Why I Break Grammar Rules-on Purpose

And Why That’s Not a Bug-It’s the Point

Playfully trying on aviator sunglasses just before Christmas; aviators like the digital glasses in my profile picture. I’ve never actually owned a pair…and…still don’t. But…who knows? ;)

Why I Break Grammar Rules-on Purpose

And Why That’s Not a Bug-It’s the Point

The Jack Hopkins Now Newsletter #714: Saturday, January 3rd, 2026-Late Night Edition

I’ll keep this short.

Every once in a while, someone on social media leaves a comment like this:

“Get rid of that comma on your headline! Great writing though and I’m a fan.”

On the surface…that looks like a nitpick.

Technically…grammatically…academically… she’s right.
The comma doesn’t belong there if you’re writing to please an English professor or score a tidy A in freshman comp.

But here’s the part most people miss:

That comment didn’t bother me.
It actually told me something important.

It told me she’s exactly the kind of reader I want.

Someone who notices the deviation…
Feels the itch…
But can still look past it and engage with the idea.

That’s not a flaw.
That’s a skill.

And it turns out, that skill…being able to tolerate small ambiguities and deviations …while staying focused on meaning…is the same skill that determines whether people can think clearly in complex…emotionally charged environments.

Which is…kind of the whole point of this newsletter.

Let’s Get One Thing Straight

I violate punctuation and grammar rules constantly.

Not because I don’t know them.
Not because I’m careless.
Not because I’m trying to be edgy.

I do it because I have a different priority.

I am not writing to impress professors.
I am not writing to win style awards.
I am not writing to be “correct.”

I am writing to get ideas to lodge inside your nervous system in a way that makes them retrievable later…under stress…under emotion…under pressure.

That requires something very different than textbook prose.

And the research backs this up.

The Brain Does Not Learn the Way School Taught You It Does

Most people were taught…implicitly or explicitly…that learning is about clarity…order…and smoothness.

Neuroscience says otherwise.

The human brain is not a passive recorder.
It’s a prediction machine.

It constantly asks:

• Is this familiar?

• Is this important?

• Does this require attention?

When something is too smooth…too expected…too perfectly formatted…the brain often skims.

It recognizes the pattern…and moves on.

But when there’s a small violation…a pause…a break…a disruption..the brain does something different.

It wakes up.

Desirable Difficulty (Yes, That’s a Real Term)

Cognitive psychologists call this concept “desirable difficulty.”

The idea is simple:

Information that requires slightly more effort to process is remembered better…not worse.

Not confusion.
Not chaos.
Just enough friction…to force engagement.

Small grammatical deviations…unconventional punctuation…unexpected rhythm…these create micro-pauses.

Those pauses trigger:

• Increased attention

• Deeper encoding

• Better long-term recall

In other words:

Your brain leans in.

That comma you wanted gone?
That ellipsis that “should” be a period?

They act like speed bumps for cognition.

And speed bumps…are how you make people notice where they are.

Emotion Is the Glue of Memory

Here’s another uncomfortable truth:

We do not remember information because it was logical.
We remember it…because it was emotionally tagged.

This isn’t pop psychology.
It’s how the hippocampus and amygdala work together.

Emotion…especially mild surprise…irritation…curiosity…or humor…marks information as “worth keeping.”

And here’s where people get tripped up:

Even mild annoyance can enhance memory.

Not rage.
Not confusion.
Just a little “huh… that’s odd.”

When someone thinks, “That comma shouldn’t be there,” but keeps reading anyway… they’ve already engaged emotionally.

The content…now has a hook.

Ironically, the people who feel a brief twinge…and move on…often remember the message better than people who glide through perfectly polished prose.

Why ALL CAPS, Ellipses, and Broken Rhythm Work

Written language is a poor substitute for speech.

Speech has:

• Pauses

• Emphasis

• Cadence

• Tone shifts

Traditional grammar strips most of that away.

So writers either accept flatness…
Or…they reintroduce rhythm manually.

That’s what I’m doing.

• Ellipses simulate pauses

• ALL CAPS simulate emphasis

• Fragmented…sentences…simulate thought patterns

• Rule-breaking commas…simulate hesitation or pivot

This mirrors spoken cognition…not academic writing.

And the brain processes spoken language more relationally…and more memorably …than formal text.

That’s not opinion.
That’s decades of psycholinguistics.

“But It Distracts Me”

Good.

Let’s talk about that.

If a misplaced comma completely derails your ability to engage with meaning, something else is going on.

Not intelligence.
Not education.

Tolerance.

Tolerance for ambiguity.
Tolerance for imperfection.
Tolerance for signal inside noise.

People who can’t tolerate small deviations often struggle with:

• Complex systems

• Emotional nuance

• Competing truths

• Real-world uncertainty

They need rigid structure to feel safe.

That doesn’t make them “bad people.”

But…it does mean this newsletter…will feel uncomfortable to them.

And that’s okay.

Audiences self-select.

This Is Not Sloppiness-It’s Patterned Behavior

Here’s another thing that matters:

This is not random.

At one point in my life…this was conscious.
I thought about every pause.
Every emphasis.
Every disruption.

That stopped a long time ago.

