Conversion Journey: My Word-to-E-book Workflow

by Joel Friedlander on April 8, 2011 · 33 comments

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by Chris O’Byrne

Have you been stumped by e-book formatting, frustrated trying to do your own conversions? Chris O’Byrne is a frequent commenter here and has provided some in-depth help for other readers on questions with Adobe InDesign.

One comment in particular caught my attention because Chris spelled out in a systematic way the workflow he used to create e-books. I asked him to write it up for publication, and here it is. Chris’s easy-to-follow steps may be exactly what you need. Enjoy.

My workflow for creating an e-book is much more complicated than it is for a print book. For a print book, I use Adobe InDesign and because the software provides so much control, I’m able to design the book on-screen almost exactly the way it will look printed.

Everything starts with Microsoft Word for two main reasons:

  1. Smashwords requires a Word file (in the older .doc format)
  2. Word produces (so far) the cleanest HTML file.

Chris O'ByrneThere are other tools available, but this is the program I’ve mastered and in which I’ve invested the most time and money.

My work starts with styles. I follow the guidelines suggested by both Smashword’s Style Guide and Joshua Tallent’s book, Kindle Formatting. I often have to start completely from scratch with a text file. Here’s one simple way to do this:

  1. Save the Word document you’re working on as a text file,
  2. Close that file, open it again in Word,
  3. Then select all and assign the Normal style.

There is something about the process of closing the text file and reopening it that prevents Word from assigning any extraneous styles.

Working With Word Styles, and a Brief Detour

The styles I use most frequently are:

  • Heading styles for the chapters,
  • The blockquote style for indented text,
  • List styles for various lists.

Some documents require as many as 10 styles, others only 2 styles. I also go through and assign italics and bold where required. These can be assigned character styles, but I’ve found that simply using the italics or bold option works just as well.

The last step is to create the table of contents and assign hyperlinks. I use Word’s option to auto-create a table of contents, but then I copy that into a text editor program, delete the table of contents in Word, and then paste the text-only version back into the Word document. I do this because I don’t want to use Word’s other table of contents features, I just want the list. I then create hyperlinks from each of the table of contents entries to the respective chapters.

My next step seems strange, but I discovered it by reading online forums to solve my problem with Smashwords. For some reason, Smashwords does a lousy job of converting the linkable table of contents when those links are created solely in Word. But if you first import the Word file into Apple’s Pages program (part of the iWork suite) and then export it back as a Word file, that usually takes care of the problem. Strange, but it works.

Pages and e-book conversion

Pages Styles - Click to enlarge

Forking of the Three Streams

From here, my workflow splits into three streams:

  1. One stream is to upload the Word doc into Smashwords and let it do its thing. I don’t use their Kindle (mobi) version yet, but I do use their ePub version, especially for Smashword’s relatively easy process to get your files uploaded to Apple iBookstore and Barnes & Noble—two sites known for being fractious to work with.
  2. The second workflow stream is to use the previously created Pages file to export as an ePub file. I would simply use the ePub file created by Smashwords, but they won’t let you do the conversion without using the phrase “Smashwords edition” in your front matter and most authors don’t want that. Before I export the Pages file as an ePub, I add the cover to the first page and Pages will use that to create your cover.
  3. The third workflow stream is to export the Word file as an HTML file. I open that HTML file in BBEdit and spend the next couple of hours cleaning the code and adding additional code where appropriate. Again, Joshua Tallent’s book, Kindle Formatting, is invaluable here.
BBedit for ebook conversion

Cleaning code in BBEdit - Click to enlarge

Once the HTML file is ready, I open Parallels (I use a MacBook Pro) and run MobiPocket Creator to make the Kindle version. It took me a couple weeks of experimenting to finally figure out MobiPocket Creator’s idiosyncrasies, but now that I have it figured out I get a working Kindle book every time.

