5 Hard Truths About Essay Writing

What You Need to Know in Today’s Tough Publishing Landscape—Plus Events You Won’t Want to Miss

Photo by Johannes Plenio on Unsplash

Hello, fellow essayists and happy last day of February.

The Challenges We Create in Our Essays—And How to Overcome Them

Lately, I’ve been thinking about the challenges we create in our essays—the structural and conceptual roadblocks that make drafting feel like wading through wet cement with heavy rubber-soled boots. Not the productive kind of difficulties that generate tension and engage readers, but the self-imposed obstacles that make our work feel like it's caving in on itself.

I’m reflecting on this now because I’m preparing a TEDx Talk, which I’ll be presenting next month at Boston College. Here’s a video where I announce the talk and its subject. If you’re in Boston or the surrounding area, let me know—I’d love to connect.

As writers, we naturally build challenges into our work; that’s part of the craft. But what derails us isn’t the problem-solving inherent in essay writing—it’s the problems we impose on ourselves. These are the patterns that stall our progress, sap our confidence, and make us second-guess every sentence.

Time and again, I work with my writing students (and myself) to overcome these common missteps in early drafts:

Overcomplicating the Structure

Weaving in too many threads or trying to balance multiple, conflicting ideas can make an essay feel convoluted and unmanageable.

Fix: Identify the main argument or question your essay explores. If an idea doesn’t serve this purpose, cut it or save it for another piece. Outline your essay to ensure each section contributes to the whole.

Example: Instead of weaving together three different childhood memories in an essay about grief, focus on one pivotal moment—like finding your father’s old baseball glove in the attic and realizing how much you miss playing catch with him.

Intellectualizing the Stakes

Focusing too much on abstract musings rather than grounding the essay in tangible stakes can make it feel distant or detached.

Fix: Anchor abstract ideas with concrete details. Instead of broadly discussing loss, narrate a moment when you realized something was truly gone. Use personal anecdotes and sensory details to bring the stakes to life.

Example: Instead of philosophizing about memory and nostalgia, show a moment—like finding a seashell on the beach that reminds you of the last time you saw your father before he passed away.

Drowning in Logistics

Over-explaining how you arrived at an insight rather than simply presenting it in a compelling way.

Fix: Trust the reader. If backstory is necessary, keep it brief. Read your essay aloud and remove any sections that feel like unnecessary detours.

Example: Rather than detailing every step of how you discovered an old letter in a box of family keepsakes, describe the moment you unfolded it and recognized your grandmother’s handwriting—how your hands shook, how the ink had faded, how it smelled of old paper.

Constantly Shifting Focus

Trying to cover too much ground, jumping from one theme to another without giving any a chance to fully develop.

Fix: Choose one core theme and stick to it. If you find yourself introducing new, unrelated topics, ask whether they serve the central message. If not, set them aside for a separate essay.

Example: Instead of an essay that attempts to cover your relationship with your mother, grandmother, and sister, focus on one defining moment with your mother—like the day she taught you to ride a bike and how that lesson stayed with you long after she was gone.

These challenges, though part of my own writing struggles, are familiar to many writers. When they take over, they lead to three frustrating outcomes:

• The essay stops feeling meaningful.

• The writing process feels stuck in limbo rather than flowing forward.

• The piece becomes difficult to place—whether in a publication, a contest, or an anthology—because its impact is diluted.

I’ve been spinning in circles on one essay for over a month now—okay, maybe two—but I finally found my way forward by stripping away an extraneous thread that was adding complexity without contributing to the core argument.

I was able to complete an essay that is connected to my memoir in progress and that went up on the Next Avenue/PBS site, which is a fantastic site. It is called I Was the ‘Dating Diva.’ Now I’m Married 20 Years. I share the dating advice that I taught and that worked for me. Here’s a photo from my days giving advice, decades before I went blonde. And make sure you check out my podcast episode #118 with Next Avenue’s managing editor. Several of my students have been published there.

Upcoming Events: Writing Throughlines, Publishing Insights & More

Structure and coherence matter deeply in essays. The right threads and throughlines elevate a piece, guiding the reader through layered ideas and emotions. That’s why I’m hosting a webinar on April 24th for Writer’s Digest called Layering Throughlines and Timelines into Your Essays and Books to Pack a Punch. If you’re looking for ways to refine your narrative’s shape, sign up here. It will be generative, informative, and interactive—I’d love to see you there.

I’m also hosting another editor-on-call online, free event in collaboration with NYU, where I teach writing classes. This one is April 10th from 12:30 pm-1:30 pm with Willa Bennett the editor-in-chief of iconic publications, Cosmopolitan and Seventeen Magazines. As an FYI, I once had the honor of perusing through Cosmopolitan founder, Helen Gurley Brown’s famous “Book,” so this will be an extra special and nostalgic conversation for me.

Snag your spot now before space runs out, by clicking on the QR code. Or signing up here. Hope you read about my last editor-on-call with an editor from The Cut.

Podcast: How to Submit & Get Published

And before I get to the hard truths about essay writing (hopefully, you’ve already read my post on My Predictions for Publishing in 2025)) check out episode #128 of my podcast where I talk to Rachel Kramer Bussel, editor of Open Secrets Magazine about how to submit and what she is looking for, and her excellent advice on crafting essays. Plus, details on the Open Secrets Magazine Live (event). Find that here.

Five Hard Truths About Essay Writing

1. Your essay needs a central argument or question that evolves.

Without forward movement—no shift in understanding, no tension building toward a revelation—the piece risks feeling static.

Fix: Ensure your essay moves forward by introducing a shift or realization. If your ending looks the same as your beginning, consider how your perspective or understanding has evolved.

Example: Start with a narrator who believes they are indifferent to their hometown, then gradually reveal moments that show a deeper connection—such as revisiting an old diner and realizing how much its closing affects them.

2. Your essay needs a structure that supports clarity, not confusion.

Even fragmented, nonlinear essays need a guiding framework to help the reader follow the thread.

Fix: Use signposts to guide the reader (e.g., "At first, I thought..." "But then I realized..."). Experiment with different structures—chronological, thematic, or circular—to see what best serves your essay.

Example: A braided essay about motherhood might alternate between personal experiences and historical accounts of motherhood, with clear transitions tying them together.

1. *There’s more, plus an opportunity to have the beginning of your essay analyzed by me to make it stronger.