2011-06-25

Publishing a Word Doc for Smashwords

This is a follow-up to the previous post, which covered formatting a book for Amazon’s Kindle Store. It comes with exactly the same caveat, because nothing has changed in the previous week:

I actually don’t know anything.

This article covers one specific topic — creating a good-looking epub or mobi ebook for Smashwords directly from a Microsoft Word document. I’m not an expert in e-book formats and coding. I’m not teh hardcorez with XHTML or the specific container-based formatting that all e-books comprise. As a one-time technical guy, i have a passing familiarity with all this crap, but i don’t have the time or the inclination to become an expert. However, experts exist, and if you want the advantage of expert advice, that’s where you should be looking. In particular, if the book you’re trying to format is something other than a straight-up chapter-by-chapter text work with no-to-minimal inline graphics, you probably want to avail yourself of a professional e-book formatting service.

Everything in this tutorial is based on my own experience and a certain amount of trial and error. If your own experience or information from another source contradicts or further illuminates what’s discussed here, just drop me a line.

Actually, another caveat — This process uses the venerable Word 2004 for the Mac (the last workable version of that application). However, following along in newer versions of Word and/or in Windows shouldn’t be overly difficult. (If anyone wants to rework this tutorial to incorporate updates/changes for other versions of Word, likewise drop me a line.)

And a third caveat — As mentioned above, these guidelines are specifically for producing mobi and epub files, the two most popular e-book formats. Two other e-book formats that Smashwords will produce are for Sony Reader and Palm, neither of which i have the ability to test. If anyone uses these guidelines and notes their success or failure at producing a good-looking Sony or Palm e-book, drop me yet another line.

Having said all that…

Smashwords creates ebooks in a variety of formats, including the industry-standard epub, the Mobipocket format made effectively dominant by its use by Amazon, and the venerable PDF. The flexibility to create numerous ebooks from a single file is a tremendous boon to anyone wishing to see their work in as many electronic hands as possible. However, it comes at the cost of conversion software (cheerfully dubbed Meatgrinder by the Smashwords folks) that needs things plain and simple.

Making things more complicated is the fact that although epub, mobi, and most other ebook formats have the same basic setup — they flow text in a reworkable, reshapable format in sections (which will translate to chapters for most books), PDFs are a fixed-page format that more closely resembles an actual book. Trying to come up with a single Word document that can make beautiful e-books in all formats is thus a challenge. And on top of that, the otherwise excellent Smashwords Style Guide actually has some advice that i personally find unforgivable (including using a combination of blank lines and asterisks to mark your chapter breaks because you supposedly can’t count on being able to summon up an e-book page break when you need one).

This tutorial is not meant to replace the Smashwords Style Guide, which you must read. (Like, right now. I’ll wait for you.) It merely focuses and shortcuts a couple of things, while also making a few recommendations that aren’t in the style guide (and, in one case, a recommendation actually forbidden by the style guide), but which in my experience produce good-looking ebooks.

The following steps are involved but not overly complicated. Barring unforeseen complications, they should help you produce a good-looking ebook with a minimal amount of fuss and bother.

Getting Started

Your Word file should be formatted in the traditionally straightforward manner that I hope most people employ for their long-form prose writing — a minimal number of well-named paragraph styles, and chapters divided into sections.

Avoid drop caps. They don’t work in e-books. In each paragraph with a drop cap, remove it with Format > Drop Cap, and select None. To give your chapter starts a little bit of non-drop cap pizzazz, considering making the first few words of the first line all caps (but see the note below).

Don’t use tabs to indent your paragraphs. I’ll repeat that, because it’s important — don’t use tabs to indent your paragraphs. If you normally do so, you’ll want to search for and delete all tab characters, then reformat your body copy style with a first-line indent.

Avoid anchored pictures and text boxes, as these will get lost in the e-book conversion process. An ebook in any format is very much like a traditional HTML web page — pictures must be run inline with the text, so that if you make the text bigger or smaller, the picture moves with the text it’s a part of.

Avoid Word’s table of contents feature (or if you use it for your main document, be prepared to replace it with a manual TOC for your Smashwords document).

Create Your Smashwords-Conversion Word Document

Make a copy of your book, appending the file name with “Smashwords Version” or some such. If your book has drop caps or non-inline images that you absolutely can’t live without in the “real version”, convert them now for this version.

Your images should be imported with Insert > Picture > From File. Don’t place pictures in your Word doc using cut and paste from another application. Select the Link to File option in the dialog box before you insert your picture.

Copyright Page

In the course of converting your document to a Smashwords conversion document, don’t forget Smashwords’ specific requirements for the copyright page. See the Smashwords Style Guide.

