Dear Meeting Room,

I’ve always been confident in my writing. Especially emails.
I’m clear, professional, and usually get straight to the point.
So why do I sometimes lie awake at night thinking,
“Should I have written that differently?”

It’s usually after I’ve sent something that felt completely fine when I wrote it…
and then got a weird or angry response.

Maybe it was a question about a project or a customer.
Or a comment on a deliverable.
Or just a normal follow-up that apparently wasn’t read as “normal.”

Suddenly, I’m re-reading every sentence I sent.
Trying to figure out what part hit a nerve.
And if other people were cc’ed, it’s even worse.
Because now I’m not just second-guessing the message — I’m worrying about how others read it too.

It’s happened with leadership.
It’s happened with colleagues.
And in almost every case, the email I sent was misinterpreted.
Completely.

And even though I feel like I didn’t do anything wrong,
I immediately start wondering:
Should I respond?
Should I explain myself?
Should I say nothing?
Should I call them?

I’ve done all of it.

I’ve written back firmly putting the sender in their place

It usually ends in a phone call where things are smoothed out.
Sometimes the person admits they overreacted.
But somehow, I still feel awkward after.

I’ve also written the same kind of email, just more polite and less sharp.

Still clear. Still standing my ground.
That’s led to calls too — where the other person ends up feeling a little embarrassed.
(And I feel a little guilty for making them feel that way… even though I was just being professional.)

And I’ve tried saying nothing.

That’s the hardest one.
Because while I stay silent, I’m still thinking about it.

Recently, a colleague asked for help writing an email to her manager.
She had some concerns about how her role was being handled and wanted to push back respectfully.

She showed me the draft.
And while I knew what she meant — because she explained it to me in person — I told her:
“This could be misunderstood. I’d take this in a conversation instead.”

She sent it anyway.
And it turned into a real issue.

I don’t think we need to sugarcoat everything or walk on eggshells.
But email culture is a weird thing.
It’s supposed to make things efficient, but most of the time, it just makes things more tense.

People misread tone.
They read way too much into punctuation, bold text, or who’s copied.

Now, I always ask:
Would this be easier to just say out loud?

Usually, yes.

And I’ve learned to spot the people who don’t do well with emails.
Sometimes it’s the ones who are more senior or protective of their team or area.
Sometimes it’s just people who are easily triggered by written feedback.

At this point, I write fewer “loaded” emails.
If something’s sensitive, I’d rather just call or talk in person.
It’s less stressful for everyone.

And the best part?
No follow-up spiral at 2 a.m.