Blogging With Ulysses

Blogging With Ulysses

There are a slew of blogging solutions out there in the world. In this post I share mine—but that doesn’t discredit whatever you find is your solution.

Long time readers at will have noticed that the website layout has changed in recent weeks. A couple of years ago I switched to the site being hosted on Squarespace and now I’ve switched away from Squarespace to a self-hosted WordPress instance.

Squarespace turned out to not be as good of a podcast hosting solution as

Yeah, took me a while to realize that there are platforms that specialize in podcast hosting. It’s not just a feature it’s their purpose.

The move was also a cost saving one. I can host the WordPress on a cloud service for about $6/month. By self hosting I have the freedom to install plugins and themes to make the site more functional and meet my visual expectations. It means I have to run updates the operating system as well as to WordPress in order to keep it running, but that trade off seems worth it.

It’s super easy for me to login and run the commands to update the underlying OS and both WordPress and its plugins have options now for automatic upgrades. Things have certainly improved over the years.

Fingers to the Keyboard

The next component for me after hosting was to have a clean and elegant process for creating content. Blogging involves typing. A good keyboard is important. For most things I write I find myself switching between a Magic Keyboard attached to a 2020 iPad Pro and an M1 powered MacBook Air. Both have excellent keyboards.

When it comes to apps, quite a few people would start with a word processing app like MS Word or LibreOffice Write. Digital natives might find themselves using an online collaborative tool like Google Docs. I’ve been in both camps when it comes to creating content. Each app’s workflow has its advantages. There’s a balance between presenting the user with a lot of formatting options and a clean interface. Word, despite having a low-distraction mode, has a lot of formatting decisions it wants you to make while in the app—while trying to focus your ideas.

With regards to the online solutions, Google doesn’t provide the same experience between the iPad and the MacBook. The iPad apps provide an inferior experience. Considering how good the Google engineers are I’m starting to think this lack of polish is intentional.

Thankfully there are folks who have managed to review the situation from a workflow perspective.

Workflow Perspectives

A workflow perspective is one that looks at the process of idea to delivery instead of individual technical challenges. Since workflows are made up from recipes of individual technical challenges/solutions it’s no wonder that so much of the software industry has focused on developing those out-of-context solutions. Since the success of the smartphone we’ve seen a huge propensity towards apps solving the workflow problem instead of simply providing the user with the technical means to overcome a particular obstacle.

Adobe has a long history of being masters of creating technical solutions. Their engineers and software can work magic. But developing a workflow that leverages those solutions often requires a large investment in training. Microsoft and Adobe both know how much money their training divisions pull in through publishing and certifying their professional cadre.

By contrast, an untrained user can likely navigate around Apple’s professional level apps without a lot of tutorials. I might just be getting old, but I literally tried to use Adobe Premiere for years and found that the cost of watching all the tutorials I would need to in order to get proficient was pretty high. I was running a Windows machine at the time and wanted to get back to content production. So I simply spent the extra several hundred dollars and bought another MacBook where I already had Final Cut Pro.

Narrowing Down the Options

In the writing space there are a few apps that have focused on the actual workflow of writers. Hint: authors don’t use Microsoft Word. Word is a business application designed to produce memos. In my experience it absolutely chugs at documents that stretch into the hundreds of pages.

There are two competing authoring apps that I looked at. The first was Scrivener. Scrivener has a lot of features for long-form writing—long articles and books. It allows you to capture your research and your content and it’s a single-purchase application instead of a subscription. Scrivener was a strong contender. It’s also the app I didn’t pick. Their iPad offering and MacBook offering didn’t clearly indicate that the two would be synced or that the feature set would be complimentary.

The app I did pick was Ulysses and it’s designed for publishing online or in a long form format. What kept me from picking Ulysses initially was the subscription model. At $49.99 for an annual subscription it’s cost effective but only if the app gets used. Ulysses has a feature that will allow your post to get formatted at the end of writing and have it published to your blog. This feature will connect to Ghost, Medium, and WordPress—some of the most popular blogging sites out there. One site that’s not supported is Squarespace.

Leaving Squarespace

Squarespace is an excellent site for those who appreciate the workflow it provides. I found their apps to be feature lacking and workflow frustrating.

You can’t publish directly to Squarespace from Ulysses or anything other than the Squarespace app.

I also found Squarespace’s website to be less responsive than I would prefer on the hosting side. It would take several clicks to get to the content that I wanted to and there wasn’t a clean way to duplicate and publish for the podcast. Squarespace provides solutions that appeal to a lot of diverse users and there are times when I really appreciate their offerings, but now it was time for me to move on.

With a self hosted WordPress site and Ulysses I can now write and publish directly to my blog in one of the most frictionless ways possible. Once I’m done typing this post on the iPad I can easily preview and sent it off to the interwebs. That low cost to production is one of the most pleasant parts of this experience the fact that I get it at a lower price point is just another example of how the world keeps getting better.

So, now it’s time to export. Select the destination and work on the next post. This one will be easy to publish.