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Battles against hope: philosophy in prison

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Essay | 25 minute read
Teaching philosophy to prison inmates inspired some profound, and challenging, topics of conversation

The man standing next to me inside the elevator looks uncannily like my father, who I have not seen for twenty years, since he was sent to prison. He is short, has yellowed fingertips and the sleeves of his oversized suit jacket brush his knuckles. I have seen men who look like my father before, while I was on buses and trains, or standing at urinals in pub toilets. I’ve seen them in London, Manchester, Berlin and Rio de Janeiro. In the elevator, I glance at him and I recognise the permanently clenched jaw, the emphysemic wheeze in the breathing. I pull my shirtsleeve over my wrist to conceal my watch and ask one such man for the time. He doesn’t answer with a Scouse accent and therefore is not my dad. Neither were the men in Germany or Brazil. We travel up another five floors in silence. The elevator stops, the doors open and he exits.

Tomorrow morning I’ll be going into a prison for the first time. I’ll be teaching philosophy to men. I have written before about my dad and the other paternal men in my family having been in jail; a few months after a piece in the Guardian, a philosopher called Jamie from a local university asked me to co-teach in jail. I assume I have been invited to work on the project because I’ll be a good fit culturally, because I might know philosophy and yet at the same time understand convict logic in a way that many Tractatus-clutching types wouldn’t. After Jamie asked me to work with them, I noticed a pair of heavy ankle-length black boots in a shop window. It was spring and I was in the habit of wearing soft leather Oxford shoes with stonewashed jeans twice rolled up at the bottom. The shop only had the boots in a size ten and I’m a size nine but that doesn’t matter to me so I bought them.

The next morning in prison, Jamie and I wait for our students in a classroom that doubles as an art room. It’s like the art classrooms from my school days except there are bars on the windows and the pencils and paintbrushes and anything else with a pointed end are kept in padlocked cupboards. I look over our lesson plan on Locke’s and Hume’s theories of identity. I imagine my dad trying to make sense of it and with a pen I strike red lines through entire paragraphs. ‘Keep it accessible,’ I say to Jamie. ‘There’s going to be a lot of illiterate guys, men who didn’t finish school. Don’t overwhelm them.’ I hear the clanking of heavy metal doors being opened and the echoing voices of men talking in the corridor outside. Our students are approaching. I’m wearing my new boots, the unworn toecaps have a first-day-at-school shininess.

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The men trickle in through the door. A man gives me a bone-crushing handshake and looks past my shoulder. Another man has morning breath and bloodshot eyes. Another says he’s here for the psychology course and I tell him it’s actually a philosophy course and he shrugs, walks into the class and takes a seat. There is one man with sallow skin and receding gums. Another who clutches a plastic bag with ‘Leeds University’ printed on it; the bag is split at the seam but he still carries his library books in it. I walk around my new class introducing myself but wince at a pain in my feet. My boots are rubbing my skin. I feel the sting of fresh blisters on my heels. More men arrive until there are twelve. Jamie and I take a last look through our notes for today’s class. ‘Accessible,’ I say again.

The men all sit in a circle and I explain Locke.

‘That’s not quite right,’ says a student called Macca.

‘Excuse me,’ I say.

‘Locke didn’t only care about memory.’ He points at my whiteboard. ‘It was more consciousness.’

All twelve men are looking at me. I walk over to the whiteboard, tiptoeing to avoid the shooting pain on my heels, wipe out the word ‘memory’ and write ‘consciousness’. The men laugh and whisper to each other. I try to explain Locke again, moving only in small strides, careful not to land my whole foot on the floor. A few minutes later, another student who has just finished a distance learning degree explains how Rousseau might disagree with Locke. Twenty minutes in we have run out of material. From across the room, Jamie’s eyes meet mine and the word ‘accessible’ silently rings out between us.

Jamie sets the students some work in small groups and suggests we go over to the desk in the corner of the room to confer. Jamie goes to the desk and I tiptoe behind.


Six months later, I wear the same soft leather Oxford shoes to prison every week that I wear most other days. I’ve just returned from three weeks travelling solo in Thailand; my skin has bronzed and my hair is caramel brown. I walk through the strip-lit corridors of the prison to my classroom. A prisoner escorted by guards passes me from the opposite direction. He has a pallid forehead and flaking skin underneath his eyes. I roll down the sleeves of my shirt to hide my suntan. I get to the classroom and write the theme for today’s lesson on the board: ‘Freedom’.

