Ex-magic circle lawyer lifts lid on City law’s psychological impact in candid debut novel

By on

Book may seem extreme but covers very real problems in the profession, author tells Legal Cheek’s Katie King

City law, despite its marketing, grad recruitment and social media pushes, is an opaque profession. Being Simon Haines, the debut novel of Tom Vaughan MacAulay, gives readers perhaps the most candid, albeit fictitious, account of solicitordom on the market.

Tom’s certainly well-placed to write it. Having studied languages at Cambridge, the now 37-year-old then converted to law and completed his Legal Practice Course (LPC) at BPP Law School. A decade as an associate and then senior associate at magic circle giant Slaughter and May, plus a stint at Linklaters (in its Milan office), followed.

Like its author, the novel’s namesake too studied languages at Cambridge. After completing a year abroad in Naples and graduating with a first, Simon moved from Lincoln to the capital to study law at City Law School. Being Simon Haines begins and ends with the driven associate vying for partnership at boutique, but top, top paying firm Fiennes & Plunkett, at which he both trained and qualified.

Katie King and Tom Vaughan MacAulay

And thus we follow Simon through the ordeal of “Campaign”. Ordeal is the right word: striving for the million-pound-a-year light at the end of the gruellingly dark associate tunnel costs Simon his relationship with childhood sweetheart Sophie Williams (“she could no longer bear my presence”), his sleep (“twenty-four-hour days were not rare”) and his lungs (“I was getting through a packet of cigarettes a day in the Fiennes & Plunkett smoking pit”).

It’s undeniable Tom’s education and career path aligns pretty closely with character Simon’s, and on the way to meet him for drinks at a Browns restaurant just by Bank station, I was expecting to be told the novel was autobiographical. I even warned Tom I’d probably call him Simon at least once during the conversation.

But I was wrong. “The book is not autobiographical but rather it’s based on anecdotes I’ve heard about, that have been reshuffled and fictionalised,” Tom explains. “My personality is not very much like Simon’s, I’ve never had a girlfriend like Sophie, and I didn’t spend a year abroad in Naples.”

The themes the novel, published by Red Door, covers are very familiar and very true to City professionals, though. On readers tracing Simon’s Campaign-induced descent into lonely, drunken exhaustion, Tom tells me:

Because the book is fiction some of it is quite extreme, but then you ask yourself: is it? There are lots of firms in the City where staff work all night and are incredibly tired and stressed. The psychological elements of the book do draw attention to issues that are very real in the City, such as the reliance on alcohol as an escape. I walk through the City even at lunchtime, and it’s packed out with people boozing. It’s a real concern.

The characters feel real too. The jarring, slightly bumbling but ultimately loyal trainee; the well-meaning partner who has become lost in his work — I’m sure they exist at every London firm.

The most interesting character, though, is Simon.

Not your typical Oxbridge student, his time at Cambridge is a blur of reluctant involvement in seedy drinking societies, on-off girlfriends, cigarettes and booze, academic achievements and a few Starter for Ten-esque awkward social interactions. Late into his degree, Simon is lured into City law by BNOC, lothario and soon-to-be Fiennes & Plunkett trainee Dan Serfontein, much to the shock of his professor. Once there, he’s hooked; in his words:

I was a man who had become addicted, a man who had submitted. A man whose primary emotion was now terror of getting it wrong.

I found Simon both incredibly easy and incredibly difficult to warm to depending on page number. My experience seems shared by others, Tom telling me he has received a lot of different feedback about whether Simon is a liked character.

Anyone else read this? It’s by a former magic circle solicitor 😱

A post shared by Legal Cheek (@legalcheek) on

Tom is split too. “To me, Simon is meant to be a character with good values but one who is lost in his own City dreams,” he says. “His big problem is that he has no self-reflection or self-awareness and is inherently incapable of understanding the impact his plight for partnership is having on his life.”

You can’t fault Simon’s tenacity, though. With much of his life crumbling around him Simon stays hypnotised by his City law dream, at the total disregard of sneer-worthy in-house roles. Yet, part-way through the novel long-time friend Dan ends up making this exact move (“‘I just can’t do it any more,’ he gasped. ‘They’ve broken me.’”).