Kindle-for-Mac e-book conversion

In the Kindle for Mac App - click to enlarge

There are other tools available and other ways to get to the final product, this happens to be mine. The process is still far too complicated, however, and I’m excited for the day when we have one or two superior tools for creating e-books.

For me, the perfect solution would be a tool that allows us to design the file the way it will look as an e-book and then exports to any format. It would also prevent using features such as text boxes that simply don’t work with the current e-book formats.

For this reason, I don’t see InDesign as being the right tool for the job unless it comes up with an e-book template that limits available features. On the other hand, e-book formats are slowly allowing more features and perhaps the two will meet in the middle some day.

Chris O’Bryne is a former chemical engineer and teacher, and now provides book editing, e-book conversion and other services for e-book publishers at his site, The E-Book Editor (

All Amazon links are affiliate links. Photo by Kodomut

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    { 33 comments… read them below or add one }

    bowerbird April 21, 2011 at 6:10 pm

    i’m about ready to release my free e-book creator-program.

    as soon as 100 people sign up saying they want to see it…


    plain-text files as your input and then button-click simplicity.



    Joel Friedlander April 21, 2011 at 6:21 pm

    Interesting. Congratulations. I’ve put it out on Twitter.


    George Maxwell April 18, 2011 at 1:44 am

    Great article and excellent feedback. My intent is to modify plain text directly with HTML as I am soon to publish to Kindle. I have already practiced with the first 2 chapters on KDP and got a clean format with a cover pic.

    I agree with Kate that Word HTML is heavy so I prefer raw HTML – Atlantis sounds interesting especially as it outputs other formats. For a free HTML editor for PC that I was recommended by another blog, checkout Having some HTML knowledge is helpful. Here is the link to the blog.


    deborah davis April 16, 2011 at 10:34 pm

    Thanks, Chris, for your input. I’m wondering what is the best way to create an ebook? Word and Smashwords?


    deborah davis April 16, 2011 at 1:52 pm

    Does InDesign allow you to export to an epub format that works on Kindle, Nook etc? I’m wondering because I would rather use what I know. Thanks.


    Chris O'Byrne April 16, 2011 at 2:48 pm

    Hi, Deb.

    InDesign does have the ability to export to ePub and the Kindle format. The ePub export option is built in and you can get a free plugin for the Kindle export. I haven’t tried either one because it wouldn’t help with my workflow. But I’d love to hear from others how well it works.


    Joel Friedlander April 16, 2011 at 2:56 pm

    Deborah, you might be interested in Liz Castro’s book that discusses in detail how to use and modify the ePub that InDesign exports. Here’s an article that tells more about the book:

    Liz Castro: EPUB Straight to the Point


    deborah davis April 16, 2011 at 10:35 pm

    Thanks for the link. Looks to be a great resource. Thanks, Joel.


    Tom Evans April 15, 2011 at 12:38 am

    I’ve dabbled with most ways and many of the above but keep coming back to working on the raw (bit basic) HTML in Dreamweaver. I like the control it gives and ability to embed a Table of Contents and forced page breaks using Kindle’s special tags.

    My next project is to create an Enhanced Edition book when I know it will be essential. I also understand you can use limited CSS which I fancy a dabble with too.


    Ken McConnell April 13, 2011 at 11:22 am

    I’ve had good luck opening a .doc in LibreOffice and saving it as an .rtf. Then I just cut and past by chapter into Sigil. Sigil produces clean tags that I then modify with my own CSS into page indents and chapter headings. My book designer uses InDesign and has no trouble importing the text from an .rtf file, complete with italics. I’ve also been known to take the .xhtml files that Sigil makes and just hand code my own ebook.

    If your end result is an ebook, stay away from Smashwords. Do it yourself and you can control the look and feel better. But then that’s coming from a programmer’s perspective. So do whatever you know. But if you hire someone to build an ebook, make sure they do it right and know their CSS. My two cents worth.


    Chris O'Byrne April 13, 2011 at 11:34 am

    I heartily agree about the CSS. If I didn’t have my web design background, it would’ve taken me a lot longer to figure this all out.

