Perfectionism is killing your writing

Stop writing to impress, and start writing to connect

I once spent days writing what I thought would be my breakthrough Medium post.

The topic was close to my heart: "doing work that sets your soul free." I was trapped in a bank job I hated, desperately wanting meaningful work, and I knew my audience felt the same frustration. Every sentence in that article was deliberate. Every transition was smooth. Every example was carefully chosen…

And the post flopped.

In four years, it’s gotten a total of 350 views.

Later that week, I had another terrible day at the bank. That night, I sat down angry and wrote for an hour about my frustrations. I ranted on the page about building someone else's dream, about companies that preach "happiness" and “wellbeing” while firing your coworkers, about the myth of job security.

I edited the whole thing once, and published it without a second thought.

To date, it’s gotten 25,000+ views.

A magazine editor even reached out wanting to republish it.

The post I cared least about became my biggest hit. Honestly, I didn’t want that post to do well because it was so negative. But after years of writing online, I’ve learned it connected with readers because it had something my "perfect" post didn't—the rough edges that make writing attractive.

Look, I’m all for editing for spelling and readability. But the more time you spend polishing your content, the more likely you are to polish away the very thing that helps readers connect with it. Call it your energy, POV, or whatever you like. But it’s entirely possible to edit the life right out of your writing.

The Problem with Polish

Most writers and entrepreneurs believe imperfect work reflects poorly on them. So we edit and re-edit, smoothing every rough edge until our writing sounds professional, authoritative, and (unfortunately) completely forgettable.

Think about it: what’s the last company-wide email you remember reading? Exactly.

Polishing is literally the act of hiding flaws. And readers can unconsciously sense when you're hiding something. Stephen King says it’s a writer’s job to tell the truth, even when the truth displeases “polite” society.

My viral post worked because it captured three years of pent-up frustration in real time. It was written during The Great Resignation when millions of people were questioning their jobs, and I gave voice to what so many were thinking but couldn't articulate. The raw emotion came through because I hadn't spent days analyzing and sanitizing it.

Meanwhile, my carefully crafted post about meaningful work—despite being more strategic, more beautifully written, and more aligned with my brand—felt manufactured. I had edited out everything that made it feel urgent or personal.

This follows what Aldous Huxley called the Law of Reversed Effort: "The harder one tries to do something with their conscious will, the less likely they are to succeed."

The more I needed that meaningful post to succeed, the more I squeezed the life out of it. I removed the rougher edges of my voice and the spirit of my writing in favor of something that sounded impressive but had no edges for readers to grab onto, nothing to drive comments or interaction.

Impressive doesn't connect. Authenticity does.

I know it sounds cliche, but people aren't drawn to your polished information—they're drawn to your authentic story. They want to see the human behind the advice, the struggle behind the insight, the mess behind the message.

When you over-edit, you think you’re fixing grammar. In reality, you're erasing yourself.

The 80% Rule for Writing That Connects

It’s not easy to put perfectionistic tendencies aside. But I’ve found a few practices that help capture that raw energy without publishing garbage:

1. Write with Energy First, Edit for Clarity Second

When you sit down to write, don't think about your audience or how you'll sound. Think about what you actually want to say. Let yourself rant, ramble, or get excited. Capture the emotion first—you can always clean up the grammar later.

When I’m working on a draft, I have one rule—no judgment. I write quickly, using the first word, first sentence structure, or first illustration that comes to mind. This works because if you allow your creative brain to override your analytical brain (for just a little while) you’ll write without inhibition an capture that raw energy.

If you’re struggling, try this:

• Set a timer for 15 minutes (or 30)

• Write whatever comes to mind without stopping

• Avoid editing or fixing mistakes

This can help you get comfortable with spilling words onto the page without judging them. When you go back and read, notice the good ideas the inevitably found their way from your brain to the page.

The goal isn't perfect sentences. It's preserving the energy that made you want to write in the first place.

2. Identify Your "Squeeze Points"

Pay attention to the moment your excitement about a piece starts turning into anxiety about how it will perform. That's when you start squeezing out the juice that makes it good.

I don’t usually edit more than three rounds, and it’s usually more like two. Any more than that, and I start fiddling with the wrong parts, rewriting sentences, moving paragraphs, and squeezing out all the good stuff.

If you’re writing a post (long-form or short-form) you’re done when you’ve:

• Made your topic obvious (usually in the headline or hook)

• Stated your main point explicitly (a problem your reader is facing)

• Fulfilled your promise (solved the problem)

Ask yourself: Am I editing to make this clearer, or am I editing because I'm scared of how I sound? If it's the latter, step away. You're about to edit out what makes it worth reading.

3. Apply the Reversed Effort Principle

The posts you desperately need to work rarely do. The ones you publish without attachment often surprise you.

I’m not going to tell you that I don’t check my stats or that I don’t care how my writing performs—I do. But I’ve learned that if you’re willing to accept your big wins and learn from your flops you’re a winner either way.

You’ll write best when you don’t need a specific outcome from your writing. If you want to sell a product, do it. But if your post doesn’t bring in any sales, try to make one thing better the next time.

When you catch yourself thinking "This HAS to be perfect" or "This post will change everything," that's your cue to lighten up. Share it because you want to, not because you need it to perform.

4. Preserve Your Rough Edges

Edit for readability, not personality removal. Fix typos and tighten structure, but don't smooth away your natural voice.

I’ve learned that writers get weird about “finding” their voice. Some don’t care, and others meticulously craft documents to explain every nuance and turn of phrase. You can probably guess which type actually connects with their reader.

Here’s my best advice for finding your voice:

• Write regularly (how else you develop your voice)

• Lean into your influences (the things you like give you personality)

• Write in different locations (scenery can change your tone)

If you find yourself thinking "Should I really say this?" about something honest but not inflammatory—that's probably exactly what you should say.

5. Publish at 80%

Share when your content feels almost ready, before you polish away what makes it uniquely yours. If it feels too raw, clean it up slightly. If it feels too polished, you've probably gone too far.

Always pay attention to spelling, basic punctuation, and clarity. If you miss these, you just look like a slob. The internet is an unimaginably big place, and there’s room for your voice.

Remember: people don't engage with perfection—they engage with humanity.

Leave some Juice

You can care so much that you squeeze out all the juice that makes your writing worth savoring. Your rough edges aren't flaws to hide—they're features that make you memorable.

The next time you're tempted to spend another hour perfecting that post, ask yourself: Am I making this better, or am I making it boring?