Kindling: Converting a Word Doc to a Kindle Book

Occasionally, I have serious thoughts. These times usually pass quickly and are soon forgotten, and they're certainly never posted here on my humor blog.

But in this case, today, the serious thoughts were around the comedy book I just published, so it didn't seem unwarranted to post the thoughts here. More importantly, the thoughts were around the incredibly tedious and frustrating process of converting a book written in Microsoft Word to the format that Kindle accepts. I've gone through this pile o' fun three times now: once for the first book, and now twice for the second book (once when it was first published, and again when I realized I really needed to fix some of numerous, tiny errors in the first edition). I'm getting sick of re-learning all of these steps each time, so I thought I'd write them down this time. And what better place for me to find them again when I do this next time than on my blog?

If anyone else finds their way here in search of the same information, or otherwise finds this a fascinating read worthy of posting on this gripping humor blog, so much the better.

Assumptions

• You wrote a book. I can't help you with this one. I can barely help myself with. So let's just assume that you got this far already. If not, you might want to stop reading right now and go write that book. Come back when you're done.
• You wrote the book in Microsoft Word. This is not a requirement for books, or writing, or anything. In fact, I regret using Word for many reasons, and spent precious hours fighting with it over the course of trying to ready my book for publication (especially the $%*%&?!$!!! non-deterministic Picture placement functionality. How hard can it be, really?) But it's a decent way to do a fair job of formatting something reasonably complex, and many people know how to use it, so it's a reasonably place to start.
  By the way, I used Word 2008 on a Mac for my book. I'm not sure how much of my experience is specific to that version (although I believe the Table of Contents issue described below may be specific to the Mac).
  Note that many of the steps below apply regardless of whether you use Word, but some of the steps were specific to my situation of using Word and some of the corner cases I ran into were because of the specific (creaky) process used to convert from Word into Kindle-friendly HTML. So even if you didn't use Word, maybe the following points can help you ... but you could also just go to the KDP site and start there. For example, this page provides a starting point with various formatting tips for Mac users.
• You feel the need to make the book available on Kindle. It's a fantastic book. The world is dying to read it and it will surely be voted Best Book Ever, except for this one fatal flaw: it's not available on Kindle. Of course, you started writing because you love books: you love the way they feel, you love the turn of the pages, and you love the fact that they stare down at you from your shelves, showing you in glorious color what you've already read and what you will read soon.
  But the rest of the world doesn't share your love of books: they take up too much space, and they just aren't as trendy-cool as content that they can access on their many electronic gadgets.
  So you want to provide them a way to read the book on Kindle.
• You're using the Amazon's Kindle Direct Publishing service. I have no idea if there's a better service. This is the one that CreateSpace sends you to after publishing through them, and it's the one I used. I recommend it because I don't know what else to recommend. And what the heck; it's free (like CreateSpace, they take their cut off of the copies sold, not off of the creation/uploading process).
• You have a half day to kill. You're already so incredibly sick of your book that you'd just as soon burn it as read it, but you fortunately have nothing better to do on a Saturday morning than review it one more time as you walk through the various steps to convert it to Kindle format. This shows not only the strength and fortitude which made you an author, but also the lack of social life which also makes you a good author.

Caveats

This is not a comprehensive soup-to-nuts description of what to do to post the book to Kindle. For that, please refer to the Kindle Direct Publishing site (or whatever other service you want to use for this). In fact, the KDP site covers some of the items below, and in much more detail; I've honed my list to the real pain points that I ran into, whether covered there or not.
Instead, this article is about just getting the damn Word doc converted into HTML that looks reasonable on Kindle. Period.

