Writing Sucks — A Practical Approach to Sucking Less

Writing advice is a dime a dozen on the web. Seriously. And most of it is well-meaning. But I’ve seen precious few articles with execution-level details that specify not only what you should do, but a plan on how to do it. With that in mind, here are a few lessons I’ve identified from teaching developmental (read: “remedial”) English/writing to college students over the past half-decade, as well as grading an avalanche of under-written papers over the past 14 years.

In 1985, a guy named Craig Vetter wrote a column about “Bonehead Writing” in Playboy Magazine (let’s all marvel for a moment about the fact that yes, there actually are real articles in Playboy!) and I’ve put it in front of almost every writing class I’ve ever had. There’s a quote in there — the “money shot” if you will — that I focus on:

Writing is thinking, which means every time you sit down to it, you get another chance to find out how perceptive you aren’t

It’s hard because we don’t do enough of it to get any easier. And we don’t do enough of it for the same reasons that people who just “want to work out” never seen an improvement in their health or weight or physical condition because they just randomly and occasionally take a walk, or go for a jog, or lift home weights, with no real plan to guide them.

The first conclusion I’ve had to force myself to accept, and that I try to impress upon all of my students, is that it’s not your fault that you’re not a great writer. It’s never been expected of you, and you’ve likely never put in much time to get any better. How you got to this point is out of your control. What you do going forward from here, though, is.

1. Writing is like painting a wall

You can’t slap one coat of paint on it the night before and expect it to look good. You can’t slap 3 coats of paint on it in the same night, wrap up around 2am, and expect it to look good. Solid, polished writing is the result of a process over time that intentionally breaks the work into multiple iterations. Brainstorming to outlining to sentences to paragraphs to adding introductions and conclusions to revision for coherence to copyediting is not a one-night process. And yet how many of us block out the evening before a writing assignment is due and tell ourselves “I’ll do it Thursday night…”?

When it’s time to write, the first step is the writing plan. It has to be. Now, you might truncate or skip certain steps, especially if some of the work is already done — you might not need a big brainstorming session if you’re given a specific, detailed topic. But I’ve rarely seen excellent writing that didn’t include at least a brief genuflection in the direction of an outline — five bullet points in an intentionally-decided sequence counts — to establish both the sequence of the writing and the scope. I’ve also seen people paint a wall without taping off all the edges, but if you’re installing baseboards after the painting, the bottom is allowed to look a little ragged.

The key here is a process. Military guys are already used to planning backwards from the due date. When planning a writing assignment, the backwards timeline needs to be longer than “the night before” and needs multiple steps. At a minimum, you need an outline and two drafts. Anything less is insufficient and fails to do justice to your thoughts.

2. Writers read, and readers write

Writers read for a variety of reasons: sometimes you’re on the hunt for a nice turn of phrase to plunder; perhaps you’re looking for inspiration; it may be a quest to broaden your general knowledge for future writing; and occasionally you just want to be reminded what you’re aspiring to.

How often are you intentionally finding something to read that’s more than a clickbait headline, a 160-character text from the kids, or a half-paragraph caption on a friend’s social media photo at last night’s dinner? Many of us have favorite book authors we enjoy reading, but how many of us can name long-form journalists whose writing we enjoy? How many of us are regularly tracking and subscribing to particular columnists in the media, or short-story writers online? How are you keeping your brain engaged between bouts of boredom?

Find a go-to source of enjoyable, informative, and thought-provoking reading. You might set up a few channels to follow on Medium. You might set up some RSS feeds or an email subscription to a particular journalist or recurring column. Get a good news magazine that regularly runs long cover stories and subscribe — not everything needs to be read on the web!

What you should be aspiring to is at least one evening each week that’s just a reading/exploration night, where you pick up something you might not otherwise read, and explore where it takes you. I’ll include a few of my go-to sites at the end of the column, but please develop your own, and get past the headlines.

3. Writing maintenance

Professional basketball players shoot free throws every day in practice. Playground basketball players only shoot them when/if they get called in a game. We do maintenance on vehicles with our regular oil change and tire rotation, on weapons in the military, on our bodies at our annual checkups, and on our houses when we swap air filters and blow out the vents. Some people get their spiritual maintenance at a worship service every week. When was the last time you did any writing maintenance?

How many of you write performance appraisals on subordinates at work? How often do you practice writing about your subordinates until it’s time to write their appraisals?

How many of you are responsible for writing business proposals at the office, and have a standard color-by-numbers form you work through? How often do you take an old request for a proposal and write a new one from scratch just for the practice, or to try out a new format?

When was the last time your professional development seminar at work talked about writing? Seriously. Don’t get your company PR flack, or marketing manager to do it, either. Bring in an editor from a local newspaper to look over your writing, not for stray commas or typos, but for internal coherence, development of thought, and reader engagement. Find a local magazine editor to come talk about how to write for a specific audience. And make sure they give you a homework assignment! There’s no point in hanging out in a conference room bloviating about how important something is, and then not bothering to practice doing it.

