Journaling: Analog/Digital

For a few years I wanted to start journaling. I read lots of articles and listed to lots of podcasts that highlighted the benefits of the practice. Intellectually it made a lot of sense, but I was never able to get myself to do it for more than a day or two. I decided to really focus on what might be holding me back, and this helped me to come up with a system that is working for me. The purpose of this post is to share some of the thought process that went into me coming up with my system, and to give some specifics on how I put it into practice.

Abstract / TLDR / Summary

I wanted to write long hand instead of typing, but didn’t want to worry about keeping a journal private. I write long hand, then use the Office Lens app on my phone to scan directly into a designated section in OneNote. I then move the scans into password protected section of the same Notebook. Finally, I shred the paper.

Privacy / Security

I definitely wanted to write long hand, but the big thing that held me back was privacy. I certainly don’t consider myself paranoid –  my journal actually ends up in the cloud. However, I didn’t want to have my journal sitting in some notebook where one of my kids (or wife, or co-worker, or other random person) might read it. Putting privacy notions aside, as an IT guy, the thought of not having a backup was pretty disturbing. Given that a journal is really just text, it seemed crazy to leave it in a form that could so easily be lost.

Analog to Digital

I don’t remember the exact point at which I made the connection between scanning a document into my computer and scanning a journal entry into my computer, but I’m surprised it took as long as it did. I use OneNote pretty heavily, so it seemed like a natural place to store the journal. It just took a quick Google search to learn how to password protect a section of a notebook.


Most people have heard the expression, “Don’t let perfection be the enemy of the good”. For some reason, I allowed all sorts of trivial details about how I should journal hold me back from getting started. What kind of physical journal/notebook should I use? What kind of pen should I write with? Should I write in the morning or evening? What if I run out of things to say? What I realized that I needed to just get on with it. The details didn’t matter – I could just use some trial and error to determine what worked best for me.


I started with a pack of 6’ x 9” unlined memo pads from Amazon. I wanted something unlined, but I didn’t want to use copy paper because I didn’t think I’d have enough in my head to fill a page. Almost immediately I found that I typically wrote several small pages, and that I preferred good old 8 1/2 x 11, college ruled paper.

At this point, the only thing I consider to be really important in paper selection is that the pages be easily removable. This makes is much cleaner to remove the pages without messing up the notebook. I did recently purchase an 8 1/2 x 11 notebook with the spiral at the top, and I really like it. As a right-hander, the spiral in a conventional notebook really gets in the way when I’m writing on the back of the page, which happens much more frequently than I initially expected.


Of course I also thought I needed a fancy pen for journaling. I suppose it was just a search for an affectation of some sort. I bought some disposable fountain pens, since they are at least conceptually fancy. They made me feel cool for a few days, then I realized just how badly they wrote on most paper. I soon found myself just grabbing whatever pen happened to be close by, eventually gravitating to an old Cross style pen that I was given as a groomsman’s gift about 20 years ago. I like the weight and the size of the barrel.


I use a password protected section in a OneNote notebook to store my journal. This could just as easily be done in Evernote, but for reasons that I may write about at some point, OneNote fits in better with my workflow. I create a page for each month, and scan the paper right in.


I used to have a sheet-fed scanner, but now I just use the Microsoft Office Lens app to scan. The app doesn’t let you save the file into a password protected section, so I save it to a different section and copy it over. The scans are perfectly readable on the screen, and while the file sizes are considerably larger than plain text, I expect free cloud storage to grow much faster than I can fill it up.

I then crop the image to get rid of excess white space. OneNote does not have a built-in cropping tool for images, but there is a free plugin that adds this function. Onetastic adds a tremendous number of features to Onenote, and lets you just right-click on an image to bring up a cropping tool.


I try to do most of my journaling in the morning when I first wake up. I start by writing the date and time at the top of the page as a reference point. When I’m done, I’ll scan the page into OneNote. Sometimes I’ll write for a few days, then scan and upload the pages in a batch. Once the pages are safely in the cloud, I shred them. I find that shredding the paper afterwards provides a nice sense of completion to the process.

Occasionally I’ll do a little writing at work if something pops into my head. In these cases, I’ll usually just type directly into OneNote.


The journaling started to pay off in just a few days. I found that forcing myself to write about what was going on in my life, personally and professionally, enabled me to have insights that I simply couldn’t’ tap into just by thinking. It has also helped me to become more action oriented. Seeing the same “I really need to do X” statement written over the course of a few days or weeks often gives me the push to actually do it.

I also found that journaling enhanced my capacity for writing public facing content. I have another site when I post some tech tips, but wanted to start a non-techie blog (i.e. this one). I was reluctant to post things that might be too personal online. As I journaled, I started to recognize that there was a fairly clean line that could be drawn between what was intensely personal versus what could appropriately be shared. It’s no coincidence that after years of wanting to start a blog, I finally started doing it after journaling became a habit.

Finally, my penmanship has improved tremendously. I never had good handwriting when I was younger, and it’s only gotten worse over the years since I use a keyboard for just about everything. I still type much faster than I write, and I don’t expect that to change. However, even in this day and age handwriting is still important, and I am very pleased that I can actually read the bulk of what I write now.

Other Tips

As I write, ideas frequently pop into my head that belong on a to-do list. As a loose follower of GTD, I want to get these ideas out of my head, both to prevent them from being a distraction, and to make sure I don’t forget them. I now make it a point to keep a separate notepad nearby so that I can quickly jot these things down as they come up. I can then deal with them after the journaling session.

I don’t write every day. Looking through my notes I’d say that I write about 4 -5 days a week. I used to worry that meant that I wasn’t doing it right, but there really isn’t a single right or wrong way to journal.

Journaling: Analog/Digital