Lose Any Template Attachments

Check to see what template your document is based on through Tools > Templates and Add-Ins. Make sure that “Automatically update document styles” is off. You’ll likely be changing the size of your styled text momentarily, and you don’t want it changing back the next time you open the document.

Check For Hidden Text

If you have hidden text in your document, the Smashwords converter will cheerfully un-hide it and run it in your e-book. (This is particularly annoying if you’ve hidden embarrassing notes to yourself. Not that i’d know anything about that.) Use Show All to reveal formatting characters, then use Find to search for hidden text (pull up the Format > Font dialog from within the Find and Replace window) and eliminate it.

Set Up Your Document in Sections

Hopefully you do this already and you’re only checking to confirm that the sections are set up properly. Use the “new page” option to separate your sections and start each one on its own page. This will create proper page breaks before each chapter in both epub and mobi format, no other formatting or special styles needed. (This directly contradicts the Smashwords Style Guide, which talks about section breaks creating unnecessary blank space in an ebook, and the need to use a Heading style. The former might refer to continuous section breaks, but i work only with new-page section breaks. The latter does work, as i’ve tested it, but the conversion likewise works fine without it.)

This is what the beginning of A Prayer for Dead Kings looks like, as an example.


Italic and Bold Are Fine

The conversion process recognizes and translates regular italic and bold text no problem. One thing to note is that Meatgrinder formatting puts the larger chapter headers in bold even if you don’t style them that way.

All Caps Needs Manual Conversion

Word’s All Caps style, on the other hand, is lost during the conversion process. As a result, any text in All Caps style needs to be either retyped with Caps Lock on, or hard-restyled through Format > Change Case.

Embrace the Normal

I avoid Word’s “Normal” style like the plague, and so should you. Except that the Smashwords Meatgrinder specifically and exclusively likes to work only with the Normal style. Oh, irony.

I’ve done some tests with simple styles under other names (Body, Chapter Title, et al), and the results have been both frightening and inconsistent (the same-style font showing up in an ebook at different sizes in different places). For better or worse, or until the Meatgrinder gets its stuff together, you want to stick with Normal in your Smashwords document.

I’ve played around a bit with trying to find the easiest way to use Normal in a way that makes Smashwords happy, and the following process seems to work best.

  1. Set up the Normal style in your document as Times or Times New Roman, 10 point, with a first-line indent of 0.3 inches. Though you don’t set the font size for an e-book (because the reader gets to change the font size to suit himself or herself), selecting 10 point to start establishes the baseline size that the Smashwords conversion will use. (Note that this sort-of tutorial isn’t a short course on how to use Word styles. If you’re not comfortable with doing so, you should consider looking for a good online reference and spending some time with that before creating your e-book.)
  2. Select All to highlight the entire document.
  3. Select “Normal” from the style menu or Format > Style and apply. This should turn all of your text into 10 point Times/New Roman
  4. With all the text still selected, manually make the font Times or Times New Roman (whatever you selected for the Normal style) and 10 point. This step is technically redundant because you’ve already restyled the text. However, it cleans up text that might have been previously manually resized, which often keeps its resizing even after a new style is applied.

Set Up Manual Text Formatting

Once your document is entirely Normalized, you want to go back and manually recreate whatever styles you’ve lost (typically first lines, chapter headers, titles, and so on). Because most of this text is at your chapter starts, you’ll likely just need to move from section to section and repeat a short process of manual formatting.

(If you have interior heads or text that’s larger for effect sprinkled throughout the book, you’ll need to spend more time working through the document to find it. In that case, it’s often easier when you first make your copy of the document to search for larger text and make it a particular color or highlight to make it easier to find after it’s been turned to 10 point Times.)

For text where you want no indent (including any text that’s going to be centered), highlight the text, then Format > Paragraph and look for the Special drop-down. Change it from “First Line” to “None”. (You can also adjust the first-line indent on the ruler.)

For text that you want centered, highlight the text and select the centered format from the Formatting toolbar or Format > Paragraph. (Make sure centered text has no first-line indent, or it will look off-center.)

For chapter titles and other heads, select the text, center it (as above), then change the size from the Formatting toolbar, with Format > Font, or with the appropriate keyboard shortcut. For sizing heads, i use the following guidelines:

  • Chapter Number — 12 point.
  • Chapter Name — 14 point.
  • Title — 18 point.

However, as with body text and the Normal style, this won’t be the actual size in your e-book — just a guideline for the conversion process.