The class is underway. I tell them a story from Homer’s epic in which Odysseus and his crew must get past the Sirens. The Sirens’ song makes any sailor who hears it drunk with love and prepared to do anything they can to get to the source of the music. They will jump overboard and swim to the Sirens where they will be eaten if needs be. To stay alive, Odysseus’s crew put wax in their ears so they don’t fall under the spell. But Odysseus wants to hear the beauty of the song, so he gets his men to tie him to the mast which means he’ll be able to listen to the song without jumping overboard and swimming to his death. They set sail. Odysseus hears the music and begs to be untied but his crew are under orders not to grant him this wish. One man, who has been at sea so long that his homesickness has turned to numbness, sees how passionate Odysseus looks and he wants to know what the Sirens sound like. He takes the wax out of his ears and, intoxicated with the sound of the Sirens’ voices, jumps overboard to his death. After they have passed the Sirens and Odysseus is untied, he spends weeks brooding over the fact that he will never again hear anything as beautiful as the Sirens’ song.

As I tell this story, one student frowns and looks out of the window. Another keeps fidgeting in his chair. Everything about telling this story in prison is loaded. Men away from home. Men gone numb. When I describe how sailors are lured to their fate by their desire for the Sirens’ song, I try not to look at those students who are in jail because of drug addiction or sexual crimes, yet I when I say the word ‘desire’ I find myself staring directly into the eyes of those very men.

The prisoners listen to the story and I ask, ‘Who is the most free – the men with wax in their ears, Odysseus, or the man who took the wax out?’

‘None of them are free,’ says Grant. ‘Odysseus is tied up. Blokes with wax in their ears are just doing what Odysseus tells them and the man who jumped off was free when he took the wax out but now he’s dead.’

‘I disagree,’ says Junaid. ‘They are all free in their own way. Odysseus was free because he knows how beautiful the Sirens are. Men with the wax are safe. The man who took the wax out knew what he was doing and so made an informed choice.’

Grant says, ‘How can you be free if what you do ends you up dead? How can you be free if you’re tied up?’

‘It’s like us,’ says Junaid. ‘We’re in jail so we ain’t free but we’re more free than if we were in another worse jail. The people who ain’t in jail, they gotta do things like pay bills or do the school run. We got freedoms they ain’t got.’

I hand a student called Keith the talking stick. He rests it on his lap and says, ‘Now – there are several ways of looking at this.’

When I first started in the prison, the librarian told me that Keith is thirteen years into his sentence, lives in a single cell and goes through a book every two or three days. Keith sometimes says words like ‘nomenclature’ in a working-class Glaswegian accent. ‘You could look at it from a neuroscientific perspective,’ he says. He talks with the speed that autodidacts often do, as if to unburden himself from his own mind, but other students are beginning to slump and stare at the floor.

‘The one who jumps off is free like how in Shakespeare the jester is free in a way that the king isn’t,’ he continues. I want to interrupt him. I would love to interrupt him. For me, interrupting people is one of the perks of being a teacher. Outside of my professional life, I’m a soft-voiced and slow-speaking person who is forever being interrupted by loud, fast-talking people, and one reason I teach is so I can legitimately interrupt people and exact revenge for this. Keith continues: ‘Quantum physics tells us that things aren’t actually determined,’ and I am unable to interrupt him. How do you say ‘I’m aware of the time’ to a man who has lived in a cell for thirteen years?

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The guards knock on the door at the end of the lesson and most students shuffle out, but half a dozen linger for a moment. One points at my suntanned face and asks me where I have been. I try to keep my answers as clipped as possible, worrying that a group of jailed men might smart from hearing about Phuket’s tropical beaches and full moon parties. But they keep asking me for more information. ‘Did you go snorkelling?’ ‘What was your favourite part?’ ‘Would you ever move there?’ Then one says flatly, ‘Did you go with your boyfriend?’

I search his face for a smirk. But there isn’t one. He’s being sincere. ‘I was alone this time,’ I say.

The men keep asking me questions about Thailand. A few have been themselves and want to know if this or that karaoke bar is still open in Bangkok. They ask if I got a good deal on flights, if I got the shits while I was there. As I answer their questions, I consider dropping into the conversation that I have a girlfriend but the atmosphere in the room now is so genial and tolerant that I don’t have the heart to not be gay.


In a class a few months later, a security officer tells us that time is up. The students leave but for one called Gregg, a man with a bright scar striking through his dark stubble. ‘This philosophy. What’s it for?’ he asks.

‘Well, ’I say ‘Philosophy is ancient Greek for—’

‘What can you do with it? What jobs?’

‘Some friends, some people I know, they work in the city now. I think.’

‘What job do you have?’ he says.

