I’ve had a few questions from fellow writers about self-publishing, so I’ll be doing a series of posts on this. Obviously, it makes sense to begin at the beginning, but in this case I’m starting near the end as Smashwords is asking for a series of blog posts on formatting tips, and this is one I want to share before anyone else tears their hair out trying to figure it out. (I’ll do an index of the self-publishing posts when there are more of them, so that you can read them in order)

OK, so jumping in at the end: You’re formatting you’re manuscript to publish via Smashwords. Smashwords takes a Word doc (note: the old .doc file type, not the newer .docx), and then runs it through its ‘meatgrinder’ conversion process (their term, not mine!) to produce e-book files in several formats.

Smashwords has a Style Guide to help you through this process, but there are a few things missing from the guide. Do read the whole style guide, though — even though it’s long — because all this information is important. To follow the guide, you do really have to know your MS Word. If you don’t know what Styles are, you may want to get a Word-savvy friend to help you.

Rather than me trying to cover off things that are already in the style guide, I’m going to focus on one tiny formatting issue… that can cause gigantic headaches, and that’s em-dashes and em-dashes. (I’ll do a post on the larger issue of special characters later, but that gets quite techy. Basically, some e-book files allow for special characters and others don’t, so you have to be careful which ones you use.)

First up, a quick refresher: what is the difference between hyphens, en-dashes, and em-dashes?
Hyphens join two or more words to make a compound word: top-heavy, well-heeled, not-for-profit.
En-dashes are the width of the letter ‘n’ (hence the name) and represent the word ‘to’: 1997–1999; May–December; the Paris–London train; ages 12–18.
Em-dashes separate a phrase or clause from the rest of the sentence (there are other uses too, but I won’t go into a long grammar lesson here). Example: “Do read the whole style guide — even though it’s long — because all this information is important.”

Do not rely on Word to insert the correct type of dash! If you type hyphens or double-hyphens and watch Word ‘convert’ them to en-dashes and em-dashes… it gets it right about 50% of the time. Not very good odds! So you need to insert them yourself. How do you do this? Go to Insert-Symbol and scroll down (graphic below) to find the en-dash and em-dash. (The good news is that once you’ve used each, they’ll appear in your recently used list). You can also use the shortcut keys Ctrl + Num + minus for the en-dash, and Alt+ Ctrl + Num + minus for the em-dash (which I think is the longest ‘shortcut key’ I’ve ever seen… so I just use the Recently Used dropdown).

Now here’s the important part for e-books: if you’re choosing from the Insert-Symbol window (above), you have to be doubly sure you’re inserting the right type of dash and not another type that looks the same. Confusing? Let me explain…

In the graphic above (click to enlarge), the character I have highlighted is the en-dash. Near the bottom (where I’ve highlighted), it tells you it’s an en-dash. If you have the correct dash selected… click Insert.

Now, you’ll see that to the right of the en-dash is another dash that looks exactly the same. If you click on it, you’ll see in the descriptor text that it’s called a figure dash. Do not use this one! Why? Because most e-readers won’t read this character, and will instead display it as a question mark. So while your Word file will look correct to you… you’ll end up with question marks where you thought you had en-dashes. So instead of “the 2000–2002 period saw a boom in the dot-com industry”, you’ll see “the 2000?2002 period”

Same for em-dashes… if you click on the em-dash, the text at the bottom will confirm that this is what you have selected. But to make life complicated… next to the em-dash is an identical-looking dash called a horizontal bar. Do not use this, for the same reason: some e-readers will display it as a question mark. Which means that instead of “Do read the whole style guide — even though it’s long — because all this information…” your e-book will say “Do read the whole style guide ? even though it’s long ? because all this information is important.”

So what is the simplest way to deal with this? If you’ve been using the shortcut keys all along, you should be safe. But if you haven’t, I suggest going through your manuscript and replacing all your dashes. This may sound a lot of time and effort for such a small issue, but I assure you it will save time (and headaches) in the long run!

Insert one em-dash into your manuscript, copy it, then go through and paste it in place of any potentially incorrect em-dashes you may have (and remember, just because it looks like an em-dash doesn’t mean it is an em-dash). Ditto for your en-dashes. And this is a good time to check that you have been employing the correct type of dash. If you didn’t know the grammatical rules for dashes, then you probably have a lot of stray hyphens in your manuscript!

Well, there’s a long post on a short issue… but I hope it saves you from encountering a whole slew of ‘surprise’ question marks in your e-book, and teaches you how to fix them. On that note, remember to proofread ALL versions of your e-book after conversion. Just because the .mobi file looks fine does not mean that the .epub file will (I only encountered this issue in the .epub files, not the .mobi files).

And feel free to post any questions on this topic if you have them!

Addendum: Find/Replace

I had a question about how to use Find-Replace to fix those pesky dashes, so here’s the answer:

If you suspect you have some rogue figure dashes and/or horizontal bars, then yes, you can use Word’s Find-Replace function to replace them with em- and en-dashes. The tricky part is that , the shortcut keys won’t create dashes when you’re in the Find/Replace window (at least they don’t with my keyboard; if they do with yours, then you have a quicker way of doing this). So what I recommend doing is typing the following text at the beginning of your document:

…using the Insert-Symbol function to make sure that you have the correct dashes (and adding the words so to make it clear which is which; the last thing you want to do is replace correct ones with incorrect ones!)

Now, we’ll have to do this in two stages, once for en-dashes and once for em-dashes. For the en-dashes, copy the first two words and their dashes. Now open Find-Replace (Ctrl + H) and paste the words into both the Find and the Replace boxes, as follows:

Now, delete the words/symbols you don’t need so that you’re replacing figure dashes with en-dashes, as such:

…and now hit ‘Replace All’.

Repeat the same process for the em-dashes, and you are done!

Now, I still do recommend doing a manual check to make sure you don’t have en-dashes where you should have em-dashes and vice versa, because the Find/Replace won’t take care of this issue (and remember, Word does a very poor job of choosing the correct type of dash if you’ve been letting it autocorrect your hyphens as you type.) Also, you’d be surprised how many proofreaders don’t know the difference between and em- and en-dash, so you can’t, unfortunately, always rely on proofreaders to catch any misuses.

Well, that’s a lot for one little issue… but as I mentioned before, it should save you mystery-solving and headaches in the future. Good luck!