I've never written an email that was too long and then later realized it should have been way more concise. I generally know my intentions prior to writing the email, so if it needs to be short, I'll write it short. The reverse situation probably happens more often though (i.e I write a short email, realize it doesn't make sense due to lack of details, then I elaborate).
Interesting. I have a different experience than you -- I often find myself writing an email that's way too long and trimming it down later.
For the design of this tool, it was important for me to "not get in the way" if you're already writing a short email. That's why I designed the widget so that it will only appear in your gmail window if you go over 100 words. It can serve solely as a "reminder" for the rare cases you might go over... almost like a training to help you form short email habits over time.
> I've never written an email that was too long and then later realized it should have been way more concise.
I kind of think we'd have to poll the recipients, not the author, for that sort of analysis.
I find myself trimming down lengthy emails frequently. Not because the information is excessive or irrelevant, but because I know most people in most contexts tend to not read or engage with lengthy emails. Myself included.
It has actually backfired on me in the past: because I didn't define and explain the entire space of the matter at hand, I was overcome by other arguments or ideas that I'd already considered and dismissed. That led to followup discussions that didn't need to occur.
It seems that context matters, sometimes long-form is better.
I tend to write longer e-mails - but I agree with you, long-form and short-form e-mails are both optimal for different situations.
The problem seems to be that it's a judgement call - and I'm not exactly sure of all factors/variables that are involved in that judgement call. The subject at hand, the audience, the depth of the e-mail thread to which you're replying, time-sensitivity of the subject, etc. - they all play a role. But my default position tends to be that I'll save time explaining in future e-mails by providing all relevant details at hand now.