For the past two weeks, I’ve been on a mission to discover more about myself through the process of self-assessment.  As part of the process, I wanted to cultivate a habit of self-reflection through journaling.

I’ve never been one to keep any sort of journal.  So when Grid Diary promised to be “the simplest way to get started keeping a diary,” it sounded like the perfect solution.  It did live up to its promises, but even so, if you’re just getting started in journaling, developing a habit can be challenging.

Here are some tips that I picked up along the way to set myself up for success and to journal more effectively.

Define the “win.”

The “win” of journaling isn’t to write a Pulitzer Prize-winning article.  It’s to get your thoughts, feelings, ideas, and fears out of your head and onto paper.

When I began journaling, I felt a strange pressure to write something profound, as if someone was going to be judging me based on the eloquence of my ramblings. As I wrote more, I became less outcome dependent and started developing a habit of writing without editing. If I didn’t feel like finishing a sentence, I’d leave it half-written and move onto the next prompt.

Paradoxically, the more pressure you put on yourself to journal, the less effective it becomes. That’s why I don’t believe that blogging is a good journaling outlet — there’s too high a pressure to perform and too many expectations to meet. Journaling should be a private exercise that fuels writing meant for public consumption.  Approaching this the other way around generally leads to imprecise writing and overshare.

Choose a tool that works for you.

The best journaling tool is the one you’ll actually use.

There are thousands of journaling tools out there — productivity journals, diaries, apps, journaling bibles, devotionals, prayer journals…  You get the idea. Finding the “perfect” solution isn’t the goal — the goal is finding a solution that’s good enough for you to use in the long run.

Here are a few criteria that I would recommend that you consider.

  • Format. Will you be more successful with a digital journal or a print journal? Digital journals are always with you, but there’s something special about putting pen to paper that you lose with a smartphone app.
  • Features. Some journals consist of blank pages to allow for free-flowing thought.  I found that I needed a starting point — some basic prompts for getting started. Try each — or even a combination of both — and discover which is best for you.

Digital journals to consider

Print journals to consider

Stick with it.

Don’t expect to get into the swing of things right away. Just like any exercise of body or mind, it takes time to develop a routine.

My first few days were rough; I didn’t know how to reflect on my day. I found myself confronted with straightforward prompts — “What was good about today?” — that I had absolutely no framework for answering. What was good about today?  I scribbled a shallow answer and moved on.

Despite not writing much and feeling inadequate, I persisted.  I soon discovered that the mere act of committing words to paper (or screen) was a discipline that forced me to be reflective, even if I didn’t feel like answering every question.  After a few days, my brain caught up.  I had successfully trained myself to be at least a little more reflective. As a result, I found myself enjoying the process of reflection.

Commit for at least two weeks, and put pen to paper whether you feel like it or not. It’s the act of writing something — anything — that will lead to deeper responses.

A picture of persistence.

One benefit is that Grid Diary tracks the number and the length of entries over time so I could measure my progress.  The chart below charts my progress over time. Not only did I write more, over time I answered more prompts in each session.

Change in journal usage over time, measured in number of entries and number of characters.

Introduce novelty

If you’re the consistent type, this may not apply to you.  But if you’re distractable and prone to boredom as I am, you may want to consider introducing novelty into your routine.

For the first several days of using the Grid Diary app to cultivate a habit of end-of-day reflection, I found myself answering the same pre-set list of prompts. As I answered the same questions night after night, I grew lazy in my responses — often writing some variation of the same response several nights in a row.

On day 6 of my experiment, I found a feature that randomizes a day’s prompts, selecting a new set from a larger pool of available prompts.  This was interesting. I found myself looking forward to what new questions I would encounter.  Some of them were particularly thought-provoking.

The app includes the ability to add custom prompts as well, so you can include prompts that are meaningful to you — or drop in some silly questions to keep yourself on your toes.

Have you explored journaling?

What tips have worked for you, and how has journaling improved your life?  Drop a note in the comments or catch me on the Twitter @roblaughter.


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