Books – MetaGrrrl

Some lessons drawn from the how-not-to-do-it example in Tony Horwitz's New York Times op-ed, "I Was a Digital Best Seller!"

If you've had a negative digital publishing experience, talk to a wider range of those who've published in digital format before concluding that your experience represents "a cautionary farce about the new media and technology we’re so often told is the bright shining future for writers and readers." It's possible that the farce wasn't entirely about the platform, but also your use of it.
Ensure when you're contracting with a publisher that the expenses they've said they'll cover are covered as you go and that you are contractually well-protected should they not publish the piece as originally planned.
Also budget your own expenses and degree of risk and, with those and what you've agreed on with the publisher, stay within the boundaries.
Use potential future income as motivation to complete the contracted work, but by no means assume that that compensation will actually come to you. This holds true also for dreams of glorious enhancement of your reputation. Bear in mind, also, as expected sales figures get tossed about that the typical non-fiction physical book sells less than 3000 copies. Be excited about potential upsides, but be realistic—and don't count on them.
Once again, ensure your contracts exist and that contingencies are in place which will incentivize the publisher to honor their deal with you and, ideally, publish and pay, or at least pay an exit amount and revert rights to the work to you.
If you aren't great at the contractual/financial sides of the business, make sure to involve professionals who are on your side, and preferably with whom you have a long history of working together. They, like you, should be taking the long view of building your success and security. They, like you, should not assume that a single project will guarantee that success or security.
Get realistic estimates of potential sales and income not only from the digital publisher who wants you to do work for them, but from others with experience in that industry and with that publisher. Get an understanding of how volitile sales indicators (such as Amazon Kindle best sellers) are and what kind of total sales they represent. It's important to know what kind of sales spike can shoot you to the top of a list and how those spikes relate to aggregate sales of the work over time. Do not assume any understanding you may have of physical book sales indications will translate to these new areas.
Do not assume your publisher—digital or traditional—will put in the effort to bring readers and buyers to your work. Get a clear picture of what they will be doing to attract readers to your piece specifically. Above and beyond their planned effort (which like the potential returns must be taken with a grain of salt), you need to prepare to promote the work yourself.
Before you take on a project, research and understand the audience(s) for it. What do they like? What formats will they pay for? How much will they pay? Use this as a reality check for the proposed compensation and expenses for the project.
Before you take on a project, get a basic plan outlined of how you will reach those audiences. How do they learn about new works of interest to them? Whose recommendations do they trust? What communities do they participate in, and are you excited about participating in those communities too as you promote the work?
If your past experience is with traditional publishing only, talk to a variety of authors who've had both success and failure with digital publishing. You should pay particular attention to their experiences with promotion, both what they did and what their publishers did, as well as to what worked and what did not.
Thanks to frequently poor online browsing setups for ebooks—yes, iTunes Store, I am looking at you especially—random discovery of your work will be one of the least common ways for a reader to find it. People aren't generally poking around the shelves the way they do in physical bookstores. It's word of mouth and reviews on which you need to focus.
Plan to prime the pump for those reviews by building enthusiasm for the piece through your own professional social network. (You have been building a Twitter following around your past work, yes? And you don't have that all muddled up with your personal tweeting, right? Ditto for your professional blog or regular community participation in your areas of expertise.) Thank your readers and encourage them (without being pushy) to review the work or spread the word about it.
Work with the publisher to ensure that review copies will be sent out as quickly as possible, including—if you'll be releasing a physical version of the work as well as ebook—a giveaway through Goodreads.
Do not assume that enthusiastic readers, the kind who'll recommend your work repeatedly, will be fooled by fake glowing reviews written by publicists or pals of the author. Build enthusiasm in those whose opinions would be trusted and whom you can expect to engage with the work in detail, writing a review that is clearly by someone who cares about the topic.
Ensure that you have a contracted and reliable way to get copies of the work for yourself to use in direct sales (for example, at speaking engagements) and as another means to get review copies in the right hands.
Once again, make sure that your rights to the work are very clearly spelled out in your contract and that there is a clear path for any rights the publisher has to revert to you under conditions of them ceasing to publish the work.
Bottom line: Know the kind of writing you want to do, the hats you're willing to wear in the course of getting it in the hands of readers, and the realistic market for compensation for that writing with different kinds of publishers and (important and different!) through self-publishing.
Writing is a tough job to make pay; don't enter into the profession with just a dream and crossed fingers.