That he asks this immediately after I’ve taught him for three hours makes me think the answer ‘philosophy teacher’ isn’t going to count. I say, ‘Some people do law conversion courses after a philosophy degree.’

Gregg stares at me expectantly, as if I am a man who has only said half of what he has to say.

The security officer puts his head around the door and taps his watch at Gregg.


Tonight I do my online tax return. I click the complete button and immediately feel depressed. I go to bed but I cannot sleep. I’m certain that I have done it wrong, have underpaid, and that I will be prosecuted.

In the morning heavy rain falls sideways and I leave the house without my umbrella to walk to prison. The back of my ears and neck are wet. I arrive at the prison’s security gate, take off my soaked shoes, watch and belt and walk through the metal detector, feeling the hard floor through my wet socks. I feel faint and my heart races. I’m in the grip of wild, irrational guilt. My rucksack passes through an X-ray machine. The security officer gives me a stern look and working backwards from it to what my crime might be I imagine the light on the scanner is about to go red and beep and the guards will find a kilo of heroin in my bag.

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The alarm doesn’t beep. I hold my arms out limply to be searched by the security officer, the sleeves of my jumper damp. I pass security, but that doesn’t exonerate me from the panic. I go through the prison grounds, past a wall with rows of cell windows and hear the sound of multiple televisions all at once, yoghurt advert jingles, emergency news reports, canned laughter.

It’s been several years since I have had this paranoia that the sins of my father will be handed down to me no matter what choices I myself make. The grim assuredness that I’d go to prison was strongest when I was eighteen and I used to worry not if I would get arrested but how. I hoped it would happen in the daylight rather than at night, when I was alone rather than with friends. I’d become distracted when I heard police sirens, pausing to try and tell if they were getting closer. In the corridor of the prison, an officer holding an Alsatian on a leash comes from the other way and I slow my pace, as if to invite the dog to bark at me. As it passes, it stares at me with its black eyes.

My student David won’t be able to attend today because he has a legal visit, so I go to his cell before class to give him some reading. His cellmate opens the door and I’m hit by a smell. They have four purple air-fresheners on their windowsill and the lavender has mixed with the smell of socks, cooked instant noodles and two men in a small space. He tells me David is still on lunch-serving duty. I go to the food serving area where there is a long queue of men waiting in line and wonder if it might be better to come back later. I ask a gangly older man what time lunch normally finishes. ‘We was supposed to eat half hour ago,’ he says. He has the same Liverpudlian accent as my father. ‘I’ve asked them what time we was gonna have lunch and they said in a few minutes and that was twenty fuckin’ minutes ago. No such thing as time in this place.’

I leave David for later. I get to my classroom and find a woman is packing toys into a box: Lego bricks, teddy bears, a rainbow-coloured xylophone and a Fisher Price telephone with wheels and a smiling face on the front. She says she teaches the men how to play so they know what to do with their children on visit days.

Half an hour later, with my students, I tell them the story of Pandora’s Box, my voice thinner than normal. Pandora opens the box and seven evil spirits come out. Hatred, Shame, Greed, Boredom, Laziness, Delusion and Pain. She opens the box again and Hope comes out. I ask them, ‘If you could put one back into the box which one would you pick?’

Jerome picks hope. ‘Hope is what makes the other evils worse,’ he says. ‘Hatred and pain wouldn’t be so bad if there wasn’t hope. We’d just live with them instead of hoping we weren’t in pain.’

‘Without hope nothing changes,’ replies Keith. ‘You can hope not to hate and you can hope not to be in pain.’

‘But if you hope and then nothing changes anyway then the hope has just made everything worse.’

I tell the students that Nietzsche thought that hope was the worst thing to come out of Pandora’s box too and this makes Jerome sit more upright and voice his ideas with more volume.

‘Put hope back in the box then you’d lose delusion automatically too,’ he says.

My gaze falls on the spirals of barbed wire I see through the window. Coils of it on rooftops and walls, loops of it everywhere above you in the prison.

‘Without hope, pain would be less painful,’ Jerome says and my attention comes back to the room.

‘I’d put shame back in the box,’ Ed murmurs.

‘Then you’d just keep doing bad things,’ Jerome says.

‘I’ve known before I did bad things that I’d feel shame after doing them and I still did them anyway,’ says Ed.

‘But you’d never learn to be good if you didn’t feel shame about the bad stuff you do,’ Jerome says.

‘Maybe it’s shame that makes you do bad things.’

‘How the fuck you supposed to be good then?’

‘Empathy, maybe. Remorse. Not shame.’

