I sucked at English in school.

Like, really sucked. I was that kid staring at the blank page, heart racing, hoping—no, praying—that the teacher wouldn’t call on me. The one they’d pull aside after class with that “Maybe stick to numbers?” look.

It wasn’t that I hated English. I just felt dumb. Like I didn’t even belong. So yeah, I ran toward numbers and formulas—safe, predictable, no creativity required.

But somehow, here I am, writing for a living. Probably as shocking to me as to my high school English teacher.

And it’s not because I nailed the perfect five-paragraph essay or memorised the NYT style guide in my sleep. Nope. I was never great at following the rules. Turns out, I didn’t need to be.

What changed? I realized writing isn’t about sticking to every rule you’re handed—it’s about knowing which ones to break. And once I stopped treating writing like a test I was destined to fail and started to break some rules, it got a whole lot more fun.

And let me tell you, so many writing rules are just begging to be broken.

You know the kind I’m talking about: polish every word until it’s so shiny you see your reflection. Curate your bio like you’re applying for the Met Gala. Plan your social posts down to the second for maximum engagement.

It’s exhausting. And there’s no finish line.

Here’s the thing: striving for perfection sucks the life out of your work. You second-guess, you tweak, you obsess—until there’s nothing left but a lifeless, overworked draft. Perfection doesn’t just slow you down—it stops you cold.

I’ve been there. I quit writing this newsletter years ago because I got stuck in that same loop. Every word had to be flawless. And guess what? I ended up not writing anything at all. But the minute I hit “Post” on something raw, the response was unreal. People didn’t just read it–they felt it.

Why does imperfection work? Because it’s real.

Our lizard brains are wired to notice what’s different. When something’s messy, raw, or honest, it stands out. You’ve felt it. When something feels raw, you feel it too.

Think about it. When’s the last time you felt an emotional connection with a perfectly polished brand? (I’ll wait.) Now, think about the last time someone admitted they were struggling, unsure, or learning. Hits different, doesn’t it?

That’s the magic of imperfection. It builds trust. You’re saying, “I’m not perfect, and I’m okay with you knowing that.” People respond to that–it’s freeing. Because let’s be real, we’re all a bit of a mess.

Now I’m not saying you should start intentionally making mistakes or oversharing every awkward detail of your life. But sometimes, the “wrong” word is what makes your writing human. It’s about being real, not careless.

Here’s the truth: Your audience, clients, and colleagues don’t want perfection. They want to trust you. And trust me, they can tell the difference between being honest and just not giving a damn.

So, proofread, sure. Fact-check, of course. Keep things clear and professional. But don’t sand away all the edges that make you, well, you. Those “imperfections” might just be your greatest strength.

I’ve tried a ton of tricks to keep my writing real, but nothing beats starting with the “shadow draft.” And no, I don’t mean your standard-issue “messy first draft” (gags). I’m talking about the version where you say what you really think. The one that’s way too honest to show a client or a boss. The unfiltered, unpolished, brutally honest version.

That’s where the good stuff hides.

Once it’s all out, I pick through it, keeping the pieces that feel true. For example, when I ghostwrote a piece on the science of binge-watching, my shadow draft was this full-on rant about work-life balance and how we use Netflix to dissociate from reality. Was it polished? Fuck no. But some of that truth snuck into the final piece–and guess what? It struck a chord.

And hey, it’s okay to leave some threads hanging. Let your readers in on your process. Share what you’re still figuring out, and invite them into the conversation. I’ve started doing this on LinkedIn–saying things like, “I’m still figuring out what I think about this. What’s your take?” It’s raw, and people respond to it because it feels real. We’re all still learning, right?

So yeah, I sucked at English. And honestly? I still don’t follow the rules. And every time I hit “Post” on something raw, part of me wants to hide under my desk.

But then the responses start rolling in, and I remember why I do this. I remember that’s where the connection happens.

Because honestly? I'm tired of how serious business is all the time. We're not robots (yet), so why do we insist on sounding like them? The whole "embracing imperfection" thing isn't just about writing better newsletters or more engaging social posts. It's about remembering that we're human. It's about connecting, not just marketing.

So, let your guard down. Write something messy. Share an idea that you’re not 100% sure about. Break some rules. Be a human, not a brand.

That’s the kind of writing people feel. And trust me, that’s always worth a little mess.