Today is the launch of Sideways Dictionary, a project I’ve been working on with Jigsaw, the technology incubator at Alphabet.

Sideways Dictionary is a collaborative online tool that explains technological issues using everyday analogies. I worked with Jigsaw to develop the concept and name for the dictionary and populate it with entries for the launch – covering about 300 analogies for 75 terms ranging from ‘API’ to ‘zero-day’. Some adapt analogies already in popular use, while most have been developed for this project.

Part of the mission at Jigsaw is to increase public understanding of the technologies that shape our lives. When I got involved, there was the seed of a thought about using analogies to explain technology in an accessible way. One of the examples was email being like sending a postcard, whereas sending an encrypted message is like sending a sealed envelope. People instinctively use analogies like that when explaining new concepts, but there was no central bank where they could be stored, searched and shared.

So that’s what the site aims to do. It’s now open to public contributions, with a voting facility to rate the best analogies – resulting in a shared resource for everyone to use.

The project has been developed in partnership with the Washington Post – the best analogies will be used on their site whenever a technical term comes up. And there’s a Chrome extension you can use to have Sideways Dictionary explain things across the web.

At this point, you should probably go off and play with the site. But for those interested, I’m now going to get geeky about analogies.

Analogies are fascinating things. When they’re good, they feel like magic – like discovering an underlying connectedness in all things. But they can also be frustrating – as a reader, you experience something close to physical pain when an analogy goes wrong, like it’s hurting the synapses in your brain.

The thing we kept coming back to throughout the project was that all analogies are inherently imperfect. The more perfect an analogy is, the less useful it is. The best analogies shed light on one aspect of an issue, but can never capture its totality. One of the advantages of Sideways Dictionary is that it gives you multiple analogies per term – each one may be imperfect, but together they have a cumulative effect. Even the process of working out where an analogy falls down leads you closer to an understanding of the issue.

The Art of Looking Sideways – image via It's Nice That

Throughout the project, and particularly when it came to the title, I kept thinking of Alan Fletcher’s The Art of Looking Sideways – the classic book about design and lateral thinking. This is more like the Art of Writing Sideways.

It’s a head-hurting form of writing. Analogies usually happen by serendipity – they occur naturally in conversations or in the course of thinking deeply about a subject. So to sit down and generate analogies mechanically is a weird process. But I found it’s like a concentrated version of what happens in creative thinking generally.

You take an issue like ‘secure socket layer’ or ‘wiki’ and that becomes your anchor point, like the end of the compass that stays in the centre of the page. Then you move the other end of the compass in a slow circle, passing through lots of areas – household objects, films, fairy tales, sports, games, cities, the natural world, pop culture, human interactions. All the while your mental compass is scanning through these worlds and trying to find matches back to the term at the centre.

When a match occurs, you try to capture the analogy in a single sentence and then expand as needed. Some colour and humour adds to its memorability and jaggedness. A good analogy can serve a twofold role – it’s partly about explaining the issue, and also about making it linger in the mind.

Fairytales are a rich source of analogies:

Others are rooted in shared human experiences:

The natural world provides some poetic analogies:

While the human world is harder-edged:

Some analogies involve real-world research:

Others find parallels in earlier forms of digital:

Some analogies enter surreal territory:

Others are more to the point:

The seed of the analogy is often in the name itself:

Analogies can reveal ancient parallels, between sheep farmers and programmers:

Some analogies are already in popular use:

Others took some imagination:

Like chess, analogies can feel like a beautiful game, or mental torture:

You can explore more analogies, and contribute your own, at sidewaysdictionary.com

Site design: Hello Monday
Films & animations: Google Creative Lab, London
Thanks to Alfred Malmros and Justin Kosslyn at Jigsaw for their patient support throughout the project.