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Three Daily Journaling Experiments

Discover The Right Method That Can To Enhance Your Creativity, Productivity, And Sleep

Imagine a practice that boosts creativity, enhances productivity, and fosters clarity—all in just a few minutes a day. Daily journaling promises all this, but it's not as easy as it sounds.

I experimented with 3 daily journaling methods. Here’s what I discovered, rejected, and stuck to.

I spent 41 minutes writing this post. You will need 6 minutes to read this post.

Daily journaling with a pen.
Daily journaling with a pen.

Related:

The Power and Pitfalls of Daily Journaling

Daily journaling is considered a cliché because it's one of those buzzwords people love to throw around, much like self-care, meditation, or mindfulness. Everyone who does it says it's life-changing, yet it's hard to tell whether they say so from social pressure. I’m not sure how many stick to it or see results. People promote it as a cure-all for stress, a way to boost creativity, or even a secret to achieving life goals.

The challenge lies in consistency. It's easy to start, but sticking with it daily can be tough. Life gets in the way.

Matthew Dicks motivated me to try daily journaling.

Describing 3 Daily Journaling Techniques

I describe 3 ways to journal daily below. For each, I share:

  • Method

  • Execution

  • Benefits

  • Challenges

My goal is not to rank, but to share how my process changed over time.

Take 1 - Finding Your Storyworthy Moment

The first method is by Matthew Dicks. Matthew in "Storyworthy" says,

"What is the most story worthy moment from the day? What is the moment that, if forced on a stage, and required to tell a story about something that happened on that day, what would it be?"

You write down a five-second moment each day that could be a story worth telling to someone. See illustration from Zsolt.

Zolt’s infographic of lessons from Matthew Dicks’ Storyworthy, including “Homework for Life”.
Zolt’s infographic of lessons from Matthew Dicks’ Storyworthy, including “Homework for Life”.

Example:

“Avyaan Exercise:

Avyaan exercised in the back garden with us in the morning. He also played on the slide and swing on his own. Now I know why he didn't like me pushing him on the swing.

Only count number one one one for exercise, not one two three. We might make him like exercise. We watch a truck at creche. Made him get in the car seat by promising we would go see the scooter. Lie. He wanted to drive car before that."

Benefits:

  • Helped me tell better stories to my friends or family.

Execution:

  • I used the Diary++ Android app to write from anywhere.

  • I set a daily reminder for 7:15 pm to retrospect the day’s moment.

Challenges:

  • I often ignored the daily notifications due to work or meetings. I tried a few different times of the day but couldn’t find a better one where I would act on it.

  • As a remote-working solopreneur and a parent, my story-worthy moments often revolved around my son. I felt the stories needed to be more diverse and less repetitive, so I stopped writing those.

Screenshot of Diary app from Android.
Screenshot of Diary app from Android.

Take 2 - Capturing Daily Epiphanies

The second method came from a mentor who is a product management leader at Salesforce. He suggested writing down epiphanies throughout the day.

“If you can’t measure it, you can’t improve it.”

We cannot improve what we do not measure or retrospect. So, I kept my eyes and ears open for revelations and wrote those down. I sought revelations about my:

  • productivity, 

  • relationships, or 

  • career prospects.

Archimedes’ eureka epiphany moment.
Archimedes’ eureka epiphany moment.

Example:

“Challenge to write book reviews

I was forgetting the content of books by the end of the year so I thought, let's write reviews of each book as and when I read it about what I learned from it. Still, now it's becoming a big inertia point for me. In some ways, it's reducing my enjoyment of books, which is fine because my goal is to learn, not enjoy, but in other ways, I am Dr dreading the end of a book. I am piling up a list of books I need to write reviews about but have not written about, but it is also not suitable for me to spend time writing reviews during work time."

Execution:

  • I noted my thoughts any time of the day. Anytime I had an idea, like a "shower thought," I wrote it down. Sometimes, I got these ideas when brisk walking after lunch.

  • I kept the daily evening reminder as a safety net, in case I forgot to write during the day.

  • I used voice typing to lower my barrier to writing.

Benefits:

These epiphanies were helpful.

  • I increased my productivity, relationships, and meeting performance.

  • I executed better business ideas.

Take 3 - Putting Your Day To Rest

I came across this in a book or blog in 2023, but ignored it at first. Then, my sleep therapist prescribed the same method in May 2024, so I started using it.

The approach involves putting your day to rest (or ‘to bed’) to help you unwind in the evening. You do this by writing down 3 things in your journal:

  1. Gratitude journaling: Write what you are grateful for. I have the habit of “Writing down things I appreciate my spouse for each day.” I added other factors, such as a) the weather being good so I could go for a walk, b) I met a client, or c) I had coffee with a friend.

  2. Tomorrow’s To-dos: Make a to-do list or a priority list for tomorrow. I plan each day and week, but I now also do part of it each night. Write one step you’ll take towards each item on your to-do list.

  3. Rationalize your Anxieties: I am left-brained and structured, so I got even more instructions here.

More on 3: Steps to find and rationalize your anxieties:

  • List your anxieties and stressors.

  • Look for evidence to support each item on your list.

  • If you don't find evidence to support a worry, it is irrational.

  • What is the probability that the worrisome event will happen?

  • What controls can you put in place to limit the damage if the event occurs?

  • Accept items where you cannot change the event. Accept the outcome.

Night journal with dim lighting.
Night journal with dim lighting.

Example:

“Night Journal

1 - I'm grateful for the pleasant weather and good company today. We also got amazing pictures. My son was mostly well-behaved, especially when we were outside. I also applied the storytelling tactic today to help him think about the overall day experience instead of focusing on the injury. 

2 - Tomorrow, I want to think of how to take my son outside so my wife can finish meal prep. I want to prepare the Amazon returns and discuss a few things with her if I have time. I want to tackle the 'delayed shopping list'. I also want to read CRM notes before the lunch get-together. It is possible for the lunch get-together to extend if friends say let's go for the ice cream in Dundrum Mall

3 - I'm worried about waking up in the middle of the night and thinking about not going to sleep. Instead, I should get out of bed and test that. I am worried it might get too cold, so I know I should instead get up and close the window if that happens. If I am awake around 4:30 a.m., I should get out of bed for the day. I'll probably be more tired by the next night and sleep better, but I didn't want to condition myself to force it that you are sleeping if you are in bed. Otherwise, you don't even get that option. But, if I get out of the bed, I am anxious about what I will do because there isn't much physical work to do. I should not exercise, I should not listen to audiobooks, I should not work on the laptop, and I should also not do cardio. The last time when I woke up and started walking around, I did not fall asleep.”

Execution:

  • Ideally, I should stop work at 7 p.m. and write this daily journal. But I work until 9 p.m., so I do this after 9 p.m. I sleep soon after writing this.

Benefits:

  • I used to think about the next day and stressors between 2 a.m. and 5 a.m. My mind was conditioned to have a meeting with myself at that time. My hope is that I can recondition the brain to have that meeting at 9 p.m. when I’m awake instead of 2 a.m. when I want to be asleep.

What Works For You?

I shared three ways I use daily journaling to reflect on my days and improve my life.

What works for you to:

  • Review your progress towards your big picture goals?

  • Be productive?

  • Have a sound sleep?


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