Make Your Reader Work for It

Does advice for clarity make your writing boring?

The Saturday Brunch: a figurative flat white or fizzy to start your weekend

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I originally published this article with The Writing Cooperative on December 21, 2022. It seemed to really speak to people! For this reason, I’m sharing it here with you. Apologies to those who may have already seen it. Many thanks to editor Justin Cox and Matterhorn reader Jennifer Unger (you’ll see the reference in the article).

Although this article is written with a writer-audience in mind, it may be interesting to consider from the reader’s perspective. What kind of text do you want to spend your time with? What settings or topics or even moods change the type of writing you want to read? I’d love to hear your thoughts!

I’ll be investigating other ‘writing workshop’ style ideas in my new project on Substack: Yoga & Writing. You can sign up now to hear more about it and join the community.

Coming soon

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Make Your Reader Work for It

‘I don’t understand this!’

‘My head hurts.’

‘What does this mean?’

‘Where are you going with this idea?’

Can you imagine those comments on a piece of your writing? Ouch. Those are not the statements and questions one would typically consider positive feedback from your readers. Writing is about making ideas clear, they say. Make your writing a riddle and people will stop reading.

In the ancient art of theZen kōan, a teacher — or sensei— poses a riddle to a student. Not only is the riddle unclear, but there is also no clear answer.The importance is in the act of discovery.

Poststructuralists do something similar in their writing. Through methods of deconstruction and difference, dichotomies and questions are presented versus clear answers and solutions. Jacques Derrida, for example, is famous for finishing essays or lectures with many questions, irritating some and enrapturing others.

I started thinking about this concept in regards to writing articles or essays when a reader of my newsletter with whom I also used to teach English told me, ‘You really make your reader work for it.’ She had given me constructive criticism that was hard to take before. Eek, what had I done? How could I fix that? Then she quickly clarified: ‘That’s a good thing! I really have to think when I read your work. It’s fun.’

It became one of the best compliments I’ve received. This style, though, also likely means I put off a lot of readers who might not be used to it or feel they lack the time. I’m willing to trade-off some potential readers for others who will be highly engaged. How about you? It might depend on what kind of writing you are doing and for what purpose you are seeking an audience.

Active reading is more engaging. It allows your readers’ creative and critical thinking to shine. You might also get more out of writing this way, creating a sort of ongoing discourse, even if you may have less people who stick with you. The paradox, however, is that the riddle itself, the tensions and questions posed, should all be exceptionally clear in delivery, even if that clarity includes nuance and double meanings. You can (and should, in my opinion), for example, include a clear thesis and paragraph points whilst allowing other spaces of deeper thinking to open up. The point is not to confuse but to illuminate possibilities.

Lessons from the classroom

As an English literature teacher for twenty years, I found that what motivated kids to read more and be ready for an engaging class was challenging reading. If it’s too easy, they’re bored. It doesn’t matter how long or short the book or article is. For example, I’ve had reluctant readers hanging onto every word of the 467 pages of Haruki Murakami’s Kafka on the Shore. The book is filled with riddles and unexplained phenomena.

There are (still) teachers who like to give reading quizzes that challenge the students on details to see if they have ‘read well.’ Instead, I liked to give oral ‘quizzes’ simply challenging students to think about some of the big ideas presented in the book. Those who had read actively were excited to have an opportunity to share their ideas. Others were encouraged to go back to the text, searching for quotes like detectives, to support or refute their points through details. Or, we would look at challenging excerpts together to model what more could be taken from a text in understanding, for example, its dichotomies, so that student’s could discover layers of the texts on their own.

I was, however, meticulous in teaching the structures of writing — five paragraph essays as an anchor and a variety of text types all with different formats and rules. These structures help ideas to be clear but also allow one to play with the structure, to make it their own, and to push the boundaries of where that structure can lead a reader.

While their essays — especially for examination — had to provide clear ideas with clearly analyzed evidence, the deeper their explanations went, the more they might make us consider more than what they actually said. Examples of evidence should make your reader consider others they know about themselves or want to research further (either in support or opposition). A great conclusion should allow some fresh clarity on the thesis that makes the reader think after finishing.

How to do it yourself

Avoid just adding in a bunch of (eek) SAT words to your writing. I mean, if a challenging word fits well, then go for it! But a more effective focus would be on how the words are used rather than the lexile score itself.

Sometimes we call this distinction ‘lexical- versus discourse-level processing.’ The former includes more than simply vocabulary. It also refers to the complexity of the sentence structure and length of the paragraphs. You might then be thinking: ‘Well, Hemingway used short sentences; why can’t I? A long Dickensian sentence isn’t always the best.’

Sentence variety

The short answer to the above question would be: ‘Yeah, short sentences are absolutely fine and often challenging.’ A longer answer might include a discussion about the awareness of different types of sentences on your reader in terms of meaning and even sound. It might also look at the nuances of sentence types and lengths that both Hemingway and Dickens really used. You might start by taking a look at the first two chapters of Hemingway’s Death in the Afternoon and those of Dickens’ A Tale of Two Cities. In each you’ll see a great variety of structural ways to entice the reader with their twists and turns. (See what I did there? Congratulations, you get to figure it out. I trust that you can find some great ideas yourself!)

