Guide: Building a Journaling Habit in 2019

Guide: Building a Journaling Habit in 2019

2019 is now upon us. While I think you can start a habit any time of the year, the beginning of the year is an ideal break point to start something new.

One habit I’ve found invaluable over the course of the last few years is journaling. It helps me tame distractions, get a grip on my inner world of emotions/thoughts/feelings, and gives me an introverted outlet for all my inner thoughts.

If you’re looking at starting a journaling habit in 2019, you may be wondering how to get started.

Well, friend, this guide is for you.

Know Your Why

The key to any long-lasting habit is knowing the reason for doing it in the first place. While you can get yourself to do things for a period of time out of sheer willpower, there will come a time where willpower won’t carry you through alone. That’s the moment you need to know the purpose of the habit for your life.

Journaling has countless health benefits, plus has the added value of creating a lasting historical record for yourself and your family.

I journal because I need it to help process my internal world. I have so many thoughts, feelings, emotions, and ideas that hit me in any given day. Without journaling (and honest, authentic relationships), I’d just bottle them up until they came out in ways I wouldn’t want them to.

So before you even set foot on the path journaling, spend time to figure out your why. Resting on this vision when you don’t feel like building the habit will give you energy to push forward.

Decide When

A habit without a scheduled time is just a good intention. If you intend to keep the journaling habit going, make sure you add it to part of your routine whether daily, weekly, monthly, or however often you choose. I recommend at least a few times a week, if not daily, as you can see patterns better when you choose to review your journal later on.

Having a scheduled time for a habit doesn’t necessarily mean you have to journal at 3:30pm every single day. I have my journaling set as a task in my startup and shutdown routine.

Find a place that works for you to fit journaling into your routine. Maybe it’s at 5:30am every morning, or maybe when you’ve put the kids to bed. Whatever it is, having a time will help you stick to the habit and make it part of your routine.

Pick Your Medium

This is usually the biggest question: how are you going to journal?

There are many roads to take when approaching journaling. Naturally, they break down into two categories — analog and digital.


When most of us think journaling, we think of notebooks, paper, and pens. Grabbing my trusty Leuchtterum1917 and a Lamy Safari is one of my favorite ways to journal. There’s something about the tactility of journaling on paper which makes the process of dumping out everything on my mind more effective than digital variants.

Paper doesn’t come with notifications, sync issues, or any other distractions which can plague digital journaling solutions, but a notebook can easily be lost or destroyed. On the bright side, a paper notebook will have no problems being read (if intact) 100 years from now for your descendants or stark raving fans to enjoy.


While the tactile process of journaling on paper is satisfying in one way, digital journaling offers so much that paper can’t, like sync between devices, searching, surfacing of old entries, and better organization.

Day One is the app of choice for most who journal digitally, but other note-takers like Bear, Evernote, Drafts, and Agenda offer ways to journal as well if you’re not ready to invest in yet another app.

The major downside of digital journaling is there is no guarantee the files will be available or even readable in the future.


If longevity is something you desire out of your journaling but you still want to have paper copies, either hand-write your entries on paper and scan them into your journaling app of choice or print your digital entries every so often and store them safely.

Start by Experimenting

Once you have selected your medium, start experimenting with journaling. The experimental phase is the “dating” phase of a new habit. You’re not quite ready to 100% commit to the ritual, but you definitely want to see what it’s like.

People also handle starting something new in shorter chunks. In fact, I think most people give up on big goals because they leave them big. The best way to accomplishing a goal or building a new habit is one small step at a time.

Start journaling by taking your desired frequency and do that for two to three weeks. Then check in with yourself to see if it’s something you find value in or can find ways to improve. If you decide to keep going, do it again for another two weeks or so.

After a few cycles of experimentation, you’ll know if you for sure want to commit to journaling long term. From there, just go!


One thing I forgot to do early on (and still sometimes forget to do) is review my journals on a regular basis. This isn’t something I’d recommend doing weekly or even monthly. I find journals have the best value to me when I’m reviewing them months later.

