Five things high school didn’t teach me about writing

10 March 2018
10 Mar 2018
West Lafayette, IN
13 mins

In those eight months since I left high school, writing has been a huge part of my day to day work. I write at a personal level on this blog; I write about tech, design, and startups for the Anvil, I write documentation and technical descriptions at work as a software developer, I write talks and pitches when I’m invited to speak or present, and that’s excluding the myriad of typing I do to keep myself up-to-date with the several teams in which I’m involved today, through email and messages.

Being dropped right into the deep end of the pool out of school, one of the things that stuck out to me the most was that the kind of writing that helps you in the things we do for most of our lives — work, selling your idea, and communicating — is not the kind of writing we’re taught to do best in school.

Fortunately, I also think this other kind of writing is a lot more interesting than the pretty dry, academic writing we practice most through high school. So, here, I’ve compiled a short list of some of the most important things I think everyone should know to write well, that I didn’t get to practice in school.

All writing needs great structure; most don’t need the exact same structure

Someone who hasn’t done much writing outside of school will usually structure their writing very dryly, in a strict sequence of Introduction -> Main point 1 -> Main point 2 -> Main point 3 -> Conclusion. If you go back to my earlier writing on my blog, you’ll see this three-point, five-paragraph structure in almost every post, because it was the only way I knew to structure my writing. And that’s fine, if all you want to do is to deliver an idea from inside the grey matter of your brain to the grey matter of the reader.

But when I’m reading, I don’t want to just feed my grey matter. I want to be interested. I want to read something not because my grey matter needs information, but because something about the thing I’m reading gets to me. And when you’re trying to make something interesting, it turns out complete uniformity, all the time, is not a very good strategy.

Usually, people have better luck getting my idea or understanding an argument when I present it in a way that’s logical for that particular circumstance, instead of as a prose version of a bulletted list.

In a typical piece, a broad introduction comes first, and a concluding section comes last, with the core ideas in the middle. But sometimes, I’ll open with a strong statement of my thesis, and sometimes, I won’t get to my main point until the very last sentence. In articles like this, I throw out the established structure almost completely, because I’m presenting a list of items, each with a probably unique structure, from anecdotes to generalizing patterns.

The pattern we learn at school is a useful starting point, but almost always, to make your point in the most interesting or engaging way possible, you’ll want to step outside of the basic box.

Grammar is the least important of all important things

The way I see it, there are two reasons to care about correct grammar and punctuation:

  1. If you can’t spell or conjugate your way into a subject-verb disagreement, you won’t help your case that you’re a credible writer with credible ideas to tell.

  2. When you have a grammatical mix-up, you risk your ideas being misunderstood.

In writing, the end goal is almost always to transmit some opinion or idea from your mind to the minds of the reader or listener. And if you can effectively and concisely achieve that goal, it matters little how you do it.

Skilled writers can achieve this even while bending the rules. Especially in more casual settings, like an informal talk or a blog post, it might actually help to bend the rules of formal grammar to make a point, or to set a tone. But this only works because the bending of the rules of grammer serves your end goal of making your point clear and interesting. The reason grammar is such a sticking point in school is, 1) you’re most likely not to be a great enough writer to be able to bend these rules effectively yet, and 2) you can’t break the rules before you know them. That was certainly my case.

It’s possible to write well and make a great point while bending the rules of grammar, but perfect grammar doesn’t necessarily guarantee a well-expressed idea. Nonetheless, there’s a reason these rules exist. Grammar exists because it almost always helps you express your idea with more clarity and precision. It’s a starting point for bending the rules, rather than something to avoid by default.

Citations are way more important than you think, even outside of research papers

Of all the writing that you’ll ever do in your lifetime, a great many of them will involve you making a compelling argument. And whether that argument is that you should order pepperoni pizza for your company’s game night, or it’s to persuade a senator to invest more in schools, having evidence makes your case stronger, and evidence can only help you if they are credible.

Citations make your evidence credible. They are the legs on which your arguments stand, research paper or not.

There are way more ways to cite your sources than the typical, MLA / APA style we’re taught in schools. Especially online, when I’m citing a source, I’ll just mention it and link to it in-text, or leave a footnote, because it’s easy, and most of the time, it’s enough to precisely reference a single source. But no matter the method, citing a source for my evidence always helps my case.

Like having good grammar, well-cited sources make your idea or argument stronger, and help your writing stand on more solid ground. It makes it more challenging for someone else to come along and say, “You’re wrong,” which, in my opinion, is always a plus.

Great writing is not a word longer than it needs to be

Reading your words should save people time, not waste it.

When you’re done writing, read over each sentence and ask, if pulled out onto its own, does it say exactly what you want it to say? Does it add enough substance to your idea that it makes up for the extra time the reader has to spend reading it?

Everyone is busy. Your readers almost always have something more important that they could be doing than reading your words. And as a writer, it’s your task to make your point in as few words as possible, and make the case that the reader should invest their precious time in reading your words, because it helps them in some way.

Here’s another way to say this that I’ve heard:

The role of your first sentence is to make the audience read onto the second sentence. The second sentence should then make them read the next one. This should continue until you’ve gotten to your last sentence, and your reader stayed hooked the whole way through.

If you can do that, you know you’ve written something so engaging and interesting that it was worth the time to read it.

People don’t read from start to finish

Think of the last few times when you clicked on a link to read something online. What percent of the words on the page do you thin you read? How many sentences? Where they consecutive sentences?

