Aligning behaviour with a dream future state using the Pennebaker Journaling Method

Hello, this is a write up for a long term behaviour change and transformation experiment.

Please hit me up with any questions, feedback, input etc. I will do my best to remain not-too-emotional-yet-still-authentic.

TL;DR: I’m going to identify my problem behaviours, trace them to core wounds, tear them open in a controlled journal setting, knit myself back together, reload, re-calibrate and re-engage.

To see if it’s helping I’ll use a pretty heavy-duty level of self observation and tracking.

The whole point? Align my character more toward my dream lifestyle. And also, why not? Let a thousand blossoms bloom.

Questioning: What can I do to heal destructive aspects of my character?

Avoidance, intolerance for negativity, defensiveness, dopamine addiction…

Is it possible to transform these behaviours from their core?

Like pulling a weed from its roots rather than breaking off the top above ground…

What ‘signs and symptoms’ would illustrate successful transformation of my core character?

As much as I’ve accomplished in the past few years, there remain many aspects of my behaviour and character that don’t serve me or my loved ones.

Doomscrolling, food-as-medication (basically any quick-source dopamine addiction…) the list goes on.

I’ve had a little success in treating these symptoms with things like the Pomodoro technique, or The Get $#!7 Done Method (my gateway drug into Personal Knowledge Management, PARA by Tiago Forte and Life OS by August Bradley). But overall… ‘Treating’ these actions with new productivity or task management tools doesn’t change my behaviour in a lasting way.

Ideally, when I’m done with this experiment I’ll have a reliable, consistent way to identify, outline and transform the root memories beneath any behaviour.

I want a method to edit my subconscious.

Since I journal plenty already, I’ll start there.


To transform myself using journaling techniques.

Aim expanded

To build and refine a templated transformation process. increasing high leverage habits and decreasing low leverage habits using the Pennebaker journaling method.


  1. Track and record standard behaviour in minute detail for a baseline of habit data.
  2. Identify characteristics which hold me back in life by writing about core memories attached to low quality behaviours (typically destructive or quick-dopamine seeking).
  3. Target one such characteristic using the Pennebaker Journaling Method by writing about the worst, most traumatic memory related to it once per day over four days for fifteen minutes a day.
  4. Plan and initiate self care options on the hourly, daily and weekly level to handle potential re-traumatisation or possible ‘kickback’ after stirring trauma memories.
  5. Update the experiment log to capture lessons, examine efficacy of self care, refine strategy or technique and pivot experiment design for another targeted behavioural transformation.

Rinse and repeat steps 3, 4 and 5 until I get bored, achieve the aims or find a better option.

Method expanded

I’ll use Simple Time Tracker and Notion.

Simple Time Tracker.

A free offline android app for time tracking. This app will be in constant use throughout the experiment phase. Over the first week of the experiment I’ll be capturing baseline behaviour and habit data, building out the database of what I spend time on. By the end of the week I expect all my behaviours and habits will have a button of their own.

Using the app is very simple, it’s colour coded with fancy hexi-stuff as well so I have the same colours for the same categories of time tracking as I currently use in my Google Calendar system, noice.

Previously, Google Calendar was my go-to for time tracking by recording my behaviours at the category level, now with Simple Time Tracker I’ll have much more granular data capturing the exact level of minutes I spend checking incremental games every day. :stuck_out_tongue_winking_eye:


A free online pc / android / ios app for database management to write, track, manage projects or do so many things.

I’ll use Notion for writing the trauma-targeting journal entries directly into a database to easily tag and categorise the experiment inputs.

Perhaps in the future I can run statistical analyses on the journal entries.

I have a daily habit tracker I’ve used for a couple years now, to that I will add a new metric for whether today is a ‘yes’ (+1) day or a ‘no’ (-1) day.

I currently manually count and tally all the hours I spend on different tasks by using Google Calendar so lowkey I’m super excited to have Simple Habit Tracker’s robust automatic data analysis tools.


The main data point for this experiment will be a simple +1 or -1 every day.

