An Opinionated Guide to the Journaling Habit
1,000 pages and 2.5 years later, my experiment has become a lifetime habit


Last week, Journal #4 hit the shelf, and I realized: I've journaled every single day for ~2.5 years. I've hand-written over 1,000 pages. The consistency was surprising to look back on. The surprise was that before this, I had never been a Reliable Randy, I had never journaled, and I had never stuck to any habit long-term (though I'd tried many times). So, what changed?

It's not a stretch to say that a single book and one wholehearted decision was responsible for all 1,000 handwritten pages. There's some grit and strategy in the credits column too, of course, but it's less than you think. This post is the distillation of my experience, focused primarily on the habit and my best practices for keeping that habit.

So, if you're interested in journaling everyday, or if you just wonder what cosmic benefits would become yours if you did journal everyday, then this guide is for you. I discuss what book and choice started everything, my rules for journaling, as well as the tools I find most useful.

The Book and The Choice

The book was Atomic Habits by James Clear. It offers many practical techniques on how to pick up a new habit or stop an old one, and at the end of reading it, I was bursting with new information on the subject. But, it's not enough to read. It never is. I knew several people who'd read the book, calling it "brilliant" and "life-changing", who did not change their lives at all. They had the theory but never had the practice. I knew I wanted to put this book into practice.

When setting out, it's important to choose a single habit. Starting with several goals is a common, human mistake. "Oh I'll just diet, exercise, and meditate 23 hours a day." Yeah, that plan is doomed. My imagination loved the idea of a skinnier, more flexible, journaling Super-Self, but I told myself that focus is powerful and forming habits is hard.

So, I was determined to put the book into practice, and I knew I could only pick one. I made a serious decision, "I will journal every day."

My Rules for the Journaling Habit

There are many techniques and guidelines that Atomic Habits offers, but I've found that the most powerful rules for me were "Make it Easy" and "Don't Break The Chain". From there I came up with my fundamental rules for journaling, which haven't really changed since I began. I'm convinced that without them I would have stopped a long time ago.

  1. Write something on the page every single day. Really, anything. A single sentence counts. You might think that this will get you into a useless habit of writing short entries, but I've found that a). you will very rarely do the minimum, and b). this rule is vital for keeping the habit alive. It is for those days when you're physically ill and have work the next morning.
  2. Same time, if convenient. For me, journaling at bedtime (yes, in bed) was a good routine because it was the LAST possible moment. There was no putting it off. I think this is a good choice for procrastinaters because when you're getting into bed, you don't have other important things to do, and you don't have anymore time left. At that moment, you just have two simple options: to fall asleep and fail or to write and win.
  3. If inconvenient, plan ahead. There are inconvenient nights, like when you're going to someone's house, or going to a bar. At times like this, I try to plan ahead and journal early in the day.
  4. If you failed to write yesterday, you have to, HAVE TO make it up today. This is the final backstop on not breaking the chain. You don't want to ruin your streak just because you pulled a spontaneous all-nighter with friends. It's important that the make-up day feel like a moral imperative. You HAVE TO make it up. That means creating two entries today.
  5. Don't share. You'll be tempted by your own hubris (and our make-everything-public culture) to share your journal. Resist this urge. Believe me, by knowing that your dumbest thoughts aren't going to be read, you will write entirely for yourself.


Figure 1: Rule #5 - Don't Share. This is the only "proof" I'll be sharing that the journals are actually full.

The Pen is more Habit-Forming than the Keyboard

Digital journaling is tempting, and I did try it. You get search functionality, an efficient input a-la keyboards, and everything can be backed up, encrypted, compressed, and now iPads draw like paper, blah, blah, blah.

I'm here to say, for the sake of the habit, journal by hand. The #1 reason for handwriting is actually because of the physical properties of a journal and the two things it gives you: Progress and Bankruptcy.

Progress is something that propels us. It's what writers strive to give readers, a sense of narrative progress, Mr. Hobbit getting closer to Mount Doom. Progress is why you keep reading late into the night. But it's not just in fiction. Even the dryest books still have progress, the page count, telling you how long before you finish! The problem with digital journaling, is that there is no "finishing". Every day I get closer to finishing my journal, a supremely satisfying experience. When you're building a lifelong habit, trust me, the landmarks of "Did X for 30 days, for 100 days, for 1 year" start to fade. I don't think about the streak much anymore, but I still find it rewarding and continually helpful to have physical progress that I can see.

