Smart quotes aren't that smart

If you're publishing an enewsletter, make sure smart quotes don't get you. Here's how to avoid the ugly results of "smart punctuation" gone bad.

First of all, "smart quotes" are those pretty quotation marks that are automatically substituted for normal quotation marks in Microsoft Word and some other programs. Some people call them curly quotes. Likewise, if you've ever put two dashes together in Word and then hit the space bar, you'll note that it automatically substitutes an em dash...which is a longer dash. Same goes for apostrophes -- those are often substituted as well.

So what's the problem? If any of those characters end up in your newsletter (or if you're advertising, your enewsletter ad), they'll give you yucky results. Quotation marks can turn into question marks, and em dashes might end up looking like this: â€". This happens because the special characters are non-ASCII characters...essentially they're not part of the normal character set that your enewsletter software uses. You'll see an example of a smart apostrophe gone bad in the image within this post...the smart apostrophe became a question mark.

So how do you keep this from happening to you?
1. If you're writing the text from scratch, use a plain text editor instead of Microsoft Word or a program that substitutes smart characters. Windows Notepad is a basic plain text editor. I like EditPad Lite because it has more features but still gives you plain text output.

2. If you're taking someone else's text and incorporating it into a newsletter, simply cutting and pasting it into a plain text editor will not solve the problem. It might appear that the smart characters are gone, but they might not be. A lot of people recommend going into the Word settings and turning off the smart quotes and other substitutions, but I still think this can lead to errors. To ensure bad characters are eliminated, here's the process we use at IndustryWeek:

• Paste the text into Microsoft Word
• Choose Save As... and go to the "Save As Type" dropdown menu below the filename. If you're using Word 2003 or earlier, you should be able to choose "MS-DOS text" from that menu. If you have Word 2007, choose "Plain Text". After you click Save, it'll pop open a dialog box where you choose MS-DOS.
• After you try to save, it should give you one or two warning boxes about how some characters will be lost when you save as text only. That's fine, so hit OK.
• Close Word. Now open the new text file you've created and make sure everything looks right. Sometimes, depending on the smart character and how you composed the message, you'll still find stray question marks in your plain text file. Look for them before you paste into your enewsletter sending interface.

Finally, test it! Before you send the final email to your full list, do a test deployment to yourself (and preferably someone else at your company too) and look for these nasty little buggers.

This process can be a pain, but it ensures you don't end up with embarrassing question marks or other strange characters in your newsletter.