On this day journaling means rereading the entry you wrote on today's date in previous years, then adding this year's entry alongside it. Each date becomes a small anniversary of itself, observed in your own words.
Some apps do a shallow version of this. Every so often, a photo from years ago surfaces on your screen: a younger you, doing something half-forgotten. It's a small feature, almost an afterthought, and yet many people find it genuinely moving.
There's a reason for that. And it's not just nostalgia.
What does on this day journaling look like?
Here is a real-shaped example. Imagine opening your journal on October 14 and finding this above today's empty page:
October 14, three years ago: First day at the new job. Got lost finding the office kitchen. Everyone seems kind. Exhausted.
October 14, two years ago: Presented to the whole team today and my voice didn't shake. A year ago I got lost finding the kitchen.
October 14, last year: Handed in my notice. Terrified and certain at the same time. Funny that it's the same date again.
Then you write this year's entry, knowing your future self will read it on some October 14 to come. No other habit gives you this view of your own life. A photo library shows you what things looked like. A journal read this way shows you what they felt like, and how the feeling changed.
Perspective is the rarest thing
We live inside our experiences. When something is happening, a difficult relationship, a career transition, a period of grief or joy, it's very hard to see it clearly. We're too close. The future feels uncertain, the stakes feel high, and our emotional state colors everything we perceive.
Time provides distance. And distance provides perspective.
Reading what you wrote five years ago, you see things your past self couldn't. You know how the story turned out. You can see which fears were unfounded and which were worth taking seriously. You can notice patterns in your own thinking that were invisible at the time. And you can see, sometimes with startling clarity, how much you've grown. That noticing is the heart of journaling for self-reflection, and the on this day format does the hardest part for you.
"The curious paradox is that when I accept myself just as I am, then I can change."
Carl Rogers
What "on this day" actually shows you
The specific power of seeing what you wrote on this exact date in previous years is that it creates a kind of time-lapse portrait of your life. Not the edited, curated version you present to the world, but the raw, honest, daily version you recorded for yourself.
You might discover that you've been worrying about the same thing for three years and that it still hasn't happened. You might find that a relationship you barely remember once occupied your every thought. You might find a version of yourself who was braver, or more hopeful, or more uncertain than the person you've become.
All of this is useful. All of it is information about your own life that no one else can give you.
How do you build your own on this day archive?
You need two things: short daily entries, and a format that resurfaces them by date. The classic way is a paper 5 year journal, where each page holds the same date across five years. The digital way is an app built around the same idea. YearDiary is a private digital 5 and 10 year journal for iPhone, iPad and Mac that shows what you wrote on the same date 1, 5 and 10 years ago, so the looking back happens automatically every time you open it to write.
Either way, the entries themselves can be tiny. One or two lines about an ordinary day is enough, because the value is not in any single entry. It is in the stack.
The idea has a name people search for in a few different ways. Our guide to the personal this day in history journal covers what separates your own record from an almanac, and if you currently rely on Facebook or Timehop to do this for you, it is worth reading why you should keep your own on this day memories instead. For the reader's side of the habit, we look at what happens when you read a year-old entry and why it so rarely matches the version you remember.
The compounding value of consistency
A journal you've kept for six months is interesting. A journal you've kept for five years is something else entirely. The value of a journaling habit doesn't grow in a straight line. It compounds. Each year you write adds a new layer of perspective to everything that came before.
This is why people who keep journals for decades speak about them with such warmth. It's not that the writing is particularly good. It's that the archive, over time, becomes a mirror unlike any other. One that shows not just who you are, but who you were, and how you became the person writing today.
What to do with what you find
When you read an old entry, you don't have to do anything dramatic with it. Sometimes the right response is simply to sit with it for a moment. To acknowledge the person who wrote it. To be grateful, or forgiving, or simply curious.
Sometimes the right response is to write something now. A reply to your past self, or a note about what has changed. The conversation between who you were and who you are is one of the most interesting conversations you can have.
You can also write in the other direction, deliberately. A letter addressed to your future self is an entry written to be opened later, and returning to the same handful of dates every year turns birthdays and hard anniversaries into a record rather than a blur.
The entry you write today is a gift to your future self. In a year, in five years, in a decade, they'll read it and understand something about themselves they couldn't have seen any other way.
That's worth five minutes a day.