Bankruptcy, for me, refers to clearing out your life and getting a fresh start. Going "bankrupt" on your Mac might mean resetting it from the factory defaults and re-installing only the programs you actually need. Going bankrupt on your To-do list means starting fresh, leaving behind all the ancient projects that linger as disappointments . In the journaling world, you achieve bankruptcy every 250* pages. By finishing and archiving the old journal, you can forget about that regrettable decision to drink coffee near your journal. Or you can decide that "This time I'm going to make one drawing per journal entry" and try that. The new journal gives you a fresh start. For me, shelving a journal and starting a fresh one is a chance to reflect on that time period, rethink my entries, and to commit to more or less effort.

I'm sure some people will still go digital, but if you abandon the analog journal, consider incorporating some Progress and Bankruptcy into your system.

*250 pages if you pick the best journal (see below)

My Journal Choice

The Leuchtermm 1917 (A5, ruled) journal is my ride-or-die choice. It is great to write on and sturdy enough to be archivable. There are many reviews out there raving about it, but simply put, if it's good enough for Neil Gaiman, it's good enough for me. I'm also a big fan of the pen loop Leuchtermm sells, and I unstick/restick it to use on multiple journals.

My Style Guide

Now, about style. If you're looking for a big ol' style guide or a "journaling framework", you're in the wrong place (you can talk to the Squares over here in bullet-journal land). I've found that only a couple of basic rules are necessary:

  1. New day? New Page. Even if you just write a sentence, don't start the next day's entry on the same page. Move on to a new page. I found this out when reviewing my first journals, it was difficult to search for certain days, and the appearance was messy. You'll lose a little paper to blank-space (although I usually fill blank-space with doodles), but this rule will give you a much more readable, clean journal.
  2. Draw horizontal breaks to separate thoughts. When you're journaling, you'll find that sometimes your thoughts skip around. First you're writing a quote, then you're recounting your trip to the zoo that day, then you're imagining about how stressful it would be to get trapped in an elevator with the 600lb gorilla, Frank. Some of these thoughts will be logically distinct, all will be on the same page, and so you'll want a consistent style to separate them. For me, the horizontal line is visibly distinct and quick. You don't want to use paragraph breaks, because otherwise all connected thoughts have to be smooshed together. The horizontal line is small enough that you don't need to waste a newline separating thoughts, and if you're feeling artistic you can fancy it up.


Figure 2: Horizontal lines can be a simple dash, or more elaborate…

Personally, I like to keep "style" loose and open-ended, and I recommend you do the same, especially in the beginning. Get scribbly and messy, go bulleted and neat, turn loopy and colorful. Do it all! Experiment!

Cosmic Benefits

Here's what you can expect as benefits when journaling:

Instant +10 to Emotional Intelligence

Better self-reflection. You'll quickly realize how bad non-journalers are at this, because what we think about our past is frequently skewed. Real insight into your past can be a powerful tool for change in the future.

You'll win arguments because you'll be able to say with certainty, that yes your spouse did say that on October 9th because BAM, it's written right here!

You'll gain skills in both calligraphic and wrote-this-while-reeling-in-a-fish handwriting.

Major memory benefits that almost no-one else has. As the ancient Chinese proverb sayeth, "the faintest ink is more powerful than the strongest memory."

More quiet, unplugged time in your day. Let's be honest, I think we could all use more of that?

Secret ultra-rare attributes that only reveal themselves to journalers. (a long list of et-ceteras and ephemerals)

What Makes a Lifetime Habit

Most people want to "change for good", to change permanently. When people talk about "becoming a better person", generally they're talking about a habit without an expiration--a lifetime habit. Unfortunately most habits aren't designed well to be lifetime habits, and they're going to eventually get dropped.

Why? A good lifetime habit must be adaptable.

For example, "pumping iron" is rarely a lifetime habit because people are rarely interested in going all out at the gym when they have kids, or turn forty, or turn sixty. Priorities change, interests change, and you will change, profoundly over the decades.

Journaling is a good lifetime-habit candidate because the blank page is very flexible. You can use it as a to-do list, a simple record of memories, a place to draw, or a scrapbook. It can be as short and quick or as lengthy and loquacious as you like.

By keeping your idea of "journaling" flexible and adaptable, your journal can change and grow with you.

Closing Reflections

I said at the top that all the pages over two and a half years were thanks to a book and a choice. Some people might disagree with that. No, they might say, it was because you were "putting in the work", because you were "choosing" to journal everyday. But it doesn't feel like a choice to journal now, and it hasn't for a long time. It's not work, it's just something that I do, every night.

To me, looking back, there's a clear date that separates me before for whom writing for one day was a big deal and me after, for whom shelving another journal is entirely ordinary. The date, January 29th, was unremarkable except for that the day I just started. Looking back, my only regret is that I didn't start sooner.

I hope that you found something useful here, and that if you are interested in journaling, you can just start and carry on. Good luck to you. For myself, I hope to carry on journaling into the deep future, and I hope my journals look entirely different in ten years. Here's to the next 1,000 pages.

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