Long Read: Insightful Reflections on a Law Career – Why Many Lawyers Aspire to Be Writers?

Christopher Jackson looks back on his long and chequered experience of the law career and lawyers and gives some advice about the profession

I remember everything about the occasion. The little meeting room at Stevens and Bolton LLP, the excellent provincial law firm in Guildford where I had trained for two years. I remember the kindly faces of the HR manager, Julie Bowden, and the partner in charge of trainees Beverley Whittaker. I remember being asked if I would like to take on a seat in the family department at the firm.

This was, to put it mildly, generous of them, since I hadn’t been a particularly good trainee. One reason was that I was just out of university and found it hard then, in ways I wouldn’t now, to relate to the problems clients faced: the need to structure a business, or transact a probate, or litigate a minute point of commercial law. It was hard then, with life just getting going, and owning no businesses and having little money myself, to detect the relevance of it all to my own life.

But really there was a deeper reason for my misgivings about the law. It was the wish to be a writer. To be young is sometimes not to accept the absurdity of our dreams, and I had decided I wouldn’t let go of mine, just yet. But still as I went into that meeting I hadn’t decided for sure what I would say. Mightn’t it be better, if offered a role, to continue to write in the evenings alongside a well-paid job?

At Finito, we often encounter these sorts of crossroads where one’s wishes and commercial reality vie with one another for the upper hand.

I think one often forgets when one looks back that one’s path wasn’t certain – it only seems so retrospectively. In my case, I remember being put the question about whether I’d like to join the firm, and I looked out of the window, vaguely hoping the answer might lie there. I wanted a prompt.

This almost never works: the answer is more reliably found within than without, a fact which tends to be a bane for the indecisive.

But that doesn’t mean we shouldn’t pay attention to the external world: though it won’t absolve us of responsibility, it’s always giving us hints, if only because its very existence is a constant challenge to our need to live in it.

On this occasion, there were some schoolchildren crossing the River Wey towards the Odeon, on their way to the Friary shopping centre. Had I not looked out the window at that point, I might well have not had a sudden sense of what it had meant to be a child, and what it had meant to dream of the life you want for yourself. Children, I have come to learn from having my own, are visionaries compared to adults: they see time stretching ahead and expect to succeed.

But time has an annoying way of narrowing. John Updike, a writer I would come to admire in my late twenties, called reality ‘a running impoverishment of possibility’. One always vaguely knows this, of course; what is surprising is how quickly crucial choices have to be made when life really gets going after school or university.

So it was that I found myself saying I would leave the law firm. It followed directly on from this that I had no plan whatsoever about what to do next.

At such points, the world, which had hitherto seemed to hold two options like a sort of everlastingly balanced paradox, alters forever: one way closes, and the reality of the way chosen crystallises. The road I had decided against had contained: 9-5 hours (or longer); likely financial security, though as shareholders in Credit Suisse know that’s never a certainty; the possibility of being a partner in a good firm, like my father and grandfather before me; and the camaraderie of the law, which I have since seen and sometimes envied.

But the legal profession had also seemed to me too staid, too predictable – a too-safe choice for someone who longed to do other things and who only had one life in which to do them.

And the way chosen? It was then unknown, but over time it would mean the writing and publishing of books (a great reward in itself but not exactly the most lucrative of professions); reams of journalism; financial uncertainty; the unexpected need to become entrepreneurial; the chance to meet people from every walk of life; and the feeling, as I write this at the age of 43, that I made the right decision for me.

Nevertheless, I’ve never stopped being interested in the law. And my professional career has involved encounters with the profession to an extent I wouldn’t have predicted back in Guildford all those years ago.

*

Due to the nature of my own story, I’ve often thought about the relationship between law and literature, a topic which I feel is fascinating in itself, and would merit a book one day, if someone – perhaps me – could find the time and inclination to write it.

It is an untold story about the relationship between two professions, both antagonistic and fruitful, which stretches back millennia.

In order to tell it, you’d have at your fingertips an impressive cast list. Your opening chapter might discuss Cicero, but would also have to delve into the fact that Virgil’s father had wanted him to be a lawyer, but that Virgil turned to philosophy finding the law uncongenial to his temperament. For every lawyer-writer who has found themselves able to incorporate into their writing, there is someone who found that impossible and sought escape.

