Why Most Writing Falls Flat (& How to Avoid Boring People)

On blind spots and working through frustration

The faces that make up the latest Write of Passage cohort (an online writing course designed to help people “publish quality ideas, find your people, and 2x your potential”)

Whoever said “Hindsight is 20/20” was a genius because I’m two weeks into my Editor gig with Write of Passage, and I’m having all sorts of revelations. I took the course as a student two years ago, and the more feedback I give on essays now, the more I see the “errors of my way” back then.

I see so much of myself in our new students, and there’s one blind spot most of us struggle with initially. In today’s edition, I’ll share what that is and how to overcome it (using a tip from real estate).

The Rules of Real Estate

Everyone knows the three rules of real estate are “location, location, location.” Writers benefit from a similar mantra of “specifics, specifics, specifics.”

The number one problem new writers run into—and hell, I was one of them—is being too generic in their writing. No stories, no examples, no visuals. This is a super relatable challenge because writing is an act of convergence and it’s natural for us to take a bunch of great stories and strip them down to overarching lessons and takeaways.

We think we’re doing readers a service by sharing things in general terms. After all, they apply to so many scenarios, right?

But we have to remember, our readers don’t have the same bank of stories (and thus context) that we do. So it puts the burden on the reader to add colour and dimension to these supposedly profound takeaways. In the absence of that, our writing falls flat and we bore people.

The easiest way to avoid this is to use “specifics, specifics, specifics” as a mantra. Bring your readers into a moment where you learned X. Paint the scene. Don’t just describe it but make them see what you saw, feel what you felt, and let them connect the dots before you explicitly share a takeaway. Gift them with a walkthrough of your journey so they can arrive at a similar, memorable destination.

Example

As a student in my first Write of Passage cohort, I thought I was doing a good job of being “specific” from the get-go. After all, I was telling readers what happened. But it wasn’t until a fellow student,

ANTHONY POLANCO

, said “You’re telling me, but you’re not showing me,” that I registered my blind spot.

After some initial frustration for having worked hard on my first draft only to have it met with a call for more, not to mention a baffling feeling as to how the hell I was supposed to do that, I questioned whether Anthony’s feedback was legitimate.

But fortunately, once I gave myself time to process it, I realized he was right. Determined to implement his feedback, I rewrote my essay with more specifics.

Here’s a side-by-side comparison of my introductions from left to right (before and after):

(Here are the full before and after posts if you want a complete comparison.)

Anthony was thrilled with my progress and that made me happy. I look back on how our exchange went from exasperated to ecstatic as one of my top Write of Passage moments.

Writer Spotlights

Of all the great essays I’ve read—and there have been many in the thirty-four I’ve given feedback on—there are two I’ve been thinking about a lot. I shouted out both within the Editing team as “great craft” and now I’m keen to share them with you:

1. ‘When The Teacher Becomes The Student’ by

TheCalisotaGirl

The first essay that gripped me was about a teacher’s “rude awakening” after making the switch from teaching “fresh-faced” students on track to join a prestigious Baccalaureate program in favour of a night program where most students have been involuntarily moved after failing “so many” classes.

Here’s the introduction to the essay:

“If you want to know what your physical flaws are, become a middle school teacher.  If you want to know what all of your mental and emotional flaws are, become a high school teacher.  Bonus challenge: teach students at an alternative school where they give zero fucks about, well, anything really.”

Read the full essay here and drop a like or comment to support this budding Substack writer in getting her publication noticed.

2. ‘Unblurred Lines’ by

Erin Rupp

This essay was so vulnerable and beautifully written, I felt as if I were reading the lyrics of a song. The words flowed down the page with the gentlest melody. The piece centers on how a blind spot the writer describes as a “longtime silent companion” has impacted her friendships from childhood through adulthood—and through love and loss.

Here’s the passage that hit me the hardest:

“Widowhood. When the unimaginable happened, I was left reeling; I never thought it would happen to us. The knock and the uniforms only existed in movies. Yet there I was, a widow at 25 with a baby to raise on my own, lost. People tried to help. Oh, how they tried. The same sweet ladies who patiently invited me for coffee appeared within hours, moving in unrehearsed choreography to prepare my baby and me to board a plane to greet my husband’s casket.”

Read the full essay here and drop a like or comment to support Erin in growing her Substack.

(Erin is a fellow Editor for Write of Passage and needless to say, I’m honoured to be on her team.)

Thanks for reading and have a wonder-full week,

Alexandra

P.S. If you enjoyed this edition, please like, comment, or reply to let me know.

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