Guest Post by Ilana Long

Ilana Long is a versatile creative who started her career in comedy, performing stand-up and sketch comedy in Chicago and Seattle before transitioning into writing. She has authored the children’s book Ziggy’s Big Idea, numerous essays in Chicken Soup for the Soul, and her forthcoming debut novel Pickleballers. In addition to writing, Ilana has taught in several countries and enjoys a wide range of creative outlets including singing, acting, and watercolor painting. Currently living near Seattle, she balances her passion for pickleball with outdoor adventures and family life.


There are two potential outcomes to every comic bit. The joke lands. Or the comedian dies. Every sketch is riddled with the ultimate comedy risk; it won’t be truly funny unless there’s a chance that it won’t be funny at all.

When I think about those days waiting in the wings to jump onstage at Chicago’s Second City and improvise in front of an audience, a cool shudder still ripples through me. What if? I worried every time. What if nobody laughs? What if I get out there and I’m tongue tied? What if they don’t invite me on stage for this sketch? Or the next. Or the next. Or worse, what if they call me into the blind date scene and say, “Ilana, go sit at the table.”

Because every improvisor knows the straight role sits at the table, and the entering character, the blind date, calls the shots.  Why was I consistently cast as the table date? Because my improv teammates knew spontaneity was not my bag. And improvisation is not about acting. It is about re-acting.

The Funny Wanted Out

Sure; give me a funny script or let me write it out ahead of time and I could rip up the audience with laughter. But on the spot, I didn’t dare.

My ego sustained some bruises, but my funny bone was still intact when I decided to leave improv and delve into writing and performing stand-up and sketch comedy. But stand-up was laden with its own land mines: the instantaneous Ilana-killing effect of the heckler. With awe and envy, I watched my fellow standups improvise heckler take-downs with ease. But for me, the instant an audience member engaged in a heckle-battle, my act was shot.

The funny in me wanted out, but each time I tried, I couldn’t relinquish my need to control the outcome. If there were any outside factors interrupting my trajectory, I tanked.  I kept proverbially scratching my head. How did the improvisers and heckle-responders do it? And why couldn’t I?

So I threw over the uncertainty of a career as a comedian and moved into teaching English and drama. I found I could use my classroom as a controlled stand-up comedy platform where my students were grade-inspired to laugh. Writing became my hobby, and for a long time that was how it went.

Lions, Pirates and Writers

And then one day, I noticed a dog-eared, much-neglected book on my classroom bookshelf. I mean, there was mold behind the cover. I almost threw it out. The book titled If You Want to Write by Brenda Ueland, was a reprint, but I smiled at the original publishing date. 1938! In the photo at the back of the slim paperback, the author wore an old-fashioned hairstyle and a determined expression that contrasted her surprisingly contemporary and sassy writing. And my flipping of pages halted when I spotted a catchy chapter title. Be Reckless, Careless! the author urged. Be a Lion. Be a Pirate, When You Write.

I wanted to be all those things.

Brenda Ueland described the rough draft process like improv on a page. To write with heart, one needed to be bold, and put direct thoughts onto the page without self-censorship. There would be time for revisions later, but for now, write without that nagging self-judgy voice that says this sentence is too silly, too descriptive, overly flowery, or flat out impossible. Rein it in later. Or don’t. But for now, get it out of your head and onto the page.

Side-Stepping Self Censorship

My students became the guinea pigs for this method. Instead of asking them to write 200 words on topic X in Y amount of time, I changed it up. “You have ten minutes for a writing warm up. Here’s a topic, but you can write about another one if you like. I will not be grading this. Do not stop writing.”  This daily writing prompt became a habit for my students, and when I began joining them without the self-censoring risk factor, the fluidity and energy of my writing changed. Why not take a situation to the extreme? Why not be brave? Be a pirate. Be a lion. Who’s gonna read it like this anyway? I had all the time in the world to move my improv into a fully formed script.

I no longer had to plot out a story ahead of time. I could go with the flow to use my instinct and guess at my characters’ reactions. And now my story could move beyond the improviser’s basic task of “What comes next?”

Because improv is the short game, and novel writing is the long game. To practice creating plot complications, improvisers play a game called “Yes, and.” It goes like this: Person A: “Doctor, I’m having the baby right now.”  Person B: “Yes, and I can see the tentacles crowning already.” Or, Person A: “Hands in the air. This is a stick-up.” Person B: “Yes, and this is why I don’t invite you to Thanksgiving dinner, Uncle Harold.”

But as writers, we have to take way-out-there responses and risks one step further. Because a novel’s storyline is sustained much longer than a comedy sketch, “Yes, and” becomes “Therefore” and “But.” With “Therefore” in play, every event becomes a reaction to the plot, and every character’s response happens in real time. The word “but” is the key that makes the conflict come to life. “But” is the twist, the surprise. It is the lion and the pirate around the corner.

Write Bold and Brave

Like in improv, your novel’s character’s reaction is key, but because we writers get to draft and revise, we can run the scenario any number of ways. There are a thousand potential outcomes to every sentence. And there are a million ways your writing might be received by a reader. The writing lands. It doesn’t land. The editor thinks it can be massaged into landing. The editor hates it, but you love it and so does your mom.

But in all circumstances, the author will never stand in front of the audience waiting for the laugh. She’ll never know how every reader perceives that sentence. So she might as well go bold, be brave, be authentic. Writing with broad strokes is a risk. But there’s nothing at stake except the truth.

Pickelballers

Pickleballers by Ilana Long

Meg Bloomberg’s life takes an unexpected turn when a pickleball trip to Bainbridge Island, meant to lift her spirits after a breakup, leads to a new romance with local environmental consultant Ethan Fine. Despite her growing feelings for him, Meg discovers Ethan is undermining her home court, prompting her to end the relationship. Determined to take charge of her life, Meg focuses on her own path, with the possibility of love returning on her own terms.

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