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  • Julius de Jong

How Journaling Makes You Smarter and Happier (Episode 19-39)

...and doesn’t have to be perfect

For some time, I journaled. It was great. I started the practice of habitually reflecting in the evening on all the meetings I had throughout the day. It was immensely valuable. Through writing about these meetings, I recalled things already forgotten, and gained new perspectives and insights. It brought me a lot. I therefore know from personal experience that journaling is very beneficial. However, I lost the habit. Which is the difficult thing with journaling, at least for me. That’s why the Sustainable Journaling Project of John Casey really appealed to me when I found it while researching journaling. ‘Sustainable Journaling is a set of easy strategies that effectively help create a daily journaling practice that can be maintained over an extended period of time’ (Casey, 2021).

Like me, Casey tried journaling on and off, but was never able to do it on a regular basis, and often found himself overthinking the process of journaling. I have had that too. As I learnt, I wasn’t the only one with thoughts like ‘that perfect looking journal is too nice to write in’, or ‘is this really important enough to write about?’ which all kept me from finding a consistent rhythm for my journaling. My talk with John about journaling has really helped me gain another perspective on the practice of expressive and reflective habitual writing. You’ll find the main insights here below.

Why sustainable journaling

When I asked how his practice of sustained journaling developed over time, John shared with me that he sometimes forgot what he had done in the past week or the last month, and how this made that time feel somewhat meaningless. In order to keep up the practice of journaling over time, John created some simple strategies concentrating on habit forming in the first place (Casey, 2021). ‘When talking about journaling, the most heard response was always, oh, I can’t keep it up’ (Casey, 2021). Due to a close of the barbershop where he works because of the pandemic, John decided to start sharing the practice of journaling by teaching others. As I’ve shared in my introduction, keeping up with the habit is the tricky part. Some of the insights shared by John during our talk therefore really hit home with me.

Benefits of journaling

Journaling creates anchors for your past experiences and the past day in written form, but it also anchors for self-care and honoring yourself (Casey, 2021). ‘Journaling is not […] performing for history’ (Daily Stoic, 2020). It’s about reflecting and processing your experiences. As John said, ‘[i]t provides the space for structured reflection’ (Casey, 2021). I think this is very important and beneficial. We often don’t do this enough, as I know from personal experience. Creating a habit and routine for doing so on a daily basis is therefore very beneficial. Having documentation of your life and knowing that you have something to refer back to for tracking experiences, events, and feelings, is a very good thing according to John Casey. Over time, this will allow you to notice patterns and help you with processing experiences. More about that below. Journaling also is a means to give you permission to know that you are worth having these moments of self-care. Apart from processing experiences, journaling also helps us improve our performance and skills. It also improves our executive functioning. Journaling helps us with remembering our to-do’s and the promises we’ve made (Casey, 2021). Journaling is ‘a strategy that has helped brilliant, powerful and wise people become better at what they do’ (Daily Stoic, 2020). It provides a way to practice our principles, be creative and purge our mind of agitation (Daily Stoic, 2020). ‘Keeping a learning [or training] journal encourages and enhances deliberate learning [and progress]’ (Di Stefano, et. al. 2014). Increasing our reflection on our day and training practices by only 15 minutes enhances our performance by over 23% as illustrated in a Harvard Business School study. That’s a big deal! And it makes sense. Think about it. What if we’d make conscious time daily to reflect on our life, work, encounters and more? Imagine all the learnings we can take from this process. We have so many times when our heads are just spinning with ideas, thoughts, and concerns (Casey, 2021). Journaling then provides with a place to write them down, and know that they’re safe. You can go back to them when you want and see what needs most attention. Writing things down helps you honor the experience but also see things for what they are (Casey, 2021). Journaling therefore can afford for some much-needed perspective. Author Derek Sivers has been journaling for over 20 years, and has shared some interesting points in this regard. As he stated, '[w]e so often make big decisions in life based on predictions of how we think we’ll feel in the future, or what we’ll want. Your past self is your best indicator of how you actually felt in similar situations. So it helps to have an accurate picture of your past. You can’t trust distant memories, but you can trust your daily diary. It’s the best indicator to your future self (and maybe descendants) of what was really going on in your life at this time' (Sivers, 2019).

