3 min
October 16, 2022

How To Make Your Writing POP

My dearest writing friends,

Whatever you do, don’t be boring. 

This isn’t a game where you get multiple lives. Lose the reader and your essay is dead. 

You’ve got to make your writing POP by being Personal, Observational, and Playful

Share personal experiences to connect with the reader. Observe the world around you and search for parallels between two seemingly unrelated things. And make the reader smile with fun and playful writing.

I learned about POP Writing from David Perell in Write of Passage. That session jolted me into the realization that I was just typing up diary entries and hitting publish. My writing was rarely observational and about as playful as a Catholic Church service on a Wednesday night. 

Since then I’ve published 80+ essays. 

In this essay I’ll reveal how to capture and maintain the reader’s attention and make reading fun again.

Personal: Give your writing a sense of humanity

Write from the gut and share stories to make your writing personal. If you skip this pillar, your writing will read academic or unrelatable. 

Dear Diary Snippet

When people think of injecting personal stories into their writing, they think of Dear Diary Snippets. These are the most intimate, confessional thoughts you might be hesitant to let anyone else read, like how I loved molly so much I would secretly take it on a Tuesday night and not tell my friends. 

My favorite writers shine in this category: Glennon Doyle, Brene Brown, Cheryl Strayed, David Sedaris. They write the stuff we all go through but are too uncomfortable to share. In Doyle’s memoir, Untamed, she wrote about her indecisiveness on whether or not to stay with her then-husband after he’d been unfaithful:

“That is how I found myself in bed at 3:00am, shoveling Ben & Jerry’s into my mouth, typing into my Google search bar: What should I do if my husband is a cheater but also an amazing dad?”

Specific, relatable, and vulnerable. The juiciest kind of writing.

Fly-On-The-Wall Insight

But personal writing doesn’t always have to be vulnerable. It could just be a Fly-On-The-Wall Insight. Think of details in your everyday life that capture a moment in time, the way Joan Didion did in Slouching Towards Bethlehem:

“I could taste the peach and feel the soft air blowing from a subway grating on my legs and I could smell lilac and garbage and expensive perfume…”

Didion carried us to New York City with her. She alerted our senses of sight and smell. She transported us to her world. The tiny, seemingly unimportant specifics of our lives can add a personal touch to our writing without confessing our deepest, darkest secrets. 

Tortoise And The Hare Experience

Finally, personal writing can exhibit wisdom. Stories from your life that resulted in a universal lesson are your Tortoise And The Hare Experiences. 

In his essay, The Three Sides of Risk, Morgan Housel told a tragic story from his late teens in which his two friends died in a ski accident. The entire point of his story was to illustrate the consequences of risk in investing:

“I don’t know if Brendan and Bryan’s death actually affected how I invest. But it opened my eyes to the idea that there are three distinct sides of risk… Once you go through something like that, you realize that the tail-end consequences – the low-probability, high-impact events – are all that matter.”

Just listing the three distinct sides of risk would not have landed with readers without Housel’s powerful, personal story. 

So share your stories. Give an inside look into your life. Whether it be a Dear Diary Snippet, a Fly-On-The-Wall Insight, or a Tortoise And The Hare Experience, personal stories are entertaining and relatable. Readers will root for your success. 

Observational: Make the reader think about something in a new way

Use your unique perspective and put your own twist on an idea to make your writing observational. If you skip this pillar, you won’t share anything the reader hasn’t already heard before. You have to give them something beyond a self-indulgent diary entry.

Metaphor And Analogy

I cringe at the thought of my old blog posts the way I cringe when someone recognizes me from college: I’d rather we all just forget about it and move on.

People weren’t interested in my day-in-the-life posts. Readers want to be entertained but they also want to learn. They want to think about something in a way they never thought about it before. Metaphors and analogies are a writer’s secret weapon here. In Derek Sivers’ essay Don’t Quote. Make it Yours and Say it Yourself, he used an analogy to make his point:

“If I hear an idea, have considered it, and integrated it into my beliefs, it’s mine. I’ll say it succinctly in my own words, and stand behind it. Like adopting a child, I will take care of this idea and raise it as my own.” 

The adoption analogy allows me to imagine a child being welcomed into a new home and family. Think of metaphors and analogies as explaining something to a 6-year-old. By simply comparing something to something else, it becomes easier to understand. 