It’s a move Tom, now legal counsel at financial services company Legal & General, in 2015 made too. Did City law break him?

No, nor did Fiennes & Plunkett break Dan. “It’s self-dramatising”, Tom thinks. “Is it really that big a tragedy to not make partner?”

Now working more manageable hours, Tom is able to dedicate more time to his writing and is working on two new novels, one in Italian and one in English. As for his debut, The Times has said Being Simon Haines may become “the defining novel… about what it means to be a driven corporate lawyer”. I’d be hard pushed to disagree.

For all the latest commercial awareness info, and advance notification of Legal Cheek's careers events:

Sign up to the Legal Cheek Hub


Get a grip

Another narcissistic romp, trying to mimic city boy. I’m sure telling the tall tale of ‘promising, bright-eyed grad to grey, hollow, office slave’ is a good way to peddle books, but I am sick of this well trodden drivel.

No-one is asking you to become a partner, or sit on the partner track. If you don’t want to do it, don’t. And if you do, don’t then turn around and bite the hand that feeds you. I’m sure you’ve had a hard life, earning way above the national average, retiring at 37 and write this twoddle. Not exactly a day down the mines though, is it..



Middle aged people don’t need to run law firms as they do, but because they do young people get drawn into them. There is little else for those with a certain intellect and drive.
Once In, it is soul destroying. You can self medicate with alcohol or elite children, nut there it is. You become more Soros than Moses, more Gates than Jesus and more Mittel than Gandhi en route. This is even though it should be an arbitrary decision for someone bright to become one or the other 🙂



“There is little else for those with a certain intellect and drive.”

Right. One of the great failings of western capitalism is the complete lack of economic diversity and the fact that you are more or less forced into a predetermined career. You wanted to be an architect, a doctor, or an entrepreneur, but no. BigLaw is your only option. /s



Law is a big employer. In cities like London and Milan there are far more legal jobs than doctor or architect jobs. There are far more legal jobs than jobs in politics, which is a similar magnet.

A man who speaks fluent Italian and English and is interested in events rather than buildings or people’s illnesses and injuries, will be drawn to law.

I referrd to a certain intellect and drive.

I make a more solid point than you realise.

The second part of the point about personality choices is harder to argue with….it is hard to think of a famous dispenser of pills, like a doctor, but I will try

Architecture makes you more Prince Charles than Martin Luther King, being a doctor makes you more human vending machine than Hippocrates. Yet it should be an arbitrary choice for a person’s soul to make.



Ridiculous. There are plenty of challenging and interesting jobs out there other than law (and plenty of way to do challenging and interesting things other than in one’s job) — law is not more interesting but simply more lucrative than most other life paths. That’s why people go into it. I’m not denying that money is a powerful pull – but it’s a pull that lots of young people resist if they think that law (or city law) is not for them.



Money, status, prestige – it’s like crack for the insecure overachiever with no specific direction. The law firm tells you what to do and tells you how you’re doing. If you get enough positive feedback you’re conditioned to keep seeking it until your identity is wrapped up in winning these competitions. Partnership is the ultimate prize for the law firm addict. They’re deluded into believing they’re the best of the best, even though from the outside, most people see law firm partners as salaried labour.


I think insecure overachievers burn out by the time they are a senior associate. Partners are often well rounded people with a balanced view of their careers who have a clear set of priorities that prepare them for a long career in the profession. They’re not the obsessive types who freak out at the slightest hint of a mediocre appraisal – these associates often throw a fit and leave. They show up, do their job, go home to their families and repeat. Generally they have a plan but not an agenda. If they don’t make partner at their firm they will just reassess and do something else.


Not really trying to mimic City Boy though is it. The protagonist in that novel was a markets analyst not a lawyer. There’s a world of difference you plonker



Yeah, because city boy is ALL about being a market analyst, isn’t it.. It’s about his journey from hippy to self-loathing arsehole.

We want the biggest plonker of the year.
You know….

I’m not a plonker.



Oh alright you win. You’re not a plonker at all but actually a great bloke.

Let’s go and have a pint and a laugh..



