1,000 days of logging my life
How I finally managed to maintain the daily practice—and why you should too
👋 Hey, it’s Matt. This is Working Theories, the weekly newsletter where I share stories, ideas, and frameworks for accelerating your career or business.
For as long as I can remember, I’ve been enamored with the idea of a daily journaling practice. It has always struck me as one of those atomic habits—a simple daily act that compounds over time, magically unlocking creativity, increasing mindfulness, and deepening understanding of oneself.
Unfortunately, I’m inherently lazy and lack the discipline to stick with something like that for more than a week. I admire those among us who rise before the sun each day to sip their pour-over coffee while filling their Moleskine with their innermost dreams and reflections, but I’ve accepted this ain’t happening for me.
Still, I’ve never been able to shake the feeling that I should do something.
I’m not sure what prompted me to start my current process back on New Year’s Day 2021. Perhaps it was stumbling across yet another Stoicism threadboi tweeting about how Marcus Aurelius wrote in his diary each morning from a tent on the frontlines of war in Germania. More likely I was inspired by Austin Kleon. Or maybe I was simply caught up in the spirit of a new year.
Whatever the reason, I decided to try something so simple that even I could do it every day. And it worked! I’ve managed to maintain my daily log for more than 1,000 days.
What follows is how I got started and what I’ve learned along the way.
Choosing a format
I knew an analog tool would never work for me. My office is littered with fancy, half-used paper notebooks; despite my love for such items, they tend to devolve into nothing more than repositories for doodles and scratch math.
As for digital options, I once maintained a Notion “journal” for a few months, but since Notion is primarily a tool I use to run my business, I would inevitably open it and get lost in a work task. I’ve also tried journal-specific apps like Day One and while I thought it was great, it was yet another app I had to remember to open.
I landed on Google Sheets for my daily log because it’s a free, low-friction tool I can access anywhere. Plus I have been using it for personal things like budgets and weekly reviews for more than a decade so I knew it was more “sturdy” than other digital options.
The process
My daily log is intentionally simple. It has eight columns, but I only update three of them manually:
Log Entry
Sleep
Daily Score
The log entry is nothing more than a few sentences about what I did the day before. Here is my very first entry:
Kid free morning with Caroline. We walked Leo and got bagels. She went to pick up kids in afternoon, leaving me with an empty house all day. Got lots of work done then watched bowl games and basketball.
The sleep column is how many hours I slept the night before. I don’t own a fancy tracker so this is just my best guess, but it’s directionally accurate.
The daily score is (obviously) subjective and I have no idea if the scale is statistically sound, but it works for me. I don’t overthink it, quickly rating based on how I’m feeling that day. (My average is 1.183 if you’re wondering.)
The additional five columns are:
Number (1 to 365)
Date
Day (Monday, Tuesday, etc.)
10 Day Sleep Average
10 Day Score Average
Most of these are self-explanatory. I like numbering the days because it gives me perspective as to how far along I am into a given year and it seems to help me fight that “time flies” feeling (more on that later).
All of these cells populate via formulas or autofill and I added some basic conditional formatting that gives me a quick visual warning if I am veering into sleep debt or a stretch of poorly rated days.
Why keep a log?
Occasionally I add commentary to the daily entry about how I am feeling, but for the most part it is nothing more than a record of what happened each day. This means I capture a lot of things that seem meaningless or mundane in the moment, but over time as I review the log entries, patterns emerge and I am able to extract significance from an event or a period of my life.
When I filter the log by score, additional trends emerge. I can see at a glance which activities (or lack thereof) lead to higher or lower scores. Recently I’ve begun experimenting with AI to take this idea even further.
I dumped my entire log into ChatGPT and asked it to identify any patterns from my higher-rated days.
Here’s what it said:
On your best days, there's a clear mix of rewarding work, personal hobbies, and genuine connections with people. Activities that combine your love for writing and tech often lift your mood. Additionally, exploring spiritual and philosophical topics, combined with spending quality time with those you care about, contributes significantly to an amplification of positive sentiment.
I never told ChatGPT that I enjoyed writing or had an interest in tech—and honestly I’m not sure I’ve ever articulated the tech interest to myself before, but it’s definitely true.
Next I asked it to look for patterns in my lower-rated days.
Interruptions in routines, reduced focus, less exercise, and an increased sense of being overwhelmed, potentially stemming from deviations in expected work outcomes or external stressors were present on lower rated days. Additionally, the emotional toll of interpersonal conflicts, even if minor, seems to have a profound impact, overshadowing other positive aspects of the day.
I knew most of this already—I crave routine and I hate conflict—but it was a nice reminder. Seeking a bit more, I asked it to go deeper and look for any additional patterns that might be less obvious.
The results were impressive:
A secondary pattern is the pronounced effect of unmet expectations, whether they relate to productivity, interpersonal dynamics, or personal goals. There's a clear linkage between ambition and satisfaction; when high-set goals aren't achieved, the day's rating often declines. In essence, your momentum and sense of achievement seem to be crucial determinants of your daily contentment. While external factors like weather or minor inconveniences appear in the logs, their impact is less substantial than the internal metrics of relationship harmony and personal accomplishment.
Instead of manually poring over years of notebooks to find such a nugget, ChatGPT found it in seconds. It then recommended a shift from a focus on striving and goal setting to one of mindfulness and gratitude—something I’ve been contemplating and trying to put into practice ever since.
Of course, sometimes ChatGPT goes too far. Here it is with a thinly veiled suggestion I limit my pizza intake:
On -2 rated days, there's a common occurrence of eating both dairy and gluten, often with reduced exercise.
Slowing down time
While it helps me with pattern recognition and self-improvement, my primary motivation for maintaining a daily log is more immediate and poignant: it anchors me in the swiftly passing moments of my day-to-day life, particularly those involving my rapidly growing children.
In other words, my daily log helps me slow down time.
At the conclusion of every month, I read each of that month’s daily entries. By starting at the bottom and pressing the ‘up’ arrow on my keyboard, I can read the entire thing in about five minutes. It’s astounding how this simple act always triggers memories and highlights that I would have forgotten otherwise.
As I scan through the log I am transported back to a night where we cooked homemade pizza, a walk with my daughter where we saw a hawk swoop in front of us, or a game of catch with my son where we found a half dozen baseballs in our neighbor’s ivy patch.
It’s also fun to go back even further when I feel like it.
Do you remember what you did on May 7th, 2021? I don’t either, but I just looked it up and I now know that I read to my son’s kindergarten class, went to the gym, ordered Chinese food, and watched The Mitchell’s Versus the Machines with my family.
I believe that keeping a daily log has also helped me become more observant and present throughout the day. There are many times where something happens and I think, “that would make a great log entry.” The moment might not make it into the log, but at least it didn’t go unnoticed.
Logging my daily life has added a richness to the progression of time while also tethering me to the reality and significance of the present moment.
That’s certainly worth the three minutes a day it takes me to do it.
Great read!!!
Glad I read this. I have the same issue of having notebooks and don't use them regularly for journaling. Will try this method you wrote about. :)