Secondary data will come from journal entries (qualitative) and time spent in habits and behaviours (quantitative).

Observations evaluated

This experiment will generate three forms of data. In terms of observation value, +1 / -1 per day is relevant, trustworthy and convenient. The data from Simple Time Tracker (time spent per behaviour) is also relevant, trustworthy and convenient, but less so of all three. I expect the journal entries will be relevant, trustworthy and inconvenient - highly likely that writing about trauma will be disruptive in ways I don’t yet predict.

Something to note: I have completed a massive time tracking experiment in the past, I’ll cover more detail in the Problems section below (because it was bloody intense! Almost broke me NGL).

As for the all important question, data relevant to what exactly?

I’m glad you asked.

Observations expanded

The plus or minus habit judgement is built from a simple gut feeling yes or no to the following question: ‘When I’m living my dream life in 2034, will I be grateful for the actions and behaviours I chose today?’

In other words, +1 days reflect yes and -1 days reflect no to this highly personal evaluation.

I’m curios to ask, what do you think about this phrasing and also this data point? Does it look valuable to you? Why, why not?

How you might phrase a similar question for yourself will depend on your inputs (subconscious and otherwise), goals and intentions.

To create clarity around this gut feeling I’ve spent many hours writing about my future in varying degrees and forms. Using ‘The Airport Exercise’ written about in Pat Flynn’s book Will It Fly and via journaling both on computer (yeah, in Notion) and with pen and paper. The more clearly I can sense my future in my imagination, the taste, smell, sight, sound and feel of it, the more clearly I can evaluate whether I’m on the right path to get there.

How can I know for certain whether this path is the right one? I can’t! But I never let something as fun as uncertainty stop me from taking a leap of faith.


This experiment hinges on consistency.

Tracking habits and behaviour is the only way I’ve defined a proof / disproof. Highly likely that qualitative measures will begin to appear when I have the baseline week of data tracking recorded and beyond. I’m relying on sheer will power to continue and maintain tracking consistency. I expect this will be fine until life gets busy or hectic (during travel, large project deliveries etc).

Self observation can be tiring.

This experiment relies on lots of unbroken self observation. Experience tells me this kind of tracking has a high emotional toll. What experience, you ask? I once wrote every single thing I did every fifteen minutes for three weeks. This experiment almost broke me, with very high highs and very low lows, yet the reward of self knowledge was immense. The rollercoaster I believe had much to do with maturity and attachment to outcomes. With more experience, patience and detachment this time I think I’m much better prepared for what to expect.

Alignment requires articulation and isn’t very scientific.

To define a +1 or -1 day (aligned or misaligned to my dream future) I need clarity on what 2034 looks like. This clarity isn’t easy to come by. While I am naturally a dreamer, articulating in enough detail to cause real vivid expectation and vision costs a lot of brain power and concentration. Plus, nobody can help! I feel like I’m setting sail into the night sky with only my guts to guide the direction.

Value judging my behaviour offers unknowns.

Actions and behaviours aren’t black and white. By trying to answer the question of whether a choice is aligned with my dream future or not, I’m introducing a wild forcing function into the ecosystem of my consciousness. I have no doubt this force will be a net positive pressure, but it comes with costs I haven’t experienced before. Tracking my actions each fifteen minutes is one thing, defining and articulating their inherent value is completely another. I’m not sure what to expect here.

Wishing life away.

If you’re going to try something like this, keep an eye on how self-observation affects you. Constant self awareness and continuously asking ‘is this behaviour aligned with my most ambitious future?’ can do funny things! For me it’s really important to remember to appreciate and enjoy the life I have now, even while building and focusing on the life I want in the future. This balancing act requires conscious effort in the art of being - which sounds like a bunch of wank. In practice this means I track some very simple behaviours like ‘Mindful Breathing’ and ‘Delight Someone’. If I gain financial freedom and physical fitness but don’t have good relationships, who cares?

Sheer time cost.