Using sentence length and type for effect is one way to bring your work to another level, where readers can negotiate layers of meaning. If you’re not sure where to start, here’s an introduction in The Writing Cooperative that goes quite a bit deeper than length and second one that discusses sentence mood in an interesting way:

• Sentence Variety Cheat Sheet: Adding Spice to the narrative tempts the readers and brings them back for seconds

• The Ultimate Guide to Getting The Mood of Your Sentences Right: This might be your chance to decode your partner’s message correctly.

Figurative language

So how else can we add challenge to our writing? Of course, it depends on what kind of writing you’re doing. In fiction, we talk about ‘show vs. tell’ where you allow your readers to discover ideas through sensory details and figurative language rather than spelling it out.

To some degree, you can try this in nonfiction essays as well. But even when you have to deliver important content information, why not add extensions after you’ve delivered the key points to challenge the reader to engage on a deeper level? Anecdotes or imagery might enhance pure ‘content’ information.

Embed questions

Ask direct questions of your reader. Sometimes these rhetorical questions — those often used for effect in speeches — will have potential answers either explicitly or implicitly presented in your text. Other times, you might allow the reader to simply consider it on their own.

How might you include a question about a reader’s personal experiences? Or their fears? When might a question about an unknown future allow the reader to interact with your points?

Rich references

Any time you mention a reference to another article or a fact, you embed a layer of meaning in your text. This both makes your writing clearer through example and reliable through research; but it also opens up inclarities if the reader should choose to do some digging themself. In other words, by investigating your research as well, the reader might seek different conclusions than you do in your essay. It doesn’t mean their conclusion will be at odds with yours.

You might provide more information through hyperlinks or references included in the language of the text. You could in this way mention other texts that talk about a similar topic, even if they oppose your points, and allow readers to debate themselves by using critical thinking. Footnotes providing or expanding on references can also be an art, as the master of structural creativity David Foster Wallace taught us.

The above references might not be facts at all but references to other reading material, films, myths, or celebrities. What the hyperlink can do almost invisibly, allusions can do explicitly. Of course, a hyperlink can provide an entire written text or video for your reader. The allusion, however, is more sure to be seen, and may help your reader tap into previous knowledge (like the DFW reference above).

Liminal space

The spaces between — the transitory moments of your writing — are the places you can also focus on allowing readers to open up their minds.

The transition is where meaning is often made. While clear connections can help your reader follow your line of thought, you might want to use these places for deeper thought beyond your own explicit conclusions. If you don’t connect every single dot, you can allow space through transitions or quotes.

We naturally pause at the end of a paragraph or a break to the next heading. Even a sentence or pausing punctuation within it is a split second to cue reflection. In a book, this would be stronger at the end of a chapter or section. Our brain starts to put meaning together in these places.

Take Robert Frost’s poem “An Old Man’s Winter Night” as an example:

One aged man — one man — can’t fill a house,
A farm, a countryside, or if he can,
It’s thus he does it of a winter night.

Frost is a master of caesura as well as leaving the reader with questions; the purpose of his poems are rarely clear and often loved because of their ambiguities.

Two roads diverged in a wood, and I —
I took the one less traveled by,
And that has made all the difference.

Which road are we supposed to take again?

What AI exposes about ‘good’ writing

Poetry to texts written by artificial intelligence feels like quite a leap. One would posit (er, hope!) that a computer could not write a master poem like Robert Frost.

Can we fight the bots in this way, through examples of creative language that leaves the reader thinking? AI writing appears to threaten who we are as writers. We thought we had uniqueness and ideas; instead a machine can apparently express similar thoughts. Is writing an art form anymore or have we understood it so deeply through AI that it has become a formula, albeit a complicated one, that simply lives within our neurons and leaks out on the screen?

The bots are focused on creating clarity for readers. This is an important skill, and one — at least for now — that humans are still better at achieving.

But what if we posit that the best writing outside of the important information discerned through medical pamphlets or immigration directions (often read in a person’s foreign language aka Google translate) is the kind that isn’t so obvious at first? The kind that isn’t quite clear until we think about it? And maybe the clarity we seek is slightly different for each reader.

I have to admit that the idea of AI writing makes me cringe not only as a writer but as a teacher and parent — isn’t the process of writing a space of discovery in itself? Will the next generation miss out on this brain development, personal discovery, and even joy? Will they all become cheats, only to have that cheating accepted or even endorsed? I used to fight for handwriting, proven to help brain development, but now I might just settle for writing at all.

However, maybe the answer isn’t so black and white. Swiss Cognitive discusses the pros and cons of AI writing, including research within an educational setting. The answers here aren’t clear, but what they do suggest is that AI might enhance our work as writers (more than a simple spelling and grammar check) to offer us more opportunities. This would require a human mind to make choices from those possibilities presented to us, offering potentially a faster way of achieving a great piece of writing.

If your goal is to appeal to — or even subversively create — careful readers and readers who think rather than passively ingest information presented to them, please try some of the above techniques. It may be a small way we can help the infowars and the lack of critical thinking available to many people today. It’s not their fault; it’s a shift in the way we expect to receive information.

How else do you challenge your readers? Do they love you or hate you for it?