Fast-forwarding into the Middle Ages, Geoffrey Chaucer studied law at the Inner Temple; for him, coming from an upwardly mobile family, it was an aspect of being a courtier, as it can sometimes be today if you happen to end up somewhere in the unsung Government Legal Department. Dante Alighieri, the author of the greatest poem of all The Divine Comedy, was both a lawyer, and had much to say about law – consigning members of the profession variously to Hell, Purgatory, and Paradise.

This hypothetical work would then have a chapter devoted to William Shakespeare, and try to decide to what extent one might co-opt him to the profession. For many, there is a lot of linguistic evidence within the plays that Shakespeare may have studied law at one time: it was Mark Twain who observed that nothing comes to Shakespeare’s mind so readily as the law, so much so that he decided he was actually the Lord Chancellor Francis Bacon.

Conversely, the cry issued by a minor character in Henry VI Part III – ‘Kill all the lawyers!’ – has sometimes been taken as a possible indication of Shakespeare’s low view of the profession, perhaps arrived at after acquaintance with its drudgery. As always with Shakespeare, we know so little about him that the desire to speculate is irresistible.

And as you go through the centuries, the law keeps cropping up as a profession of writers: in the 19th century and early 20th century, Gustave Flaubert and Henry James. By the 20th century, you have John Mortimer. Today lesser known but fascinating writers like The Secret Barrister, Christopher Wakling, Douglas Stewart and Martin Edwards have all done time – sometimes a lot of it – in the legal profession.

There is also a sort of watershed moment for the species of lawyer-turned-writer around the middle of the 21st century. Before the invention of television when literature was the primary form of entertainment, a writer was more likely to leave the law and establish an income as an author – as Charles Dickens, who would also get a chapter in my book, did.

Dickens had worked as an articled clerk, and if anyone wants to know how interesting he found that, they should read David Copperfield, paying particular attention to the character of Uriah Heep. What he seems to have loathed about the law was its pace, so at odds with the frenetic pace of Dickens himself. But it also put him in an ideal position to write that great satire Bleak House: he could laugh at the slow progress of Jarndyce v Jarndyce because he’d seen such things first hand.

Dickens, of course, established a readership in a world when people read books voraciously. That’s not the case today, to put it mildly, making the dream of ‘being a writer’ somewhat heartbreaking, and commercially mad.

*

So what do lawyers-turned-writers think today about the overlap between the two?

For Christopher Wakling, author of six acclaimed novels including On Cape Three Points, Undertow and Towards the Sun, and who worked as a litigator before turning his hand to writing, the relationship between the professions should come as no surprise. “Law is about morality, conflict, evidence, persuasion, point-of-view and precise use of words, all of which applies to story-telling, too … it’s always seemed unsurprising to me that many lawyers also write fiction,” he says.

Meanwhile, Douglas Stewart, author of superb novels such as Dead Fix and Hard Place, specialised in employment law, and founded the immensely successful Stewarts Law, which still bears his name. In his view, it’s important to make a distinction about the sort of linguistic skills required for the law. “To become a lawyer, one of the first prerequisites is having made the most of a good education with particular emphasis on English Language but, in my view, less on English Literature,” he says.

But for Stewart, it’s not so much this immersion in language as the immersion in human nature which the law requires, which can be of such benefit to writers. He continues: “In their daily lives, lawyers (and particularly litigators like myself) have seen the best and worst of humanity. We have the advantage of being able to ask questions and assess the honesty and integrity of answers. Even those who do other legal work such as probate may (rarely) encounter fraud and forged Wills. Dealing with a cross-section of the community also gives an insight into the lives of the rich and famous through to those who are in need of Legal Aid.”

Stewart also cites other benefits to remaining in the law when it comes to wanting to write. “For me, having the financial security of a job as a solicitor also enabled me to devote time to writing. Very few writers starting out are able to survive on their income from book sales.”

