Blog from your iPad on your own platform for $88


I run my primary website on Squarespace. It looks great, and I like the module approach to building out things like my speaking page. It’s been working well for me. So when I decided to start blogging again, I made my first few posts there, using the blog I’d initially set up many years ago. I remember that it was glitchy back then, especially the Markdown link handling, and I always felt friction around actually getting content into the blog.

Nothing has changed. If there are new features since I launched my site years ago, Squarespace has hidden them well. The blogging app never worked well and still doesn’t. I’m sure Medium has taken some of the pressure off, and that a lot of Squarespace customers blog only infrequently. But I really can’t recommend it if you plan to publish more than once a month.

So I went looking for an alternative with these things in mind:

  • I want to focus on writing
  • I want to spend as little time as possible configuring and maintaining things
  • I want to blog on my own platform, not a social media site
  • I don’t want to spend time learning anything new (for this project, anyway)

I’ve been liking Ulysses, and WordPress is one of its built-in publishing options. So I went over to and signed up for a free account. I connected Ulysses and published a post from my iPad that I’d previously published to Squarespace. It worked great. Significantly fewer steps, no copy-and-paste malarkey, and no errors that I could find.

One hour later I’d signed up for the personal plan ($48/year), configured the name and theme, added a couple of old posts, and pointed to the WordPress site. The hardest part was figuring out what I actually had to do to set up the custom domain. I was overthinking it, as usual, as there are only two steps:

  1. Add a single CNAME record within the DNS settings. You don’t have to “create” a sub domain or anything like that; everything happens in that single record.
  2. Add the sub domain address within your account and set it as your primary domain.

I briefly considered registering a new domain, but I kind of like keeping it generic in case I want to rename it in the future.

I left my old Squarespace blog alone save for moving it out of the main nav, then replaced it with a Link component pointing here.

The costs: $40/year for Ulysses, and $48/year for the WordPress account. And of course the domain name, which I’d have been paying for anyway.

I’m playing with static site generators for another project, and maybe I’ll move to one of those in the future if I get the hang of it, but right now I want to focus on writing, not technology. I’d rather that Squarespace had an amazing modern blogging engine so that I could run it all in one place at a lower cost, but $88/year to have my own low-maintenance, iPad-friendly blogging system feels like a reasonable expense.