Now…it’s just how I communicate.

Because once a pattern aligns with how brains actually work…including my own…it becomes automatic.

Just like good speakers don’t think about every inflection…
Good communicators stop thinking about “rules” and start thinking about impact.

Why This Filters the Right Readers In (and the Wrong Ones Out)

Here’s the quiet upside no one talks about:

This style self-screens.

People who can engage with ideas despite minor discomfort tend to be:

• Better thinkers

• Better listeners

• Better at nuance

• Better at long-form reasoning

People who can’t get past punctuation rarely contribute meaningfully to deeper conversation anyway. That’s not condemnation. It’s science.

They don’t add signal.
They add friction.

And over time…they filter themselves out.

That’s not arrogance.

That’s ecology.

The Comment That Got This All Started

Let’s come back to that comment:

“Get rid of that comma on your headline! Great writing though and I’m a fan.”

That’s not a complaint.

That’s a signal of cognitive flexibility.

She noticed the deviation.
She felt it.
And…she stayed.

That’s the reader I write for.

The Real Point

This newsletter is not about being “right.”
It’s about being oriented.

In a world flooded with noise…fear…outrage…and manipulation, the ability to stay focused on meaning…despite minor discomfort…is a superpower.

If you’re here…
If you can read past a comma…
If you can feel a little irritation…and keep thinking anyway…

You’re already doing the work.

And I’ll keep breaking the rules…
Not because I don’t respect language…
But because I respect how your brain actually works.

#HoldFast

Back soon,

-Jack
Jack Hopkins

P.S.

If punctuation violations drive you up the wall…this probably won’t ever feel comfortable…and that’s okay. But…if you can tolerate a little friction…in service of clarity…insight…and long-term understanding…you’re exactly where you’re supposed to be.

Resources & Research (Why This Works)

The ideas in this piece aren’t stylistic preferences. They’re grounded in decades of cognitive psychology, neuroscience, and psycholinguistics.

Here’s a non-exhaustive map of the science underneath the claims.

1. The Brain as a Prediction Machine

The human brain is fundamentally predictive, not receptive. It is constantly forecasting what comes next and conserving energy when patterns are familiar.

• Friston, K. (2010). The free-energy principle: a unified brain theory?
  Shows how the brain minimizes surprise and disengages from overly predictable input.

• Clark, A. (2013). Whatever next? Predictive brains, situated agents, and the future of cognitive science.

Implication: perfectly smooth…expected prose often gets skimmed because it generates no prediction error.

2. Desirable Difficulty and Memory Encoding

Information that requires slightly more effort to process is retained better than information that is effortless.

• Bjork, R. A. (1994). Memory and metamemory considerations in the training of human beings.

• Bjork, E. L., & Bjork, R. A. (2011). Making things hard on yourself, but in a good way.

Implication: small disruptions (like unconventional punctuation or rhythm) increase attention and long-term recall.

3. Disfluency Can Improve Learning

Material that is not perfectly fluent can trigger deeper processing.

• Alter, A. L., Oppenheimer, D. M., Epley, N., & Eyre, R. N. (2007). Overcoming intuition: metacognitive difficulty activates analytic reasoning.

• Diemand-Yauman, C., Oppenheimer, D. M., & Vaughan, E. B. (2011). Fortune favors the bold (and the italicized).

Implication: minor friction forces engagement instead of passive consumption.

4. Emotion as a Gatekeeper of Memory

Emotion tags information as “important” for storage. This includes mild irritation, surprise, or curiosity-not just strong feelings.

• McGaugh, J. L. (2004). The amygdala modulates the consolidation of memories of emotionally arousing experiences.

• Dolcos, F., LaBar, K. S., & Cabeza, R. (2004). Interaction between the amygdala and the medial temporal lobe memory system predicts better memory for emotional events.

Implication: even small emotional reactions improve recall.

5. Spoken Language Is Processed Differently Than Formal Text

The brain evolved for speech…not academic prose. Written language that approximates speech patterns is processed more relationally.

• Levelt, W. J. M. (1989). Speaking: From intention to articulation.

• Chafe, W. (1994). Discourse, consciousness, and time.

Implication: rhythm…pauses…fragments…and emphasis cues improve comprehension and retention.

6. Tolerance for Ambiguity and Cognitive Flexibility

The ability to tolerate small inconsistencies is associated with better reasoning in complex environments.

• Furnham, A., & Marks, J. (2013). Tolerance of ambiguity: A review of the recent literature.

• De Dreu, C. K. W., et al. (2008). Cognitive flexibility in complex decision making.

Implication: readers who can stay engaged despite minor discomfort tend to reason better under uncertainty.

7. Attention Is Not Infinite

Attention is a scarce resource. Pattern breaks reallocate it.

• Kahneman, D. (1973). Attention and effort.

• Posner, M. I., & Petersen, S. E. (1990). The attention system of the human brain.

Implication: micro-disruptions function as attentional resets.

Bottom Line

Rule-breaking that is intentional…patterned…and meaning-directed…aligns more closely with how the brain actually encodes…retrieves…and applies information- especially under stress.

This isn’t sloppiness.
It’s applied cognitive science.

I’m glad you’re here. Truly.