Long story short, I decided to move my site from being built with Jekyll and hosted on Github Pages to being built with WordPress and hosted on Pressable.

Jekyll on Github

I originally picked Jekyll because I liked the purity of it: I like that my site was statically generated and that all of my posts were just plain text files. Hosting on GitHub was also obvious because I already used them for storing code and because their Jekyll hosting is free.

The first problem with that setup that I ran into was actually posting to the blog. I theory, it was easy: just push a new commit to my repo with my new post. In practice, getting all of the YAML front matter for every post needed up being pretty annoying. I made a little utility app that did the heavy lifting here, but there was still too much friction to getting my text from my devices to my site.

Another big issue with Github Pages is that they do not support SSL for custom domains. So they only way to get my site to severed via https instead of standard http would be to use the domain rosskimes.github.io instead of rosskimes.net. That was a non-starter.

The last problem I had was just performance. I post a lot of photos to my site and they were always pretty slow to load.

I could have fixed the SSL and performance issues by just moving my Jekyll site to another host but I figured if I was going to pay for hosting I should pick something that would fix all of my issues.

On to WordPress

After doing a little research, it was clear that WordPress did everything I wanted.

Posting is easy. For longer articles like this, I can post directly from Ulysses on my iOS or Mac. For shorter microblog posts, I can post right from the Micro.blog app. For my photoblog, I can use the new Sunlit app. I can even use Workflow for quickly posting specialized posts like photos and links. I also was able to start using MarsEdit to handle more in-depth posts on the Mac¹.

The host I landed on, Pressable, performs well and has built in support for SSL via Let’s Encrypt. It also includes a Jetpack for WordPress plan, which has some nice bonuses like site monitoring and stat tacking.

What’s Next

When I decided to move, I just wanted to get the site running as close to what I had on Jekyll. Now that I am done with that, I can work actually improving the design and adding some features. The first thing I plan on doing is making the homepage look a little nicer and adding in support for posting quick links with little commentary (this is inspired by the new Fresh Links section on The Newsprint, which is excellent).

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If you subscribe via RSS, old posts may show up again. I did my best to make sure all my URLs stayed the same so that wouldn’t happen, but it is hard to cover every case in big migrations like this.