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Real, Counter-Intuitive Advice on How to Keep a Journal

The Whys and Hows of Forming a Writing Habit Forever

Finding romantic spots to write in my pre-laptop journaling days

There are three things no one tells you about how to form a habit of writing—particularly in a journal, which I think, anyway, is the most fertile loam for stories, poems, profound realizations, and anything else one could desire to write. These insights run counter to a lot of the advice I read in articles and books on this subject, but the only argument I’ll offer is that my advice comes from over twenty years of non-stop journaling, and represents the key elements I’ve found are needed to free your inner record-everything deep-thought beast. Without further ado, here are my biggest tips for becoming a hardcore addicted-to-writing journaler.

1. Start with the Boring.

People come to a fresh, new, beautiful hand-painted glorious blindingly white blank-paged book with a lot of hopes for unleashing long-blocked creativity, and immediately getting down every profound thought dreamed up while driving or showering or chasing children or running errands for the boss. But profundity doesn’t work well under pressure. Start with the boring. I mean, really boring. Start with the mundane crap that if anyone who ever found your journal read, would think you were the lamest person ever.

Examples of things to write about:

  • Your crappy commute
  • The crappy songs on the radio during your commute
  • Your boss and the weird shit he/she says
  • Your two-year old hitting their head again
  • The damn printer that broke again so you had to make up a totally new lesson for your nightmare class on the fly
  • The fact that you went all afternoon running errands trying to catch up with your life and you may have forgotten to breathe that entire time, but you don’t actually remember
See? It’s already starting to get profound on its own! Writing is easy. No worries!

Here are some things to avoid:

Writing Prompts. Too much pressure, often contrived, and actually boring. Maybe great if you want to write a memoir, or develop ideas for a story, and the prompts are brilliant. But that’s not we’re here to do, yet—we’re here to journal. Why do you want to journal? If I had to throw a rock in the general direction of a guess, I’d say at least part of the answer would be this:

To be present to your life.

The distinct and unique gift of journaling, compared to other forms of writing, is that it is present, it is here and now, and it doesn’t look away from the mundane, the boring, the dross—a journal accepts everything. The only one reading it is you! Writing prompts take you to the far-off land of what once was or what could be. But what the journal is best for is looking squarely, honestly, unflinchingly at the now.

The other thing to avoid:

Gratitude Rituals.

Yikes! I sound like such a grouch! But it’s true. The advice in vogue these days is to write five, ten, a hundred things you’re grateful for, every day. Here is why I think this is a bad idea: writing about things you’re grateful about doesn’t actually make you feel more grateful. You’re either grateful about them or you’re not. Trying to drum up lists every day will quickly become tedious and dishonest. It artificially creates a feeling that would be better to honestly acknowledge is not there, even and especially if you feel that it should be there.

The better thing to do is just be honest. “No, I’m not grateful for my two year old today, who has been an insufferable brat all day long, but god is in the clouds, am I grateful for this third cup of coffee and the glass of wine that I’m gonna drink tonight.”

And speaking of getting to that glass of wine tonight, onto point number two!

2. Repetition is Key

This could probably have been fit in with point number one, because it’s boring, but repetition is so important, I’m gonna repeat myself!

The key—seriously, the one key needed to forming an unbreakable 'til-death-do-we-part journal-writing habit, is repetition. This is actually what journaling is: the repeated writing about your day, day after day after day. Now, I understand your ambitions with journal writing aren’t about daily record-keeping—they’re about writing your deepest thoughts, considering your philosophies, and looking at your life through a lens full of meaning. But these are the gorgeous flowers that bloom out of what is mostly muck and dirt! Your profound thoughts will come naturally out of the space that is now being held for them every day—but you must be willing to sift around the boring daily muck of your life.

And this is where one of the secrets of writing lies: but first, let me illustrate with an example. Here is what a snippet looks like, from each of my journal entries for a week:

Monday - “And then I had coffee at the coffee shop and it was delicious. And that barista was super nice again today even though the place was packed.”

Tuesday - “And then I went for a coffee on my break and sent more cat memes to my brother.”

Wednesday - “This coffee is so good, it’s so delicious. Why can’t I drink this all day looooooong?”

Thursday - “It’s raining out, but this coffee is keeping me warm and I think I should finally buy that sweater I’ve been dreaming about.”

