Career Advice

How Unlocking Your Inner Teenager Can Help You Overcome Writer’s Block

By Charlie Kasov December 12th, 2014

For the past 11 years, I’ve been helping teenagers prepare for the SAT and ACT. As part of my duties, I help them with the essay portion, in which they must conjure an organized response to a randomly chosen sociopolitical dilemma in less than 30 minutes.

If you haven’t interacted with teenagers lately, a quick refresher: They’re the ones who go from sleepily apathetic to hormonally apathetic in picoseconds. Getting them in the writing zone isn’t easy. To spur both their creativity and productivity, I’ve cultivated a few exercises that usually work.

When I started writing professionally, it took all of three months for me to get hit with my first bout of debilitating writer’s block. It took way longer than that for me to realize the tricks I’d been teaching my teenyboppers might actually help me as a freelancer.

The emotions we feel from writer’s block—the frustration, the anxiety, and the certainty that, somehow, our inability to produce content will lead to an early, painful death—aren’t much different than the emotions my pubescent pupils feel when they’re asked to cough up mini-treatises at 8 a.m. on the most important Saturday of their high school careers.

So, with that in mind, I felt it would be helpful for me to go over some of the exercises my students do to get in working mode—and explain how they might just help you overcome the horror that is writer’s block.

How does this relate to global warming?

This is a hack for dealing with the ACT essay prompt, which usually concerns education policy. At least with the SAT’s super-general essay questions, kids can write about Abe Lincoln and Martin Luther King, Jr. 80 percent of the time. When they have no idea what aspect of education policy they’ll be asked to discuss, they often struggle to come up with any examples.

To ensure they never leave the page blank, I tell them that every essay prompt can be tied to global warming.

For example, the first prompt in the official ACT prep book asks, “Should students be required to maintain at least a C average in order to obtain a driver’s license?”

While most students will have one instinctive argument in response to this question, writing five paragraphs on the topic fills them with dread. So I teach them: Assume bad students make for bad drivers, and bad drivers cause more accidents. More accidents cause more traffic, which causes more pollution, thus more global warming. Global warming is bad.

Usually after I walk them through this thought process on two prompts, they’re able to tie the next one to global warming without my input. It might seem off-topic, but both the kids and the essay-graders are happy to see a constructive argument with clear progression.

This can work for professional writing as well. If I’m having trouble thinking clearly about the topic at hand, I now ask myself how it relates to something that seems wildly off-topic, like global warming, human rights, or the 2024 presidential election. This exercise is usually silly enough to let me drop my guard, and even if the end-result isn’t usable, it at least got me thinking analytically.

Channel an annoyingly inquisitive four-year-old

I got this idea from Louis C.K., but while his daughter’s endless questioning drove him to manically deconstruct the universe, I found a different way to make it useful.

Most of my students excel at writing two-sentence paragraphs. Or eight-sentence paragraphs with only two sentences of original thought restated four times. To get them to flesh out their best ideas, I encourage them to ask nagging questions like “Why?” and “So what?” after each assertion they make. This tactic forces them to dig deeper with analysis and make unclear ideas more explicit.

When you feel like you’re being too vague or shallow, or when you’re at a loss for what to say next, ask a question about the last sentence you’ve written, or after any idea that feels too thin.

Be sure to physically type out the question in bold, then answer it in normal typeface. Continue to do this after each sentence you write until you’re writing fluidly again. Then go back and delete all the bold questions, and you ought to have something worthwhile.

The “Mafia Threat” counterfactual

The counterfactual—a hypothetical scenario of what could happen under different conditions—is a fun exercise to get you thinking analytically. You might not end up using your counterfactual, but you should still feel looser after writing a few.

With my students’ work (and my own writing), I often posit the question, “If you believe your argument is truly important, but you’re having trouble articulating it, ask yourself, how unpleasant would life be without it?” When done well, the counterfactual can be rhetorically intimidating.

If a vacuum cleaner salesman really wants to sell you a vacuum cleaner, he might not just tout its virtues. He might also remind you that without one, untold pathogens will accumulate in your home, which means they’ll accrue in your lungs, which could cause any number of problems.

Essentially, he’s insinuating that, without his help, your potential for tragic death or harm is high. It’s like a mafia threat: “Gee, it’d be a shame if something bad happened to you because you didn’t agree with me…”

Retake the test

On average, I have my students write six practice essays before they take the real SAT or ACT, but, until recently, I had only written a total of three myself. That didn’t make me less qualified to teach, but it did deprive me of a useful creative writing exercise.

Between the two tests, there are over 15 prompts in the official SAT and ACT prep books, each accompanied by a few blank pages for you to handwrite your opus. The writing space is narrow. The paper is a soothing coffee-stained beige. It’s quite inviting.

Better yet, each question strikes the perfect balance between vapidity and provocation. A question like “Can success be disastrous?” might overload your brain with ideas, but your ego will be so offended by the arrogant stupidity of the question that you’ll have to answer it. Just set your timer to 25 minutes and get to work.

Edit old papers

Teenage writers tend to think wordiness equates to sophistication, and as a result, they’ll often fill the requisite two pages with repetition rather than concise new ideas. Teenagers are smarter than we think, though, and even writers who struggle can make pretty damn good editors—as long as they’re not precious with the material.

I have them show me a paper they wrote in ninth or tenth grade, one that’s already been graded and they’ve long since forgotten about. That way, they can be objective about the subject matter. Next, I tell them to cut 20 percent of the words.

Suddenly, their cold, apathetic souls are lit by a competitive fire, and I watch them enthusiastically turn phrases like, “the problem that the governor of Florida is dealing with” into “Florida’s governor’s problem.” After they finish that exercise, I immediately have them start writing a new essay. More often than not, they churn out better work after repairing their old stuff.

I’ve managed to keep a lot of my writing from high school and college—pieces tucked away in their original binders and notebooks—and I keep them in a milk crate taking up precious floor space in my tiny bedroom. Most of the writing is embarrassing garbage, but I keep that garbage around in case I get writer’s block.

Once, I pulled out a paper I wrote in which I assumed the literary authority to claim that Yeats’ “The Second Coming” was better than Eliot’s “The Waste Land.” Those ten pages of academic drudgery were like the axe behind the glass you only break in case of emergency. I needed to get my brain going, and after nothing else worked, I pulled that sucker out and started cutting the fat.

Hacking away at my shameful past work got me in the mood to write something better that day. Sometimes you need to destroy something ugly to create something that’s, if not beautiful, then at least slightly less ugly.

Image by Thampapon
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