5 lessons learned from keeping a daily journal for 10 years

Approximately ten years ago, on the thirteenth of March 2009, I made a personal decision to keep a daily journal cataloguing my life journey. Rain or shine, happy or sad, I would document what happened in life.

Now, over 3 650 entries later, I’d like to share some of the insights that were gained during ten years of journal keeping.

Insight #1: You’d be surprised by how little you remember

Pick any random, arbitrary day in the past ten years and I can tell you what I was doing on that day. But I might be just as surprised as you at the answer.

The reality is, the vast majority of the activities of our lives lies forgotten in the heap of yesterdays and yesteryears.

You are the executive summary of the executive summary of your life’s experience.

Insight #2: Journals should be non-judgemental explorations

The style of my journal evolved over the years. New sections were created for photos, conversations or thoughts. Sometimes I did videos (“vlogs”), sometimes written entries.

But possibly the most important decision I made about journalling was a philosophical one: complete, utter non-judgement in the exploration of life and reality. 

In the beginning, I worried how my future self would think or feel when reading these entries. “Will I think this is stupid? Will I think it’s silly to dwell on XYZ so much? Will I get bored by the minutiae? Will I even take the time out to read or listen to these ever again? Will I even care — if not why do I even bother?” — these questions lead me to worry about self-judgement —  worrying about the self of the future! — (The wiser, older Shawn) I worried how this person might look cynically on my naivety.

A crucial point came later on when I realised possibly the most important aspect of journalling is complete openness and non-judgement. This lead me to a kind of journalling philosophical manifesto:

  1. Journal entries can be as long or short as I like
  2. Journal entries can contain whatever content I like (events, feelings, thoughts, conversations, anything)
  3. Journal entries can be completely true / authentic reflections of what’s going on right now, even if its shitty, even if it’s an angry rant or depressing weeping.
  4. Journal entries need not be interesting, exciting, engaging or attractive in any way for anybody in the future. The only person who might ever review them in the future is likely to be myself, and even the future self need not be interested in reviewing them.
  5. Journal entries are about pure, open, curious exploration of reality, and not primarily focused on evaluations or judgements. 

And this ties in to the next point:

Insight #3: The psychological value of journalling & processing

While I claim no formal psychological credentials, it’s my understanding that much of the value of counselling / therapy is in seeking closure with the events in our lives, and having someone guide us in telling the right/thorough stories about and processing our past life events, particularly those with high emotional or traumatic content.

This is one of the reasons why therapy takes time, you sit down with a person and tell them the story from the beginning and in detail, taking your time to get the facts right and process emotional trigger points along the way.

— Of course, I am not trying to take away from the value a qualified therapist can offer a person in counselling, but highlighting that in some way disciplined journalling can fulfil much of the same function (the thing it tends to lack is the qualified person on which you can “bounce” ideas off or who can offer guided alternative stories, meaning you can get stuck more or it might take longer to reach conclusions).

In my life I have found journalling to have significant benefits in this department. Much of the reason I’m able to approach the present moment with good stability is due to having high amounts of closure in relation to the past — it is well and truly “behind me”, relatively well documented and with little felt need to revisit it. This is somewhat ironic of course — it is by dwelling on the past (journalling) that one gains closure in relation to the past and thus feels little need to revisit anything. The past literally becomes “yesterday’s news”.

Which leads to the next point:

Insight #4: Journalling helps you progress and grow faster

Jim Collins said in one of his speeches I watched once “don’t take 5 years to gain 2 years’ experience”. Journalling helps you to do that, reducing the amount of wasted time in your life’s growth path. It shouldn’t take you 4 years to realise something it might just take you 1 year to realise.

The reason it does this is that your life experience now has secondary conceptual “overlay” applied to it — being your journal entries about it, and they help you to construct more compelling and comprehensive narratives about things that happen. In other words, journals can increase the amount of insights your life experience is able to yield to you, by improving the processing of those life experiences. In some way it’s like upgrading your personal CPU to extract deeper insights from the same volume of experience. This forms a positive feedback loop as your next experiences are then approached from a place of more insight, thus giving you more diversity etc. for your future journal entries.

In line with the idea fool me once shame on me, fool me twice shame on you, journalling can form a key mechanism by which you don’t get fooled twice, by properly understanding why you were fooled the first time.

Finally, that leads on to point #5

Insight #5: Journalling makes you a better person for those around you

The emotional and intellectual processing that journalling offers can be transformative for your life. But it doesn’t just help you, it helps those around you too.

Let me illustrate this with a theoretical anecdote:

You’re frustrated in your work because of few of the things that are going on. You turn to your journal to express your frustration. You create an angry rant video of you talking into the camera about everything that is happening, jumping from topic to topic as you explore.

There is no “desired outcome” for your journal entry. You’re not trying to achieve anything. You’re not trying to conclude anything. You’re not trying to gossip or speak ill. You’re just trying to explore, and in this case this means expressing your frustration.

The next day you get back to work and start talking with your colleagues about some of the problems. For some reason, you find yourself less emotional, and less “ranty”. You discover that by processing those events privately in your journal that you’ve gained “the upper hand”. You say constructive things instead of just complaining. You don’t get as upset when discussing the topics because that wave has already passed and had its space. Indeed because of the additional time you spent processing these events you’ve even started coming up with some novel solutions to those problems, or thought of how to negotiate better.

You find yourself more able to listen to others, because you feel you’ve already had space to be listened to yourself. Thus you’ve become a better problem-solver and a better listener.

As this story illustrates, you find yourself more sedate. And so your interactions with your family members, colleagues and friends are better as a result. They interact with a more stable, more mature version of you.


Journalling is not for everyone. I’m not recommending that anyone should do this. It also doesn’t necessarily need to take the exact form I chose for my journal (daily). But after ten years of doing it I can definitely attest to the value its brought into my life.

And finally: it can also be just plain fun — if you’re into this kind of stuff!

Shawn 20-03-2018

4 Replies to “5 lessons learned from keeping a daily journal for 10 years”

  1. This was a brilliant article, Shawn. I really enjoyed reading it as it reinforced the benefits of keeping a journal.
    I write in mine to process ideas and thoughts, as well as gain an appreciation of my life – as you said, memories all get lost in yesterdays and yesteryears.

    Thanks for reiterating the purpose. I’m so glad I’ve been keeping a journal over the many years.


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