I launched a new Jekyll-powered version of this website last October. I wasn’t unhappy with WordPress (which powered the website before the move) but aspired to a more unified personal knowledge management system. Jekyll’s main advantage in this regard is that site posts are stored as Markdown documents, which I index in DEVONthink. This allows me to discover connections between posts. The benefit is real: DEVONthink’s AI engine is quite powerful.

But there’s been a considerable downside to the move: the impact on my writing and publishing workflow. I’ve long used Ulysses for my short- and long-form writing. (Besides my blogs, it’s also where I wrote Living in Information, presentation and workshop scripts, etc.) Since moving to Jekyll, I mostly write either in DEVONthink itself or in BBEdit and have delegated Ulysses to editing posts for The Informed Life, which remains hosted on WordPress.

I miss Ulysses. For me, it strikes an outstanding balance between distraction-free writing and powerful control over a text’s structure. Ulysses uses Markdown under the hood but hides markup when you’re writing. (Some folks consider this a downside; I like how it focuses my attention on the writing.) When I write, I set my apps to go full screen so I can focus exclusively on the text at hand. While DEVONthink has a full-screen writing mode, I much prefer Ulysses’s. When using Ulysses, the words flow in a way I haven’t yet replicated with another tool.

But that’s only part of what I miss about writing in Ulysses. After all, I could continue using it to write for Jekyll since Ulyssess can save texts as plain Markdown files in a directory on my Mac. But Ulysses allows for direct publishing to WordPress (and other platforms, such as Medium, Ghost, and micro.blog), making for a much easier workflow than Jekyll.

When writing with Jekyll, I must first produce the post: i.e., write, edit, prepare images, etc. Then, I must recompile my blog locally. Then, I must upload changes to the webserver. Then, I must commit everything to Git. (I know this workflow could be better. It is what it is.) With Ulysses, I write, drag and drop images, and publish to WordPress, all within the same tool. And if (when) I must correct a typo in a post, I simply open Ulysses, make the change, and update the post. Simple.

Bottom line: although the Jekyll-based setup is closer to my ideal from a PKM perspective, it’s less effective from a writing perspective. Looking back over the last few months, I realize I’ve written and shared a lot less than I was before. It’s been partly due to work commitments, but I suspect the change to my writing workflow has also affected my productivity. Our tools and the environments they create have an important impact on our effectiveness.

I don’t know yet if I’ll stick with Jekyll. Besides the impact on my workflow, moving to a static site generator entails a significant loss of functionality. (E.g., no local search, no native commenting system, no pre-scheduled posting, no antispam control on email forms, etc.) I’ve kept a parallel WordPress-powered version of the site in the wings, just in case, and may yet switch back. In the meantime, I’ll continue tweaking my Jekyll workflow to see if I can make it better. And as always, I plan to continue sharing what I learn here.