This write up has already taken me four hours across three days (the exact number is three hours and fifty eight minutes as I write this!). This time cost will of course increase as I self observe, organise a baseline, journal to create targets, then apply the Pennebaker method and report my findings. I’ve got a lot of other things competing for my time: career, business, content to create, a wonderful partner, so it’s not easy to say no to all that so I can indulge my addiction to data collection! I justify this experiment by telling myself it will be super high leverage if I can pull this off. Easily the most valuable thing I could possibly spend my time doing as it has infinite upside, so long as I can manage the downside and still maintain my other responsibilities.


Pennebaker journaling method.

Apparently one of the most widely scientifically validated and peer reviewed methods of journaling for healing.

Brought to the mainstream by Andrew Huberman in his podcast on it. The scientist who brought this technique more attention than any other is named James W. Pennebaker who’s also written a few books I’m keen to get my hands on including Expressive Writing: Words that Heal that outlines the method and Writing to Heal: A Guided Journal for Recovering from Trauma and Emotional Upheaval.

The airport exercise.

The main method by which I articulate my dream lifestyle in 2034.

Popularised by Pat Flynn in his book Will it fly? the method asks you to cast your mind and imagine you’re in an airport five years in the future (he picks five years because that’s typically what you can somewhat realistically imagine). You bump into somebody you haven’t seen for ages, more than five years. They ask you ‘omg how’ve you been?’ and you answer from a deeply grounded and centered place ‘I… have actually been incredible.’ You think about it and realise, yup, your life is absolutely how you would design it in every way imaginable. Now you reel yourself back into the present day, pull out a pen and paper and write in as much detail as you possibly can about what you tell them.

Obliger personality temperament.

I am an ‘obliger’ which is my main reason for posting all this.

Knowing my personality temperament has been a game changer, it’s kind of like finding the hidden control panel in my brain. I can get to the secret knobs and dials and much more effectively influence my behaviour consistently than I could before I found this. Super exciting if you’re as much of a nerd for personal growth as I am! The ‘Obliger’ temperament comes from Gretchin Rubin’s Four Temperaments framework (you can do her test for free on the website). The short story is: I’m highly likely to do what I tell others I will do, therefore I tell as many people as will listen so I’m super compelled to go ahead and follow through.

The slight edge.

Heaven and hell aren’t waiting for us after we die, they’re right here in this very moment.

Reading The Slight Edge: Turning Simple Disciplines Into Massive Success by Jeff Olsen gave me a perspective I always wanted but could never find. It gave me a simple answer to the question: ‘If everyone knows what they ‘should’ be doing, why don’t they do it?’ This experiment is massively driven by ‘the slight edge’ in its examination of not just the big life changing impact of trauma healing, but also the slight, almost invisible impact by examining the smaller stuff, inconsequential day to day habits and actions.

The law of diminishing intent.

If you delay taking action, your likelihood of never taking it shoots right up.

I came across this theory through John C. Maxwell which he got from Jim Rohn. I’m regularly wrestling with the reality of this law in my everyday life because I have so many ideas so often that I don’t have the resources of time or money to pursue. This is the underlying reason of why I really want to create more freedom for my partner and I, because I’m so tired of saying no to great ideas! Imagine an iceberg where everything that I do and publish is the 1% that makes it through the resource barrier, and the 99% is frustratingly locked, hidden away in some Notion database hoping to see the light of day.

The gap and the gain.

Measure from how far you’ve come to feel good, measure how far you’ve got left to feel bad.

This book by Dan Sullivan and Dr. Benjamin Hardy has become a key defense in my mental health over the past few months. I think attempting any kind of big-and-crazy tracking or behaviour change experiment needs to include a basic understanding of these concepts.


I will post updates here as I go and on my blog.

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Preparation Phase

Baseline - Thursday 28/03/2024

Day four of habit and behaviour tracking.

Day one I recorded seven hours worth of data, the next two days recorded twenty hours worth of data. I’m getting used to it! The emotional toll so far has been very low. I think it’s important when tracking habits and time to not judge it.

