Once upon a desk, there was always a notebook.
In the older photos of my computer setups that I shared recently, charting the rise and fall of my monitor empire, you can usually spot a notebook or journal somewhere on the desk. Often it was a trusty Pukka Pad. Occasionally, when I was in my more self-consciously pretentious moods, it was a Moleskine or Leuchtturm 1917. Between 2017 and 2023 it tended to be a Self Journal, as I had been lured by their science-backed system. These were always nearby, always half-full of scribbled goals, tasks, reflections, and random facts and figures about my day.
“That’s something else that has changed,” commented Jocelyn on reading my last blog post, “you don’t have those journals on your desk any more. You could blog about that.”
Indeed, she was right. I went digital.
And I haven’t looked back.
Why I Abandoned Paper
That past version of Ian believed in paper. He liked the ritual. The tangibility. The act of tearing off the bottom-right corner of the page each day. The optimistic sensation of turning a fresh page and somehow pretending that the next thirteen weeks would be transformational.
But around early 2023, I drifted away from those paper notebooks. Not because I stopped capturing my thoughts or trying to organise my life, but because I realised that I needed something more effective and flexible than paper. Something searchable. Something that didn’t require me to keep rewriting the same handful of tasks across multiple different pages while pretending that I was being productive or “affirming” my goals (oh please).
There are a few things I still admire about paper. It doesn’t distract you. It doesn’t crash. It won’t show you a notification while you’re writing. That’s about it.
But paper doesn’t scale. Not over years. Not across locations. Not when you’re trying to remember whether you wrote your brilliant idea in the grey notebook in Q3 2022 or the navy one in Q1 2021.
I increasingly became aware of the shortcomings of relying on paper:
Search — You can’t Ctrl-F a Pukka Pad.
Repetition — I found that I kept rewriting the same to-do lists, rephrasing goals, moving half-done items to the next page like some paper-based Sisyphus. If nothing else, I suppose this was good practice for managing Scrum sprint backlogs.
Speed — I type much faster than I write, and my handwriting has never been what you’d call archival quality, more like an ECG during a wasp attack.
Access — Paper can’t sync between devices, share with colleagues or family, or ping you when you forget what past-you was supposed to remember.
I wrote in notebooks for years. Then I spent much of the last two years painstakingly digitising the contents. That process alone should tell you everything.
The Digital Tools I Use
It’s perhaps no coincidence that my migration from paper to digital occurred at the same point in my life that I was also migrating from Windows/Android to the Apple ecosystem. Everything is now so effortless and reliable that it dramatically lowers the friction involved in picking up a device to write, or relying upon it for calendar and todo lists.
Some of the use cases for which I once relied upon paper are now handled by:
Apple Notes — handles my ad-hoc notes: things I’m working on, jottings from conversations, conference notes, snippets of things I’ll probably forget, shopping lists, software keys, ideas for things to blog about.
Apple Calendar — replaced the scheduling bits from the old Self Journal layout.
Apple Reminders — took over the to-do list - sparing me from the paper-era ritual of shamefully copying undone tasks across to a new day as a form of procrastination.
But the real shift — the big change — was moving the meat of my personal journalling and logging into Day One.
Day One as Archive, Memory and Mirror
Day One is ostensibly ‘just’ a journalling app. But I use it as an archive, a logbook, and — increasingly — as a structured memory system. My exocortex.
Here’s what now lives insides mine:
A daily journal — part diary, part log, part thought-dump.
My work notes — a brief summary of what I do each day. This comes in very handy at the end of the month when I can ask ChatGPT to summarise it all into a ‘Consultant Service Report’ for submission along with my timesheet.
My daily Wordle score, because I am a creature of habit, and I like to know when I last scored a 2, or confirm that FIFTH really didn’t come up prior to Wordle 1,427.
Lists of the books I’ve read, films I’ve watched, and a compendium of favourite English words that I’ve encountered.
Every hill I’ve climbed, tagged and timestamped.
Digitised entries from years and years of paper journals (an ongoing work in progress).
My old online journal from the 1990s.
Each entry captures metadata automatically: weather, location, time, word count. And thanks to the “On This Day” feature, I get a moment of serendipity every morning — a glimpse into who I used to be one, three, or ten years ago. It’s part nostalgia, part audit, part gentle nudge to notice the passage of time.
This isn’t just digital journaling. It’s offloading my memory into something structured. Not quite a second brain, but perhaps a decent backup of the first.
The Tooling (Because of Course)
Of course, you don’t get an exocortex by starting from scratch. I wanted continuity. So I wrote some software — which you’re welcome to clone on GitHub — to import:
Facebook archives
Tweets
Old WordPress blog posts
CSV logs from scattered corners of my life, including my opinions on the 1001 Albums You Must Hear Before You Die, which I worked my way through between 2019 and 2023.
I wanted to gather as much as possible. Not only because I’m nostalgic, but also because I like completeness. The act of collection is its own kind of reflection.
Regrets, Caveats and Mild Anxieties
I’m still finishing the digitisation of my old Self Journals - a long, slow process involving deciphering my own handwriting and judiciously choosing not to transcribe lists of Jira tickets for projects that I’m no longer working on. I hope to finish this quest by the end of this year. It makes me quietly wish I’d gone digital much sooner.
Day One is now owned by Automattic, which gives me a slight itch. I think I trust them, mostly, but I don’t particularly love platform dependency. That said, the app is robust, actively maintained, and the export options are good. I keep backups. I’m not losing sleep. The subscription is reasonable. Certainly cheaper than Self Journals.
The Bigger Picture
This shift — from notebooks to Notes, from scribbles to searchable logs — isn’t just about productivity and efficiency. It’s about being able to easily find myself, years later, and remember not just what I was doing, but how I was thinking. And to use those insights to inform how I behave today.
So Day One hasn’t exactly changed my life. But it has helped me notice it more clearly. And unlike a shelf full of dog-eared journals, it never needs dusting.