I was in the loft clearing out some other stuff when I came across some of my old diaries. There were about 12 in total – a small number of pocket diaries and about ten journals. These spanned the period from the early 1980’s right up to the 2000’s. Some were complete and others had only a few entries but all were a fascinating insight into my life.
For a number of years now I have been using the Day One app to keep a daily journal. I try to also include a picture to go along with each entry to give some colour to the text. Doing this electronically means that it is easy to search and you get nice features such as “On this day” allowing you to quickly and easily see what you were doing on this day over the years.
I decided that it would be great to get all these entries from the paper diaries into the Day One app…

Why do this?
From a personal point of view my motivation for doing this was simply that I felt that it would be interesting to look back upon. Day One’s “On this day” feature allows me to easily see not only what I was doing a year ago but as much as forty years ago. It’s quite amusing to be sitting reading an entry thinking that 45 years ago I was doing my Technical Drawing ‘O’ Level!

From a Family History point of view it might, I hope, be of interest to future generations. I’m no Pepys but the diaries do give a snapshot of my life through my teens, university, finding love, marriage, having children, work and, finally, retirement.
How did I do this?
The thought of transcribing a lot of paper diaries was pretty daunting so I tried a few methods as follows.
By AI Transcription
I tried snapping an image and then running it through AI to read my handwriting and convert to text. I had hoped that this would be a quick and accurate way to get the entries into text. However, there were a number of issues with this:
- Any extra text, such as the date on the page header, was also included in the text
- Turns out AI has difficulty reading my handwriting too!
- The hallucinations could be bad and funny. It didn’t know of the “Peppard Road” and changed it to the “Peppa Pig Road”!
All of this meant that it became a longer process than I expected. I had to snap the page and then crop it to make sure only the handwriting was included. Then, I would run it through AI to get the text. Finally, I would have to read the entry and correct any mistakes made, and there would be quite a few.
After a while I found this to be too much of an overhead and so knocked it on the head. I should say that AI is improving all the time and so it might be worth revisiting this to see if it works better for you.
By Hand
This left typing in each entry manually – gulp!
I considered doing this a number of ways:
- Doing today’s date for all the diaries. With a dozen to do, this proved to much.
- Concentrating on one diary at a time and starting from 1st January. At a page a day for 12 diaries that would have meant 12 years to complete the project.
What I have done is to actually do at least two pages of the diary each day. Some of the older ones also have Saturday and Sunday on one page which makes transcription slightly quicker. It still was a mammoth task.
The way I have worked is to sit with the diary to one side open at the page I am transcribing, read a block and then type it directly into Day One.
My typing speed isn’t too bad but I am definitely not a touch typist and, it turns out, I don’t have a very large short-term memory buffer to hold large blocks of text!
Once I had completed a page I used a tool called Refine (similar to Grammerly) to find any grammar and spelling mistakes before reviewing to decide whether to keep the suggested change.
It is time consuming and, to be honest, I’m surprised I’ve stick with it to the end!
From Other Sources
I don’t have diaries for every year but I did have a complete run from 2009 – 2013 and 2015 – date. Why I didn’t do 2014 I have no idea but it was frustrating to have a year missing from what would have been a 17 year run.
Obviously, I couldn’t go back and write the missing entries but I did want to have something for this missing year. Google Calendar to the rescue!
Turns out I do have a record of what I was up to in 2014 as I have my calendar entries. It’s not perfect but paired with pictures for the same period it does help.

Other Considerations
Here are some of the other things that I have learned while doing the transcription.
Context
As I read back the diary entries I have found myself scratching my head at a name I don’t recognise or an acronym that makes no sense. If they didn’t make sense to me how was anyone else going to make sense of them?
I have decided that once this project is finished, currently I am on track to finish the last of the diaries by the end of 2026, I am going to create a document explaining all the people, places and other items that are likely to confuse.
I see this like a story plan a author might use to keep key people and dates in mind to ensure consistency. However, in order to create it, it does mean reading back 7,500 diary entries…
Revising History
Another question that has come up is should I make any corrections such as for grammar and spelling?
My diaries are littered with mistakes – some through writing without thought and other through my bad English. I laugh at the words that I couldn’t spell then and still can’t spell now but should I correct them?
In short, yes I have. Partly because some are very glaringly wrong and partly because these days mistakes are highlighted with wiggly red lines below them making it clear it isn’t right.
Backup
As ever, keeping a backup of your data is vitally important and that apples to your journal/diary too.
Here’s what I do:
- Once a month I export my journal to a format that might endure. I have chosen PDF for this as it preserves text, pictures and formatting but you may prefer to also export to plain text.
- Keep the old diaries! Not only do they serve as the source material they also give an insight into handwriting, doodles and other annotations you might have made.
Follow that and you won’t go far wrong.
As I write this I have just started transcription of my last diary and will be finished by the end of the year. It will be a relief but, I feel, worth the effort.


