Lessons Learned: My First Hundred Days of Journaling

Consistency, persistence, clarity, and self-compassion

Allison Holt
Feb 22, 2020 · 8 min read

I’ve been a writer my entire life, but I’ve never been much of a journaler. I’ve heard the advice over and over again, in every writing class I’ve taken and in every book on writing or self-help I’ve read. Sure, I’ve written any number of journal entries here and there, usually when the cacophony of stresses and anxieties in my head made it difficult to think, but never had I kept a journal with any sort of consistency.

Until one hundred days ago, when something finally clicked. I’ll admit that when I started this journaling journey, I kind of accidentally backed into it; I wrote in my notebook one day, and then the next, and it felt good to do it, so I kept doing it — and now here I am, full of lessons learned.

Consistency is key

I’ve learned the value and importance of consistency. For me, I don’t just mean consistently writing every day, but following a consistent routine. I think that the single most vital decision I made (and I didn’t even consciously make the decision as much as notice what I had been doing after a week or so) was to use a single notebook for a single purpose.

Plenty of writers can and will write anything they can in anything they can, in whatever’s handy. They’ll keep a single notebook that houses everything for them — journal entries, shopping lists, to-dos, snippets of ideas. Turns out that doesn’t work so well for me! The Moleskine notebook I started journaling had been that to me, but after a couple of days, I didn’t want to put anything else on those pages.

For me, having one concrete place to put all of my thoughts — and only my thoughts — has done wonders to remove the barriers to journaling I unknowingly had in place. I don’t have to think about it anymore at all — I open the notebook, I open the pen, and I write.

Maybe for you, that’s never been a problem, but I struggled with finding just the right place to journal for so long. Not just in paper, but online or in various writing apps; I have older journal entries and blog posts spread across the hard drive and my Internet.

Now, though, I have one notebook. (Well, I filled the first and am onto my second.) I know exactly where it is. I have a fountain pen I like attached to it (and I use that pen exclusively for journaling). I’ve removed the main barrier that kept me from writing in my journal by taking the decision-making process out of it altogether.

I now have a couple of hundred Moleskine pages absolutely stuffed with my handwriting, and it’s one of my proudest accomplishments from a lifetime of writing. Yes, really.

(I do still wrestle with finding Just The Right Pen, but that’s a battle that will never truly be won.)

Out of my head

I’ve long been prone to having negative thoughts — about others, about situations, but most of all about myself— that would slather themselves in glue and wedge their way into the crevices of my brain, sticking out their little tendrils and waving at me to get my attention over and over again. Not only were these thoughts less-than-beneficial to my overall mental health, wow, were they annoying.

Journaling has allowed me to delve into those thoughts and thoroughly process them. And then I can evict those thoughts from my brain rather than obsessing over them. I write everything down and quite often have arguments with myself debating the various points raised by different parts of my mind.

The difference between letting go of the negativity via journal instead of listening to the incessant debate inside my head is that putting my worries down on paper gets them out. It’s like those different voices have had their say once it’s written down, and they stop arguing. Much of the time, it turns out that whatever bad idea I was internally hashing out (“I should shave my head again, right?”) turns out not to be something I actually wanted to do once I’ve written it out.

And then I stop obsessing. It’s wonderful.

Strengthening the muscles

About a month-and-a-half ago, I shifted from journaling at random, convenient times during the day to practicing Morning Pages instead. Every morning, I get up early — usually 5:30 on the weekdays when the kids have to get to school, but I’ll “sleep in” until 7 or so on weekends. I push the start button on the coffee pot I prepared the night before, I sit at my desk, open my notebook, and write three long-hand pages.

Every day.

It takes me about 45 minutes to write those three pages, and the three pages average out to about a thousand words. That means I’m extracting a minimum of a thousand words a day from my head. Usually, it winds up being considerably more because I’m working on a blog post or the draft of a novel.

I can’t yet determine if there’s been an actual increase in quality from the hundred-thousand-or-more words I’ve pulled out of my brain, but I can tell you without a doubt that it has become so, so much easier to do the work. When I began the morning pages practice, managing those three pages was like wrestling a small animal from a crocodile’s teeth. Now, those pages flow like wrestling a small animal from a tub of butter. (OK, that simile wasn’t great; I told you that maybe my quality hadn’t improved yet…)

And it’s not just journaling where the words are now well oiled. Writing anything has become easier, at least in terms of that initial flow of words. The words that come may not be exactly the words I wanted — I certainly haven’t bypassed the need for the editing process — but those first drafts reveal themselves much more quickly than they used to.