Set Up Chapter Heads

Each chapter head will consist of one or two lines (depending on whether your chapters are named or simply numbered). However, you want to add another three to four blank lines above the chapter head, both to push the head down a bit and to provide a place to anchor your chapter bookmark (see below).

Using Show All, it should look like this.


Setting Up the Table of Contents

Word’s automatic table of contents generator is a tool of the devil. (It’s true; you can see comments from Beelzebub in the original Word source code.) I have read that it can be used to generate a table of contents that a Smashwords conversion will love, but setting up your contents page manually takes about five minutes and is almost certain to give you less grief in the long term.

Make a new section at the very top of your document. The table of contents must run before your title page, or the Meatgrinder’s Kindle conversion might get cranky.

Type out your table of contents manually. You can copy-paste-and-restyle your chapter names, but don’t use Word’s Insert > Index and Tables command to create the table of contents. Just don’t.

Even if you spell out your chapter numbers in the chapter head (“Chapter One”), use numerals in the table of contents (“Chapter 1”) — they’re easier to read and mentally organize.

There are any number of ways to set up a table of contents, but centered text under some sort of header (either the title of the book or “Contents”) usually looks best.


I like to add the fiddly bits (copyright, title page, et al) to the table of contents in an e-book even though one would normally never do so in a real book. This is because e-books are much harder to “flip through”, and it’s easy for a reader to miss your dedication and front material if they go the table of contents and simply select “Chapter 1”.

Set Up Bookmarks in Your Document

A bookmark in Word is like an anchor on a web page — it’s a place that a link will eventually point to. To set up a bookmark in your document, place the cursor where you want the bookmark to point to (which is to say, the start of a chapter). However — you want to place your bookmark not at the beginning of the chapter number or chapter name line, but in the very first blank line above the chapter number and chapter name.


If the bookmark actually points to the chapter text, going to the chapter using your e-book reader’s TOC function can mess with the formatting of the chapter header text. (This is owing to a difference in the internal placement of the bookmark tag between Word and the e-book XHTML, but you don’t need to worry about that as long as the bookmark points to the blank line.)

Once the cursor is placed, go to Insert > Bookmark.


The very first time you open the Bookmark dialogue box, make sure that the “Hidden bookmarks” option is checked. This is because Word loves to throw in secret bookmarks (like the one above) that will play havoc with your conversion. Select and delete all hidden bookmarks.

Type in the name of your bookmark in the field at the top of the dialogue box. Word allows no spaces or punctuation in the bookmark name, so go with simple names like “Chapter01”, “Chapter02”, and so on. (Having the leading zero makes the chapter names alphabetize properly if you have more than nine chapters.)

Click on “Add” to add your bookmark.

You can test your bookmarks at any time by going Insert > Bookmark, selecting the bookmark from the list, and clicking “Go To”. When you do, Word should place the cursor exactly where you placed the bookmark. If not, delete the bookmark and try again.

Add bookmarks for all the places in your book that you’ve listed in the table of contents. However, don’t make a bookmark for the table of contents itself (see below). When you’re done bookmarking all the places in the text that appear in your table of contents, you want to add two special bookmarks that the Kindle version of your ebook will make use of.

Place the cursor at the top of your table of contents and create a new bookmark named “toc” (lower case). This is the bookmark the Kindle uses when you select “Table of Contents” from the navigation controls.

Place the cursor at the top of your title page and create a new bookmark named “start” (lower case). (Don’t worry if you’ve already placed a bookmark for your title page. They’ll play nicely with each other.) This is the bookmark the Kindle uses when you select “Beginning” from the navigation controls. (You can place this “start” bookmark wherever you think the start of the book is. Some people like to make this Chapter One, but i like to make sure the reader gets to see the title page, the dedication, and the epigraph.)

Use Bookmarks to Create a Clickable Table of Contents

Now you want to link each of the entries in your table of contents to the bookmarks you previously set up.

For each entry in the table of contents, highlight the text, then Insert > Hyperlink. In the Edit Hyperlink dialogue, select “Locate” next to the Anchor field.

In the second box that pops up, click on the Bookmarks triangle to reveal the list of bookmarks in the document, select the bookmark you want to link to, then click OK.


You can test your hyperlinks by clicking on them. When you do, Word should place the cursor exactly where you placed the bookmark you selected for the hyperlink. If it doesn’t, check the bookmark manually with Insert > Bookmark and selecting “Go To”. If the bookmark is wrong, delete it and try again (see above). If the bookmark is correct, select the hyperlinked text and make sure you haven’t accidentally linked the text to the wrong bookmark.

