I’ve been journaling for over 15 years (and almost every day for the last 10).
At first, it was a way to track how I spent my time.I’d log everything I got done, reflect on how productive I’d been, track my workouts, etc.
But one evening when I was re-reading entries from the previous year, I realized something. The most valuable entries to me were the ones that shared stories of something my kid said, thoughts I had about a conversation with my wife, or reflections on a challenge I was working through.
But those entries were harder to surface because they were buried under a mountain of to-do's and status updates.
For a while, that kind of journaling served me. It kept me accountable to not waste my days.
But in my current season, I’d rather spend my time reflecting on moments worth remembering rather than just giving myself a performance evaluation everyday.
What I'm focusing on
I'm implementing a practice called Homework for Life.
It's a concept from storyteller Matthew Dicks. The idea is simple: when you journal, write down one story-worthy moment. It can be a moment of change, realization, or something that stuck with you.
It doesn’t have to be big or dramatic. Often, it’s small moments that carry the most meaning.
For me, an example of this practice was one night last year. I got home late from Bible study and pulled into the garage. As I got out of the car, I noticed my toddlers’ two little bikes sitting in the corner.
For a split second, I imagined my future 50-year-old self standing in that moment, wishing I could return to it; return to the season of life when those bikes were still there, when my kids were still small.
The thought only lasted a second, but writing it down made it more permanent. It’s one of those things I wouldn’t have remembered if I hadn’t taken a moment to write it down.
Everyday?
Additionally, rather than journaling every single day, I’m writing just 2–3 times a week. This shift helps me avoid the trap of just listing what I got done.
Instead, I reflect on the broader strokes of my week, thinking back to the meaningful conversations, small realizations, or moments that I want to remember.
Paper vs. digital?
Paper Journaling: There’s something special about seeing your own handwriting years later. I have journals from 2007 when I was in my 2nd year of college. Had those been Word docs, who knows if I'd still have them.
Digital Journaling: The big advantage here is searchability. And being able to document more stream-of-consciousness if you type fast.
My preference:Personally, I prefer paper journaling, but at the end of each year, I do a digital reflection where I compile the most meaningful entries into one annual review Notion doc. I can write more about that process if you're interested. Reply and let me know.
And of course, you can always print out any digital journals.
Helpful prompts
If you’re not sure what to write, try these prompts
- What’s one moment from today that surprised me?
- What’s a conversation I want to remember?
- What’s something I noticed that I might otherwise forget?
Journaling is time travel
The most useful part of my journaling is that I time travel. So every morning, I talk to myself 20 years ago, I talk to myself 10 years ago, and I talk to myself last year.
-Penn Jilette
I love this perspective on journaling. Jilette actually talked about this on the Tim Ferriss podcast and how he re-reads old journals every day.
Busting out my old journals to take the photos you see above transported me back to moments I had completely forgotten about, particularly those before 2010!
If you’ve been journaling for a while (or are thinking about starting) I hope this inspires you to do it in a way that serves you in this season of life.
And if you're a podcast listener, I went in depth with my journaling practice on the Focused podcast here.
Recommendation of the week
This app is great if there's an article or newsletter you want to 'listen' to on your commute or walk.
It's created by ElevenLabs which is the leading AI company when it comes to AI generated voices that sound super natural and real.
Just drop a link to the article or paste any text into the app and it'll read it in the voice you've picked out.
What about you?
Do you journal? Or plan on starting?
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Thom Gibson
Founder of WFH Dads
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