The Threat of Failure by a Single Errant Keystroke

Back when I went to journalism school (from 2005-2009), we had a rule that students would literally fail an assignment if they submitted an article with even a single typo.

Students and teachers alike affectionally referred to this as a "Medill F" - named as an homage to Joseph Medill himself, the namesake of the Northwestern University journalism school.

A subtle reminder of disappointing a man who would surely be turning over in his grave, were he to learn that you published the word "website" when the 2005 AP Style Guide clearly indicated it should be written an "Web site."

While I'm sure this rule was initially intended to push students toward detail-oriented writing, it had an inverse set of perverse consequences for me as a writer. Over time, this zero-tolerance threat of failure stuck with me for much of my adult life, making me almost paralyzed from pushing publish until I felt things were really perfect.

The first time I published something in a newspaper with a typo in it (back as a summer intern for my local paper, back in 2007), I punished myself so severely and then cried in my bedroom closet for an hour afterward, vowing it would never happen again.

For the first several years after school, I felt it was my noble duty as a classically trained journalism to uphold the AP Style Guide in every tech company that took me in under its wing. So, when I started on the marketing team at Stack Overflow, back in 2012, I remember fighting over even the most basic of word choices in our web copy.

Here's one example I remember.

The original line read:
Over 18 million developers visit Stack Overflow each month.

Now, technically, you should only use the word "over" in a literal manner (ie: "the cow jumped over the moon"), so AP Style would recommend that you substitute "over" for "more than."

So, I suggested this change:
More than 18 million developers visit Stack Overflow each month.

This wasn't a super popular change.

"We can't use that," I was told. "It's too many words for a single line in a heading."

"But it's the correct way to say it," I insisted.

"It's not as punchy," they said.

But I couldn't let it go. Eventually we agreed upon this passable alternative.

18 million+ developers visit Stack Overflow each month.

Never mind the fact that AP Style also strongly advises against starting a sentence with a number.

(You can start to see why this became a problem in my adult life.)

The Flex of Typos in an AI-Automated World

How times have changed.

Today, I no longer see typos as a vote of "no confidence," but as a signal of my own humanity. Proof of human, if you will.

After all, were I to use AI to write everything for me, the frequency of typos would substantially decrease. But with a few typos or weirdly constructed sentences every now and then, it actually adds a little grit and relatability to the story I'm telling. It's proof that, behind this shiny, AI-enabled veneer, there is still an actual person on the other side of it all.

The thing about rules is that they are helpful up until a point. But ultimately it's equally important to know when to break them. I didn't feel like I learned the latter part in school. I learned it while working on the job. But of course, anyone who works in a highly dynamic and creative field knows that you will never win by simply doing things "the right way" 100% of the time. In fact, that's almost a sure way to bog you down in processes and rigidity that will not enable you to adapt quickly.

The way we get work done is changing faster than ever before. And the way we learn needs to catch up. Part of that involves incorporating agile thinking into the day-to-day mindset of everyone. And maybe part of that means seeing what happens when things don't fit squarely into the neat little box.

To be clear, I'm not making the case to abandon all spelling, grammar, and conventions.

I still firmly believe that people need to know how to write and communicate effectively. This may be more crucial now than ever before.

We need to know the rules. But then we also need practice at when to break the rules. And sometimes that means showing your mistakes in public.