Write Like Hemingway or Die Trying: The 6-Word Challenge

For sale: baby shoes, never worn.

Six words. Supposedly Hemingway's. Probably not. Definitely genius.

Last month, I decided to master Hemingway's style. Not the drinking part (my liver filed a restraining order). The writing part. The part where you say everything by saying almost nothing.

1000 sentences later, I discovered something horrifying: We've forgotten how to shut up.

The Experiment That Broke My Brain

Here was my insane plan:

1. Take 1000 sentences from business emails, blog posts, and LinkedIn updates
2. Rewrite them Hemingway-style using WriteBetter.ai
3. Find the ones that actually worked
4. Understand why we suck at simplicity

[Visual: A graveyard of deleted adjectives]

The results? 994 failures. 6 survivors. And one existential crisis about modern communication.

The 6 Sentences That Survived

Original #1:

"I wanted to reach out and touch base with you regarding the proposal we discussed in our last meeting to see if you had any thoughts or concerns."

Hemingway Version:

"About the proposal. Thoughts?"

Original #2:

"Our revolutionary AI-powered solution leverages cutting-edge machine learning algorithms to deliver unprecedented results."

Hemingway Version:

"Our AI works. Yours doesn't."

Original #3:

"I'm writing to express my sincere gratitude for the opportunity to interview with your esteemed organization."

Hemingway Version:

"Thank you for the interview. I want the job."

Original #4:

"Unfortunately, due to unforeseen circumstances beyond our control, we'll need to reschedule."

Hemingway Version:

"Can't make it. When works?"

Original #5:

"This quarterly report demonstrates significant growth across multiple key performance indicators."

Hemingway Version:

"We grew. See attached."

Original #6:

"I believe there may have been a misunderstanding regarding the parameters of the project."

Hemingway Version:

"We fucked up. Let's fix it."

Why 994 Sentences Died

They died because Hemingway's style isn't just about being brief. It's about being brave. And most of us are cowards when we write.

We hide behind words like:

• "Synergistic" (means: working together)
• "Utilize" (means: use)
• "At this point in time" (means: now)
• "Circle back" (means: talk later)

Stanford researchers call this "linguistic inflation." I call it fear.

The Iceberg Theory (Or: Why Less Hits Harder)

Hemingway believed in the Iceberg Theory: Show 10%, imply 90%. The power isn't in what you say—it's in what you trust the reader to understand.

Modern business writing? We're serving ice cubes and explaining the molecular structure of water.

Example from my inbox this morning:

"I hope this email finds you well. I'm reaching out because I wanted to follow up on our previous conversation about potentially exploring opportunities for collaboration."

Translation: "Want to work together?"

27 words vs 4. Same message. One respects your time.

The Psychology of Simplicity

MIT neuroscientists discovered something wild: Our brains process simple sentences 34% faster than complex ones. But here's the kicker—we also trust them more.

When you write simply, you signal:

1. Confidence (no hiding behind words)
2. Clarity (you know what you want)
3. Respect (for the reader's time)

When you write like a corporate dictionary had a baby with a thesaurus, you signal:

1. Fear
2. Confusion
3. "Please don't fire me"

Try This Now (Warning: It's Painful)

The 6-Word Email Challenge

Take your last email. Rewrite it in 6 words or less. Can't? You're probably saying nothing with extra steps.

The Adjective Assassination

Delete every adjective. All of them. Now add back only the ones that would make Hemingway nod. (Spoiler: That's maybe one.)

The "So What?" Test

After every sentence, ask "So what?" If you can't answer in 3 words, delete the sentence.

What Hemingway Taught Me About AI

Here's the plot twist: Using AI to write like Hemingway taught me when NOT to use AI.

Hemingway's power came from:

• What he left out
• What he lived through
• What he bled onto the page

AI can mimic the style. It can't mimic the scars.

But—and this is important—it can strip away your corporate camouflage. It can show you what you're really trying to say, buried under all that business bullshit.

The Sentences That Didn't Make It (But Should Have)

Some rejected rewrites that I personally loved:

Email Sign-off:

• Original: "Please don't hesitate to reach out if you have any questions or concerns."
• Hemingway: "Questions? Ask."

Meeting Request:

• Original: "I was wondering if you might have availability for a quick sync."
• Hemingway: "Coffee tomorrow?"

Project Update:

• Original: "The project is progressing according to the established timeline."
• Hemingway: "On track."

Rejection Letter:

• Original: "After careful consideration, we've decided to move forward with another candidate."
• Hemingway: "We chose someone else. Sorry."

The Real Challenge

Writing like Hemingway isn't about being terse. It's about being true.

Every unnecessary word is a lie. Every inflated phrase is fear. Every corporate cliché is a tiny death of meaning.

The real challenge isn't learning to write less. It's learning to mean more.

One More Thing...

Hemingway once said, "Write drunk, edit sober." Terrible advice for your liver, perfect metaphor for using AI.

Let AI help you write drunk—wild, free, without fear. Then edit sober—sharp, clean, true.

The best sentence I wrote during this experiment?

"I tried. I failed. I learned."

Seven words. Everything I needed to say.

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Think you can out-Hemingway me? Send your best 6-word story to alex@writebetter.ai. Winner gets my respect and a WriteBetter.ai subscription. Loser gets my respect anyway.

P.S. This article was 1,047 words. Hemingway just rolled over in his grave. Worth it.