(The same process of bookmarks and hyperlinks lets you set up links from anywhere in your document to anywhere else. For example, you could create footnotes and cross-references.)

Whither PDF?

As mentioned above, a PDF differs from other e-book files because it locks down things like text flow and type size even as epub and mobi ignore those things. Smashwords offers the option of creating a PDF version of your book along with its other e-book formats, and it can be a good idea to do so. Virtually every computer in the world can handle PDF files, even as trying to read certain e-book formats on computer can still be a total pain in the ass. (As of this writing, the Kindle App for Mac does a great job with mobi files, but there is not a single Mac e-reader that can handle epub without sucking badly.)

The importance of this step depends on how important it is for the PDF version of your e-book to look good. If you don’t want to produce a PDF, or if you don’t care that it looks like crap, your e-book formatting is done and you can skip this section.

When you convert your Word file to epub and mobi format, it ignores everything about your file except the text and the section breaks. An epub or mobi file has no page size — the text simply flows in accordance to how large or small the user makes that text. A Smashwords PDF, on the other hand, is created using the page size, the margins, and the other physical attributes of your Word file. As a result, your page setup has implications for how the PDF looks and how readable it is.

If you do your writing in a default letter-sized document (you shouldn’t, but that’s a subject for another post), that’s how your PDF will look — and to my mind, a letter-sized PDF e-book looks unprofessional. What you want is a PDF that will resemble an actual printed book in size and appearance. To this end, go to File > Page Setup to set up a custom page size mimicking the appearance of a paperback book. The page sizes available to your version of Word often depend on your printer installation, but shoot for something close to 5 inches by 7 inches. In a worst-case scenario, you might need to set up a custom page size. If you’re not sure how to do that, you should think about working through a good Word tutorial before attempting to create your e-book.

With your custom page size established for your document, set your margins with Format > Document.


These settings will give good results, but feel free to tweak them, especially if your headers or footers are more than one line. In the Layout tab, don’t set different odd and even pages unless you really want to (the left-right format of a print book doesn’t translate to a page-by-page PDF). Make sure you set the Apply To drop-down as “Whole Document” so you don’t have different margins in different sections. If you’re not comfortable setting margins and working with headers and footers, considering finding a good Word tutorial before creating your e-book.

With these settings in place, view your document in page layout view (if you aren’t already). The layout you’ve set up should combine with the font size settings you’ve already established to look something like this.


Set up your headers and footers as you like. Most PDF readers keep track of what page you’re on when you’re reading, but adding page numbers is important in case your readers want to print the PDF. Scan through your whole document to make sure you don’t have headers and footers on pages where you don’t want them (for example, the table of contents and the title page). Again, if messing with headers and footers isn’t something you’re comfortable doing, you should think about spending some time with a good Word tutorial first.

Once you’ve scanned through your entire document to make sure everything looks the way you want it, you’re done.

Cover Art

You don’t need to place cover art in your Word document. The Smashwords conversion process uses the cover art you upload to create the cover for the epub and mobi versions of your e-books. However, for reasons unknown, it doesn’t do so for the PDF version of your e-book. If you do add a separate section at the front of the book for your cover, the PDF will have it. However, your mobi and epub e-books will then have the default cover, plus a duplicate cover on the book’s second page.

Upload and Test

With your document properly formatted, you’re ready to upload it through your Smashwords dashboard. Smashwords is usually pretty good about converting your book in short order. If your conversion generates any Meatgrinder errors, consult the Smashwords Style Guide to sort things out. (I’m told that two of the most common conversion errors are running more than four consecutive blank lines in your e-book text, and not following the required formatting for the Smashwords copyright page.)

If your book converts without errors, go to the book’s page to look at the online versions and download the e-book formats you’ve chosen to create. This is a most important last step, so plan on going through your book very carefully, page by page, edition by edition, to check that your formatting looks the way you want it to. Any weirdness, any bad breaks, extra space, text indented when it shouldn’t be, et al, go back to the Word doc, tweak the text, upload, and check again.

One thing worth noting before it drives you mad — Apple’s iBooks for the iPad has an interesting “feature” that forces centered text to run flush left if you turn on Justification in iBooks’ preferences. If you can’t figure out why your carefully centered text isn’t centered in the epub version of your book when you test it in iBooks (especially if it’s centered in another format or on another e-reader), check the setting and embrace iBooks’ limitations until Apple gets it fixed.

And You’re Done

If you’re satisfied that the book looks good, follow the instructions to submit it for Smashwords premium distribution, and you’re good to go. At least until a minute after you submit the book, at which point, you’ll remember that really excellent change you wanted to make. Welcome to the wonderful world of publishing.