On Writing: Windows, Eternal Spring, and Books (Premium)

I spoke recently with Tony Redmond, a long-time friend and the primary author of the highly recommended ‌Office 365 for IT Pros: The Ultimate Guide to Mastering Microsoft's Cloud Office System, which he self-publishes using Gumroad. I had been wanting to pick his brain about book writing and publishing for a long time, in part because my wife and I are writing an Eternal Spring guidebook to Mexico City, an interesting departure from my books to date. (More on this below.) But also because I wanted to know how he manages such a large project: His book is over 3,300 pages (!) long in print form.

It was a terrific conversation, and quite helpful. Tony handles his tome far more responsibly than I do my own books, the Windows 11 Field Guide, Windows Everywhere, and the Windows 10 Field Guide: ‌Office 365 for IT Pros is released in a new edition each year, and he and his coauthors issue monthly updates (free to users of the current edition) and a separate annual update to entice readers to buy the next edition.

My support policy has been looser but also more uncertain, though readers have at least benefitted from longer periods of free updates. Tony long ago advised me to move to a more finite (and transparent) updating model, but I am conservative by nature, and my chief aim has always been to help people with a product that is paradoxically important to their daily work lives but also something which most might not even consider paying for such a resource. So I’ve kept the books cheap ($9.99 and up, thanks to variable pricing) and amp up the value with years of free updates.

Whether that ever changes is ... well, up in the air. I supported the Windows 10 Field Guide with free updates for 6 years, and so far, I’ve supported the Windows 11 Field Guide with about 18 months of free updates, and I don’t see ending the support timeframe for this book anytime soon. But Windows Everywhere is a different kind of book, and I have many ideas for future updates. (Too many, perhaps.) I could see doing a second edition as a “new” title, though I will at least go through another editorial pass on the current version and try to clean up any remaining grammar and style issues first.

The Eternal Spring book is likewise a (very) different kind of book, and there, too, I could see a different support model, perhaps with annual releases, similar to guidebooks by Rick Steves and others. But I don’t want to get ahead of myself. When it comes to books, the Windows 11 Field Guide is my primary, ongoing concern. And it needs a lot of help: Not only is the book too long—really, too big—but there’s a ton of content I still want to add, and more coming as we move into 24H2 and then future updates. (More on the Eternal Spring book below.)

If you look at the web version of this book on Thurrott.com, you might understandably believe that I’ve taken some kind of break in recent weeks, as the last new (updated) chapter was added on March ...