Photo by Ian Schneider on Unsplash

I didn’t practice morning pages when I first started journaling regularly, and I’m not sure I’d recommend anyone else looking to develop a journaling practice start there, either. It’s certainly upping the degree of difficulty, knowing that you need to wake up and face the page first thing, and anything that might keep you from developing the habit is probably worth waiting on.

But I’m very glad that I did indeed add morning pages to my practice. It’s become incredibly important to me and is definitely one of the most important pieces of my journaling puzzle.

The second person

One of the things I’ve noticed over these three-plus months is something that’s always been present in my sporadic journaling, but I’d never been able to hone in on before: my encouraging, supportive second-person voice. Whenever I write something that’s unkind to myself or expressing doubt in my abilities, I unconsciously immediately shift into writing in the second person, talking to myself rather than as myself.

My second-person voice is frequently gentle with me, but sometimes knows she needs to be harsh. She doesn’t take any of my crap or any of my excuses. I can recognize that she parents me much the same way I try to parent my kids. I’m immensely grateful for her perspective, one that seems unclouded by the torrent of distractions and emotions that frequently pollute my head. She cuts through in a way that nothing else in my brain seems able to.

I’m sure my therapist would greatly enjoy digging into whatever childhood trauma of mine produced that voice.

Gaining clarity

I’ve long known I’m one of those people who has to write out what I think I think in order to actually know what it is I’m thinking. It’s part of what I said above about the jumble of competing thoughts and ideas; it’s often not until I put the words down where I can see them that I can make any sense out of them. (Some people go through this process verbally, feeling that they don’t know what they think until they’ve said it aloud, and I don’t understand those monsters at all.)

Given how infrequent my journaling uses to be, however, I wasn’t often able to gain that clarity that comes from working through my problems or opinions or ideas. Not knowing what I think makes it awfully difficult to explain what I think or defend it to others, and I like having some confidence that I’ve already worked through my thought process beforehand. Journaling calms the churning waves.

Writing about writing

I realize how inaccurate what I’m about to say will sound coming toward the end of a two-thousand-word piece all about writing, but: I don’t write about writing anywhere near as often anymore. Well, that’s not exactly true — I don’t write about writing in place of doing actual, productive writing.

I used to have a serious mental masturbation problem. I’d desperately want to write something, but had no idea what, so I’d pop open a Google Doc or a text file and ramble on about how little I knew what I wanted to do. And I’d think that made me productive because I’d produced something. Even if it was pointless, solipsistic crap.

Paragraphs and pages, all signifying nothing.

Now, all of that work lives in the journal. I still write about writing — about the process, about idea generation, about my frustrations and intentions and triumphs — but it all happens in those pages where no one ever has to read it. Then when it’s time for me to do “actual” writing, I’ve gotten all of that other work out of the way and can work on pieces that have something to say.

Final thoughts

I know that there’s no evangelist as enthusiastic as the recent convert, and I fully admit that I am converted. I can’t say that journaling has changed my life, because, well, let’s not be overly dramatic here.

I can and will say, however, that journaling on a daily basis has entirely changed my relationship to my writing. I have a focus and consistency now that I’ve never been even close to having before. I have a far greater idea of what it is I want to do — with my writing, yes, but also in many other facets of my life — and a much stronger idea of my capabilities and ability to accomplish those goals.

If you want to change your relationship to the words you put on paper, try starting a journal. Grab yourself a notebook — one with lots of blank pages stretched out in front of you. Find a pen that feels comfortable in your hand and makes marks that please you. Set aside some quiet, solitary time for yourself (this is exactly why I get up at 5:30 in the morning to write). Let your mind spill itself onto the paper, feel the accomplishment of having done so, and then do it again tomorrow.

And the next day, and the next. You might be surprised at what you find if you follow where your words lead.

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Allison Holt

Written by

I write words and I write code, and I’m frequently surprised at how similar those processes are. Email: medium@alli.fyi.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +800K followers.

Allison Holt

Written by

I write words and I write code, and I’m frequently surprised at how similar those processes are. Email: medium@alli.fyi.

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +800K followers.

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