4. Keep a portfolio

You can make it a digital one if you like. Set up a folder on Google Drive and upload a copy of each thing you write into there. You can post them online for others to see, share, and critique (and be prepared for some harsh words!). Personally, I have a paper copy of everything of consequence written that I would want to show off for someone asking “oh really, what have you written?” I’ve got a few short stories, a dozen or so newspaper op-eds, a few of my game reviews, a travel article, a professional journal article, at least one outline for a comic book series. At some point, the sheer volume of writing starts to overwhelm even the paper gods, and the hard copy portfolio gets unwieldy. But you know what? There are worse problems to have than weeding out articles you’d rather not show off in a portfolio.

But every time you write something of consequence, a copy of it should land in your ‘permanent record’ of writing. Revisit it on a regular basis and see what’s improved, and what still needs work. See where you can take a victory lap for getting better, and double down on the places you’ve stagnated (or worse, regressed!). Take note of the overused cliches and start swapping them out for better expressions. Trace the evolution of your topics over time and see what’s caught your interest. Compare what you’ve written to what you’ve read over a comparable time period. Stick post-it notes to the pages in the portfolio with today’s thoughts, and come back in six months and see if they still hold true.

So, what sort of “workout plan” do we have for improving our writing? My suggestion is four-fold, as explained above:

  1. For everything you write, have a process and follow it: brainstorm, outline, sentences, paragraphs, revision, copyediting. How you tweak it to fit your style is up to you. But whenever you’ve got writing to do, put the steps on a calendar, and don’t stack them all up in the same night.
  2. Have a plan for reading. Have an evening each week you set aside to curl up with a few favorite authors and read. If you’re a scribbler, then annotate the crap out of what you’re reading. If you’re a note-taker, summarize it to death. But dammit, read something!
  3. Write when you don’t have to, because it’s good practice. This is the difference between the high-performing athlete, who practices her sport because she can’t stand to just be adequate, and the pick-up athlete who fools around at the park on occasion, but never touches a ball in between. Seek out good coaching, give yourself extra homework, and revisit past performances to make sure you’re not repeating old mistakes. Even something as simple as a daily journal works; find one with some prompts to give you something to write about
  4. Keep a record of your work. It’s hard to chart progress with no record of past performance. Your portfolio serves as a record of your journey of writing and helps you identify your trends over time. As you regularly assess where you are, back up to step 3 to do something about it.

As I tell my students, writing is a pain in the butt. It’s hard. But it’s also important. And it’s too important to be tackled haphazardly, instead of with some intentional, planned purpose. We develop so many other facets of our lives — physical exercise, cooking lessons, sports practice, Bible study, small arms training, mental health therapy — that it seems insane that the only time we touch our writing is when we’re backed into a corner and covered with an automatic weapon.

Build yourself a plan. If you’re in a position of authority somewhere in a company, organization, unit, or street gang, use that authority to put even just a skeleton plan in place for your folks to help them all get better. But whatever you do, don’t sit still.

Where to find some good reading?

  • I have my personal preferences set up on Medium.com that include smatterings of articles from channels as diverse as The Ringer (sports), War is Boring (military affairs), PS I Love You (personal relationships), and Backchannel (technology). Those channels, plus the recommendations Medium throws at me, usually keep me pretty busy on days I sit down to see what’s new there. Some specific authors I follow there include Michael Peck, David Axe, and Mark Titus, whose college basketball columns are more fun than watching the games.

updated March 2019: The Ringer is now on its own site and not on Medium anymore. Ditto Backchannel. The URLs still work tho

  • I also check out Richard Deitsch on Sports Illustrated’s website pretty regularly. Deitsch covers the sports media for SI, and has a weekly column that includes his topic du jour, as well as anywhere for 12–25 links to good articles people sent him that week, and in 3 years, he’s never had a column that didn’t have at least 3 articles I found absolutely fascinating. One of my personal ‘bucket list’ items would be to appear as a guest on his podcast, but I can’t for the life of me imagine why he would have me appear on his show, considering I run a wargaming website and have precious little to do with sports media.

updated March 2019: Deitsch is now writing for The Athletic, and most of his work is behind a paywall

  • We have a running discussion forum thread over at GrogHeads.com where we share long-form journalism links with each other, and while I’m probably the major contributor to that thread, I’m been impressed by the links others have shared there, too.

updated March 2019: Find us over at Armchair Dragoons now, instead

  • I have an RSS feed for certain topics at The Economist, but since my subscription lapsed, I’m limited to 3–4 free articles each month, so I’m pretty judicious about what I pull up there.
  • Finally, I follow Doctrine Man! on Facebook, and he’s good for at least one article/day that really makes me think. Moreover, there’s usually some pretty good thoughts by the Caped Commentator himself with each of those articles, that helps provide some perspective on the articles.

Dad, husband, game commando, veteran, Army brat, writer, teacher

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