    I’m not completely satisfied with the resulting e-books from Smashwords, but I use them because of their marketing prowess and the ease of getting the books into Apple, B&N, Kobo, and Diesel all at once. And soon, they’ll also have a direct connection to Amazon.


    Ken McConnell April 13, 2011 at 11:44 am

    It has been my experience as a self-publisher that until you are well-known, you should probably stick to just a few markets. I can upload to Apple, Kindle and Nook directly and so far, that’s where the money is at. In fact, I only use Kindle and Nook for the moment. Once again, that’s just my take based on my puny sales – which at their peek amount to only a few hundred ebooks a month.

    I’ve had my books on Smashwords for over a year and have not experienced numbers from any other publisher that even comes close to Kindle. But I do know that as quickly as I type this, things are changing. So keep your options open. Gotta love it!


    Joel Friedlander April 13, 2011 at 12:49 pm

    Thanks for the detail, Ken, I’m sure other self-publishers will be interested in your results.


    Christy Pinheiro April 9, 2011 at 11:23 pm

    Hi Chris, I contacted you through your website.


    Keri Knutson April 8, 2011 at 3:04 pm

    Learn something new everday here. Thanks, Chris and Joel, this is by far the most understandable post I’ve seen lately on the subject. For those of us who are naturally technologically impaired, it’s very helpful.

    And thanks, Kate, too. I’ll try out Atlantis. (I’d give anything to be able to rely less on Word!)


    Kate @ Kallitechnes April 9, 2011 at 4:53 am

    It’s a bit annoying until you figure out how to turn the darn sound effects off, but after that? You’ll wonder why the heck you didn’t start using it sooner. Best $35 I ever spent on software.


    Kate @ Kallitechnes April 8, 2011 at 12:36 pm

    For the love of cheese, do NOT use Word for producing HTML. If that’s giving you the cleanest HTML you’ve found thus far, I shudder to think of what you’ve been working with in the past.

    Give Atlantis Word Processor a try. You can save as a .doc file, so Smashwords will still accept it, but it gives you a much, MUCH cleaner HTML output, and can also output straight to ePub. It’s a far cleaner program than Word, which is bloated and exports really terrible markup. Basically, it’s the cleanest output you’re going to get without coding that sucker by hand. I’m hooked.


    Joel Friedlander April 8, 2011 at 12:40 pm

    Thanks for the input, Kate. You ought to list your company in the eBook Conversion Services Directory, which is free:

    eBook Conversion Services Directory


    Kate @ Kallitechnes April 9, 2011 at 4:54 am

    I shall do just that! Thanks!


    Bob Wilson April 8, 2011 at 12:55 pm

    Thanks Kate. I just downloaded it and I’m anxious to check it out.


    Kate @ Kallitechnes April 9, 2011 at 4:54 am

    It let me go from spending hours cleaning up code in Sigil to creating clean ePubs in only a few steps. I’m in love…and I hope it works for you!


    Chris O'Byrne April 8, 2011 at 1:46 pm

    Whoa! If Atlantis produces clean HTML, I’ll be all over it! I’ll give that a try right now. That could save me hours of work. Thanks, Kate!


    Chris O'Byrne April 8, 2011 at 1:48 pm

    Darn, it’s PC only. Sigh. Good thing I have Parallels on my Mac.


    Chris O'Byrne April 8, 2011 at 3:43 pm

    Kate, I tried Atlantis and you are SO right. The HTML is refreshingly clean. My only complaint is that the chapter titles I styled in Word with Heading 1 do not translate as h1 tags. Do you see the same issue or is there a good workaround.

    Again, thank you so much for the recommendation. This is a big time saver for me.