What you drinking? Me, lager sometimes cider..

Different drinks for different needs…


Sounds pretty dull book



If you can’t take the heat get out of the kitchen



Harry? Is that you?



I am completely worn down and I am only 3PQE. Who wants to open a records shop up north with me?



Broken record, more like



“twenty-four-hour days were not rare”

They are pretty common on earth, I have noticed.



Good gag


Dr Patel

“I found Simon both incredibly easy and incredibly difficult to warm to depending on page number”

Firstly, top writing Katie. Secondly, that’s because you’re a girl and have more empathy.


Frustrated Writer

Only very sad lawyers cover their inadequacies and frustrations by writing stories. Oh well….

Alex had been the type of kid who had spent his pocket money on sweets and chocolate within minutes, much to the annoyance of his mum, who was working two jobs to feed him. When he was old enough for a paper round, the newsagent would simply give him his usual selection of crisps and fizzy drinks in lieu of payment, knowing that the money would be squandered on them anyway. As a student, as soon as his loan cheque cleared, all his mates would join him at the bar, knowing they would not need to put their hands in their pockets as Alex worked his way through his money until the early hours.

So when Alex got the expected spike in traffic, and the precious upturn in revenue followed, it was within character that he spent little time in dispersing his funds. Firstly, he checked himself into the most luxurious suite he could get at the Dorchester hotel, and spent the afternoon at the Armani store on Bond Street updating his wardrobe back to its former glory. He had also visited his old favourite salon in Belgravia, getting a full mani-pedi, haircut, and intimate waxing. Finally, he had returned to the Porsche dealership, taking care to find the salesman who had hounded him so much to take possession back of his last car, nonchalantly throwing a wedge of cash on the desk in front of him, demanding the keys to the best Cayenne that was on the garage forecourt. He had even paid the Reporter to get Not Amused back trolling. For the first time in a long time, he was content to look at himself in the mirror.

The next three days were a blur. He could remember entering a high class club in Mayfair, chatting up an attractive Russian woman whilst the Cristal flowed. After that, there was a void, finally broken by the sound of his aged Nokia phone ringing by his bedside, and the door being knocked insistently, matching the banging in his dehydrated head. The phone call was from his mum, the latest in a large number of missed calls. She was used to him disappearing, but this was a long period even by his standards. The door was the hotel front office manager, checking he was alive, but more importantly, demanding payment of his bill. He ignored the phone and opened the door, forgetting he had slept naked.

After calming the poor manager down from the shock, Alex had agreed to settle the bill, but it nearly wiped him out. He couldn’t be sure, but he thought the Russian woman had taken some, and then of course there was the room service he seemed to have ordered. He had taken a dressing gown and a pair of slippers, even raiding an unattended maid’s cart for posh toiletries to sell in the pubs around the Legal Cheek offices to claw back at least a small amount. But that would not be enough to replace what he had spent. He had to leave and found himself back at his mum’s place. He had vowed never to sleep on that cold, hard garage floor again, but had little option, his remaining cash would barely stretch to a Travelodge.

Alex still had a key, so did not have to knock to get in. He really didn’t want to see his mum, and in an eerie recollection of his days as a teenager coming home, drunk on white cider, was hoping he could avoid her as long as possible.

As he entered his grimy garage, he breathed in the familiar scent of paint and white spirit. He missed his plush hotel bed already. His neck pre-emptively ached from the old camping mat he had to sleep on in the garage. He looked around and noticed his mum had left a neat pile of his post near the door.

Alex flicked through the pile, with a well-practiced movement dropping those with large red letters and words such as “final demand” into the overflowing waste bin, unopened. The last item in his hands was different though. It was this week’s copy of Racing Post. Alex had never got around to cancelling his subscription. Having nothing better to do, Alex sat on the floor and pulled the publication from its plastic cover, discarding it on the floor. He idly flipped the pages until he reached the dog racing schedule. His eye immediately fell on one of the participant’s names. “Top Dog” would be running at the 2:08pm at Romford Greyhound track that afternoon. Alex couldn’t believe it. It had “top” in its name. That had to be a sign. Serendipity, almost. God was telling him to do it, he thought. Alex checked his watch. He had just enough time, if he rushed, to get to the bookies to lay a bet. He departed immediately, hurtling along the high street well beyond the speed limit, hoping that there would be no police around. The amount of alcohol still in his system would surely make him fail any breathalyser.

