Confessions of a head boy: ‘Was I to be shot or, equally tragically, expelled? I wondered which would disappoint my parents more’

The life of a head boy – or head girl – is one of strange privilege and pressure, lived against the already-challenging backdrop of the final year at school. Harry Goodwin, who has just finished a stint as head boy at Bryanston, tells all.

It was 11pm on the penultimate night of the summer term and I’d just finished a four-hour dress rehearsal of a perplexing play by Friedrich Dürrenmatt when my housemaster appeared backstage.

A quiet man at the best of times, he offered no hint as to why he was there.

‘Harry, you need to come with me right now,’ he murmured. Then: ‘Perhaps leave your microphone.’

We were out of the side door before many of the cast had come backstage. Few people saw me go. My phone was upstairs in a dressing room. I was wearing yellow shoes and a tweed suit and was confused. It struck me that this was how enemies of the state disappeared during Stalin’s Purge: in the dead of night, with no witnesses. Perhaps I was to be shot or, equally tragically, expelled. I wondered which would disappoint my parents more.

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Walking up to the main school in the dark, I had never known small talk to feel so small, dwarfed by whatever my housemaster knew and I didn’t. We passed the cafe, long closed. ‘Do you need a drink?’ he asked.

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‘I’m fine.’

‘You should get a drink.’

I was struggling to keep my eyes open. The junior boys had been ‘dorm-raiding’ the night before and I felt drugged when we turned onto the pathway to the Headmistress’s house.

Only then did I realise that I still had my make-up and moustache on and my hair was painted white. As the Headmistress asked me if I would be Head Boy, she was no doubt questioning her decision and praying for more consistency from the Head Girl.

In September, she and I discovered that we had six meetings a week: three mornings with the Head, one at 9pm with the Second Master and two with the prefects. Our first test was herding new pupils to the biometric machines that were to scan their fingerprints and faces, which perplexed my conscience a little, as well as simultaneously guiding their parents to their talks and teas. It was vital that the two groups did not mix, for fear of emotional encounters.

My back was aching from standing and talking to so many small people when relief arrived: it was now my turn to meander through the parents who were having tea. The school supplies excellent cake and I thought I rather deserved one.

I worked my way backwards, smiling and chatting, towards the cake table, whereupon an anxious mother lurched from the shadows. She had many concerns; my first lesson in school diplomacy was a brutal one. As one can never pull off cake and conversation in style, I abandoned the former and threw my energy into neutralising her fears.

Harry Goodwin

When her husband arrived, the barrage doubled in intensity. I noticed an unsuspecting prefect standing by the wall and decided to pull rank. I never apologised to Ben for dragging him into that situation, but it’s hard to feel remorseful with two cakes in your hands.

Bryanston’s disapproval of hierarchy results in a lack of privileges for the Heads of School, so imagine our delight when we discovered we could – according to legend – have a pipe, a beard and a goat. I don’t smoke and neither I nor the Head Girl could grow a decent beard, so we settled on two pygmy goats. I got as far as contacting a Welsh farmer about his wethers before realising that A levels are enough of a logistical nightmare without two goats to feed. Also, I don’t speak Welsh.

We were often tasked with giving prep-school heads a tour, visits that generally passed without incident. However, there was no tour more crucial than the once-in-a-decade visit of The Good Schools Guide that happened to fall within our tenure. We expected one inspector, but he brought his wife. I shall call them Mr and Mrs Guide, not least because their real names escape me.

During the tour, I couldn’t help feeling that I was being interrogated with unprecedented ferocity by Mrs Guide, who perhaps suspected the relaxed, creative ethos of Bryanston was hiding something and had the habit of dictating into her phone on one topic just as you were answering her questions on another.

I glanced enviously ahead at the Head Girl, who was chatting easily with Mr Guide. Had she taken on the gentler of the two or managed to tame her escort with a charm that I didn’t possess? I suspected it was the latter and wished I could subtly call for back-up when Mrs Guide informed me that she used to be a prison warden before retirement.

Bryanston ( is a co-ed boarding school (some 670 pupils, aged 13–18) on the banks of the River Stour near Blandford Forum, Dorset.