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My Most Embarrassing Business Mistake — And How I Bounced Back

My Most Mortifying Business Blunder — Yup, I Tanked a $10K Client With a Typo (And Didn’t Just Crawl Into a Hole)

Alright, grab some popcorn: here’s my dirty little secret — I managed to flush a ten-thousand-dollar client down the drain because I couldn’t double-check my spelling. Yep, a typo. Not even an interesting one.

Sounds ridiculous, I know. But that forehead-smacking moment? Kind of the punch in the gut I needed to get smarter at this whole “running a business” thing.

Let’s rewind.

The Glow Up (Or So I Thought)
When I quit my soul-sucking 9–5, I practically danced out the door. Freelancing felt like I’d just hacked the matrix. I started landing projects left and right, cash was showing up, and every paid invoice felt like Ludwig van Beethoven was playing in my head. Thrilling, honestly.

Then — cue dramatic music — they came knocking.

Not just any client. A name-brand, see-them-on-billboards kind of company. They slid into my DMs after reading a blog post I wrote (which I thought nobody read, but apparently, miracles happen). A couple of video calls later, I find myself agreeing to a $10K content strategy gig. Three months, huge name, mama-I-made-it type stuff.

Except, obviously… I didn’t.

The Facepalm of All Facepalms
First project for them. Not just an email — a full-blown, twenty-page rundown: SEO strategy, personas, content calendar, the works. I stayed up till sunrise tweaking it until every bullet point looked perfect.

Except, uh, guess what? I spelled their company name wrong. Not just once — like, everywhere. Cover page, inside pages, probably would’ve been on my tombstone had I died of embarrassment then and there.

Why? I grabbed an old template and forgot to swap in the real name. You know, rookie mistake? Only $10K was riding on it. I emailed it off in a caffeine-fueled haze, closed my laptop, and strutted off like a boss.

The Crash Landing
Their reply hit fast. “Hey, thanks for the effort, but our company name isn’t spelled that way. It’s misspelled several times.”

My insides just melted. I opened the doc. Five. Freaking. Times.

I panicked, sent a sorry-not-sorry email, promised a fix ASAP. Too late, of course. No response, just silence. A week later: “We’re moving in a different direction.” That’s corporate-speak for “you blew it, champ.”

The Humiliation Hangover
Did I share this on Twitter? Hell no. I basically turned invisible for a week, avoided LinkedIn like it was a haunted house, and binge-ate snacks like I was prepping for hibernation. It wasn’t just losing a client — it was losing my own confidence. You ever start spiraling? “Maybe I should just go back to my old desk job. They had free coffee.”

Yeah, I was there. Not my finest hour.

Turning the Ship (AKA, Coming Clean)
Eventually, sitting in shame got old. So I decided, fine, let’s just own this mess. I wrote a brutal LinkedIn post about it: “Lost $10K Because of a Typo — Here’s What I Learned.” Expected to get roasted, but people? They loved it. Turns out everybody’s got a story. Some folks even topped mine (honestly, thank God).

That’s when it hit me: perfection’s a myth. Owning your screw-ups? That’s power.

How I Bounced Back (And Stopped Crying Over Spilled Coffee)
Alright, here’s how I got my act together:

1. The Godsend of a Pre-Delivery Checklist
I built a simple, non-negotiable checklist before sending anything to anyone. It’s painfully obvious: check client’s name, scan formatting, click every link, read the dang thing out loud. Five minutes that now saves me thousands (and my dignity).

2. Hired a Proofreader (Yep, Even Solo)
Why fly solo when you don’t have to? I picked up a part-time proofreader. Total gamechanger. It’s not pricey, and my nerves thank me every time.

3. Tossed Out Old Templates for Good
No more “just update the old doc.” I built proper project templates on Notion, with actual fields to fill in actual client info. Fancy? Not really. Lifesaver? 100%.

4. Switched Up My Pitch
Instead of chasing every hotshot client, I started working with startups and small biz folks who care about actual collaboration. Honestly, they’re the best — and less pretentious.

5. Got Loud About My Own Flaws
That messy LinkedIn post? It blew up more than my best case study. People connect with real. Vulnerability = credibility, who knew?

Now? I show up as myself, warts and all. Would I prefer to not have lost $10K? Yeah, obviously. But would I go back and erase the lesson? Nah.

Stay scrappy, double-check your work, and don’t let one facepalm keep you from blowing up bigger than you ever thought possible.
 

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