At the end of the class, Gregg comes up to me and tells me he’ll be out in two weeks. ‘They gave me a job working on the underground railway,’ he says.

‘Driving a train?’ I say.

He frowns at me. I sense I have just misunderstood something in the most basic way, again.

‘Fixing the tracks at night. Criminal record don’t matter there because there’s no public around. Four hundred quid a week.’

‘Are you pleased?’

He purses his mouth. ‘Be underground so I won’t actually get that cold.’

I know this is a good thing for Gregg. I know he will be able to make money and reclaim some autonomy, like I know somewhere that my tax return is fine and that I do not have a kilo of heroin in my bag. But imagining Gregg drilling subway tracks at 4 a.m., my stomach tightens and I think of Hades, an underground world of physical labour and eternal punishment.


My students continue to think I’m gay. During a discussion on knowledge, Marlon uses the term ‘batty man’ and the others shoot him an unamused look. Marlon looks over to me and says, ‘Sorry boss’. I give him a gentle and forgiving smile. I go on teaching in prison as a closet heterosexual. The students believing I’m gay seems to make them more at ease around me and in turn I feel more at ease as their teacher.

The night before a class, Jamie and I photocopy some readings about Indian philosophy. Then we realise the pages we have photocopied have tantric images of gods and goddesses in ecstatic union. Against a blue sky, a green-skinned Bodhisattva opens her legs to receive the penis of a deity with eight arms. These sorts of images are not allowed in the prison. Pornography and any images of penetration are deemed contraband. Inmates can have lingerie models on their cell walls provided no nipples are on show. So we can make new photocopies purely of the text, Jamie and I get some scissors and frantically cut out the spiritual images, a confetti of phalluses and breasts flutter down across our desk.

Lying in bed, I wonder about sex in prison and I google, ‘Are conjugal visits allowed in UK prisons?’ The answer is no.

A few months later, I arrive in the education block of the prison and find that my normal classroom is being used for a talk by a recruiter from a healthy fast-food chain that offers jobs to ex-offenders. A towering security officer called Baxter with a wide jaw, pockmarked cheeks and a forearm full of tattoos tells me I’m to use room nine instead. I open the door to room nine and find tall bookshelves in the middle of it. The bookshelves are on wheels, so I grip the side of the shelves and try to push them but they don’t move. ‘Are you ok?’ I turn around and Baxter is in the doorway offering to help. There’s also a woman with him, who I know is called Anika, sitting at the desk.

‘I got it,’ I say to Baxter and he leaves.

Anika doesn’t look up from the paperwork she is filling out.

‘Sorry, I didn’t realise you were here,’ I say.

‘OK,’ she says, still not looking up. She has bleached blonde hair falling over one side of her face. I know her name because I’d seen her teaching in the prison before and asked a colleague what her name was. I think she is beautiful, as do all the other men in the building; men sent down for murder or arson behave like perfect gentlemen around Anika. I squat down, unclip the brakes on the bottom of the bookshelf wheels and then stand up and try to move the bookshelf again but it’s no less stuck than before.

‘Excuse me,’ I say.

Anika keeps her pen on the page and looks at me from over the top of her glasses. ‘I’m just wondering,’ I say, ‘if you know how these wheels work? I thought I’d unlocked them but the shelves still won’t move.’

She takes off her glasses and says, ‘If you unlock the wheels the shelves will move.’

‘I must be doing it wrong.’

I see her leg is shaking in irritation under the desk. She has a pointed jaw and high cheekbones. Inside a men’s prison, her already sharp beauty takes on a merciless quality. I look at her and I feel sorry for the hundreds of men yearning inside their cells. Which is to say, Anika looks at me – looks right through me – and I feel sorry for myself.

When my dad got into pub fights or trouble with the police I saw how his girlfriends grew dissatisfied and weary, so I came to believe that what women most wanted wasn’t tough guys but men who were soulful and sensitive. Using my shoulder, I press as hard as I can into the bookshelves but they still don’t budge.

Baxter is back at the door and this time says, ‘Let’s have a look,’ as I step out of the way. He grips the bookshelves and they move under his force. I can see Anika squeezing her thighs together.

An hour later the class has started. I say to them, ‘Descartes wanted to know whether there any way that we can prove that we are not in a dream right now?’

Solomon says, ‘If this is a dream, I’m gonna have a right go at myself when I wake up.’ The rest of the men laugh.

‘I remember waking up,’ says Ray. ‘I remember getting out of bed.’

‘Maybe you just dreamed that,’ says Solomon.

‘But all of this makes too much sense to be a dream. It’s physical. I can touch the chair. I can touch my watch.’

‘Dreams can be physical though.’

