Tool Friday #2 — Hemingway: The Editor That Forces You to Write Like a Human
Ernest Hemingway wrote 6 words. Made people cry.
“For sale: baby shoes, never worn.”
That’s the standard. Most copy — especially the kind founders send to prospects — doesn’t come close.
A founder asked me last week how to improve his cold emails. He was getting sub-5% reply rates. I didn’t send him a copywriting course. I sent one link: hemingwayapp.com.
Here’s why.
What does Hemingway Editor do?
Hemingway is a free, browser-based writing editor that highlights readability problems — long sentences, passive voice, complex words, adverbs — and shows your text’s grade level so you can write copy that busy people actually read.
Hemingway is a writing editor. Paste your text in. It highlights problems in color:
| Color | Problem | What to do |
|---|---|---|
| Red | Sentence too long and complex | Break it into two |
| Yellow | Sentence hard to read | Simplify |
| Purple | Word with a simpler alternative | Use the simpler word |
| Blue | Adverb | Delete it (almost always) |
| Green | Passive voice | Flip to active |
The main metric it shows you: readability grade level. The rule I use is Grade 9 or below. If it’s higher, I rewrite. That’s not dumbing down — that’s respecting the person who has 40 unread emails and 3 seconds to decide if yours is worth their time.
No login. No account. No paywall. Just paste and edit.
My workflow: cold emails
This is where Hemingway earns its keep.
Cold emails fail for two reasons: they’re too long, or they sound like they were written by a LinkedIn bot. Usually both. Hemingway catches both.
Here’s a real before/after from a cold email sequence I was running for a client in SDR recruiting.
Before:
“I wanted to reach out because I came across your profile and thought there might be some potential synergies between what you’re working on and what we do here at…”
Read that out loud. Count the syllables. Nobody talks like that. Nobody reads past it either.
After (post-Hemingway edit):
“Saw your post on hiring SDRs. We help with that. Worth a chat?”
Same intent. One-tenth the words. Three times the reply rate.
The rule: if you wouldn’t say it to someone at a bar, don’t send it in an email. Hemingway makes this test objective.
My actual workflow for cold emails:
- Write the messy first draft — get every thought out, don’t self-edit
- Paste into Hemingway — aim for Grade 8-9, check the colors
- Cut every red sentence in half, delete every blue adverb
- Read it out loud — if it sounds like me, send it
Takes about 4 minutes on top of drafting. The reply rate difference is not marginal.
My workflow: LinkedIn posts and blog editing
Same principle applies to content. The first draft of almost anything I write is too dense. Sentences that could be two become three, paragraphs that should be cut stay in because I feel like cutting them would lose nuance.
Hemingway disagrees. And it’s usually right.
For LinkedIn posts, I target Grade 7-8. The feed is noisy. If someone has to reread your sentence, they don’t — they scroll. Short sentences stop the scroll.
For blog posts (like this one), Grade 9-10 is fine. You have more space, more context, a reader who opted in. But I still run it through to catch the lazy adverbs and passive constructions that sneak in.
Passive voice is the enemy of clear writing. “It was decided that…” by whom? Hemingway flags every instance. Kill them.
What surprised me
I’ve been using this tool for over four years and the thing that still surprises me: how often I think something reads well and Hemingway shows me it doesn’t.
The grade level readout is particularly humbling. You write what feels like a clear, direct paragraph and it comes back Grade 13 — college reading level. That’s not what you want in a cold email going to a sales director who gets 80 of them a day.
The other thing: the adverb killer. “Extremely,” “very,” “really,” “actually” — these words cost you credibility. They’re hedges. Strong writing doesn’t need them.
What are Hemingway Editor’s limitations?
| What Hemingway does | What it doesn’t do |
|---|---|
| Flag overly complex sentences | Tell you if your angle is wrong |
| Kill passive voice and adverbs | Improve weak hooks |
| Show readability grade level | Know your audience or context |
| Make you cut ruthlessly | Replace thinking about strategy |
| Work on any writing, free | Catch factual errors |
It’s a syntax editor, not a strategy tool. If your email is Grade 8 but the offer is bad, Hemingway won’t save you. The thinking still has to be right. This just makes sure the writing doesn’t get in the way of it.
How much does Hemingway Editor cost?
Hemingway Editor is completely free in the browser — no account needed. There’s an optional desktop app at $19.99 one-time for offline use.
Free. Browser-based. No account needed.
There is a paid desktop app ($19.99 one-time) that works offline and has some extra formatting features. I’ve never needed it. The browser version does everything I use it for.
Alternatives
| Tool | Best for | How it compares |
|---|---|---|
| Grammarly | Grammar, tone, plagiarism | Does more — grammar, tone detection, plagiarism check. But it’s a subscription ($12/mo) and it tries to do everything. Hemingway does one thing and does it free. |
| ProWritingAid | Deep style analysis, long-form writing | Best for novelists and long-form writers who want detailed reports on pacing, readability, and style. Overkill for a cold email. |
| LanguageTool | Open source, multilingual | Works in 30+ languages. If you write in anything other than English, this is the better choice. For English-only copy editing, Hemingway is simpler. |
My take: Grammarly catches more errors. Hemingway makes you a better writer. They solve different problems. I use Hemingway for copy that needs to be short and punchy — cold emails, LinkedIn posts, landing pages. If I needed grammar checking on long documents, I’d add Grammarly.
Verdict
Score: 8/10
Minus one because it has no memory (you can’t save drafts in the browser version without the paid app). Minus one because it can be a blunt instrument — sometimes a long sentence is intentional and Hemingway flags it anyway.
But for what it costs (nothing) and what it delivers (cleaner copy in under 5 minutes), the ROI is absurd.
Every founder who has sent me an email that starts with “I hope this finds you well” should have this bookmarked.
Tool Friday is a weekly series where I review one tool I actually use in my workflow. Just tools that made my work better.