Principle of Chaotic Habits

You are probably familiar with all the routine advice about forming habits: doing it every time, staying consistent, doing it regardless, deciding to do it etc. I don’t want to go too deep because that is not the focus of this article.

When I first wrote about this principle in a Twitter thread (see it HERE), I was writing for the sake of 1 in 4 humans who simply cannot form/sustain habits independently without external pressure, or grave consequences wielded by someone who looms larger than life over them (yes, the occurrence is that common).

You see, for some people, their neurology (read brain wiring) simply prevents them from being able to do certain things like neurotypical people would (there’s a whole lecture behind this that I may or may not revisit sometime in the future).

They can try as much as possible, but the habit just never forms, which means that they either fall off the wagon very soon, and spend the majority of their lives beating themselves up inside over constantly failing at “simple” stuff, while enduring external criticism for not being able to meet up, keep up, or show up.

The constant state of self-criticism and external disappointment/low expectations make them even less likely to succeed when they try – leading to a vicious cycle of failure, a mentality of impossibility and self-defeat and a tendency towards depression; and suicidal thoughts are often not far behind. I know, because I’ve lived it. And I have spent the past few months talking honestly with others who battle the same. The worst part is in not being able to openly admit that it’s hard (or to be more accurate, a disability).

I wanted to start this body of work by highlighting how big a problem it is, and show how common it can be.

It feels like having a chain, with some of the links malformed, which means that the chain keeps falling apart. It’s a consequence of executive dysfunction, and The Principle of Chaotic Habits is how I beat the problem.

Earlier this year (2021), I ran a public experiment to test this principle in public domain. I wanted to share 21 lessons from 2020. I made the decision on the 31st of December, and the neurotypical approach would have been to drop one lesson each day from the 1st, till the 21st. Lol.

Let’s just say that while I shared the 21 lessons (outcome achieved), the habit of posting one each day did not happen. I placed the example in public domain because it is such a typical example and proof of how the principle works:

  1. you will get stuff done
  2. you will complete things

However, progress might not happen the way society has conditioned you to expect it.

This article was written as a Twitter thread using this very principle, and is just one step in the long road from an idea to a published book. (You see, rather than continue to beat myself up over not being able to stick to a “consistent” plan that gets my book out in xyz weeks, I am going to commit to continuing to write and take the tiny steps that keep pushing me in the direction of the outcome that I desire. So here’s a good point to subscribe to my mailing list, so you do not miss any updates about the book and other developments. You’re welcome).

1. Set an outcome, not the habit

The temptation is great to make the habit you want to acquire the focus (e.g. exercise 3x a week). However, when your focus is the outcome (a fitter body, or toned muscles), you 10x the likelihood that you would actually follow through. For this one, my outcome is to keep writing. Writing is how I equip my community with valuable tips, working wisdom, and tested techniques for living with autism and ADHD, for walking with God, for constantly growing and evolving into a better person.

My first few books were short, and written from the zone of hyperfocus. Not-so-short, intense busts of hyperfocused concentration that drove me at an insane pace through the execution process. But then life happened, and we all know that hyperfocus is unpredictable, and not a particularly reliable strategy on its own for steady execution.

For the longest time, I felt bad that I could not reproduce those bursts, and beat myself up for not being able to follow through with my goals of writing/meeting certain quota in specific blocks of time, and my goals to publish a certain number of books in certain time frames kept falling through.

By flipping the switch from the goals (publish a book by so-and-so date) to the outcome (write to equip), it became so much more likely that I would deliver. It did not have to be the whole book at a stretch. A tweet, a thread, an article, a chapter, a podcast episode, the book, a video course… Do you see?

Outcomes help you sit into both the immediate impact and the long-term benefits: like building a castle a beautiful block at a time.

2. Reinforce the loop with thought processes

Every time the thought of your desired outcome crosses your mind, mentally walk through the steps your plan. It reinforces the habit loop even if you are not able to get it done at the moment and increases the ease of doing when you need to. Sometimes, you remember what you want to do, or what you want to achieve. But executive dysfunction is at work, or you are stuck inside another task and cannot switch, or don’t have the tools that you need. Or the alarm you set goes off, and you are not in the headspace to do what you planned to do.

Walk through your planned action. Dream of it. Experience it. Two things could happen:

  1. you feel so satisfied/enthusiastic (dopamine rush) that you begin to make room to get to the task as soon as possible (no matter how much procrastination sets in, you eventually wind up doing it)
  2. you run into a potential snag (mentally) that you can fix, and so the next time you make an attempt, the process is not as hard to start.

