Journaling

January 05, 2020

Ever since 2012 I’ve been keeping a personal journal. It’s a pretty loosely defined concept in my eyes: just a bunch of text associated with a day of the year. Yet out of this simplicity has emerged one of the most important tools I have in my life for self-reflection and personal growth. It’s a habit I think everybody could benefit from picking up, and hopefully this post can serve as a bit of inspiration for those who have thought about trying it, or even some new ideas for those who are already into journaling.

For me, journaling comes in the form of a bunch of text files sitting in a folder on my computer; something like 2020-01-03.txt . Each file has a title on the first line, and the rest is entirely freeform text. The length and quality of each entry varies greatly from day to day, ranging from a few words to multiple thousands. I usually average 5-7 entries per month: far from a daily habit but still frequent enough to get the general idea of what I’m thinking about at some point in my life.

The medium you choose for journaling shouldn’t matter too much, whether that be physical notebooks, some note taking app, or just plaintext files like mine. The most important variables are ease of use and confidence that what you’re writing will be accessible over a long time horizon (think decades!). Since I move around a lot, I trust digital formats more than physical formats for durability. I also really enjoy some of the benefits that come from digital text: the ability to search, easily access all entries, and run various forms of statistical analysis on the text. Whatever you choose is great as long as you reliably write in it and are confident entries will stick around in the long-term.

As for the entries themselves: sometimes it’s just a few bullet points of what I did a given day, other times it’s a longer-winded analysis of some event in my life. When I’m traveling I generally try to get at least one or two entries in with thoughts about whatever city I happen to be in. Especially fun entries are ones that attempt to predict the future: whether that be how my own life will pan out or how a particular geopolitical event might unfold (of course I incorrectly predicted the 2016 election). Sometimes I’ll even ask my future self questions, left open until a few months or years later when I rediscover the prompt and fill it in. I’ve found leaving open questions therapeutic during hectic times of my life, especially when I’m nervous about how things might pan out.

Writing might seem a bit tedious and boring for the first few months, but keep at it. As time goes on you’ll find that entries become more and more interesting to read the farther away they become. Over the course of years you’ll start to notice patterns: the origins of thought processes, life decisions, and relationships that have emerged and dissolved in your present-day life. You’ll get a glimpse into the mind of a person that may seem oddly different than the person you are now (or sometimes surprisingly similar).

This is where I’ve found much of the value in journaling. If done correctly, it’s incredibly powerful tool for self-reflection and growth. Sometimes I’ve found myself reading an entry and thinking my former self sounded like a real jerk. That is growth! Other times I’ve looked back and read myself preaching about some ideal or value I was passionate about, and realized how little I care about it now. At that point, I ask myself if it’s positive that I’ve lost track of this ideal, or perhaps I’ve regressed and need to rethink my values of today.

An easy-to-spot source of growth within my journal is amongst the entries I’ve written in Spanish. Reading through past entries, I’ll feel myself getting more and more frustrated at the obvious mistakes in both grammar and vocabulary that I made. Learning a new language has been a particularly slow and grueling process for me, so any sign of progress is especially motivating. If I’m feeling bad about my level of speaking, I can go back and read journal entries for a sign that things really are moving in the right direction, even though this progress is slow moving over the course of a decade.

Journaling has also helped me uncover the seeds of deeply-rooted ideas that have had major impacts on my life. Since 2015 or so I’ve been an avid (and impulsive) traveler. Only recently did I stumble upon an old entry I had written back in early-2013, well before I had left the United States for any meaningful amount of time:

Seriously, future Steve: if you have the means, go somewhere. Just pick a place and book a flight. Get some time and just go somewhere new. I really want to book a ticket to somewhere in Europe, I just need some money for it. Maybe this internship over the summer will help out. I think I need this experience.

Maybe I could even live somewhere outside of the US, just for a little while, to see the world from a different perspective.

Looking back now, I took this advice perhaps a bit too literally in the years following, all without remembering that I had written about it years before.


It’s a great little habit/hobby, one that I have many more thoughts on that I hope to share in the future. I’d especially like to elaborate more on the benefits of digital journaling; I’ve derived numerous side-projects from the body of text that I’ve created in my journal thus far. Various forms of statistical analysis, read/write reminders, and a random button have all yielded interesting results that merit their own post.

If you’re into journaling, I’d love your suggestions on how you approach writing, reading, and analyzing yours. Reach out via email or Twitter with your ideas.