I do have an unexpected problem. The habit tracker I’m using asks for me to choose between two different forms of tracking, either concurrent tracking where multiple habits can be recorded at once, or non-concurrent where it’s only a single use of time available to be tracked.

I lean more toward single-use and the implications for mindfulness feel immediate. How often do I spend my time doing ‘two things at once’ (in which case I’m really doing less than either)?

Plan update:

The original plan was to track for roughly a week or so while completing preparation for the experiment, then to begin the Pennebaker Method next week.

After having read more about the Pennebaker Method and finishing Andrew Huberman’s podcast episode on it, I’m going to extend the period of preparation for at least as long as it takes to read James W. Pennebaker’s book on the writing method.

Trauma is no joke.

Reprocessing it can cause people to have psychotic or depressive episodes and I already have a genetic disposition toward schizophrenia.

If you’re thinking about doing an experiment like this, take your time to set yourself up for success!

Interesting post.

I have never heard of Pennebaker before although I now have a copy of hiis 2007 retrospective paper thanks to Google Scholar. Checked out the price of those books via Amazon; currently listed at over $50 US.

Will be equally interesting to see how you mix quantitive and qualitative data together.

Cheers. Yeah pricey for the journal one.

It’s actually got its own short quantitative and qualitative survey for each day of writing, cool to see. I’ll borrow what works and share about it when I cross that bridge.

Preparation Phase

Baseline - Saturday 30/03/2024

Day six of habit and behaviour tracking.

Gathering the Baseline

This time tracking app is insane. I’m learning new fancy features every day. I love how the design is so obvious and simple it requires no tutorial or lessons. Just begin, fool around and figure it out really intuitively.

It’s clear that a lot of effort from many people have gone into the Simple Time Tracker.
I’m not sure on how best to slice my day up, whether a new day should default begin at midnight or around when I tend to rise or fall etc.

Stick with midnight because :man_shrugging: If you have any suggestions or input please share!

Many small decisions like this I’m making on the fly as I go.

This can be tough because the temptation to maximise for the endgoal is strong, but doing this requires lots more brain power and time. I gotta remember that what matters today is taking the step I can, and trust the end to work itself out as I go.

Pennebaker’s book on Journaling
I’m 30% of the way through the book on journaling. The author writes in a cheeky way inviting the audience to hold skepticism for his entire life’s work. I find his tone humble and endearing.

The Flip-Out Rule

If you do intend to try something like this please do read the book by Pennebaker.

It includes a tonne of very helpful context and set up, for example ‘the flip-out rule’ (which I hope is named after this hilarious scene) which basically states ‘if you think you’ll flip-out by writing about that topic, don’t write about that topic’.

Simple and straightforward.

Don’t Share Your Writing

He has a lot to say about the risks of having other people read your writing.

Mostly boiling down to the chance of having people react in the wrong way potentially making emotions worse. I imagine this comes down to validation and depth of perception. Sometimes the feeling of being misunderstood hurts worse than the feeling of being invisible.

Having shared my own story via podcast I can attest to an enormous amount of struggle I faced after the episode aired. Found it very surprising very irrational and emotional my thoughts became for pretty much the entire day.

Of course that was only triggered by the introduction of a ‘faceless audience’ concept, before that day the expression of pain and history only happened between the interviewer / podcast team and myself.

Very interesting implications around experiment design and security of journal entries as it relates to the kinds of people around you (for example if you’re interested in trauma healing because you have complex trauma it’s probably because you have or had people in your life who have zero regard for your boundaries, invalidate your experience and use your vulnerabilities against you, all important to consider if thinking about journaling things that might be used against you).


Writing context is important enough to have a chapter of its own.

I’m not surprised given my experience with psychedelics. Set and setting are the western, fast food version of what ancient civilizations have practiced for thousands of years. Ritual matters. It’s why we bury our dead, have wakes, celebrate birthdays. It’s why tribes chant before certain practices. It’s why we have rites of passage. It taps into something deep inside us.

