How to make journaling a regular practice

In our previous article, we discussed how to build a habit of journaling but we didn’t go much into detail about the actual process of journaling. In this article, Dzhuliana Nikolova, Co-Founder & CTO of OneUpOneDown shares her experiences making journaling a regular habit, including the trigger that kick started the habit and questions that you can ask. 

If you’re someone who likes to know the exact process for how to do something, the experiences Dzhuliana shares in this blog post will be useful for you. 

Step 1: The trigger to get started

I knew the compelling benefits of journaling long before I made it a regular practice; good for mental health, better sleep, more self-confidence, and a stronger immune system. However, this was not the trigger that made me start practicing. At that time, I was working on my first start-up and I was reading a lot of biographies looking to improve my leadership skills. From Marcus Aurelius through to Benjamin Franklin, Abraham Lincoln, Eleanor Roosevelt to Warren Buffet and Bill Gates. I noticed many common traits shared by these people, but one stood out. It was that simple habit of writing. Picking up a tool used by these great people made me feel excited and that was my real trigger to start.

Step 2: Getting started – writing the first page

I felt on top of the world when I decided that journalling was going to be my regular practice. But when it came to writing the first page, it was quite difficult. Maybe this was the reason I postponed it for so long; actioning an idea is always harder than imagining it and I didn’t know how to use the tool that I had decided to pick up. So I started searching for ideas and found the following self-analysation questions:

  1. What mistakes did I make?
  2. What did I do successfully?
  3. Can I do this in a better way?
  4. What lesson did I learn from this meeting?

Having a set of questions to prompt you when you first start the practice of journaling is useful. It makes starting easier. You could try these questions, or google ‘questions to start journaling’ to find other great suggestions. Once you have started, it will be a natural progression to try new things that push your journaling practice closer towards what you are wanting to achieve from it. Which brings us to the next step…

Step 3: Letting your practice evolve

The questions I shared above were exciting and useful in the beginning, but as time went on I found that answering them every day required a lot of effort and they weren’t always relevant. As a result my writing became inconsistent. 

I also felt like I had begun to master the task, which made me feel empowered and confident. This is a trick of the mind; thinking that the job is done. The value of this task comes from consistency – mastering it as a regular practice, not a once off. 

The learning here was that the why is much more important than how. The purpose of journaling is to get thoughts out of your head and down onto paper and to use this process for whatever outcome you are wanting. Whether it be to make sense of how you are feeling, to improve behaviours and actions, or to tell a story. How you facilitate the process of getting thoughts to paper doesn’t matter so much as long as you achieve the outcome you are wanting. It is quite okay for these questions to evolve and change to support ongoing learning and improvement.

I have tried many different ideas for journaling throughout the years, including the following:

  • Writing about problems and destructive thoughts
  • Writing to my grandchildren
  • Writing to my future self
  • My opinion of a specific domain that I care about
  • Letters to people when I am angry with them
  • Past events from my childhood
  • Self-analysation questions
  • The events during the day
  • Notes from something I have read or listened to
  • Jokes
  • Daily affirmations

Today, I write 3-4 times a week, less or more depending on my schedule. I no longer have a set structure that I stick to each day; sometimes, the pages are a bit empty of words but full of feelings. Once I had built the habit and experienced the value of the tool enough that it is embedded in my mind, I could relax the rules I had set for myself. 


The first step to creating journaling as a habit is the trigger, that is realising that the benefit of the practice is worth time and effort required. This is usually driven by a desire for a better or different way of being. It is the first ‘why’ in the practice. The next steps is to find a suitable journaling process to help guide your journaling experience initially. This is the equivalent of gutter rails for bowling. It will help to keep you on track initially while you are improving your skills, so you don’t get frustrated and fed up with the practice. It introduces you to the ‘how’ of the practice. As you start to journal regularly, through self observation you will start to realise the outcomes that you can achieve through journaling and the different questions, intentions or processes that best help you to achieve this outcome. 

There are no right or wrong ways to do this. It’s a matter of trying things out, maintaining an observer mindset, and keeping consistency. 

Happy journaling!

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