Suppose you’ve written a few blog entries per week for a few years, taking a random walk to explore a slowly revealed terrain. How could you most effectively organize and compress those hundreds of insights into a truly useful and readable format?
Inspired by this blog entry by Sean Murphy and recollecting my own comment about blogging that
But mostly I’m curious to see what themes emerge! I’m trying to keep it spontaneous and authentic. ”These colors […] are not the product of some artistic conception. They are the flowers from my vine.”
I started thinking how someone like Sean (or maybe a future me) who has written 550 posts could organize a subset of them into a useful ebook.
Why? First, people I know still generally prefer to study from paper. For casual reading or searching, the computer monitor is OK. But for study, it goes to the printer.
Ok, but what else does a book do for the reader, besides making it easy to print? It has a linear organizing principle, a clear theme, and has been edited down.
One approach would be to figure out clearly what you want, then pay a ghostwriter to edit your material into a book. (I’d guess it wouldn’t cost much nowadays to hire an off-shore ghostwriter. Or, if you fly “first class all the way, baby”, you could even hire someone like this.)
But you’d probably end up wanting to give the ghostwriter the theme and an outline. And once you’ve created those, you’d probably (re)learn a lot, and get some new ideas, by rereading and categorizing your blog entries.
An outline is tantamount to a linear presentation, because a tree can be naturally flattened.
So after you’ve created an outline according to your organizing principle, you could assign to each leaf node in the outline a new blog tag, plus create one more that means excluded from the book, then go through all the blog entries from earliest to latest, adding exactly one of these tags to each entry.
Create a single page/tab that is your outline with links pointing to the associated tags, such as this, perhaps embellished throughout with some introductory and connective text.
This would not be exactly a book, but it would be book-like, and would be easy to convert into a true book if you wanted.
You could start with a broad outline, because if you wanted to refine a leaf into a new parent, you would just add new tags, and assign one to each that has the older tag, and edit the outline page to use them instead. (No need to remove the older tag from the entries.) You’d want to resist the urge to add several leaf tags to the same entry, because then the outline would lose its tree structure and not flatten naturally into something linear.
Then as you add more blog entries, you would tag them, too, and your book-like page would be automatically updated without editing it.
And if you did ever want to hire a ghostwriter, this book-like page would be a great rough draft to hand off to them.
Blog Brut 
Some interesting suggestions. Still wrestling with the best way to refactor/restructure what I have written. It could be that several smaller booklets are more appropriate and perhaps more easily consumable. Thanks, it’s definitely food for thought.
The outline idea has come up from several folks. I am currently working more or less bottom up by re-reading all of the leaves and attempting to create themes. I will probably create an e-book of quotes using the http://www.leanpub.com technology and continue to work in the wiki on the “Working Capital” book derived from my blog.
Sean, those are exciting, positive actions and for sure something good will come of all that effort.
In addition to an outline, other must-haves are two measures of success, one for you and one for the reader.
For example, for you, is an ebook enough, or do you need a publishing contract? Is it enough to have useful content, or do you want the verbal style to be outstanding, too?
For example, for the reader, what will they be able to do after that they lacked the knowledge or inspiration to do before? How will your book change their world?