Going Paperless: Digitizing Old Letters

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:

  1. I was developing a process to go paperless, and starting with incoming paper made sense, since I wasn’t actually creating new paper.
  2. 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:

  1. 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.
  2. 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.
  3. 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.
  4. 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:

Letter Search

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.


  1. Just wanted to extend my thanks for this article as it`s most timely; after the recent passing of my father, we`re downsizing my parents home and having the materials scanned means saving forever. It also means being able to share the items with scattered family members as well as scrapbooking the original for my mother.

  2. Thank you for your well thought out process! This – preserving what is precious to us – is what we all want to do, even more than whittling down the daily paper handling.

  3. Great post! I just moved and have boxes and boxes of letters and cards. I’ve been wanting to get them online but wasn’t sure how to go about it. Now I do 🙂 I love the thought of having them online because then if there’s ever a fire, flood or other unforeseen thing they are safe.

  4. Hah that letter from your grandpa is easy to read, you should see how my great uncle writes letters from Australia so only my grandmother (his sister) can read the letter to us. =D
    Oh and thanks for this guide i’m bookmarking it as my grandma has alot of these letters and could become useful in near future. =)

  5. Hi Jamie,

    I do the same with letters and greeting cards for my Evernote account, but I scan and save to jpegs (even if it means multiple images in one note. Evernote doesn’t OCR handwriting within PDFS, only typed text. It will OCR handwriting in jpegs. Discussion here: http://discussion.evernote.com/topic/23940-my-scanned-pdfs-dont-get-ocrd-by-en/

    That’s probably a large reason why it won’t interpret your grandfather’s handwriting — not a weakness in the OCR engine per se, just a PDF limitation.

    Hope this is helpful! I really enjoy your Paperless series posts.

  6. Excellent post! I’ve been digitizing letters between my grandparents while he was in the Army in Europe during WW2. Very useful for genealogy but of great sentimental value to me as well. I’m also trying to think of efficient ways to transcribe them. Am going to try voice dictation and see if that’s any faster than just typing them out myself. Naturally, Evernote is a big part of this whole enterprise!

  7. Hi Jamie – so does this mean you then destroyed the original letters? Was that easy to do or did the emotional attachment to the letters make it difficult?

  8. Thanks for this post! I started with EN 2 months ago and am now uptodate with my recent stuff. Now I’m thinking about filing the memorabilia. I see the benefits in scanning these old papers, but I am unsure whether I will miss the ‘look and feel’ of letters, postcards, stickers, pins, newspaper clips. But I think I will give it a try, without shredding the old papers but file them in the cellar…

    BTW I have been impressed and touched by the lines you wrote about your grandpa. A person who gets such commemorative words will never be forgotten.

  9. It is very wise to scan the letters, and I hope that I will do the same before it’s too late. But I sincerely hope that you and others here preserve the originals in a safe environment (special acid-free envelopes, and no plastic folders).

  10. Scanning is a duh. What interests me is that you felt you could dispose of 90% of your paper files because you haven’t needed them recently. In my experience, I might not need a file for a few decades, and then I need it again and am glad I kept it. The old files put me in touch with who I was all those years ago, both intellectually and vis-a-vis the other areas of my life.

  11. Ok, time to freak everybody out a bit and stretch our imaginations.

    Here’s my thoughts – if all my emails, blogs and journals are combined into a collective database and kept their for long enough – eventually cheap AI will arrive that will be able to recreate a model of my psychological profile that would respond to questions in the same manner that I would within a reasonable statistical variable say 3 x Standard Deviations.

    The HMI interface could be presented with a virtual model of my face… and maybe my great grand children could ask my virtual self about what life was like back in the 20’s and 30’s even in the olden days – 1980’s!

    The virtual me would also learn about new things and build upon the existing information and while my 7 year old great grandchild is depressed about something, or too afraid to bring up something with his parents, he can call up the “grand papa” app / program and talk with it.
    A lifetime of hard gained wisdom, available to the young child at the touch of a button.

