Not A Planner? Embrace Being A “Chaotic”…



I never sit down and plan out articles. I’ve now written over 200.

I never write detailed summaries of chapters of books or sections of products before I get to work on them.

I never planned a single university essay (and still got a First Class Degree and a PhD).

It’s not just that I’m lazy and just can’t face the idea of writing down a simple structure. Rather, despite every effort, planning just doesn’t work for me.

*        *        *

When I was studying for my PhD at Oxford, one of the mandatory hurdles required students to submit a detailed plan of every chapter of their ENTIRE thesis, along with titles and a condensed summary of all the major arguments and literature they intended to draw from.

My only problem? I didn’t know any of this.

I had ideas. I had a sense that I wanted to write about human rights. I had certain authors and books whose arguments I agreed and disagreed with.

But being forced to write an ACTUAL plan was one of the most unnatural and painful exercises I could have been forced to do. It clogged up my brain.

Even if I have a sense of something I’m angry about (e.g. Free Speech, Tinder, the perfect way to make a cup of tea), it doesn’t mean that I know (a) what my main arguments will be, or (b) how I intend to structure the entire piece.

Because the truth is: I don’t write to say what I think, I write in order to figure out what I think.

 This is true of many people, I’m sure. I know Kevin Kelly has said something similar in his excellent Tim Ferriss interview.

But the world is still full of “planners”. For every chaotic creative (like me), there are plenty of diligent, hard-working writers who create entire blueprints before they ever set pen to paper.

Plenty of novelists have every chapter, every twist and turn in the plot neatly summarized before they dive in and write it all out.

I spent a long time trying to copy the “planners”. I envied their ability to figure things out first, and then simply connect the dots once armed with their detailed map of the territory ahead.

Planners have maps. Chaotics just have a compass.  

As a Chaotic, all I ever know creatively is a general “feeling” of the way ahead.

And even then, I bump into some walls and have to recalculate. It’s like searching through a dungeon with a flashlight and occasionally hitting dead ends, empty treasure chests, trap doors. But as you trudge through each winding tunnel, the path gradually gets more illuminated until you come out the other side and can see the entire route as clear as day.

Of course, what’s exciting about being a Chaotic is that you just have one commandment: BEGIN. That’s it.

Begin. Write. Don’t look back. Keep trudging through and that path will eventually reveal all its secrets to you. Then go back and make it better. Do that 3-100 more times and you’ll have made something beautiful.

Sure it’s messy, but why should neat and tidy be the only game in town? Messy can work. As long as you don’t stop for too long and let your messy thoughts get the better of you.

For the Chaotic, relentless action is king. It clarifies. It lights the path forward. It puts the structure into place, even if the road to get there is bumpy as hell.


  1. Maria · January 31, 2017

    Thank you for this! I’m forever being told to write plans and I find it so restrictive – as though my creativity is being muted. Even when I do begrudgingly write plans, I always seem to deviate but eventually find my way. It allows you to be spontaneous, adventurous and imaginative. Isn’t that the fun of it?!
    That being said, I am the type of person to get on a random bus just to see where it takes me. So perhaps our approach to writing says more about us than we think…


  2. Mary Jones · February 1, 2017

    Hey Stephen, I enjoyed reading your piece. You write so beautifully. I am a planner but I find that I plan so much I don’t actually commit anything to paper. I may try your approach and see what happens x


  3. Krystle · February 4, 2017

    Absolutely Amazing, expressing artistically in words feelings that I’ve had to release as a post-order-induced-mini-brain-trauma sigh or grunt. Beautiful! Thank you 🙂


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