[wdfifteen]

I made the same mistake three years in a row.
I failed to change an LLP to a single member LLC when I bought my partner out. Three years in a row I forgot to make the change, paid my taxes late (LLPs have to file in March, single member LLCs file in April) and had to pay $7xx in penalties each year.

We had a trivia question contest and I made the mistake of saying, "Anyone who answers this question gets a free subscription" when I meant to say, "The first one to correctly answer this question...." I had to give away about $2400 worth of magazine subscriptions to the people who responded.

I don't know if I was the one who made this mistake, proofing was supposed to be done by the proof reader, but as the boss it landed on me. We ran a promotion one year and gave a way a free T-shirt with each new subscription. The ad ran in our magazine, and the copy was supposed to say, "Free T-shirt with your new subscription." Some proofreader let the ad run without the "r" in "Shirt."