Stewart adds a third reason to juggle law and writing: “Another advantage of being a lawyer is the benefit of travel to broaden horizons,” he explains. “That was certainly true in my case because I have now visited and/or worked in some 80 countries. The benefit of seeing other countries and meeting different nationalities, whether lawyers or not, has been of great advantage to me.”

All this amounts to a reasonably good refutation of my decision to leave the law, and almost makes me begin to wonder whether I made a mistake. I remember when I sheepishly told a friend of the family that I wanted to write when I was in my early twenties, and he replied somewhat brusquely: “Yes, but to do that you need to have some life experiences.”

My answer then is the same as my answer at the time: what about Jane Austen? Austen, of course, isn’t someone anyone but a fool would compare themselves to. But even so she’s something of a trailblazer in the idea that life experience is one thing you don’t need when it comes to writing book. What you need is an ability with language and plot and an insight into human nature.

However, it’s also clear that Stewart has received great benefit from the law. And he isn’t finished yet, telling me: “Finally, and this is particularly so in the case of John Mortimer QC, involvement daily in the High Court and in particular the criminal courts, is a constant source of amusing anecdotes and high drama. Mortimer used it so effectively – bringing out absurdity, pomposity, wit and cunning. I could talk for hours about my own experiences in court up to and including now where I sit as what in England would be called an Employment Judge. Most of my books have not actually involved the daily grind of the law, although my early novels did although all involved litigation.”

It is all enough to make one question whether there really are that many frustrated writer-lawyers out there. Christopher Wakling is unsure, saying: “I did work with other lawyers who had literary ambitions, yes. So do lots of other types, though: at Curtis Brown Creative I’ve taught many teachers, journalists, doctors, advertisers, analysts, as well as a fair few lawyers.”

Stewart agrees, adding: “I quite doubt that there are lots of frustrated writers practising law. I cannot give a precise percentage but at a guess, I would think that at least 70 per cent of solicitors never go to court and spend much of their day poring over law books and drafting complex documents. It would drive me mad but they seem to get job satisfaction.

That large percentage of solicitors probably does not get much opportunity to consider writing as inspired by their work in the law – because so much of it would be boring to a layman. It takes a different type of legal brain to sit everyday dealing with arid conveyancing deeds or drafting Articles of Association – as opposed to living on your wits and using imagination, essential  in litigation – these latter being qualities which will assist fiction writers.”

Even so the brilliant crime writer Martin Edwards, whose books have won multiple awards, has this to say: “I have met many lawyers who told me they intend to write a book once they retire. I doubt many of them have done so. The key ingredient that may sometimes be missing is a strong creative imagination. Personally I think creative imagination is a great asset for a lawyer but I don’t think it’s essential and in fact I think it is lacking in some perfectly good lawyers.”

It’s this which I think comes near the matter: the idea that somehow, if you go down the route which isn’t your dream, there won’t be time at the end of it all to make it right.

I remember writing a story once about someone who has been in the law their whole life: on the day the person is about to leave the firm and retire, he overhears someone saying something disobliging about him in the corridor. This chance overhearing leads to a complete panic attack about the choices he has made, and a terrible sense of having wasted the whole of life. My suspicion when I left the law – and it still holds today – is that that potential feeling of waste is worse than any financial or status uncertainty which might be triggered by ‘following your dream’.

*

Even so, according to Stewart and Wakling, I may have acquired a slightly exaggerated sense of the idea of there being numerous frustrated lawyers out there.

If I ask myself why I might have arrived at this possible fallacy, then I arrive at the figure of my grandfather Neville Jackson (1923-2013) who practised law after the war. A family member might be deemed the opposite of a workable data set: the important figures in our lives loom in outsized fashion, and their example can make us draw a range of generalisations about the world which may be true as to that specific person but insufficiently true about everybody else. In that sense they give a vivid example and a limited clarity, while at the same time distorting our sense of the world.

In this magazine we have a regular feature called ‘Relatively Speaking’ which touches on the perennial question of how the jobs our relatives do impact on the careers we ourselves attempt. If I were writing my own column of this, I would write about my grandfather and my father Gordon Jackson (1952-), who was also a lawyer for many years, ending up as managing partner of Taylor Wessing.

