadful boors” (a jab directed their way by none other than D. H. Lawrence) at social functions.
I’d abandoned law because it looked like I’d be a full-time writer, in retrospect a deeply naïve assessment. I discovered everyone from HMRC on down expects you to produce a bestseller every three years or so, something my 40K words of second novel rot made clear I wasn’t going to do. I faffed about for a few years, living off royalties and doing various eccentric jobs — from archaeologist living in a donga to interpreter at the Home Office — but in the end, responsible adulthood was necessary. I faced up to law school, paid a thirty-buck fine at the admissions office for being so dilatory (eight years after completing my arts degree), and was instantly recognised.
“What took you so long?” said the woman at the enrolments desk.
If you’ve had novels successfully published, or you even have the ability to write a novel (I’m going to assume everyone reading this can write), you are per se a member of the upper-middle-classes regardless of background. You can enter any of the professions with a modicum of effort. That means—if writing isn’t working, even if you’ve been successful as a writer in the past—you need to get a useful job of work.
At this point, a lot of writers go down the grants path rather than seeking employment—that is, they apply to Arts Council England or the Literature Board of the Australia Council or whatever—and write on the proceeds. If you’re left-leaning, this can work, but it loads pressure onto you in the same way an option clause loaded pressure on me. There’s also a sense in which you’ve been bought and paid for: if your leftism is at all unusual, or you’re white and male, you’ll struggle, including to get any sort of grant.
Would you sleep with someone for a million quid? Maybe you would, maybe you wouldn’t. But if you would, don’t pretend you’ll come out unchanged once it’s over.
Public conservatives seldom get arts grants, and if they’re at all intellectually consistent, they shouldn’t even apply. Get a job, fellow righties. It’s likely to make you a better writer.
Also, life is not fair and writing is hard work.
To be continued.
DeBoer is absolutely right about the bitterness.
But life is full of disappointments.
Heraclitus said: “Out of every one-hundred men, ten shouldn’t even be there, eighty are just targets, nine are the real fighters, and we are lucky to have them, for they make the battle. Ah, but the one, one is a warrior and he will bring the others back.”
We all think that we are that warrior.
As we get older, we realize that only occasionally do most of rise to the level of fighter.
Mostly, we pass our lives as targets.
Happiness consists of trying our best, living good (moral) lives, and enjoying what we have.
The bitterness comes from not accepting that we aren't the warrior, that we aren't lucky (in this endeavor), or that we didn't work hard enough.
I don't think I've ever known a writer, whether personally or not, who had anything like a conventional or normal path to success. The one common element seems to be the willingness to work hard. Writing is extremely difficult work, after all. Writers who make it tend to be writers who write, and publish, a lot - the ones who spend a decade working on their special novel without ever finishing it tend to go nowhere.
Related to this, the day job - or better yet, a series of them - isn't just economic fallback. It provides human experience, essential to good writing.
One thing I really appreciated here was your discussion of your readiness to deposit half a novel's worth of prose in the circular filing cabinet. Assuming 2000 words a day, five days a week, that's a month's work, if you're an extremely fast writer. Having the willingness to critically assess all of that work, find it wanting, and discard it, is crucial - a writer must also be their own most critical editor, which means regarding their own work with a certain ruthless detachment from the emotional investment they'll inevitably have with it (to say nothing of the inherent reluctance to go back to square one after putting in so much time walking down the wrong path).