This is a blog about everything digital books can do that can’t be done in print.
It’s a look at what’s currently being done—by big publishers, by independent operators—with an occasional bit of idea-mongering about what we’re not yet seeing.
I’m interested in spotlighting others’ work, and taking a serious, respectful, and enthusiastic look at anyone who’s part of this remarkable, epochal transformation from print to digital.
I’m planning on asking a lot of questions: what’s working? what’s not? how might idea A be improved by getting rid of feature B and tweaking option C?
Part short essay space, part design scratchpad, the site will hopefully be a fun place for anyone interested in questions like:
- What exactly is the job of a table of contents? In what ways can the traditional plain-text version be improved upon?
- Are 300-page long business books the best way to convey the handful of truly useful ideas that many of these authors have?
- What can information design gurus like Edward Tufte teach us about how to construct more useful, more reader-friendly documents?
- What are shopping catalogs like J. Peterman and Lucky magazine doing to merchandise products that might also be done to showcase ideas?
- If what we mainly do as readers is remember and interpret, how can books do a better job of helping us with the former without spoon-feeding us the latter?
- When does embedded video improve a book and when is it just plain annoying?
- A few years from now, when my daughters are reading on their iHolographs, what kinds of composition tools will their favorite authors be using?
- As a recovering Chekhov, Emily Dickinson, Gabriel García Márquez, Flannery O’Connor junkie, why am I spending so much of the time I used to devote to books on Twitter, Facebook, and iOS apps?
About Me
As a writer, my devotion is to clear, engaging prose. In the writing I’ve done—as a grad student at the Iowa Writers’ Workshop; in articles for the New York Times, the Wall Street Journal, and Wired; as the author of Best iPad Apps (O’Reilly Media) and Enhanced Ebooks Today & Tomorrow: A Survey for Authors and Publishers (F + W Media)—my goal has always been to “create a context in which other people can think” (Edwin Schlossberg).
I also have a firsthand familiarity with technology—its possibilities, its limitations, its own capacity for creative expression. At Iowa I earned strange looks from those in the Workshop by using my elective course credits to take much of the undergraduate computer science sequence. In the mid-90s I co-founded one of the first online multimedia textbook ventures (Digital Learning Interactive), hand-coded its first website, managed operations during the first two years, and watched in a bit of awe as it grew to 70+ employees, raised (and spent!) more than $20 million, and eventually got scooped up by publishing giant Thomson.
During a five-year tour of duty at O’Reilly Media, where I served as associate publisher of the Missing Manual series, I led a number of projects aimed at figuring out how to transition from print to digital. I conceived and oversaw the launch of the Missing Manuals’ screencast program (video teaching guides where the instructor narrates the action onscreen); designed a system to produce “living guidebooks” (continuously revised, with the latest version always available online and via print-on-demand format); inaugurated the “mini Missing Manual” program (ebook-only short takes on topics); and created a new series called “FlashGuides” in which swipe-able flash cards integrate an expert’s guidance with curated tours of great explanations online.
My undergraduate degree is from Harvard, where I studied American history and literature. I live in Washington Heights (aka “upstate Manhattan”) with my wife, two daughters, and more reading devices than I will ever have the time to actually use.