I’m a bit of an over-engineer so while I’m tempted to go all in on designing ritualistic writing practices I will resist and just go with something simple like lighting a candle and extinguishing it to begin with. In the future though if this practice works for character design and I continue with it I’d like to layer new aspects in (such as invocation or prayer).

Design Flaw

Reading the book has shown me a pretty big flaw in the experiment design.

The ties between my (little t) traumatic events and the impacts they have in my life are weak. It’s hard to trace back the reason I have avoidant or dopaminergic tendencies because it’s not like a big T trauma with a huge inciting incident like a car accident to target etc.

The links are weak at best for what I’m planning to target. But the risk is relatively low compared to the potential upside - so long as I abide by the basic guidelines (like the flip-out rule) in the book, so I’ll just keep it in mind as I go ahead.

Correlation / Causation

It could also be that successful experiment is correlative not causative, meaning higher self observation and awareness combined with decisions to pursue slow dopamine sources (such as exercise and mindful breathing) are the real heroes, even though I happen to be doing an experiment on trauma healing through writing. Or even that it’s something I haven’t really got my eyes on, in any case I’m keen to collect whatever observations I do.

Journaling yesterday I think I discovered the first topics I’d like to devote to writing about, I’ll continue to grow the list as I go, reading the book and preparing for Change Attempt One.

Preparation (:point_left:t4: you are here)
Targeting / Selection
Change Attempt One
Review / Reflection
Change Attempt Two
Review / Reflection
etc. ad infinitum.
Experiment Wrap-Up (?)

I originally expected Preparation would last a week or so, but I actually begun drafting the write up of the original post on the 26th of February 2024 (over a month ago as of right now). It took me multiple passes to write the first post (up above) and is now taking me more passes to clean and clarify exactly what I’m planning to do, while refining the how, why and desired outcomes.

I don’t mind taking something like this slow because tracking and logging the experiment is just as important as completing it.

When I’m dead I hope there’s a long list of experiments like a kind of breadcrumb trail for anyone who finds themselves facing the same struggles I have.

Picking Writing Topics

Given the now obvious design flaw (that I’m using a big T trauma-healing technique for a behaviour change experiment, which may be a scalpel when I need a hammer - or vice versa…) I want to add a bit more weight to the odds of designing character change.

Here’s a loose draft outline of how I plan to select / target a memory including a bit more around intentionality before and after.

Targeting / Selection

  1. List the specific behaviours I’m either avoiding or that I want to replace.
  2. Pick the one most significant for this week.
  3. Write about it in unfiltered journaling looking for memories to trace. Ask questions like: what emotions are present around this behaviour today and when did I first feel this way?
  4. Find a memory to target, related to the emotion, feeling and behaviour.
  5. Write about the target outcome for transformation including natural reactions to specific triggers attached to the behaviour (in other words, write from future-state Said’s perspective about precisely which behaviours happen based on identified triggers, how he experiences life, the world and decision making - this will act as a bar by which I can compare future journal entries to).

Change Attempt One
6. Do the four of days of writing.
7. Reflect / review.

I imagine over time I will build some of these processes into somewhat of a templated shape with questions etc. Pennebaker includes a simple questionnaire in the guided journal for each day of writing, including some basic quantitative questions with a space for qualitative reflection. I can clone this for ease of both input and number crunching in Notion.

FYI I have negligible academic experience so when I use the words quantitative and qualitative I’m probably bastardising them.

Being part of this community has given me the confidence to do big tracking experiments in the past, and to start using graphs and charts. I very much intend to improve my tracking, statistical analysis and data presentation skills, by doing stuff and making mistakes and learning.


It seems rather obvious now, having written all that out - what I’m really attempting to do is in the domain of NLP.

I think I’ll focus on doing Change Attempt One as soon as I finish this book (quickly as possible) and after that I will finally start looking into NLP - been meaning to for over a decade.


I suspect to begin Change Attempt One mid-way through April.

See you soon!

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