Words Gone Wild: Digging Into Whimsy for Serious Writers

[This article originally appeared in the November/December 2025 issue of Writer's Digest magazine.]

I know so many of us want to be serious writers. I get that. I’m serious with a capital S, in a dig-into-the-trauma-and-cry, self-flagellating-because-I-didn’t-finish-that-chapter-by-deadline, elbow-patches-on-my-tweed kind of way. Serious. Because you have to be serious to make a living as a writer, don’t you? You have to sit down at the keyboard day after day, banging out serious words with a frown on your face.  

I’m guilty of this, too. I’ve told my students to take their writing seriously. I meant it, at the time, just as all of the teachers who told me the same thing meant it when they said it. As writers, we’re often told to treat our craft seriously if we want to be taken seriously.  

And I agree with this concept—within reason. 

But somewhere between self-doubt, punishing writing routines, and the absolute horror show of querying, I think some of us can forget the most important aspect of writing. It’s supposed to be fun.  

In a recent workshop I taught on creative chaos, participants wrote about a talking can opener, being locked naked out of the house, and, in one oddly specific story, Ryan Reynolds’ socks. At a writing retreat, my co-author-in-residence and I guided participants through writing bad haiku, stories of the unexpected, and characters making ridiculous mistakes. When I run my Prompt-A-Palooza events, participants are encouraged to leave normal at the door and go back to the idea of writing for the thrill of trying new things.  

The stories, poems, and other works to come from these workshops might not end up being publishable. And maybe they don’t make it into the novels all the participants are working on. But these activities do something better. They force the writers to let go of perfectionism, unleash their inner critic, and simply play with words. 

Of course, some of the writers do leave with stories or scenes for their novels or poems stunning enough to submit to literary journals or contests. Some of the participants come away with what they consider results. But all the participants of these workshops leave with something far more important, something invaluable—a sense of joy, an increased desire to experiment with the majestic worlds that words can create, and renewed creativity and passion for their own writing. In other words, even when the act of whimsical writing doesn’t necessarily produce a tangible product in the form of a “usable” story, it absolutely produces something better—happiness. 

It's long been acknowledged that making art can lead to increased happiness. In an article on Harvard T.H. Chan School of Public Health, the authors cite Dr. Jeremy Nobel, founder and president of the Foundation for Art and Healing. “… the arts literally rewire our brains, changing our thoughts, feelings, social cognition, and behaviors. Making art decreases the stress hormone cortisol, and increases levels of feel-good hormones such as dopamine, serotonin, oxytocin, and endorphins.” When we allow ourselves time to write for the sake of writing, we’re increasing the feel-good chemicals in our brains.  

Science has shown that when we engage in play, we increase brain activity in the prefrontal cortex, where creative thinking happens. Tapping into those areas of the brain empirically increases our creative thinking. And what happens when we allow our creative thinking to break free? We write better stories, better articles, better memoirs, better everything.  

But how does a Very Serious Writer™ go from staring in angst at their screen and tearing out their eyebrow hairs to letting loose and creating chaos on the page? Listen, folks. You’re going to have to work at it. Play comes with practice.  

It’s easy to tell you to let go of the idea of perfection, but it can be so much harder to internalize that. When you sit down to work on your novel, or a story for a contest, or that article you’ve been putting off for three months, and now the deadline is tomorrow, you might feel you don’t have the time to set aside your quest for greatness.  

Trust me, I understand. It’s hard to be whimsical when your agent is tapping their watch, asking when you’re going to be finished with edits. It’s difficult to consider writing stories about lonely potatoes or a rice steamer who has lost its will to steam when you are deeply entrenched in the oh-so-serious business of writing for a living.  

But I propose this. We cannot become better writers if we don’t allow our creativity free range. We can’t reach the heights of skill that come from experimentation in whimsy if we don’t allow ourselves those sweet little dives into weirdness. 

This is why I recommend taking time for structured play. If it sounds like a contradiction, it’s probably because it is. Yes, I really am proposing structured time to play. Remember play dates as a kid? Think of it as play dates for grown-ups, only instead of playing with Legos and Play-Doh, you’re playing with your own ability to build worlds and create people out of words.  

To start, consider bringing together a group of writer friends. This can be in person or over the internet. Video meetings are best, but you could also do timed sprints and share results over social media or through email. However you get together, I do believe playing works better in groups.  

If you don’t have a group, or if you’re so introverted, the idea of approaching anyone about writing together feels slimier than an eel in a jar of olive oil, you can do this alone! The key is to remember you are not striving for perfection. You’re striving for perfectly unpredictable.  

Once you’ve gathered your group or set aside some time for yourself, how do you actually do this thing? How do you bypass that inner censor and break down the doors of the Very Serious Writer™ club to let your beautifully bizarre brain loose on an unsuspecting world?  

In my workshops, we work on the idea of constraint + absurdity = freedom. In other words, set a timer, use a prompt, and put your pen to paper (or fingers to keyboard) and just write whatever comes to mind until the alarm goes off.  

Here are a few of my favorite prompts from the Prompt-A-Palooza classes I give at conferences and festivals.  

Example: Greg stole my sandwich 

From the breakroom fridge again 

His head is in my desk 

In groups, all of the brainstorming can be done together. Imagine what your friends can come up with for weird hobbies or unusual modes of transportation. In a group dynamic, writing for play becomes a way to bond—laughing together. On your own, you can still unlock these moments by jotting down every thought that comes to mind, no matter how strange or ridiculous it seems.  

I have been belaboring the point that these writing exercises are meant to be fun. They’re meant to be strange and silly, and they aren’t necessarily meant to produce any serious work. But it’s important to note that in my workshops, students often do come out of these exercises with stunning stories and new scenes for their works in progress. I think this happens because when we settle in to play, and we give ourselves enough time to really dig into the ideas simmering under the self-critic and the stories that come out not because we think they should but because they burst out of our imaginations with joy.  

Sometimes, we have ideas and then we write. But sometimes, we write and then ideas come. Giving yourself time, space, and the creative freedom to simply start writing words one after another often leads to something brilliant in the middle of it. Maybe you’re stuck at an impasse in your manuscript or maybe you don’t know how to take your main character on the emotional journey they need to take to reach the conclusion of your novel. Maybe you’ve spent day after day opening your document and staring at it before closing it again to go play “Animal Crossing.” Trust me, I’ve been there. Instead of frustrating yourself further, take a play break. Playing with whimsical exercises allows you to dig into the things that are blocking your creativity and move into something new.  

Finally, consider this. Even if you don’t walk away with something serious, even if you don’t come out of your play date with a new chapter for your book, or a new character arc, or the next great article for your freelancing career, you’ve still done something incredible for yourself. You’ve given yourself an hour or two away from the very serious business of writing and allowed yourself a chance to relax all the clenched teeth, tight shoulders, and aching neck muscles. You’ve given yourself the equivalent of a spa day—only the massage is for your brain and your soul, not your body.  

So go ahead right now—set your time, grab a prompt, and settle in to write about a vengeful refrigerator who purposefully ruins all your food, or a ghost who refuses to believe they’re dead. Your serious writer self (and your deadlines) will thank you for it, I promise.