Leveraging chaos

December 13, 2020 • ☕️ 5 min read

When I first learned about the GTD methodology I embraced it wholeheartedly. There’s a part of me that loves putting disparate things into neat little boxes, but up until that point I hadn’t realised that this predilection could help me get things done. All of a sudden, I was making things happen in my life with a lot less effort.

At the time it felt like I had gained a new superpower. It was the first time I began setting goals for myself and actually following through on them. It felt amazing. I had a new insight on how to do life: organisation was the maximum good and disorder was to be hunted down and abolished at all costs.

But as I’ve mentioned before, life is too complex for such simple rules to be the secret to everlasting happiness. We can’t just look at different situations and problems through one lens and expect that it will work for all scenarios.

This is yet another situation where an epiphany that helps us level up sows the seeds for the next rut in our life. So just what do we miss out on if we idolise order and demonise chaos?

The failures of order

Well for starters, organisation doesn’t actually get anything done. We can spend hour and hours setting up the perfect system, making sure we have the perfect tags and categories, table rows and columns aligned in geometric perfection. When we’re done, we can stand back and admire our beautifully laid out strategy. If we’re being mindful though, we’ll also notice that we are no closer to our goal.

The trouble is that organisation by itself doesn’t provide any value. Yet we can fool ourselves into thinking that it does. In fact a lot of the time we will willingly (if unconsciously) dive into over-planning and stay there for as long as we can. Of course what’s really happening is disguised procrastination. Research, watching videos, reading tutorials feels rewarding in the moment. We don’t have to make any hard decisions, we’re not forced to flex our creative muscles.

So we delay the moment of starting hard work. Because we know from that point on things will feel uncomfortable. It is the phase of any project where risk increases. It is when we are forced to figure out what we personally think, what we are going to include and what we’re leaving out. It is the time to put skin in the game, and this makes us vulnerable. People might disagree with us or we might get blamed if something goes wrong. It’s no wonder it’s so much easier to stay in the safety of meticulously laid out plans.

A related disadvantage of an unexamined adulation of order is that once we have things perfectly organised, we will feel an underlying pressure to maintain this perfection. For example, we set up the perfect tagging taxonomy for our project management system and then spend more time making sure tasks are in the right category rather than taking action on them.

There are so many examples of this. Organising our picture library into the exact right folders, refactoring code for the sake of refactoring, making sure our notes are in the exact right categories. The trouble with perfection is that it tends to be brittle, or more accurately it doesn’t exist. Humans have been trying to come up with perfect taxonomies for millennia, yet reality has kept showing us that it’s a fool’s errand.

I experience this with code all the time. I write the perfect abstraction and pat myself on the back, in certainty that I’ve captured all use cases. And then the designers come in to tell me that it looks great but could the 5th row of text break the grid and jump to the opposite side of the screen. My left brain rails at this chaos while the right knows what they’re saying makes what I’m building more human.

The creativity in chaos

What we miss out when we seek perfection is the incredible value in disorder and chaos. What I’ve experienced lately is that chaos is not to be avoided, rather it is a signal that I am at my most creative.

When I am in the midst of creation bills go unpaid, clothes unwashed, emails and even bodily needs unanswered. The code or words that I write are messy, don’t make logical sense and would be illegible to others. Yet there is something being born when this happens. And this is what it takes. It could even be said to be temporary possession by our muse or daimon.

If I’m in this flow, then it would be crazy for me to come out to tidy up my to-do list. Because there is no need for a to-do list when we are in flow. We are tapped into a much higher intelligence when in this state. We intuitively know what to do next, which breadcrumb to follow and if we try to figure it out, we would just kill the magic.

Once more when in this state, sticking to our plans is not likely to lead to the best outcomes. This is because emergence is an inherent part of creation. At the outset we have no way of knowing what the best path to our goal will be, we can only start by collecting the dots with the faith that they will connect at some point. When our plans are flexible we leave space for serendipity and unexpected connections. We are able to opportunistically change directions when the perfect unexpected situation arises.

Or as Quincy Jones would say:

If a song needs strings, it will tell you. Get out of the way and leave room so that God can walk in. — Quincy Jones on the process of creation

Or for those triggered by the G word:

Get it 75% of the way there but remember to leave room for the magic.

Resolving the paradox

Let’s not throw the baby out with the bath water though. Being organised has its limitations but it can also make us much more effective at making our goals and dreams a reality.

Just how do we resolve the paradox? Part of the answer might come from realising plans serve us best is when they’re fluid. There’s a tendency to think that planning is an activity you do before you begin executing on a project and which results in a blueprint you stick to until you’ve reached your desired outcome.

In reality, strategy properly done is fluid. Planning is at its most effective when it is a lightweight and frequent back of the envelope affair. Because reality keeps on changing. Things will never match our predictions perfectly. So of course to be useful our predictions (ie plans) need to keep evolving too.

So where I’m at now is that we should maximise disorder whilst maintaining the minimum amount of order needed get things done.

I’ll finish up with a relevant quote:

The best planning is done in the midst of execution.

And some variations I’ve been enjoying playing with:

The best learning is done in the midst of creating.

The best sharing is done in the midst of learning.