When Michael Naylor tackled the last papers he’d inherited from his father, he found a leather-bound, green notebook in nineteenth-century handwriting and packed with pressed leaves. It belonged to his great-grandmother’s branch of the family, but its author was a mystery.

Had it been in the family long?
Yes, my father, who died twenty years ago, had inherited a tin box of papers from his own father, which was labelled “Mrs Naylor”. It also included some other handwritten family notes and old newspaper clippings which belonged to my great-grandmother, Nina Mather Naylor.

Had anyone tried to transcribe the diary before?
No.

What gave you the idea to tackle it yourself?
I had no idea who had written the diary and I had some time, thanks to recovery from double-hip-replacement surgery. But I couldn’t learn who wrote it until I could actually read it.

How did you first hear about Leo?
After several “ordinary” AI tools kept inventing words, I searched for something better. Google served up Transkribus and Pen-to-Print but neither worked for me. Somewhere in those results was Leo. It transcribed the first nine pages nearly perfectly and so I went ahead and transcribed the rest of the diary.

What challenges did the diary itself present?
The diary is in reasonably good physical condition but some challenges included faded ink, bleed-through (“ghost” text), Victorian spellings (the long-s), and cramped lines. The writing style also presented difficulties. I’ve been told by the few who have read it that it resembles that of Jane Austen!

Any “aha” moments?
Leo’s transcript let me cross-reference birth dates from family-tree records, including where the diary’s author refers to her father’s birthday and her mother’s anniversary of death. Eventually, I narrowed it down to two women, before reviewing the part of the transcript where the author described being consoled for toothache by a young neighbour who refers to “poor Charlotte”. That was the breakthrough moment. This was Charlotte Needham Medley (1816-1903).

Why is the finished transcript a special wedding gift for your daughter?
My daughter is also a Charlotte, so I decided to gift the original diary accompanied with a bound transcript and historical notes as a wedding present to her.