Make the journalling habit stick: 5 tips

I’ve been a bit of a personal development geek for a while. About 10 years ago, I was reading blog posts about all the benefits of journalling: how it can help you to process your thoughts and emotions, to work through difficult situations, develop a better understanding of yourself and to boost your creativity. It was no surprise that online productivity gurus like Tim Ferriss owed much of their success to daily journalling. I was struck by the vivid detail that Richard Branson described his life events in his autobiography. These productivity gurus outlined a daily ritual: wake up early before the sun rises, before anyone else is awake, sit in a quiet room and scratch away with your pen to the paper for 15 minutes. Do this everyday, and you too will be successful.

Hungry for all of the purported benefits (and the success!), I was burning with motivation to try it out. I picked up a notebook and pen and set aside time in the morning to sit down and write about my thoughts. I woke up bleary-eyed at 6.30am (at least an hour before my usual waking time) and got prepared to attack the day with my pen. With the best of intentions I sat at my table and flipped open to the page, pen in hand, ready to write and start my journey to success and then.. I just stared blankly at the page for 14.9 minutes, trying to fight through the morning haze in my brain. Eventually I proceeded to give a bland recap of mundane things from the day before: “I ate this for dinner” and “I saw this person today”. I pressed on with it for a few weeks, each day getting slightly faster at writing. The result after a month: I only got slightly higher quantities of bland words.

So I gave up on it. Granted, this wasn’t a huge amount of time that I’d dedicated, but I was young and impatient. I returned next year to try it again, reinvigorated about the promises after reading another blog post, only to go through the same motions and give up again.

Every time I went through this cycle, I found that the same issues kept coming up:

  1. I always felt tired when I sat down to journal. It was a massive mental uphill battle just to form coherent thought.
  2. I could barely read my handwriting in my journal. I would also forget to bring my journal with me, so I never had it on hand if inspiration struck.
  3. I felt like my entries would be written once and forgotten forever. I didn’t have a system of going back to review old entries, so the lessons I’d learned weren’t being remembered.
  4. Even when I wasn’t tired, I got massive writer’s block and couldn’t think of anything to write.

I found ways to overcome each of these issues one by one. Once I did, journalling finally felt easy and worthwhile. Fast forward to today and journalling is actually a habit that I look forward to doing! I don’t do it everyday, but nor do I feel like I need to in order to get the benefits from it.

If you’ve been struggling to start journalling, I hope these tips will help you to find a method that works for you.


1. Find the right time

The idea of “productive morning = successful in life” is one that’s parroted a lot in the productivity world. People draw on examples of countless CEOs like Tim Cook who are early risers. Naturally I thought that it had to be one too.

Turns out, I’m not a morning person. My neurons take their sweet time to wake up and start firing properly. So when I sat there in front of a notebook right after getting out of bed, the only thought I could muster was “this wouldn’t be a bad place to go back to sleep”.

It took years to let go of this ‘productive morning’ idea and accept that I’m just a night owl. So instead, I now journal at night or in the afternoon and I find that I could immediately get my pen to the paper and open up my stream of consciousness. It feels so much more natural for me to reflect on a day that had already happened instead of trying to desperately pull memories back from a previous day.

You might be like me or you might be an early riser. Or somewhere in between. Whatever your preference, write according to that. Don’t blindly follow people trying to recommend the same regimen for everyone.


2. Find the right medium

I consider myself a very digital person. My handwriting has always been terrible and keeps getting worse every year that I’ve finished school. It doesn’t give me much satisfaction to look at my handwritten chicken scrawl.

So now, I write my journal on my laptop as well as my iPad or iPhone (yes I’m very spoiled). I can start an entry on my phone, jotting down a note while I’m out and about, then finish it on my laptop at home. I can type a lot faster than writing by hand and the end result is a lot prettier too.

I use an app called Diarly, which has a super clean and minimal interface, syncs entries via iCloud across all of my devices, allows me to record special data like location, weather and movement. It gives me all I need in a journalling app for a cheaper price ($25/year) than the leading Day One app ($35/year). It’s a steal if you ask me.

Yes, there’s something special about the feeling of the metal ball rolling against the paper, the tactile feel that connects you to your words in a day that a digital device never could ver replace. It’s also a lot easier to get distracted and start scrolling while writing if you’re doing it on a internet-connected device rather than a paper book. But these are trade-offs that are well worth it for me.

Don’t get hung up on the whole physical vs. digital thing. If you like a paper notebook, go for it! My advice to you would be to find what works for you: like with morning routines, don’t dogmatically subscribe to a certain medium because someone else (even me) told you it’s ‘better’. Focus on what will help you get the job done.


3. Do a weekly review

I used to open my dairy, write my entry, close it and never look at it again. Again it didn’t help that I could barely read my own handwriting. The problem was, it was hard for any for it to feel that meaningful. What was the point of spending all this time writing something, only for it to be lost forever? I wanted a way to feel like all this effort was building towards something bigger.

When I started using Notion seriously in 2021, I found out about something called the Weekly Review. Yep, it’s exactly what it sounds like. I do it on Mondays late in the morning, and it allows me to think and reflect on everything that happened in the past week, as well as plan the week ahead. This routine forces me to look back on the entries I’ve made in the past week in Diarly and surface any learnings and memorable moments from them.

I also have a Monthly and Quarterly review routine that I do as well with a similar idea, but I’d recommend starting with a Weekly Review if you haven’t already.


4. Write like you’re giving advice to yourself a year ago

This piece of advice really helped me get my pen to paper (or rather, fingers to keys) a lot faster. It also helped with making the entire practice feel more meaningful. Rather than writing about what I had for lunch, this prompted me to think about what I’d learned so that I could potentially help out someone going through a similar situation.


5. Have prompts

This follows from the last idea. Have a list of 3-5 prompts to start your entries with so that you spend less time staring at the dreaded blank page and make sure your time is well spent writing insightful things.

My favourite ones are:

  • “I’m grateful for..”,
  • “Today I learned..” and
  • “I’m proud of myself for..”.

With these prompts alone, you can write a solid entry every single day.



Now, I actually feel excited to write entries. I can open Diarly whenever I’m in the mood for it and immediately note down an idea, insight or reflection I have. I know that these special moments will build into bigger pieces of my overall life, not to be lost like leaves in the wind any longer.

If you’ve wanted to get into journalling for any amount of time but have found it hard to stick, I hope these tips give you some ideas to switch it up and inspire you to find your own way to make it work.

What’s your favourite method of journalling? What elements have I missed here? Feel free to reach out to me with a comment or message.