I have finally gotten around to going through my filing cabinet, getting rid of what paper I can get rid of, and scanning the rest. (This in itself will be a topic for a future post.) When I got started going paperless, I decided from the outset that I’d only worry about new, incoming paper, and not the paper that was sitting in my filing cabinet. The reason for this was twofold:
- I was developing a process to go paperless, and starting with incoming paper made sense, since I wasn’t actually creating new paper.
- I almost never went to my filing cabinet for anything. So why spend time digitizing old paper when I never used it in the first place.
It has been more than two years now, and in all that time, I still haven’t had the need to go into my files. So why start clearing them out now?
Well, I want to get a new desk, and since my files are in my desk drawers, I am forced to go through them. The new desk I want has no drawers because I no longer need them. All of my “drawers” are now virtual.
I’d say that, so far, 90% of the paper that filled my files has been shreddable without having to scan. But I did come across some paper that I thought was worthwhile digitizing: old letters.
Most of these old letters were from my Grandpa. My Grandpa and I were very close and we wrote to one another frequently. He would occasionally type his letters on a battered old Royal manual typewriter, but most of the time, he scribble his letters in his unique chicken-scratch. It was nice to have a chance to scan the letters, for a couple of reasons:
First, I knew I was preserving the letters for much longer than they would be preserved on paper. Second, I tended to re-read them as I scanned them in (for practical reasons, as well as nostalgic ones, as you will see) and it was delightful; like travelling back in time.
Let me describe my process for scanning the old letters, which was just a little more involved than straight scanning, for reason that I will try to make clear. For each letter I scanned in, I went through several steps:
Step 1: Scan the letter
I scanned all pages of the letter to a single PDF file, which then goes directly into Evernote. As I scanned the letters, I adjusted the settings depending on the letter. For some letter, I just did the usual default scanning. But for other letters, letters types on thinner typing paper, I scanned in single-side mode only so that I didn’t end up getting “blank” pages because the text from the back of the page bled through on the thin paper.
I worried that my scanner might have trouble with the very thin typing paper some of the letters were written on, but I had no trouble at all.
Step 2: Update the note in Evernote
Once the letter was scanned into Evernote, I updated the note’s meta-data. This involved the following:
- Changed the create date of the note to match the date written on the letter. If the letter was dated June 11, 1988, I changed the create date of the note to June 11, 1988. I do the same thing for most documents I scan because it makes searching by date infinitely easier.
- Title the note “Letter from [name]”. If the letter was from my Grandpa, the note was titled, simply, “Letter from Grandpa.” If it was from someone else, I used their name.
- Tagged the note. I use a “correspondence” tag for these kinds of notes. All letters get tagged “correspondence” so that I can easily search for them later.
- Filed the note into my Filing Cabinet notebook.
Step 3: Tested the OCR for the letter.
My Grandfather had legendary unreadable handwriting. It was only because I’d been reading his letters for years that I could read them at all. While some of his letters were typewritten, most were handwritten. After syncing to Evernote and doing a few test searches, I found that the letters really weren’t very searchable.
This is no slight on Evernote’s OCR capabilities. A pharmacist who spent a life reading the scrawled prescriptions of doctors would not be able to interpret my Grandpa’s chicken scratches. So, if a letter was not particularly searchable (i.e. all his handwritten letters), I moved on to step 4:
Step 4: Transcribe the letter in the body of the note
In those notes which were particularly hard on Evernote’s OCR, I manually transcribed the text of the letter into the body of the note. I’ve done this on about 10 letters so far. It’s really not a burden as most of the letter are not particularly long.
I now have the ability to search for my Grandpa’s letters (or any letters I chose to keep permanently. I can narrow down a search for my Grandpa’s letters quite easily. I simply search in my Filing Cabinet notebook for any note tagged “correspondence” with the work Grandpa in the title. The result looks something like this:
In a future post, I’ll talk in more detail about how I’ve whittled down the paper in my files to the barest few that I want to capture in digital form. For now, if you’ve been looking for a way to preserve some history, and have already organized all of your family photos, consider digitizing you old letters. If nothing else, it preserves them for the long run and may give you some joy in re-reading them again.
If you have a suggestion for a future Going Paperless post, let know me. Send it to me at feedback [at] jamietoddrubin.com. As always, this post and all of my Going Paperless posts is also available on Pinterest.

Leave a Reply to SuziCancel reply