Either way, you lower the activation energy for the next time you would actually be able to get it done. The power of the thought processing is that it reinforces the faulty habit loop with a lot more links. The more links, the more likely the chain is to hold (it’s not fool-proof, but it’s better than beating yourself up)

3. Build systems around it

New patterns will not stay in your life, if you do not make room for them. You can think of it this way: the chain links already fall off easily. When they have room to stretch, they are a lot more likely to stay hooked.
Reorganize your space, acquire the tools that you need (within reason/budget – the affordability discussion for ADHD/autistic tools, accessibility and productivity hacks is something that we will have sometime in the future), declutter your TL (or follow some new people), join communities…

Determine what needs to go, what can stay, and what should come in to help you to make your chosen outcome become a natural occurrence in your daily life sequence.

We already know that too much pressure is counter-productive for us, and no pressure at all makes it near-impossible to get started. The systems that I found to work were those that are dynamic in nature: not some rigid “5-pillar steps to abc” that fades into white noise in a few days/weeks, but a sweetly, subtly changing background noise of some sort. You know how having a super wide music pool that randomly shuffles can jolt you back to consciousness? That’s the wisdom being transferred to be applied here.

Sometimes, the system you need is a set of acquittances oriented in the direction of your desired outcome, sometimes it’s the movies you choose to watch. Sometimes it’s your calendar’s incredibly surplus reminder system, sometimes, it’s visible lists. Sometimes, it’s public commitment, sometimes it’s an alarm

It would not always work, but if you switch things up often enough, you would be propelled towards the outcome so surely that you would arrive at it.

4. Acknowledge the weakness

…because, who are we fooling? Certainly not yourself.
We like to act strong and capable, partly to compensate for the feelings of inadequacy, and all the times balls drop because of executive dysfunction and the barrage of ND symptoms, partly because we are so used to masking that we know no other way, partly because it’s embarrassing to admit that you struggle with something so “basic” (blame societal conditioning and expectations) etc. but if you do not admit to yourself that you have a weakness, and that you need help, your mind has no logical reason to accept available help, and you’re just setting yourself up to fail.

Help is not always available, and help is not always affordable, but if we do not admit our need for help, we might fail to spot it where it is available, or accept it when it is offered, and that’s on us.

5. Celebrate tiny milestones

Remember, the goal is outcomes, so every tiny step that contributes towards the outcome is worth celebrating. You had a 3-day streak? Braaaaaaaggggg about it. you over-shot your expectations? Do a special treat for lunch.

Track the progress, celebrate, and give your brain the dopamine rush – it helps you increase the likelihood of doing more.
It’s such a game changer, and the beauty is that celebrating can be ANYTHING. From bragging to a close friend, to grabbing a favorite treat, taking yourself out to a nice place, or watching an extra episode…. As long as you know the why, and are intentional about it, it works!

6. Create time pillars

This one works when your systems are in place. Set up times/dates when it becomes unnegotiable to do something in the direction of the outcome that you want.

Use alarms, calendars etc. You’d find them more helpful now, since systems are already at work to lower the activation energy for the tasks, the outcome is playing at the back of your head, and you probably have experienced the thrill of celebrating a milestone.

This is not to say it would be fool-proof, but progress is what we’re after, right? (wink).

The other way that I use Time Pillars (another pending conversation that I would return to link into this article) is to create “pillars” or markers in my calendar/schedule to mark the passage of time. I do not feel the passage of time, so a marker (reminder) that I am 1/3 or quarter-way through the allocated time slot for a task helps me get back on track if I had fallen off.

It does not have instantaneous effect, but it brings the awareness that anxiety feeds on to get me to start. I tend to use this one for work-related tasks, as defaulting has more grievous and compounded consequences (it’s a pity I cannot use it everywhere else, because over use of any one tool turns it into white noise).

7. Do it whenever you have the urge AND the energy.

If it comes to mind, and you can do it, please do. It reinforces the habit loop. If you cannot, mentally walk through the task (see point 2). There’s the temptation to pass up on it because it’s “not the right time”. But as much as you give yourself the permission to skip when your brain, willpower, and muscles are not cooperating, balance it by leaning in when all three align – especially when it does not conflict with another important task/looming deadline in which case you hold on to the thread, as a motivator to get through the less desired task, and then sit into the habit/outcome that you are working to build.

For example, the will and energy come together, but you’ve got a work deadline in 2 hours? Layer them. Mentally walk through your outcome, then assure yourself that you would jump on it as soon as you are done with the work task. You can even gather up what you need to achieve the outcome and place it in sight (or do your work task in the spot where you would normally do your outcome activity). The sense of completion and reward now associated with the layered task means that there’s a greater release of dopamine. See? Win-win.