Converting a Word document to a Kindle book

Okay, here goes:

1. Overview: "All" you're doing is converting the Word file (.doc or .docx) to HTML. This is actually easy ... but if you look at the results of the conversion, you'll probably see, as I did, that many things get messed up in this conversion. The steps below are meant to take care of these issues so that the resulting book looks good on Kindle.
2. Start from the final version of the Word doc used to create your hardcopy version. For me, this was the final version of the Word file that I then converted to PDF, which I then uploaded to createspace (my publisher). You'll want to start with this copy because it would be really handy if the versions you're working with don't get out of sync. Also, it's common sense - you want to make sure you get all of those last-minute fixes you applied to your published version before you start on the electronic one.
   By the way, in the process of converting to Kindle format, you may want to make changes that should be applied to the original version - go ahead and do this to avoid the versions getting out of sync. For example, you may have a future edition, and you want to make sure that all of those fixes you made to get the Kindle version working don't get clobbered by starting from an older version of the hardcopy version.
3. Save As... to a new version of the document, like MyFantasticBook-KDP.doc. You're going to do things to your book that will be specific to the electronic version. These will be horrible, terrible things, things you wouldn't tell your children about, things you wouldn't want your co-workers to know about, and definitely things that you don't want to pollute the original version of the book. For example, you're going to move images around that you worked so hard on to get Word to inline them next to the text in question; you're just going to put them on their own lines, after the referencing text. Don't destroy your artwork of the hardcopy by doing this in the original document.
4. Image Insertion: For some reason, KDP suggests you "Insert" all images instead of copy/pasting them. When I have noticed problems in moving pictures around and getting them to stay where I put them (between the version I see in Word and the version I see in the resulting HTML), I've deleted the picture and done the insert operation (Insert -> Picture -> From File...), and seemed to have better luck with that.
5. Image Placement: Occasionally, I've had inlined images end up (in the resulting HTML and/or Kindle document) in a reasonable place, next to the text where I inlined them. Usually, this is when I placed the image on the left of the text. But more often, I've had the image move around unpredictably between the Word and Kindle versions, moving above the original placement, below it, to the right, and to the left. I've even had it hop a number of chapters and resize itself along the way, like it was a high school kid trying to crash a local frat party. There is something completely f'd up happening with Picture placement in Word, and it's best to just avoid the issues entirely: put each image on a line of its own near the text that references it (I put my images after the text usually, hoping that the reader hasn't yet forgotten what I wrote before they see what I drew).
6. Table of Contents: Word has this great ability to create a custom Table of Contents (TOC) based on styles that you specify and use for section headings, chapters, whatever. It's quirky, but once I figured out how to use it, it was very powerful.
   And then I converted to Kindle.
   I believe there's a facility on the Windows version of Word that allows you to carry this TOC over to the Kindle version. But on the Mac, you have to start over. Completely. Like this:
1. Delete the TOC. (Remember that part where I said you want a new version of the document for Kindle? This is one of the reasons).
2. Go to all of the items in your book that you want in the TOC and create a Bookmark for them (Insert -> Bookmark...). Name them appropriately. Note: I dumbed-down my TOC for the Kindle version and just created headings for the sections. No way was I going to go to the trouble of bookmarking all of my tiny little chapters. Huh-uh.
3. Go to where you want the TOC and create Hyperlinks (Insert -> Hyperlink...) for each of these items (go to the Document tab in the dialog box, select the Anchor field and find the bookmark you want to link. Name it appropriately in the Display field and click the OK button and voilà your TOC entry is there for that item). Keep going until everything you want in the TOC is there. Note that you can format all of these handy hyperlinks however you want (you may want different formatting for chapter headings than, say, the 96-point bold all-caps Chancery font used for the ABOUT THE AUTHOR link, because that's how important you are).
7. Create extra bookmarks for the Start and TOC locations just for Kindle. These are used by the Kindle readers and won't show up in your TOC section. Go to your TOC and insert a bookmark named "TOC" (not with quotes, those were just to call out the word in my text here). Now go to wherever you want the user to pop into the story when they start, or when they navigate to the Beginning of the book. Insert a bookmark named "Start" (no quotes. See above.)
