But then you’d have raw content with no formatting, which is a slightly inelegant solution for us, because our audience would balk at losing their bullet points and other “not quite crap” formatting.

In this particular user test, the FCK WYSIWYG actually did a decent job of stripping bad stuff, at first glance. But upon closer inspection, we found it left a couple stray SPANS in the file that screwed with our user’s line-height in a couple paragraphs.

Also, there was a completely stray, empty table just sitting in the middle of a paragraph. Since it was an empty table, it was invisible. So it looked like a bunch of dead space in her email content, and every time she hit delete to “move the paragraph up” it wouldn’t budge.

At first, our user thought it was our WYSIWYG’s fault (MailChimp’s fault), but then she remembered that she once had a table in her original Word .doc right in that very spot, and she deleted it (or at least thought she did).

See, the problem gets compounded by user error with the Word file itself.

Perhaps I’m overthinking (I’ve been accused of doing that), but I couldn’t help but ask, “Why does one feel the need to write newsletter content with Microsoft Word in the first place?”

I don’t think typing content into Word is a bad idea. I just feel the need to always ask “why?” in order to get to the bottom of the problem (and come up with new feature ideas).

Why not type content directly into MailChimp? Yes, I do realize our interface doesn’t match MS Word exactly, but it’s extremely close. There are some buttons missing, but those are buttons that do things that you can’t do in HTML email. we specifically kept them out.

Maybe our editor window is too small? Do people need more room to type?

Should we provide a “toggle to full-screen” option (I’ve submitted that to our wishlist, BTW)?

But wait—why do you need that much room to type? This is an email, not a novel we’re writing here.

So I looked at the content our accountant was trying to send. It was basically a super-duper long checklist of “how to prep for 2008 taxes.”

So we’re talking about someone who sends email once a year. Ah, so it’s basically a lot of content that’s built up over time. That’s why she needs to use Word. She’s compiling her content as she works on other stuff. Instead of logging in to MailChimp to put down her thoughts, she puts them into Word.

And the fact that she uses MC once or twice a year makes it difficult for her, because we update our interface fairly often. So we get the “OMG I’m having some serious issues w/MC” calls.

Lots of issues here. That’s what makes design so fun(strating).

Ultimately, we helped her get the email done, and urged her to setup a blog, so that she could simply post her content there as the ideas popped into her brain. Then, she could use MailChimp’s RSS-to-email tool to send emails out every time she updates her blog.

Plus, blogs are easy to update, and would allow her to show off a little of her personality (but not too much). They’re also easy to post links to relevant news, opinions on stuff, ideas, customer showcases, etc.

Another added benefit to emailing her customers a little more frequently (via RSS to email) is her list will be cleaner.

See, when you send once-or-twice-a-year emails, you have massive changes to your subscriber lists. People get laid off, they move, switch ISPs, etc. That leads to spam filtering and blocked IPs, which leads to more support calls for us.

The root of the problem is really setting a nice pace for yourself. Don’t make the newsletter a huge project that takes you several months to send (I have this problem myself, BTW). Sending in smaller chunks avoids soooo many problems.

See, I think too much.

And this is exactly why we built the rss-to-email tool.

Love the RSS to email feature.

I would also urge those same people to be careful when copy-pasting from your website as a lot of times code will be transferred over as well. If you have text in a span the span tag will often copy over and could cause problems.

I always paste either into my source code, or into notepad first like you have suggested.