    The simple act of scanning letters is a basic building block of something much bigger.
    Handwriting style alone reveals significant insights into personality traits.

    My philosophy is “capture information first – ask questions later”
    You never know what technology will be available to extrapolate and build on the information you have captured … even if it’s not in your own life time.

    1. A very interesting idea. I can think of a variation that I feel could probably be done today. It would be to capture hours of video of your face while you read selections of text that brings out various emotions – inspiring stories, jokes, serious debates, etc. Then develop a markup that specifies emotional characteristics and an app that will have you reading marked up text with the indicated emotion .

      1. James, I a big fan of the Quantified Self movement. One of the things they try to tackle is capturing emotions from day-to-day. I’ve read some of the ideas on this but I think there are two problems, one with the ideas and one with me. With the ideas I’ve seen for capturing emotion: none of them are automated in any reasonable way. Automation is critical because if it isn’t automated in some way, I’m less likely to capture it. Then there’s the issue with me, which is that since emotion isn’t as readily quantifiable as other things (blood pressure, steps taken, words written, emails sent, places visited, calories eaten, etc.) and is often too subjective, I don’t think capturing it would be particularly useful. At least for now.

        1. Jamie – I’m not familiar with this Quantified Self movement you mention. Thanks, I’ll look into it. You’re right to be a bit skeptical about the Idea I mention. I’m sure there’d be considerable noise in any set of physical characteristics one might select to provide a measure for emotion, but since our brain can do it to a certain degree I think some information must be there. It would be an interesting line of research, perhaps starting with attempting to train a neural net on audio voice tapes. Sounds like something DARPA might find interesting. I would not be at all surprised to find it’s already been done, or at least attempted.

  12. Hi Jamie,

    I really like your blog, very inspiring.

    I was wondering if you also use Google Drive or DropBox? As it seems you put all files and info directly into Evernote, what kind of personal files/documents (vs. OS files or programs etc.) do you still have on your harddrive and/or google drive or dropbox? Photos? Movies? Something else? Do you have many duplicate files. E.g. where would you put your College diploma? Evernote? HD? GDrive? Everywhere?

    Thanks a lot

  13. Enjoyed your blog discussing eReader Use Cases – a very entertaining read. My one comment is that you seem to refer to both the IPad App and the Kindle without pointing out that they differ in some significant ways. Please correct me if I’m wrong – I’m no expert in these matters – but I believe one of these ways is that the Kindle does full text indexing over all its contents while the free IPad App doesn’t. So doing a keyword search from the home page of a Kindle devoted to a large professional library provides a much more useful result (a list of hyperlinks to the entire content that can be drilled into and backed out of) than can be obtained in any way using the App. — Jim Cook (jcook@ieee.org)

  14. I have the same question as Suzi, even though I’m coming late to the conversation. I had a close relationship with both of my grandmothers, and I have great quantities of paper correspondence sitting in a large box. I do want to preserve these documents (largely because the cat has figured out how to get into the box and likes to sleep inside of it), but will I be able to bring myself to recycle the originals?

    Maybe you’re less sentimental than I am, but the fact that you’ve kept your grandfather’s letters all these years leads me to believe we might be on the same page…?

    I did have the unfortunate experience several years ago of a new dog (husky-wolf hybrid) eating one of my father’s letters to me, so I am definitely pro-digitizing.

    1. Jennifer, there is absolutely no reason to recycle the originals if you are uncomfortable with doing so. (I have not yet done so, in part because of the lingering memories of the close relationship I had with my grandfather.) Going paperless is not an all-or-nothing project. There are degrees of value we put on paper, and sentimentality is only one of these degrees. Do what makes you feel most comfortable. For me, I’m just glad knowing that even if the paper goes away some day, what’s written on the paper is preserved in Evernote.

  15. Old letters are very important to most people especially when coming from family or friends because they usually contain great memories and sentiments. Thanks for showing us how to digitize letters. This is so useful since I also have lots of letters to digitize.

  16. what kind of scanner did you use? i want to do exactly this project; don’t currently own a scanner and have many letters to scan (front and back sides). any suggestions would be great!


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