8. Use Page Break. Freaking Word, I swear. In fact, I swear all the time. At Word. One of the reasons is its insistence on using Column Break instead of Page Break when I specifically used the keyboard shortcut that it says is for Page Break. (Note: you can see what kind of breaks you have by going into Outline mode).
   Anyway, use Page Break whenever you want to start at the top of a new page. This may be between sections or chapters or whatever. I found that Section Break and Column Break worked similarly in the hardcopy version of the Word doc, but were completely wrong in the Kindle version. Fortunately, it was easy to use Find/Replace to replace the mistaken Column Break things with Page Breaks. And where I did have a Section Break instead of a Page Break, I deleted it and inserted a Page Break instead (Insert -> Break -> Page Break). I had some issues around Page Breaks inserting an extra line afterwards that was tricky to delete, but some fiddling around will fix that when it occurs.
9. Watch for custom-formatted fonts/characters. I had one single character that I custom-formatted several times in my book to get it to look right. Basically, I wanted a huge W, italic and bold, at the beginning of some of my sections of text. I got it to look right (without too much padding around it) in the hardcopy version by doing a Format -> Font on the character, going to the Character Spacing tab of that dialog, choosing Spacing: Condensed and then specifying 8 pts for it to do the right thing. Looked great. Until I converted to Kindle.
   Kindle displayed this same text by placing that character several characters over to the right, over the following letters in that word. Icky. Totally icky.
   The fix was to simply remove that formatting before converting. This made it look bad in Word itself, but the converted HTML, and resulting Kindle, text looked great.
10. Save as HTML: Now you've done all of this (and probably many more things besides) and you're onto the final step (oh, so you hope). Save as HTML by doing Save -> Save As Web Page....
    This will create a .htm version of your document, along with a folder that is similarly-named which contains all of the images used in the doc. You're almost done, except for a couple more steps...
11. Review: Open up the resulting HTML page in a browser (double-click on the file in Finder) and see how it looks. It won't be paginated, but you can at least see how things like the images and text look. This preview may also show you things like messed-up HTML which I found in my conversion. Just look for anything that looks screwy and deal with it.
    In fact, this step may be useful several times between the steps above - you can always save as HTML and see how things are going, just to check in.
12. Image sizes: I found that converting to HTML converted several of my images from their original, large PNG files to much smaller GIF files. But I also found that it left the originals in the folder with the other images, giving me about 6.5 MB more image bulk in my upload than I really needed (remember: time is money. And so is upload size. The KDP pricing is based partly on download size, so getting rid of huge images can save some of the overhead cost). I simply deleted the images that I knew I didn't need anymore (because there were smaller versions also saved) and everything was fine.
    However: You should always check the resulting HTML to make sure that you haven't deleted an image that it was actually using. Refresh the HTML page in the browser after these changes and make sure you don't have any missing-images problems.
13. Upload to KDP: Now you're almost there (ha!). Compress your htm file and images folder into one single zip file (I did this by selecting both the file and the folder in Finder and compressing them together, which created a file called Archive.zip). Upload this to KDP (use their UI for this - there's a step where they tell you to browse to this file and upload it). This will make available both online and offline preview versions. You really need to preview it. Really.
14. Preview: Preview your resulting Kindle file. Trust me, the HTML-in-browser version does not show all of the problems that can result from the double-conversion step from Word, and you really need to see what your book looks like on actual Kindle devices (or even these emulated offline/online devices that KDP offers).
15. Finalize: Once you're satisfied with your eBook, you're ready to go - follow the rest of the steps in KDP and publish the damn thing.

Now you're ready for the final two steps. These are by far the most critical in the entire process, so pay attention:

1. Sell millions of copies.
2. Use your unbelievable profits to come back here and buy my latest comedy book. Or my other comedy book. In Kindle format, even, because I'd hate to have wasted all of the steps above and that Saturday morning I spent doing this instead of wondering what to do with my Saturday morning if nobody actually buys the Kindle version.

I hope this was useful to you. If not, I have no idea why you've read this far.