September 15, 2020

Prompts and questions to help you journal better

It has been several years of on and off journaling, but recently, I finished my first notebook full of notes. As I looked through, I realized that my journaling has come a long way.

My first foray into journaling was through the five minute journal. It had five questions, three to answer in the morning and two to answer in the evenings, including what I was grateful for, what would make today great and how could I have made today better.

The great thing about the journal was that it really took five minutes or less. Although this deserves a bigger post, the best habits are ones that you want to do and are simple to do.

Then, when I completed the five minute journal, I decided that since I had a bevy of empty notebooks, I would just use one and adapt the questions to ones that were important to me. To understand what questions were most helpful to me, I did research looking at the journaling practices of Tim Ferriss, Ryan Holiday and others and took a look at the different journals out in the market, including the five minute journal, the two minute journal and others.

Although my questions change from day to day, here are the ones that I have found most helpful in writing down my thoughts and feelings to:

What did I learn today? What have I read recently that surprised me?

Before I journal, I open up a book and read a chapter. It usually does not take me a long time, but I try to read for at least 30 minutes to an hour every day, reading bits and parts of different books to develop my concentration and focus. For example, today, I completed spark joy by marie kondo, which is an illustrated master class on organizing and tidying up. Inspired by her chapter on the bathroom, I decided to take some plastic boxes and organize the cupboards underneath the guest bathroom. What she said made a lot of sense to me: since it is a guest bathroom, the cupboards are more apt to be opened and seen by guests than any other bathrooms so organizing and tidying it up not only helps you, but the guests as well.

After reading, I will think about how I can apply it to my life, and then I will open up my journal to note down what I learned and how my life might change as a result.

It is rare that I don’t learn anything from reading a book, but sometimes I will note down other things I learned, such as when friends share big news or I learn something new about my partner or family (or even myself).

How could I have made today better?

Since I typically journal in the mornings, the question may be changed to “how could I have made yesterday better”. I will reflect on some of the mistakes or failures I have made the day before. One thing for instance I noted was leaving the house before checking I had everything. I have often left the house without my wallet, my phone, maybe even important documents I was supposed to bring along.

Therefore, I will write down what I did, and then what I should do in the future. I’ll make sure that I mentally check off a list of the things I need before going out.

What decisions am I grappling with?

Journaling is especially useful for big decisions in my life. What projects should I take on? What books should I write? What can I learn today that will be useful to me in five years?

Writing down all the details about a decision helps to give me clarity on what I am considering. And as a plus, it documents my decision so I can look back after to understand whether my thought process was correct or not.

What are my ten year dreams?

This is something that I learned from Mel Robbins and her Best Decade Ever program. I signed up at the start of 2020 and she advocates writing down our ten year dreams every single day. When we write down our dreams, we start to visualize and ‘make it real’ how we are going to achieve these dreams.

There is a part of our mind that tends to focus in on things that are top of mind. For example, when you are looking to buy a car, you tend to see that car on the road more so than before when you were not considering purchasing one. Or when you are looking for different opportunities, you tend to hear more about opportunities from others.

As a result, I have been writing down my ten year dreams every time I journal and even though it has only been several months, I can see myself working towards them every day.

What’s bothering me? Why? How can I change myself to change the situation?

One thing about me is that I tend to bottle up what I have inside. If things frustrate or anger me, I try not to let it show (though people that are close to me can see right through me). I often do this because I have a hard time telling if the frustration, impatience or anger is justified. I am rational enough to understand that my feelings can be irrational at times.

When I journal, I write about these things to see if my feelings are rational or irrational. Why am I so impatient? Or frustrated? What is it about me or the other person that makes me feel this way? What can I do to control the situation or my feelings better?

There’s an important rule I learned a long time ago: you cannot change other people, you can only change yourself. So even if someone was making me frustrated, I would write in my journal how I could change myself so that I do not get frustrated in the future. One example: I am frustrated whenever I am in the middle of something and then I get distracted from an interruption. I don’t like being in the middle of blogging and then getting called upon to do something that could have waited until lunch or the evening. One way around this is to wake up super early so that I can do the things I need to do without anyone bothering me (one great benefit of waking up early).

What ideas do I have?

Adapted from James Altucher’s daily practice as described in Choose Yourself, James, talks about coming up with ten ideas every day to make your brain ‘sweat’, similar to how you would lift heavier and heavier weights to make your muscles grow.

If you come up with ten ideas every day, that’s 3650 ideas every year. Are all of the ideas going to be winners? No. But there’s going to be a high chance that a fraction of those ideas will be decent. This is all about the process of generating ideas, because the more you can grow your ‘idea muscle’, the better off you are going to be in different situations. Any problem, challenge, project or activity you are involved in, if you can generate more ideas, the more options you will have.


What questions do you like to use as prompts in your journaling practice? Or is your journaling completely unstructured and free form?

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