Neville died in 2013, and as I approach the tenth anniversary of his death, I find myself thinking of him more and more: he remains a daily reference point against the world. He was, in fact, a very successful lawyer serving as President of the Westminster Law Society, as well as acting as one of the first film lawyers representing Universal Studios. Through this client, he was able to meet some names of astonishing fame, including Charlie Chaplin, Peter Ustinov, and David Niven.

These people didn’t especially impress him, anymore I suspect than some of my generation would be impressed by representing a boy band. His favourite by far was Marlon Brando, who in my grandfather’s telling couldn’t have been nicer; Niven and Alec Guinness he once had to tell to shut up after he caught them arguing outside his office. Ustinov, meanwhile, ‘thought a bit highly of himself’ – something which, for my grandfather’s generation, was very bad form.

At the same time, my grandfather also became a leading expert in planning law. In those days you didn’t have to specialise so much as you do today, which made the profession more attractive for a certain kind of mind than it would be today.

His attitude to it all engendered in me mixed views about the law. In one sense, my grandfather could be Eeyoreish about it, as he was prone to being pessimistic about many things: humorous disavowal of his own achievements was an undeniable streak of his character. Well into eighties he would opine about alternate lives he might have lived given better luck. He would imagine his would-be life as a farmer, or racing car driver, historian or Latin professor – just about anything besides the successful career he had actually had.

In actual fact, I suspect he had loved his career. “He was certainly much more a lawyer than a farmer,” laughs my father today. “The thing you have to remember about that generation is that, he would have almost certainly done Classics at university, had it not been for the Second World War, so there was that sense of a road not travelled for all those people who had fought and won the Second World War.”

This in turn makes me recall a copy of Horace’s Odes which was handed down to me after my grandfather’s death: it sits on my shelf now like a set of intentions he never quite got around to. It’s an interesting point to note when we see the widespread discussions in Westminster today surrounding apprenticeships and skills that it has already been tried on my grandfather’s generation.

And tried, it must be said, with some success. They rebuilt the country, and expertly ‘got on with it’. For the post-War generation, the theatre of battle had been their university and I remember my grandfather being pretty unsentimental about it. Naturally bookish in any case, he never had any trouble educating himself.

In those days, the interview process was extremely literary, reminding me that law and literature were bound up then in ways which would be gradually ousted in the second half of the 20th century. My grandfather once told me there were only two questions: “Do you like English poetry?” When my grandfather replied: “Yes”, the second question was: “And do you like this modern stuff?”, presumably referencing things ike TS Eliot’s Wasteland. When he shook his head adamantly, replying “Oh no!” he was offered the job.

It is an image of how rapidly the world has changed and how in those days, it would have been far easier than today to juggle the career of a writer with a daytime job as a lawyer. My grandfather was articled, my father now tells me, to one Sir Samuel Gluckstein, who had a successful career as a lawyer, and an unsuccessful career as a politician, failing three times to win a parliamentary seat in the interwar years. Perhaps it was Sir Samuel who came up with those questions all those years ago.

Of course, the case was different for that generation. In those days, there was real money to be made in writing, and so there wasn’t quite the same necessity today’s writers experience of needing a ‘day job’ or a ‘paying gig’ alongside what they really want to do. Today’s generation of writers has it harder both ways: there is limited market for books, and the jobs you need to do to earn a living while you write them have also become more specialised and therefore more consuming.

In post-war London, the life of a lawyer has an undeniably leisurely feel. The day would begin, or so he told me, in post-war Piccadilly, with the opening of one’s physical post – without the constant demands of emails whizzing back and forth. One imagines offices of relatively uncluttered desks – and uncluttered minds.

Lunchtimes would be spent patrolling the streets of Piccadilly, pursuing his other great love: Persian carpets. The afternoon might involve a client meeting, then a sedate train journey home. No doubt there was work to be done, but how quiet and untroubled it seems compared to what it is today.

For my father Gordon Jackson’s generation, the Reaganisation of the law had come along, and the profession was no longer the sedate gentleman’s sport it had once seemed to be. It was the era of Wall Street, of Gordon Gecko and big deals – all of which seemed to suit my father, whose energy continues today in his seventies, now diverted away from the law towards his great passion for the Surrey Hills.