Twilight Zone Moment

Observational writing also lends itself to hot takes, or as I like to call them, Twilight Zone Moments. When you look to your left, look to your right, and think, “Surely everyone agrees with me??” Only to realize you’re all alone. Everyone thinks you're crazy at the same time you think everyone else is crazy. 

David Perell had a Twilight Zone Moment at the Thanksgiving dinner table when he found himself trying to explain to his family how the world worked. The conversation inspired his essay, What The Hell Is Going On?, which detailed the shift from information scarcity to information abundance. 

Just because something is obvious to you doesn’t mean it’s obvious to others. As Peter Thiel famously asks interviewing candidates, “What important truth do very few people agree with you on?” 

When you interpret something strongly and differently from the majority, you allow the reader to understand it from your unique perspective. 

Expert Edge

Finally, observational writing reveals your Expert Edge. These are things you know a lot about because of your experiences.  

Tim Ferriss spent years editing cookbooks by some of the world’s best chefs, so he had an insight about why readers should (obviously) choose the cheapest wine on the menu: 

“The cheapest is often a good, smart value; the second cheapest is sometimes a sucker’s play – a bad deal put specifically on the wine list for all the people who don’t know wine, don’t want to ask, but don’t want to look cheap by ordering the cheapest.” 

Ferriss was on the inside of the restaurant business. It made him uniquely qualified to share his insight with readers. 

What insights do you have? How can you make something easier to understand by comparing it to something else? Recall your Twilight Zone Moments and use your Expert Edge to your advantage.

Playful: Make your writing delightful and easy to read

Add a splash of fun and put a smile on the reader’s face to make your writing playful. If you skip this pillar, your writing will be dry and hard to get through. Playful writing is the fuel that moves the reader from one sentence to the next. 

Pop Culture

At first, I focused on the pop culture aspect of playful. How could I incorporate Harry Potter, The Bachelor, and Seinfeld into my writing?? Anthony Bourdain made it look easy in his essay, Eat To The Beat, about the “shameful” 1977 New York City music scene: 

“Every douche bag in America who could buy a white suit or some heavily adulterated cocaine was suddenly empowered to show you his back fat and chest hair. It was the triumph of the Ron Jeremys.

The first sentence could have stood on its own just fine, but referencing a famous porn star in the next sentence took it to POP status. Perhaps you’ve never heard of Ron Jeremy? Well congratulations, that just means you’re an upstanding citizen who doesn’t watch porn. 

If you’re a fan of something in pop culture and it applies to whatever you’re writing, why not reference it? But there’s no need to force it. Pop culture references are not the only way to write playfully. 


Best Friend Talk

Imagine you’re at a formal event. You’re all dressed up and wearing uncomfortable shoes. You’re hyper aware of your posture. People pass by and you exchange polite hellos. And now your best friend is standing next to you. After the pleasantries with strangers, what might you whisper to your best friend? 

This is Best Friend Talk. It’s almost an aside to the reader, as if you’re breaking the fourth wall and inviting them inside the process. Maybe your writing has a more formal or professional tone, but every once in a while you give the reader something that makes their lip curl. 

In their book, Like Brothers, filmmakers Mark and Jay Duplass reflected on a movie they wanted to make:

“We wanted it to have the raw, emotional truth of a John Cassavetes film but also carry our sense of goofiness and humor. We didn’t want people to have to eat their vegetables with this one. Or at least if they were vegetables, they would be roasted with lots of salt and olive oil and be super crispy and fun! (Can’t believe we just wrote that, but you get it.)

Addressing the reader directly and using self-deprecating humor made the Duplass brothers more relatable.

Read your text messages and emails to friends. Best Friend Talk is informal, direct, and might even feel lazy. One or two-word sentences can be playful.

Dr. Seuss Experience

Sometimes playful writing is less about content and more about style. A lot of Dr. Seuss stories don’t make much sense, but they’re always fun to read:

“Think of black water. Think up a white sky. Think up a boat. Think of BLOOGS blowing by.”

Provide a Dr. Seuss Experience for the reader with visuals and sounds to make your writing sing. J.K. Rowling did this in Harry Potter And The Sorcerer’s Stone by using descriptive alliteration:

Harry had never imagined such a strange and splendid place. … The tables were laid with glittering golden plates and goblets. … As Harry helped himself to a treacle tart, the talk turned to their families.”