Alex parked illegally in a disabled spot outside the bookies, and burst through the door almost causing an elderly member of the shop’s clientele to have a heart attack. Quivering, Alex threw a bundle of notes at the cashier, demanding she hurray as she took his bet. Alex grabbed his slip to a high stool with full view of the TV screens showing the dog races.

It was a short and inglorious culmination of the afternoon. Top Dog far from lived up to his name, coming a distant last place. Alex felt himself slip into despair, not for the first time realising the folly of his ways. He had indeed been given a signal. As he double checked the screen for confirmation of the result, desperate for his eyes to have deceived him, he saw that message loud and clear, taunting him. He should’ve known. He left the bookies penniless and shamed.



Boring. Try harder.



Yeah that was a bit shyte to be honest. I think Frustrated Writer might be running out of narrative ideas.




Quite. This piece just seems to be a constant attack at Alex, nothing clever or law related about it.



First one I have disliked. It seems to be an attempted backstory merged with current plotlines. Either way, thought it was overly rude to Alex.



When are you giving our boy Frustrated Writer some coverage?



I always wanted to be a lawyer, that’s why I studied languages at Cambridge.



I think a lot get tricked into thinking that international work = lots of language-speaking. Nope, you’re just in a boardroom with lots of other people speaking English of varying quality.



There just aren’t enough articles where the journalist takes a selfie with the subject. Thank you Katie, for the being the brave trailblazer of journalistic integrity.



Where is her other hand?



I have lived and am currently living all of this. it is perfectly possible to find a balance, if you have a strong enough character. people in this business rarely realise that most stress is self inflicted, even at the top.



Calling bullshit on that.



I love my desk. I love my desk. I love my desk. I am not allowed plants or decorations but I love my desk. Please don’t make me hotdesk. Please. NO!!!!!



Are you at Freshfields?



All true. Been through the mill in earlier years, learned how to stay calm and recuperate efficiently. Booze and other self medication lead to a vicious circle. Honestly, nowadays i try not to overthink anything, trust instincts and not beat myself up for procrastication. Its the overworkers who crash and burn.


Katie we could run to the hills post-Brexit and build a house out of materials we can scavenge and start a hunter-gatherer life together. We could build a raft and see where it takes us.


Not Proudman

Not gonna lie, would be a lot more interested in this if the protagonist were female. Just another androcentric, wannabe Firm-esque book.



This book would be better if it were about an exciting profession like a fireman or astronaut.



How can you claim that being a City solicitor is not a glamorous and exciting job ?

You get to wear a suit, you get to sit with one arse cheek on a colleague’s desk talking about crap to them, you get to be a complete dick most of the time, you get to sit in a conference room and marvel at the depressing nature of AV technology, you get to kiss the IBS-ridden arses of various senior/equity partners who return the favour by treating you with barely-concealed contempt, you get to not really put what you learned about law into practice to any great extent at all, you get to work yourself into the ground, you get to get depressed, you get to alienate yourself from your family through having no time to interact with them, you get to get all Machiavellian about your colleagues while maintaining the pretence that they’re sort of friends.

Who could want for more ?



I do the sitting on one arse check on a colleague’s desk talking crap! 😀



The same bleak outlook on professions/jobs’ profiles could be applied to describe a lorry-driver.

If one is negative and sees the act of working from this perspective, any nod will be described exactly with the same cinical and caustic way.

Go on then…write your next review on a McDonalds sales assistant or a school teacher. I’m curious to see if there is going to be any change of style and inflections. K



From his publisher’s own website:

“Our authors underwrite the cost of the production process of the UK edition of their book. This is the element we take from the self-publishing model; it shares the initial commercial risk for us, meaning that our sole consideration can be: ‘will this be a great book?’ It also gives the author immense control over every aspect of the process.”



– British London?

– Yeah?

– Sounds a bit…

– What? Too patriotic for you?

– A bit made up.


Comments are closed.