While being a talented photographer, he was able to practice the law without constantly imagining himself in other careers. He rose to be managing partner at Taylor Wessing not once but twice, moving offices as his last hurrah before disappearing into a life animated by passion for a locality he had seen too little of while commuting into London and back for the previous decades.

There was an element of Walter Mitty in my grandfather’s makeup – a tendency to wonder aloud about other lives, and insodoing to create little moments of escapism for himself. But it was all along an inconstant vein of fantasy which could make him imagine other lives but this streak was never stubborn enough to nudge him into a creative career. I remember his second son Andrew, also a lawyer, when he was dying of cancer in 2008, saying of my grandfather: “Well, he was a born lawyer, actually.”

*

The same could not be said of me, in whom its practice caused resentment. I sometimes imagine that the law gets an unusually bad press in English literature partly because it is written by people trying to escape it.

Yet leaving the law didn’t mean that I got to escape it: in fact it only altered the way in which I enacted with it. Having completed my journalism studies it looks inevitable in hindsight that I turned out to be especially suited to legal journalism, starting out at one of the directory companies which publishes among other industry publications, the Legal 500, which I joined in 2011.

The job was often very dull – but I found I could do it quickly and ably, and still have time leftover for the writing of books. Open at my desk would always be the Legal 500 document I was working on – a summary of the solicitors working in family law or tax law or for the US Supreme Court – and a book of poems, which I would tinker at all day long, headphones in, surreptitiously determined on things other than the job I was ostensibly there to do.

That book of poems, which would eventually be called The Gallery, would be published by the University of Salzburg in 2013, about three months before my grandfather’s death. I remember, though he was emaciated and very sick, that when I showed it to him in the hospital, he did a very good look of wild surmise, eyebrows raised with delight. I always think how that book arrived just in time.

But what I didn’t know is that many of the people I was writing about in the directory chapters would turn out to be people I’d get to know, become friendly with, and learn from as my career proceeded to the deputy editorship of Spear’s magazine, and beyond.

The private client beat in London turned out to contain a marvellous cast of characters, quite distinct in glamour from the sort of people, much as I liked them all, who I had seen at work in Stevens and Bolton.

Private client always seems to me, because of its personal nature to attract delightfully wacky individuals. Having got to know the people who work in tax and trusts law, art, divorce and reputation, I can see what a desirable life it is, if you happen to be constructed that way.

Here we find the always sumptuously dressed Baroness Fiona Shackleton, sweeping into the boardroom, in a blaze of colour, but always giving kindly attention to me as a young person and almost certainly the least important person in her day, though you could tell from her energy that every day was equally busy. Then there was Mark Stephens CBE, who’d always greet you with a ‘Hello, mate’ and always hint at a zone of confidential knowledge which was his and his alone which he was quite unable to share while seeming also to share something of the thrill of it all: a sort of legal Willy Wonka.

With Mark, possible disclosures seemed to whizz by:  the identity of Banksy, what Rolf Harris had really been like, what it meant to consider litigating the Pope. He’d fascinate you, then leave you standing outside the gates of confidentiality, wondering what he really knew. All this seemed desirable to me in a way that provincial law had never done. In short, I began to be interested in the law at a point when I had moved too far away from it realistically to return.

True, it wasn’t always enviable. Family law, in particular, perhaps because of the deeply contentious nature of cases, seems to give rise to rivalry which often spills over to animosity. It was a world dominated by the Queen Bees – Fiona, Helen Ward, Sandra Davis, Diana Parker, Frances Hughes – all of whom I grew to like personally, but then became aware that they were often at loggerheads, and in some cases, mortal enemies.

The men involved – the charming Stephen Foster, the wise and kindly Michael Gouriet – seemed to be sitting to one side, watching all this gladiatorial combat rather wryly, ultra-smart men bemused to have landed somehow in a woman’s world.