8. Have a plan for interruptions ahead of time

Would you write down the intrusive task, delegate it, set an alarm for it? Would you allow it, dream of it, or use it as the excuse you need to take a break?

When you have a plan for intrusions, you are much less likely to abandon your habit half-way. The first set of options are useful for when it’s will power driving you to get it done, the second set of options work when you are in hyperfocus zone with our outcome’s task, and need to work breaks in.

(This really belongs under the “systems” point, but then again, why should it not stand alone?)

9. Set the bar loooooow.

Then slowly raise it.

  1. It’s easier to hit the dopamine rush when you first start with a low bar
  2. Getting to raise the bar becomes a sub-challenge in its own right (even more dopamine)
  3. There’s a lot less likelihood of failure

Cheap wins are better than no wins, and a little dopamine is better than none at all. The next few points would show you why setting the bar low works super great for us.

10. Start with the easier stuff

This is simply another variation of the last point, but I think it bears repeating. Start where you are, with what you’ve got, and ease into it.

If you want a healthier body, taking walks comes easier than signing up for cardio 4x a week. Eating more fibre per meal comes easier than jumping head first into an unfamiliar diet. If the outcome is more knowledge/awareness, adding a podcast to your favorite Playlist is easier than aiming to read 50 books in a year.

There’s that part of us that resists change, and you want to tease engagement by keeping things as familiar as you can (unless it is a mortally dangerous situation), and then slowly replacing one bit at a time until all of the unwanted parts are gone (this methodology is at the heart of the Intentional Life Design coaching track, and you might want to check it out HERE).

11. Lean into the chaos

Leverage what you have. Find ways to incorporate what you want into what you already enjoy. It does not have to always follow some rigid structure recommended as the ultimate step-by-step methodology, and the more you enjoy it/look forward to it, the more likely you’d be able to get started. Make your brain your ally, not the enemy. You want to move around more? Turn exercise routines into dance or (virtual) social gatherings depending on the level of your social anxiety. You want to eat healthier? Put new ingredients in your favorite food. You want to write more often? Write about your favorite topics (this one is a personal hack. It gives me enough content for when I need to put out a structured body of work at near-impossible deadlines).

12. Turn it into a game

…then make a game out of seeing how many games you can turn your desired practices into

The more, the easier

You know why? I shared it earlier. You are several times more likely to do something that feels fun, than something that you feel obligated to do. And gamified tasks are the height of fun. Gamified tasks are also easy to teach to others, so if you want to consider building an income source out of your process, here’s a good point to pay attention to. (For more about building income sources, subscribe to my newsletter and you’d get my signature blueprint for working from home and the Future of Work delivered to your inbox in my welcome email. For a deeper dive, sign up for Money Management)

13. Completion energy

Do you remember that feeling of “I’ve come so far, I might as well finish”?

Use it whenever it shows up. It is such a game changer, that it can propel you through tasks and shorten your time lines in ways you did not imagine. (Inside gist: I’m running on that energy right now, and it just might get me through the article tonight instead of in 8 more days like I initially planned for)

14. Use lists

Sometimes, listing out the components of the next major step would help you to actually get something done. It helps you mentally walk through the task, demystify it, & borrow some extra executive function. So, if the earlier suggestion to dream about the task/outcome was sorta challenging, this is a much easier alternative.

For me, lists get me through unfamiliar tasks, and help me when my thoughts are all over the place. Like this article started as a list of things that work for me and wanted to share, then each point acquired a sentence, and then each point became a paragraph, and it all grew from there.

Another way I use lists is when there’s a barrage of tasks associated with a particular outcome, and brain fog is showing me pepper. I’d write down as many tasks as I can understand/recall, and then the list becomes an anchor to wade through the brain fog. (it’s probably why my boss thinks I am able to constantly execute without excuses: I’ve got a “crutch” for my “missing leg”).

Bonus: you get to spot the progress being made and celebrate each tiny milestone.

15. Each trial is perfection in itself

This one is from Water Walker (by Ted Dekker, the Outlaw Chronicles).

Accept that it is okay to be imperfect on the first try. Aim at better, not perfect

The ND struggle with perfectionism is a lifelong one, so take this as today’s reminder that it’s okay to not have 110% the first time you tried.

(The Outlaw Chronicles book series make a good read with valuable related lessons)

16. SEE your current reality, and count the cost.

This one ties into point 4. Recognize and acknowledge your current reality, hindrances, possible obstacles, AND THEN, work out a way to beat them.