Or you can add rhyme and repetition. Matthew McConaughey included a little poem called Oneinarow in his memoir, Greenlights:

“Any success takes one in a row. Do one thing well, then another. Once, then once more. Over and over until the end, then it’s oneinarow again.”

By looking at your writing as music rather than words, you can guide the reader from one line to the next. Make it pretty and poetic and punchy. 

Original Language

Speaking of punchy, this section cannot exist without naming the master of playful writing: Tim Urban. 

Urban is one of the few writers where I belly laugh multiple times during one sitting and about halfway through need to share it with a friend because it’s so funny and they need to read it RIGHT NOW. I’m not kidding. Read anything on his site. A good starting point is Why Bugs Ruin Everything

Wait, don’t read it yet! I need to set up Original Language. Urban is the king of acronyms and coining terms.

Here’s an example of an acronym from the above essay:

“A key skill of The Guy Who’s a Huge Pussy When it Comes to Bugs is to control the ‘initial involuntary horror reaction,’ or the IIHR, which happens when you suddenly notice a large bug on or near you. When I’m alone and see a bug, I let the IIHRs fly. I think probably the most mortifying thing that could happen to me would be for someone to show everyone a video montage of every private IIHR I’ve ever had.”

And here’s an example of a coined termed from his popular essay, Taming The Mammoth: Why You Should Stop Caring What Other People Think:

“Humans evolved an over-the-top obsession with what others thought of them—a craving for social approval and admiration, and a paralyzing fear of being disliked. Let’s call that obsession a human’s Social Survival Mammoth.”

Original language encompasses more than just acronyms and coined terms. It can also give something a very specific name rather than the obvious generic version of what it is. For example, instead of talking about an elephant, you might say Dumbo. Or instead of describing a character as Australian, the writer might refer to him as a “Bloomin’ Onion with feet.” 

Playful writing is the opposite of cliches, but we think in cliches so we write in cliches. We can’t help it. We’re creatures of habit. (See??)

That’s why playful writing often happens in the editing phase. Create a new document and put each sentence on its own line. Transform bits of your writing into a Dr. Seuss Experience. Are there any opportunities to add in pop culture references, Best Friend Talk, or Original Language? 


The best writers POP. 

They include all three pillars in their writing. Some might lean more towards one over the others, but they are all there. The Crane Wife by CJ Houser is a perfect example.

Hauser started: “Ten days after I called off my engagement I was supposed to go on a scientific expedition to study the whooping crane on the gulf coast of Texas.”

She then jumped back-and-forth between two stories: the demise of her relationship with her fiance and her trip with strangers learning about a species going extinct. Both stories were personal accounts (the breakup was very personal), but what made it interesting was the observation throughout the essay in which Hauser drew parallels between herself and those birds. 

If I were to have written that essay before learning POP Writing I would have easily written about the breakup with my fiance. I would not have thought about the metaphor with birds. 

But now I see metaphors everywhere. Every story has a lesson. Every story has something universally relatable in it. By simply asking myself the question, “What will the reader get out of this?” I’m able to naturally bring the observational piece into my writing.

And of course, Hauser spiced up her essay with some playful writing, like when she referenced my favorite reality television show. Hauser said yes to the engagement to her ex “even though he turned our proposal into a joke by making a Bachelor reference and giving me a rose.”

And then she snuck in a little Best Friend Talk:

“I didn’t leave when he wanted to invite [the woman he cheated on me with] to our wedding. Or when, after I said she could not come to our wedding, he got frustrated and asked what he was supposed to do when his mother and his friends asked why she wasn’t there. Reader, I almost married him.

By using all three pillars, Hauser wrote an essay that popped. 

Anyone can become a POP writer. It takes practice. And patience. And lots of shit writing. 

It’s a challenge. 

But as the great Ted Lasso once said, “Taking on a challenge is a lot like riding a horse. If you’re comfortable while you’re doing it... you’re probably doing it wrong.”

So get on that horse. Get uncomfortable. And get poppin’.




Thank you David Perell for your eyes on early drafts and full support of this essay. Thank you Michael Dean for your encouragement and brilliant idea to include more coined terms. Thank you Stew Fortier for a final pass to help make it really POP! And thank you to my editor, Sam Bleecker.

One final shoutout to my amazingly supportive and sarcastic writing crew for the final punch: Matt Tillotson, Nate Kadlac, Scott Krouse, and Florian Maganza. I appreciate you guys. :)