And the money was undeniably attractive. There were the lunches (‘Would it not be criminal if we didn’t begin with a glass of something rather good?’ as one partner put it to me once); there was the tennis with Stephen Foster at the O2 when, having written an entire book about Roger Federer, I finally got to see him play (and win) thanks to Stephen’s exceptional kindness and thoughtfulness; and the general sense that this, and not literature, was the good life. I could never after all the experiences I had quite concur with ‘Kill all the lawyers’ and never any longer imagine Shakespeare had ever agreed with it himself.

The Legal 500 was also international, meaning I would travel to Japan and Israel, meeting lawyers who had built astonishing lives overseas: young people mulling a legal career should know that it’s hard to think of a career which has such readily available international opportunities as the law.

My favourite beat was the US trial lawyers and US Supreme Court. It was the French philosopher Jean-Jacques Rousseau who stated in his Confessions that if someone were to peer into the heart of man, he would want to travel down in life and not up: Rousseau was peddling the idea that the successful are necessarily hard-hearted.  He was wrong about that just as, so far as I can tell, he was wrong about more or less everything.

Certainly, that US beat taught me that the opposite is frequently the case. People do well in life because they’re kind and polite, and therefore people want to work with them – and promote them. I noticed when interviewing the very top lawyers, those who’d argued 40 cases before the Supreme Court, or risen to become name partners of New York or San Francisco firms, and find them delightful. In my experience, it was the person who was toiling as a debt recovery solicitor in Derby who was rude – and there was a strong sense that being rude was why they’d ended up in that position.

Sometimes, there would be comic moments. I remember one lawyer boasting about his representation of Lance Armstrong one year; by the following year, by which point Armstrong had been disgraced by his cheating scandal, he affected not to remember ever having done so. Young lawyers may not know that one day they’ll be required to ‘go after’ clients. I remember having coffee with Jenny Afia of Schillings several years ago, telling me with steely determination her desire to represent Meghan Markle. She now does, and when I found this out by watching her appear on Netflix documentary about the Sussexes, I remember thinking it was never in serious doubt that she would.

*

‘No genius is required for the law except common sense and relatively clean fingernails,’ as John Mortimer put it. As usual, he was joking.

Actually, much more is required and I would sometimes glimpse it in these individuals I was privileged to meet. All were immaculately dressed, with the possible exception of Stephens, whose dishevelled look was part of a sort of Columbo-ish charm, making him the exception that proved the rule. I remember Fiona’s brisk manner, the way she filled a room, and how any client would feel that they were buying, alongside legal nous, an tigerish indefatigability allied to kindness.

I recall how Frances Hughes, meanwhile, had a sort of detached cool which I sensed could easily turn terrifying. And I don’t think I’ve met anyone quite so precise as Helen Ward, someone who seemed to take such care over everything – language, manner. It was as if she took note of what was required in each successive moment and expertly provided it.

No doubt this form of precision was all along what I was lacking. Creativity, when we are in flow, still has a slight flavour of throwing things at the wall and seeing what sticks. You might subsequently revisit and refine, but creation just isn’t like the law; I think in its essence it’s too impatient. My grandfather had a sort of deliberation about him which meant that when he did finally get around to painting he did it slowly: I could never understand why he wouldn’t work on a canvas every day. But just as it wasn’t in my nature to be a lawyer, it wasn’t in his nature really to be an artist or a writer.

Similarly, my father whose energy reserves are considerable, has an ability I can hardly fathom to be confronted with a document and laser in on the detail which will prove problematic later, and to engineer the words to tweak that contingency and solve the problem. There’s a bit of clairvoyance about the law; a need to pause in the present, peer round all the things which are likely or even unlikely to happen, and to pin those down to the advantage of the client.

For writers, getting into a flow in the present is more important than getting too hung up on where the book is going. When Gore Vidal wrote Myra Breckinridge, he had no plan. He simply wrote: “I am Myra Breckenridge whom no man shall ever possess” and went from there. It had the flavour of something to be getting on with.

Today, I realise that my life then is impossible to imagine without law – it has enriched me and frustrated me in more or less equal measure. But if I could go back to that twentysomething years ago, and be at his shoulder in the room in Stevens and Bolton LLP at the moment I was offered a job in the divorce department, with the opportunity to reverse his decision, I wouldn’t interrupt him.