In my experience, most people don’t read from start to finish. People generally don’t even read things in order or read individual paragraphs at once. Unless you’re writing a story that needs to be read in chronological order, most people will scout for the information they want, rather than reading one word after the next from the beginning.

Since people won’t read your words sequentially, your writing can be more effective when it’s structured with that in mind. There’s a few tricks I use to help people who jump around for information through my articles:

  1. Use headers. We don’t do this often in writing for school, but it’s incredibly helpful when your readers are skimming the article for information that might be useful, or just trying to get a basic sense of your points. This also helps structure your writing into smaller sections, to break up the wall of text that becomes of longer pieces and hinders legibility.

  2. Bold or highlight passages that are important to you, so they stick out to the reader when they’re scanning. In print journalism, people will use pull quotes for this purpose. In everyday, more casual writing, I find that bolding my important points helps people find them faster.

Writing is super not a linear process

Almost all through my high school, I wrote linearly. I started writing with the first word in my essays, and I finished writing when I typed the last word of the last sentence in my report. And I read over it a few times, fixed some awkward wordings or mistakes, then hit print.

But that’s a linear way of writing, and it turns out, it’s a pretty inefficient approach to writing well.

Imagine if songwriters were taught to start composing by recording the very first measure of their song, then go on to the next one, then the next, until they wrote the last measure, and then tweaked a few notes in the middle until they were satisfied.

Imagine if artists started painting by laying down the paint on the top 2 inches on the canvas, then moved on to the next 2 inches, and so on, until they covered the entire piece.

Or, what if a director filmed their movie by taking the first shot, then shuffling everybody around to get the next shot, and then moved everybody again to get the next shot, until he worked his way through every frame of the movie, sequentially?

It’s beyond obvious why no sane person would think these are great ideas, but almost everyone I knew in high school wrote like this, including myself. We started from the first word, and ended on the last word. And if you compare it to the way we do almost every other kind of creative work, it seems ridiculous in comparison.

Good writing is never done sequentially. It’s done in steps.

The best writers I know start without typing a single word on the page. They spend half of their writing time or more on compiling ideas and researching the background to their case. Then they write a rough first draft by picking and choosing from the collection of ideas and research, and arranging them into order, which usually ends up around 3–4 times the length of their final draft (at least!) Then they spend the majority of the time left to cut out any irrelevant points, distill their idea down to its most effective bits, and rewrite the parts that are the most important. For me, this takes about 3–4 passes through my draft.


In the end, all of these points can be distilled down to one thing: writing is about delivering an idea or opinion from your brain into someone else’s brain in a clear and interesting way, and as a writer, that should be your highest priority.

I think the baseline rules we learn in school can help you produce good writing. But like anything that follows the basic guidelines, these training wheels are sometimes helpful, and other times limiting.

And once I realized how I could work around the basics to make my point clearer or my tone more interesting, my writing became more interesting to read, and my ideas could be better represented on screen or paper.


A note to those who teach writing

In my experience, at least 95% of the writing I practiced up to my graduation was what I’d call academic writing. Academic writing is incredibly important. It’s how the world’s researchers exchange and discuss information, and it’s a vital skill set to be able to both write and read in a way that enables us to participate in that discourse. Not to mention, it enables us to study further into our interests in college and beyond.

But it’s a reality that 95% of the writing we do — even if we become researchers — will not be academic writing, and it’s also true that many academic writing is not the epitome of great writing in general. We won’t always be writing purely to deliver information rigorously and precisely. We’ll be writing to sell ourselves or our opinions, or to deliver an idea to an audience from a stage, or to ask for meetings to be cancelled or for Papa John’s to be the definite supplier of all pizza-related deliveries to our offices.

And in my view, those equally important types of writing require a different approach than academic writing requires, and personally, I don’t remember being very familiar with these other circumstances in school.

So when I abruptly stepped out into the working world, I found myself having to learn quickly how to write for people who weren’t reading my words for a grade, were short on time, and probably had better things to do than read what I had to say. In these situations, perfect grammar and argumentation give way to the more important skills of keeping the reader’s interest with structure, tone, and specifics.

Writing is so important because it’s a fundamental skill in any line of work, and in its ubiquitous form, I think good writing is much more diverse, interesting, and immediately useful than I think students are led to believe in school.

In my sophomore year, I founded a small student-run online publication with a dozen friends to expand the avenues through which we, as students, could write about what mattered to us. And even though it shuttered its doors a few years thereafter, and with only a few dozen pieces under our belt, to date, that remains one of my favorite projects, because I think it was a step in the right direction toward exposing students, of which we were all one, to the kinds of writing we’ll have to do well for the rest of our lives: writing not necessary meant to score highly or deliver precise hypotheses, but nonetheless to tell engaging stories and make compelling arguments about what we believe. It gave us all an audience of our peers that cared about our writing at a higher level than mechanics.

Technology and social media enables the kids in your class to have reach that could span thousands of people across the world, and I think it’s a tragedy that most of the best writers I met in high school did their best work for class and grades, rather than to get their ideas out there. It leads most students to believe that writing is inherently academic and standardized, when in my opinion, writing at its best is a combination of artistic, organic, and diverse.

It’s my hope that, as technology empowers students earlier and earlier in our lives each generation, the way we teach what great writing is also changes, to include not just how to write to the rules, but when to bend the rules, and when to rewrite them entirely.


If you enjoyed this piece, you might also enjoy my next post, Saying no to almost everything is the most important skill I was never taught.

Have a comment or response? You can email me.