‘Not physical-physical. Not like real life.’

‘The other night,’ Solomon says, ‘man in my cell woke up screaming his woman’s name and he was wet in his shorts. Said he had a dream that he was with her.’ Solomon holds his hands out in front of him as if gripping something the shape of a watermelon. ‘He could smell her and taste her. Feel her.’

A grin breaks out across my face and I look around the room to meet the eyes of another so I may share this moment with someone else. But the rest of the men are earnestly listening to Solomon. ‘Dreams can be physical. Man had to get up and change his shorts.’

Ray leans back in his chair and strokes his chin.

‘So what do we think?’ I say. ‘What does the wet dream mean for Descartes’ argument?’


I go to my friend Chloe’s dinner party. Opposite me sits a doctor called Paul, elegantly dressed in black. I tell him what I do and he says to me, ‘So your dad was in prison and you teach in prison. Are you trying to save these men you teach?’ I don’t think so, I tell Paul.

My next class, I wear an ironed shirt, something I have not done in years. Rather than do the register by sight I call it out, like a professional would. I stop calling my students ‘fellas’ and start referring to them as ‘gentlemen’. I interrupt students who interrupt other students and tell them that they must not interrupt. ‘You’re in the mood, aren’t you?’ one students says to me.

In the afternoon, walking home, I listen to loud sweary music on my earphones and in my head I re-enact a fantasy version of my conversation with Paul.

‘Are you trying to save these men you teach?’ says fantasy Paul.

‘What did your parents do, Paul?’ I reply.

‘They were both doctors.’

‘And you’re a doctor too. How funny that you don’t pathologise this type of inheritance.’

Fantasy Paul doesn’t know what to say back. He looks six inches shorter. Chloe offers me a second slice of cake. I eat it and gulp down lapsang souchong. Nobody wants to talk to fantasy Paul anymore and he gets his coat to leave, but I put my arm around him and tell him to come and have a drink with me on the patio. Outside, under the stars, I tell him, ‘It’s not a matter of saving anyone, but a matter of what knowledge has been planted in your system. You don’t get to decide what you have to digest.’

‘I’m so grateful you taught me all this,’ fantasy Paul says. He looks shy now, almost like a child.

Two months later I go to another of Chloe’s dinner parties and Paul is sitting at the table. I pick the seat furthest away from him.

I first sat in a prison visiting room when I was seven years old and when I went back to school the following Monday, I found hardly anybody else who had had the same experience. I knew there was one universe that I and most people lived in every day and took for granted, but I had also glimpsed the edges of a second, more disturbing world that many people didn’t know about. Aware of the doubleness of things, I grew up to be ambivalent about what most people told me. When I was seventeen and attended my first philosophy class, I met other people who shared this ambivalence.


I am back in prison, and in the doorway of the classroom. A student called Matthew tells me that he wasn’t able to shower before class because security kept things on lockdown until the last minute.

‘Oh god. That must just be so frustrating,’ I say.

‘Just that way sometimes.’ He shrugs and walks into the class.

I’m embarrassed at how naive I must have sounded to him. He is trying to let things go in order to survive this place and my words probably don’t help. I’ve been teaching in prison for three years now, but I feel as if I’m just as capable of saying wrong and naive things as I was on my first day. Visiting prison in my childhood but never having been a prisoner myself has left me with complicated feelings. This might be the reason why today I respond to Matthew with such self-consciousness. I’ve been exposed to the effects of prison life – my dad didn’t like to sleep without his baseball bat beside the bed – yet I gasp when Matthew tells me about going without a shower.

For many of my students here, their days consist of battles: battles against the justice system, against physical violence, against their own desires for the world outside or sex; battles against hope and shame. To survive those battles, some wear a kind of armour. I see it in the way they walk and the ‘trust nobody’ terseness in how they speak. In these philosophy classes, I have seen some of these same men open up, share their feeling and opinions, even at the risk of sounding soft and I have seen them grapple with newly appreciated uncertainties. They have gone from talking with vehement conviction to using a more hesitant tone: one of tender confusion and humility.

Today is the end of the course that Jamie and I are leading. At the end of the lesson, a security guard knocks on the door and says that time is up. The men shake my hand on their way out. They file through a corridor that leads them back into the belly of the prison, a metal door clanks shut behind them and I wonder if they have already put their armour back on.

*Names and identifying details have been changed to protect privacy

Thank you to Peter Worley for the Sirens, David Birch for Pandora’s Box and to Mike Coxhead, Andrea Fassolas, Kirstine Szifris, George Pugh and Emma Worley for their dedicated support.