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The book began not with a concept but with a habit. Shelby enrolled at St. George’s School in Middletown, Rhode Island, as a sophomore in 2021, and the volume of calls home gave Hilderbrand a front-row seat to institutional life she had never experienced herself.
Shelby would call home several times a day to fill me in on all the drama, and at some point I said to her, ‘We should write a book about all of this.’
Hilderbrand had attended public school in Pennsylvania and had no boarding school experience of her own. That gap between the insider and the outsider is the structural premise the collaboration runs on.
Once she committed to the project, Hilderbrand identified a generational hole in the genre she wanted to fill. She placed the book in a lineage that runs from John Knowles through Curtis Sittenfeld’s 2005 novel ‘Prep,’ which follows a scholarship student navigating class and power at a New England boarding school, and then stops.
There hasn’t been a boarding school novel for Gen Z... ‘A Separate Peace’ and ‘Catcher in the Rye’ are beacons of a certain generation. Curtis Sittenfeld wrote ‘Prep.’ That was sort of the millennial version... there hasn’t been a deep dive into a boarding school, a literary boarding school novel that’s set at Gen Z. [paraphrased from audio]
The project also arrived at a professionally charged moment. Hilderbrand had announced ‘Swan Song’ as her final Nantucket-set novel, closing a 27-book cycle that had defined her career, and the boarding school book was the first thing waiting on the other side.
It’s like somebody plugged me into a socket — I’m so energized, so excited to be able to take my writing skills, which now at the age of 54, are pretty, pretty advanced, and be able to take them to a different topic. All of a sudden, writing has become new for me.
Before either of them drafted a scene, Hilderbrand went back to the source texts. Rereading ‘A Separate Peace’ for the first time since high school revealed an absence that became the book’s first organizing principle.
I read ‘A Separate Peace.’ I hadn’t read it since high school, and the number one thing I realized: there is not a single woman in it. It’s almost exclusively men... So we wanted to make ‘The Academy’ female-forward. I reread ‘Prep’ by Curtis Sittenfeld, a book I’ve loved for 20 years.
The writing process divided along the lines of who knew what. Hilderbrand ran it with the structure of a classroom: she outlined the characters and their arcs at a dinner on Nantucket, then handed Shelby specific scenes to draft while she handled the adult characters herself.
I gave Shelby writing assignments: ‘Okay, now you’re going to write a scene from Davi’s point-of-view.’ Shelby was instrumental in getting the kids right.
When the drafts crossed back over to Shelby for editing, the corrections were specific. Hilderbrand described Shelby as her translator, and the word landed literally: the generational gap showed up in the wardrobe.
She had people wearing Converse and listening to Rolling Stones, and I’m like, They’re wearing Golden Gooses and listening to house music.
One structural challenge was carrying over the sensory texture her Nantucket novels are known for. Those books move through named restaurants and specific dishes; a boarding school dining hall offered no obvious equivalent. Her solution was to import the food through a new character rather than through setting.
I was thinking: What do people love about my summer novels? One thing: the food. So any Elin Hilderbrand book set at a boarding school is going to have incredible food. How do I do that? I thought: ‘We’ll have a chef who’s fallen on hard times and takes this job because he has no other recourse.’
The school itself is fictional. She and Shelby moved the setting from Rhode Island to western Massachusetts to avoid legal complications with St. George’s, and the name Tiffin was chosen partly to pair with the sequel’s title, ‘The Thoroughbreds.’
Hilderbrand has written every one of her more than 30 novels alone. The collaboration with Shelby required her to hand over creative territory she had never shared, and she described what that exchange cost and gave back in a single sentence.
Well, it combined the two things I love the most: writing books and parenting. [paraphrased from audio]
The collaboration worked because the experiential asymmetry was total. Hilderbrand had spent three years receiving dispatches from inside an institution she could not enter; Shelby had lived it. That gap was not a problem to solve but the condition of the project.
She went to a very fancy and snobby New England boarding school. I went to public school. So we wrote it together.
Hilderbrand has been direct about who the book is for and what question it is actually asking. The boarding school is the container; the subject is a generation.
I think it’s really about... coming of age as a Gen Z person in the 2020s. That’s what it’s really about. It’s really about what is growing up like now, what is the boarding school experience like now? [paraphrased from audio]
She has also pushed back against readers who might approach the book as a younger audience’s genre. The Nantucket novels carry adult themes, but Hilderbrand wanted to be explicit that moving to a school setting did not mean softening the content.
It’s not Young Adult. If anything, it might be more adult than my summer novels. There are adult themes and language.
Part of what generates those themes is the architecture of boarding school life itself: students and faculty sharing the same physical space around the clock, with no afternoon exodus to reset the social temperature. The intensity of that proximity, she has said, is exactly where things go wrong.