Journaling as a means for processing feelings and emotions

Writing about our feelings and emotions has proven to have long-term beneficial effects. Although in the short term, it can stir our feelings and emotions more, over time the effects of writing and reflecting are beneficial. Writing habitually gives yourself the time and space to just sit with something (Casey, 2021). This helps one process experiences. It is also helpful and beneficial to know that at the end of the day, we can write about a particular experience which makes it less intense when experienced in the moment (Casey, 2021). The fact that you know that you’ll have a space later to reflect on-, and learn from-, the experience can help calm you down and deal with whatever is in front of you better in the moment. This releases the pressure of having to make sense of it all that instant. The structure of regular journaling provides this.

A study from Cambridge University found that ‘[w]riting about traumatic, stressful or emotional events has been found to result in improvements in both physical and psychological health’ (Baikie and Wilhelm, 2018). This study shows that expressive writing results in significant improvements in long-term physical heath, improves blood pressure, our lung function, liver function, and reduces the number of days in hospital. It also produces significant benefits for our immune system functioning. ‘Confronting a trauma through talking or writing about it and acknowledging the associated emotions is thought to reduce the physiological work of inhibition, gradually lowering the overall stress on the body’ (Baikie and Wilhelm, 2018).

Journaling doesn’t have to be perfect

What made me lose the habit of journaling after attempting it in the past were my fixed ideas about what journaling should look like. Silly as it might sound, it was a big eye opener for me to hear John share with me during our talk on journaling that sometimes his entry for a day was simply ‘Stayed at home and did my taxes’ (Casey, 2021). Pfffh! So, it doesn’t have to be perfect?! Obviously, we make up our own rules. But I know I can get locked into thinking things should be a certain way. For instance, that when I’ve written fluently, and was so articulate, inclusive and reflective one day, the next time should be at least the same. Of course, it doesn’t work like that. Knowing then that merely a few words can also be sufficient, and that our writing doesn’t have to be perfect really was an eye-opening thing to hear. As John suggests, at least write the day and date for each day helps us build the habit. This allows one to get back to an entry later and possibly add something. It also helps honor the practice and have the day accounted for. This is called retroactive journaling, which means as much as adding missing information later (Casey, 2021). I really like this. It takes the pressure off from things having to be a certain way and allows for flexibility and frees us from a striving for perfection. Yet at the same time, it helps us keep a structure in place, and reinforces our habit of journaling. Again, this really doesn’t have to be perfect. It can even be just key words at times. They’ll function as triggers for remembering later and will still have their role in terms of accounting for our days, and processing (at least some of) our experiences.

Product and process

John Casey distinguishes between the product and the process of journaling. The product is having the documentation of everyday, keeping track of things, and having your day accounted for. The practice of journaling helps you honor and appreciate the day. Being able to come back to this later will help us be more aware and present.

The value in the process is having the space for structured reflection, having the time to sit and remember what the day was about, what was important, and what you felt and learnt. As mentioned above, this helps us deal with feelings and emotions, and has proven long-term beneficial health effects. Doing this also reinforces our learning experiences and helps our performance improve over time. Be it in business, relations, sports or whatever. When we consciously reflect and process, it improves our outputs and state of mind.

The habit of journaling

As John shared, many people have the idea to journal when something interesting happens. However, as we know, it’s in those times when we’re most occupied with that particularly interesting thing that’s happening. This doesn’t help our practice of journaling. Also, it brings in the burden of decision making. Namely, now we have to judge what is interesting and what is not, and this doesn’t help the practice of journaling, nor does it make the experience nicer or easier. Instead, when creating a habit of journaling, which we routinely do, ideally daily, this frees us from the burden of decision making. As John said so beautifully, ‘[f]reedom though discipline is freedom from decision making (Casey, 2021). How I love that, and how much I can relate! When something is a habit, it’s one less thing that we have to decide or worry about.