Friday - “It’s raining again, big fat raindrops in the windows. Man, I really love this coffee shop. They always have soft music and the barista is so sweet and this counter with these wide windows is perfect for watching the rain and, ugh, I wish I could have a cat again. I miss my cat. God, I loved snuggling her when she’d jump up on the counter at breakfast and start purring immediately for no apparent reason, and her fur was so beautiful in the window light and she could just stare at the rain for hours and… she had the most delicate shin to scratch and she trusted me completely, and she never hurt me with her claws, even when we were playing rough, and her eyes were like jewels and… ugh… I don’t know if I’ll ever have another cat like her. She was my one experience of cat-happiness, four years of soft furry bliss. God, there were days during that horrible break-up, when she was my only solace. What I wouldn’t give to kiss her little nose again.”

Aaaahh this article just got real… aaaaannd… (takes a deep breath), that’s the beauty of repetition.

Repetition is crucial to everything about life. We are repetitive creatures, and it’s out of those iterations that truth arises. And the secret I learned, more important than whether or not we have a profound breakthrough, is the fact that the repeated occurrences of our lives are valid, beautiful and inherently worthy of our attention.

If you want to be more present to your life, you have to pay attention to the things you repeat day after day—and the best way to pay attention to them is to write them down unself-consciously. That way, you honor them and respect them as the underpinning, the foundation for your life that they are. That daily coffee? Supremely important. That creepy but thrilling murder podcast you listen to on your commute? Life-saving. The chores you love to complain about? Honor them, the crap in your life that they seem to symbolize, and the angry resentment you feel towards them, that bolsters your courage in other areas of your life, or your gratitude, or your relief. Everything is profound. Everything in life is worthy of note.

And the more you write down the boring repetitive crap, the more you’ll see patterns, the more you’ll take note of your life and the more you can appreciate everything about your life, the place that everything has in creating you, and the story you are creating every day as you live it, and hopefully now are also writing down. ;)

One last piece of advice, really briefly, is a pro tip I only discovered this year—after twenty—one years of journaling, no less! Who’s the idiot, really? :P

3. Write on a Laptop!

But writing in those beautiful handmade journals is so romantic, you moan! How can I curl up in the window alcove with my blanket and coffee and ten cats (okay, this is a fantasy) with a laptop??!

Here are the many awesome benefits I’ve found about writing in a laptop:

  • You write closer to the speed of your thoughts
  • Because of this, you’re less likely to float off into a reverie
  • The lack of romance to writing in a laptop also inhibits said reveries
  • You can outline your journal, holy moly! When you ramble about a thing and then come to a profound realization, you can go back and put in a header with a pithy title and it’s easy to find later and add to later, it’s amazing!
  • Not only can you find those realizations later, you can more easily turn them into articles! Like the one I’m writing right now!
  • Along the same lines as this, you can use the word-find function. Can’t remember that special instruction for your taxes that you jotted down? Never fear losing jots again.
  • A creepy benefit: your journal feels more accessible by others. At least for me, I leave my laptop around everywhere, I don’t keep it password protected… hmm, this is actually starting to sound really irresponsible. But my point is, my significant other and friends can easily and quickly access my journal and everything I’ve ever written about them. So if I’m having a conflict with anyone, I’m more careful about how I write about it. In this way, my laptop habit becomes my conscience, even when I’m trapped in an intense emotion.
  • Because of this, I find that I’m also more rational when detailing a conflict in my journal.
  • And later, when I’m no longer in conflict, I will often go back and delete angry rants, even though it might seem dishonest. I do this because I may get angry at the people in my life, but I also love them. It’s a fine line, to balance the validity of my feelings as they were in a moment, and the enduring arc of feeling I carry for someone in my heart. Both are valid and important. You have to remember conflicts because if you forget too easily, you’re prone to letting people walk all over you. But forgiveness is equally important, especially when it’s fully deserved. Writing on a laptop, I get to make that choice daily, about whether I will keep a conflict, remember it, honor it and let it serve as a warning, or whether I will let it go, and delete it fully in a very real way.

So that’s it! Two absolutely foundational things everyone needs to understand about keeping a journal and keeping it forever; and one awesome advanced journaling hack that I wish I discovered ten years ago.

To be honest, you can totally throw this advice out the window and curl up in your romantic nook to all the writing prompts and gratitude lists your heart desires. Those are valid, and it feels great. I know, because I’ve done it for years! Especially the romantic nook part.

But I wanted more than anything to give you permission to not feel pressured by those things, and to enjoy the other incredible benefits of a repeated writing habit. The beauty of writing in a journal is it’s extremely personal and there are as many different ways to do it as there are people on the planet. So go enjoy your life, your particular life, and happy writing!

Bella helping me with my calculus homework <3 

Bella at the window <3

Bella at my desk, distracting me from my writing <3

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