    Kate @ Kallitechnes April 9, 2011 at 4:52 am

    I’ve never had a problem styling headings as Heading 1 and having it export properly from Atlantis…it’s odd that it’s giving your trouble! I always just style my chapter heads as Heading 1, generate my TOC, and off I go on my merry ePub way…

    (SO glad you like Atlantis. When I found that program, it was like a gift from above…clean HTML, and easy exporting to ePub that passes ePubCheck EVERY SINGLE TIME. Cuts hours off my process, I’ll say that. Worth working in a PC environment for!)


    Chris O'Byrne April 9, 2011 at 12:03 pm

    I was referring to the export to HTML option. I tried again and it doesn’t export the chapters headings as h1, but instead creates paragraphs that are styled the same as the Heading 1 style was. That’s a minor complain, however, because the little bit of extra time it takes to fix that is far out-weighed by all the time saved cleaning up the code.

    Joel Friedlander April 8, 2011 at 12:26 pm

    Thanks to Chris and Bob both for filling in more details in this process.


    Chris O'Byrne April 8, 2011 at 9:44 am

    Hey, Bob. I’m pretty sure the .doc is the only format that Smashwords accepts.

    Have you checked the validation of your ePub version from Calibre? I know Apple won’t accept a file that doesn’t pass validation—and sometimes not even then! I use the Threepress site to check the validation:


    Bob Wilson April 8, 2011 at 11:35 am

    No problems. My books are on Apple, but they get there through Smashwords, after Smashwords converts them to ePub. I convert to ePub to submit to Barnes & Noble.

    Yes, .doc is the only format that Smashwords accepts, but when you save your document from Word it will normally save it as “Word Document (*.doc)”. Instead, when you click Save as in Word, select “Word 97-2003 Document (*.doc)” from the “Save as type:” drop down list on the Save as dialogue. (I hope that makes sense.) After I started doing that I’ve had no problems with my hyperlinked table of contents in Smashwords. When you tell it to save as “Word 97-2003 Document (*.doc)” you’ll probably get a warning asking if you’re sure you want to save in that format. Just click yes. When you do that I think it strips out some newer features of Word that cause the problem. I think the same thing happens when you import the Word file into Apple Pages and then export it back as a Word file – you’re stripping out some newer Word features. You can skip the Apple Pages step if you save as “Word 97-2003 Document (*.doc)”.


    Chris O'Byrne April 8, 2011 at 2:16 pm

    I think the reason I don’t have that step, Bob, is because I use Word 2011 for the Mac and my Word format choices are either .docx or the .doc, which it lists as ““Word 97-2004″ for me.

    Good discussion!


    Bob Wilson April 8, 2011 at 9:20 am

    My process is similar to yours, but I don’t tinker with the HTML and after I create the mobi version with MobiPocket Creator I use Calibre to create the ePub version. I also copy eveything to Notepad (including the Word generated table of contents) so I can get rid of any weird styles.
    I had the same hyperlink problems with Smashwords until I read on their forum that you should save your Word file as a “Word 97-2003 Document (*.doc)”. Since I’ve started doing that my books are going through Smashwords beautifully and the linked table of contents work properly. I’ve also created a couple of Word templates with styles that I’ve created. That’s helped to keep things working correctly in each format. I think everyone has their own way of doing this and they usually end up in the same place at the end. I’m also waiting for the day when we have one or two superior tools for creating e-books.
    Great article. Thanks Chris and Joel.


    Kent April 8, 2011 at 5:12 am

    I’d like to hear about people’s experience in e-book formatting with Scrivener 2. It allows you to compile to most e-book formats and handles the cover art. So far I’ve only exported to epub for my Nook and my wife’s ipad. The Nook looked pretty good, ipad had some odd alignment issues on opening pages but the body of the book looked good. Now, this was just for proofing the writing, so I wasn’t too picky. That will change when I compile for the readers.


    Chris O'Byrne April 8, 2011 at 5:20 am

    Kent, I’d love to hear more about how well Scrivener works, also. I recently bought a new copy of the program—partially to use it as a developmental editing tool and partially to learn and use the e-book conversion feature.


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