The biggest benefit I’ve found for reviewing your journals is to see how much you’ve grown. I love looking at old journals and seeing how I’ve overcome certain situations in my life and how those obstacles matured me into the person I’m into today.

One reason I like Day One for journaling is they make it super easy to review past journals through their “On this day” feature. You have the option to see journal entries from years past on today’s date when you go into the app. This makes reviewing journals a lot easier.

Are You Ready?

Journaling has the potential to be a powerful habit in your life. I know I wouldn’t have some of the mental and emotional clarity I do today without building a journaling habit years ago.

That being said, do I journal every day? No. I journal periodically, and largely only when I feel I need to. I started off by documenting lots of little details and things that happened in my day, but found that to be too laborious. Instead, I tend to note just what’s on my mind at that moment, from thoughts to feelings to experiences.

The practice of journaling can be anything you want or need it to be, as the habit is ultimately for you, not anyone else.

If you get your journaling habit going this year, give us a shout on the Productivity Guild Community. Tell us how you’re doing, what you’re using, and how journaling has helped you grow.

I’ve been trying to start a journal habit off and in for a few years now. That means I’ve had Day One from version 1-3, experimented with tools etc. In 2019, I may have finally gotten it to stick:

I decided a time and tool - every day, as I start to wrap up around 10, on the iPad, in Day One. I also time bound it to five minutes on the prompt, max, and five minutes on the thoughts of the day. That makes it feel not intimidating.

The prompts have been key for me, my wife got me a set of journaling prompts from Best Self as a stocking stuffer. I don’t want to let them go to waste, which was also a motivator. It looks like they are out of mine, but there are other series.


I have the Due app set to start nagging me at 4:30 pm to do a journal entry. It’ll nag me every 30 minutes until I finally write an entry and dismiss it. If I have a one-time alarm, it’s easy to disregard it.

There have been days where I’m still busy and I can’t do my 4:30 pm end of day journal entry. I love the nagging reminder every 30 minutes to keep me on track. I’ll more likely finish my journal entry after 4:30 pm and hopefully before bedtime.


I had tried for years and would go a month and stop for one reason or another. About mid 2017 or late 2017 it finally stuck. These days I have a list of tasks in OF for morning (reminds at 8am) and one for evening (reminds at 7pm). In the morning I bootstrap my journal for that day and add a list of items that would make the day “awesome”, gratitudes, what time I woke up, how my morning run went, etc. In the evening when doing my OF closeout list for the day, I complete the days journal entry. I’ve found that by bootstrapping it in the morning, I don’t feel so pressured to get an entry done and in the evening, since it’s half done, it’s not much of a commitment.

The side effect of writing the “awesome” list is it sets my mind in motion for what I’m working on that day. I don’t list everything, just the things I feel would make the day great. OF keeps the full unaltered list.

I still feel dirty for using DayOne and not paper but recently I’ve utilized the weather features that DayOne logs with the entry and I’ve enjoyed going back to look at photos attached to old entries.

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I have the same feeling sometimes, but DayOne is just easier right now. Plus, it’s automatable :smiley:

The best thing to do to encourage journaling (or any habit) is to make it as easy as possible. Put the physical journal tied with a pen in an easily accessible place. I have a notebook that sits on my desk. I always make room for it. I have a pen that is clipped on to the notebook elastic band that keeps the journal closed. It’s a visual cue that my journal is ready to write in.

I also have a Keyboard Maestro macro that opens Day One and creates a new Day One Entry, tags it with “End Of Day Review” and then inserts text questions for me… Anything to make life easier. This macro was part of my Daily Review that I perform at the end of the day. It’s described here…

Here is the YouTube video. I fast forwarded to the part of the video where I click on a Keyboard Maestro macro and it automatically starts my Day One template.

Here’s a screenshot of my Day One macro…

Download the Keyboard Maestro Macro file here:

You can generate a TextExpander macro that can also create the journal template.