Building strategies to move forward without acknowledging your present reality and sitting into it is simply setting yourself up to fail. It’s like building a bridge from the centre of a chasm. You’d hit burn out so fast, that you drop off, and it would not be because the principle or methodology that you are attempting to deploy is wrong/does not fit/does not work, but because you have not accounted for the stating leg of the journey, or the stretch it would take to get into the path you have crafted.

So SEE yourself, and then begin from there. You will not beat the obstacles by ignoring them, and beating the obstacles is also progress

17. Count the cost

Every decision/choice/habit is a decision/choice/habit against something else. No decision occurs in isolation. Every single choice is a trade-off. Sometimes, the trade off is an obvious good vs bad decision, but sometimes, it’s harder: low-road vs highway (should I teach about this? Let me know in the comment section). Sometimes, it’s a safe vs significant decision. Sometimes, it is a choice of good vs great.

Whatever it is, you need to consciously count the cost, and make peace with the trade-off, or you would constantly self-sabotage throughout your journey without even meaning to.

18. Give yourself a long rope

Make room for all of your symptoms. This is part of setting the bar really loooooooow. It feels better to finish before your set deadline, and have room to tweak and improve, than to have to race and burn out and not be able to double-check.
Here’s why. When the feelings of woe-is-me-I-did-not-even-do-that-right come swinging around (like they always do), you would have tangible proof that you actually did your best, double-checked, and you can go to war with facts rather than just sweet words that you may have become cynical about.
Secondly, if the symptoms (executive dysfunction, brain fog etc.) do kick in, they would not mess seriously with deadlines, or affect the morale of your team (if you are working with a team).
Thirdly, unless you’re using tight deadlines to propel yourself to get started on a difficult, oft-procrastinated task, tight deadlines are not a very sustainable long-term strategy to move towards an outcome.

Sit into the process, get thorough, and do good work that you would be proud of when you look back.

19. Know when to take a break

Don’t let your need for an unbroken streak blind you to the need to take a break when you need to. Intentional breaks (with defined plans to restart) help you to sustain your new Chaotic habit, rather than waiting to fall off.

On a final note,

The guilt of falling off is a thing. However, do NOT let it stop you from going again when you are ready to.

Go again. And again. And again.

You don’t fail because you fell off. You fail when you give up

With so much love,
Jane Hadassah OLUWADARE

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P.P.S: You can now pre-order the book Principle of Chaotic Habits HERE



Author: Jane Oluwadare
Jane solves hard problems so you don't stay stuck Jane (Hadassah) OLUWADARE is an autistic, dyslexic multi-dimensional woman who uses her different dimensions to amplify one another, and is committed to showing other neurodivergent people how to replicate working wisdom in their respective contexts. In the PKH Network, she brings her various facets, strengths and skills to work together in viable business models, creating solutions for other visionaries, and providing platforms for young people to grow into their own strengths, develop experience and expertise As a data analyst, strategist and business development consultant in PKH Consulting, she sits with business structures to help them identify the gaps in their processes, build the blueprints, strategy, process flows and structures that will get them from where they are to where they want to be. As a productivity and execution coach in PHRONESIS Lighthouse, she works with neurodivergent people to get more productive, and do more with less effort, with particular attention to autistic people and people with ADHD. As a fashion consultant in HSFH, she styles, illustrates, and brings 15+ years of sewing experience to bear as she works to produce and sell stylish clothing that meets sensory, functional and fashionable needs. She teaches creative and trade skills in CriArt Skill Academy, working with neurodivergent children (with particular attention to autism, dyslexia and ADHD) to show them how their natural talents and tendencies can be an advantage inside and outside of the classroom and school curriculum. Utilising games and play as tools, as well as drawing from her own personal experience as a designer, chef and writer she helps them transfer the skills from the creative arts into school subjects and real life. She writes extensively, sharing her thoughts in books, articles and through her various enterprises as creative stories and non-fiction think-pieces available in Books By Hadassah. An International Youth Council member and former Global Youth Ambassador, she sits on the boards of several youth-led organisations in an advisory capacity; and continues to work with others to help develop children and young adults to create a life of impact. At the very core of her being, Hadassah keeps chasing after The One who keeps her balanced and finds the ultimate fulfilment in her fellowship with the Holy Spirit. She quips that He is the real super power that keeps her functioning as an autistic, dyslexic person with ADHD, and often shares the insights He teaches her on Personal Development, Business Development and mindset reorientation according to the Word with Deborah's Court (her ministry expression)

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