The Weekly Review

by Chris Bowler

3 ways to make the journaling habit stick

My most read piece on Medium is How I Journal. Since writing that, I’ve received a lot of questions about my journal, Day One, and how I put it all together. But there is one question that comes up more than all the others.

How can I start journaling and make the habit stick?

A lot of people see the value of keeping a journal, but struggle to fully adopt the habit. It’s very easy to try out an app like Day One, add several entries over a week, then forget all about it for a month. The world is full of empty paper journals with a couple of notes scratched into the first 3–4 pages.

So how does one adopt this habit?

There are plenty of good articles on this topic. And people like James Clear spend a lot of time talking about how to start a new habit. But as someone who has struggled with journaling regularly, I can share you with you what has helped me make this an almost daily occurrence.

Start Small

If you do not journal at all, envisioning yourself suddenly scribbling 800 words per day is not realistic. The best way to start journaling (or any other habit) is to start small.

This could mean a quick couple of lines at the end of your work day to sum up what you did. This would also apply at the end of the day before you go to bed, but you write about anything in life. Or it could mean adding a couple of images of your kids to an app like Day One without any commentary.

The important thing is to get started and to get some entries into whatever tool you’re going to use.

Use automation

One great way to achieve this very goal is to use some automation. There are activities you perform every day that can make good journal entries.

The perfect example for me is my reading journal. I have 5 journals in Day One, one of which is where I put quotes that resonated with me. I sometimes take pictures of a physical book I’m reading, but most of the entries are populated automatically without any work from me.

Using tools like IFTTT, I can populate my journal based on my reading habits. When I read an article in Instapaper, I can highlight sentences that I enjoy the most. A few minutes later, that highlight is added to Day One by an IFTTT recipe.

Quotes from Instapaper

I’ve done the same with my runs in Strava or my daily Fitbit summaries. The options are vast: your posts to Instagram, your tweets, posts to your blog.

With workflows like this, I’m building up a library of information that is of interest to me, but with no effort required on my part.

Review your entries

As I mentioned above, I have struggled myself to adopt the habit of journaling consistently. From 2012 to 2014, I wrote a lot of manual journal entries in Day One as a part of my morning routine. For whatever reason, I dropped that habit in the years after.

I still had Day One on all my devices. And when special occasions took place, I would tend to make a note or add some pictures. But I was not writing regular daily entries.

However, I was seeing the On This Day banner in Day One.

Day One includes this nice prompt to review all your entries for the current calendar day

And it was this banner that helped me see the value of keeping a journal. Every time I opened the app, I could see the 3–4 entries that had been written over the years on this specific day. The nostalgia from these captured thoughts and events immediately showed me how wonderful it is to have a repository for things your mind has forgotten about. Not every entry brings this feeling, but there’s value in the mundane daily activities as well as the special moments.

It’s all gold.

Over the past 3–4 years, I’ve persisted in increasing my use of a journal based largely on the value I’ve gotten from regularly reviewing my journal entries from the past. This is why starting small and using automation is so vital: you simply need to get some entries in there to see the value.

This is why building habits is hard. The return on the investment can take time. Even with Day One, you’d have to create a few entries and wait one year to see the value using On This Day.

So in order to see the value more quickly than that, force yourself to add some short entries, add some automation, then ensure you take some time to review what you’ve added.

Why Day One is so effective

I’ve mentioned the app enough times here already, but it’s worth pointing out why it’s so good. But let me state it plainly.

Day One makes it easy to get started, enables some nifty automated workflows, and even works well if you prefer a paper journal.

How I Journal now is a mix of paper and digital entries. But they’re all in Day One. When I sit down for morning devotions, my journaling starts in paper. But I always snap a picture of my notebook in a Day One entry. And my weekly review habit is also on paper, but each week also exists in Day One.

It's really the best option.


And that's how I've been able to keep journaling a regular part of my life over the last 8 years.

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