A Simple Plan

2026-02-08

“For sale: baby shoes, never worn.”

That sombre six-word story is sometimes discussed as the world’s shortest story. It’s also misattributed to Hemingway, although he isn’t behind it.

Nonetheless, I’ve found it quite moving and, more so, a perfect example of the power of words.

And recently, it’s also gotten me to think about the relationship between simplicity and creativity.

If you’ve ever read a copywriting guide, any one of them, really, then you have undoubtedly come across the advice of ‘keeping things simple’. To all of you who might not be writers (or specifically copywriters), this statement is often code for: “edit out all the unnecessary words”.

As the world’s shortest story shows, short is beautiful.

A single word really can express a thousand when done right.

So, how do you keep things simple when you’re trying to be creative?

The creative dilemma, I think, stems from the tendency to make two assumptions about it.

First, creativity is often equated with thinking outside the box and letting go of all constraints. While there’s certainly a lot of truth in terms of not letting yourself get tied down and instead trying different things, sometimes this freedom to do whatever stops you in your tracks.

The second assumption, equally bad in my opinion, is equating simple with easy. I don’t think there’s anything particularly easy in keeping things simple, especially in writing. I’d argue that the ‘simpler’ you want it, the harder it might be.

Moving past these assumptions, I often find myself being creative through constraints and a healthy dose of ‘making it harder’.

In essence, the stricter the constraints and the more difficult the task might seem on the outset, the more creativity I squeeze out.

A good example of this is a 5,000-word whitepaper vs. a 30-character subject line.

While 5,000 words is a lot of writing, it’s not that much of a box in terms of word usage. The length alone gives a bit more leeway to get to the point or expand on it.

On the other hand, ensuring everything important is on into those 30 characters really puts your gears spinning. Ensuring you inform, entertain and hook with extremely limited wording really makes you think each and every one of them carefully.

Having a broad goal of writing a sad story gives you plenty of freedom to be creative, but the objective of writing a tragic story in six words really challenges your storytelling.

If I feel stuck on a writing project (or many other life goals), I sometimes zoom in and, so to speak, artificially build a box around me.

What if I had only a paragraph to tell the findings of this study? What if the sole reader is a 40-year-old lawyer thinking about adopting a dog named Twiggie? What if I had to eat 100 grams of protein every day, and I couldn’t eat meat?

And if you’ve been reading those copywriting books, they teach you to do this as well. This box is evident in the buying personas we create. Instead of defining the target audience as “a 40-50 year-old man that has disposable income and likes golf”, the better example is a fictional person like “Matt who is 45, works as a financial advisor at a boutique firm, playing golf at a country club every Saturday with his mates”.

Sometimes staying inside a box can be a powerful catalyst for creativity. Limiting your options can actually open many more doors.

It’s not that you should or even could write a comprehensive case study with 100 words, but by challenging yourself with constraints, you might realise the things you can’t omit or the points that do require expanding. You’ve suddenly energised your writing and opened up opportunities.

Matt’s habit of playing golf on a Saturday might help identify unique patterns in shopping behaviour or tell that weekends really matter to him. Crafting copy only for people who like golf can be less emotionally appealing to them than discussing how vital that weekend retreat is for wellbeing.

With a box around you, you realise that you don’t always have to write a whole book to move people hundreds of years later.

You may end up doing it with just six words.