A moment of silence and reflection, and time for oneself is beneficial for anyone I believe. Therefore, creating a habit of writing to do this is an easy way to reap the benefits of this and stay true to the practice. As John shared during our talk, only two minutes of time will already get you a long way. Better would be around 15 minutes of quiet space to write and reflect on the past day. This could be done in the evening, before bed, or as John does it, as part of the morning routine the next day. This practice will result in more clarity during the day, and an overall more grounded state of being and as John shared, increased sense of gratitude and (self-)compassion (Casey, 2021). We benefit from building good habits. According to Derek Sivers, journaling ‘works best as a nightly routine. Just take a few minutes and write at least a few sentences. If you have time, write down everything on your mind. Clear it all out. But if you miss a night, make time the next morning to write about the previous day’ (Sivers, 2019).

Re-reading your previous writing

According to John Casey, as he learnt from his students, rereading entries is not something that many people do. John himself has created the habit of re-reading the last month’s entries on the first day of the new month. This offers a great opportunity for reflection, learning and gratitude. As John shared, he often wonders of all the things took place (which we forget), and how much appreciation and gratitude he experiences while reflecting on the past month. ‘When it’s looking back, our brain always goes to the things that it wants to fix’ (Casey, 2021). Our eyes always focus on the fault and the imperfection, and the speck of dirt on a clean white table. We see the errors first. This is our safety feature of the survival mechanism of our brain. By recognizing there is more good than we sometimes think, through the process of reflecting on our writing, this helps us shift our focus and create more good from there moving forward. Where focus goes, energy flows.

‘Thoughts on …’ journals

In his article on keeping a journal, author Derek Sivers also shares his way for tracking how his thinking grows and develops on particular topics. In my view, this is an interesting approach for keeping your notes, thoughts, and ideas on certain topics organized and accessible for later review. As he wrote, ‘If you care about your thoughts, keep them’ (Sivers, 2019). ‘I find it so useful to keep my thoughts on each subject together, because I can see my past thoughts and current thoughts in one place. I can see how my thoughts on this subject have evolved or keep repeating. Sometimes I think I have a new thought on a subject, so I open up the file and write it down, then afterwards I see I had that same thought a year ago and had forgotten about it’ (Sivers, 2019). Together with the daily entries and monthly (digital) filing of these entries as suggested by John Casey, I really like this approach to structuring one’s thoughts and making them accessible for later consultation and review.

Do it, and see

In conclusion, I’d like to end with an invitation. Why not give it a go for some time? Agree with yourself (or together with some other people for accountability) to try out the practice of keeping a daily journal for some time, to see what it brings you. Of course, there is an effort required, but as with everything, effort is rewarded. I’m curious to learn what it will bring you. I myself will also start again too with keeping a daily journal. I’m curious what I will find, reflecting back, later. Join me?



To learn about journaling, I’ve talked to John Casey from New York. John is an avid practitioner and teacher of journaling, and the founder of, a place where one can learn easy strategies that effectively help create a daily journaling practice that can be maintained over an extended period of time.

This was a very interesting and practical talk for me, and I’ve learnt a lot about how to build a habit of sustainable journaling and what typically gets in the way from this. In case you’d like to learn more about how this simple daily practice can make you more effective, happy and even smarter, you’ll surely enjoy this recording!



Baikie, Karen, and Wilhelm, Kay, 2018, Emotional and physical health benefits of expressive writing, Published online by Cambridge University Press.

Daddona, Matthew, 2021, How a Barber and Journaling Expert Spends His Sundays., accessed on 30 November 2021.

Daily Stoic. The Art of Journaling: How To Start Journaling, Benefits of Journaling, and More., accessed on 2 December 2021.

Dee, 2021, 17 Journaling Tips For Beginners (And How to Start)., accessed on 2 December 2021.

Di Stefano, Giada, Gino, Francesca, Pisano, Gary, and Staats, Bradley, 2014, Making Experience Count: The Role of Reflection in Individual Learning, Harvard Business School Working Paper.

Sivers, Derek, 2019, Benefits of a daily diary and topic journals., accessed on 3 December 2021.

Watson, Renee, Fraser, Marianne, and Ballas, Paul, 2021, Journaling for Mental Health., accessed on 2 December 2021.

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