Why I Switched to WordPress.com

I spent the entire weekend trying to sort out why changing my WordPress theme brought down my site. There was this error and I just couldn’t figure out what was happening. I exported my data, moved to a temporary free WordPress.com account as a backup, and re-installed WordPress on my self hosted site.

Before we get to far into it, to clarify, WordPress is a technology that lets you create blogs. You can either run WordPress on your own server (in the cloud) or let a company manage your installation. WordPress.com is a company that manages WordPress installations, so you can blog away and let WordPress.com handle the technical details of running the site.

Getting back to it, I reinstalled three more times because each time I ran into a different problem. I think the issue came down to a database incompatibility, but it was just one in a series of problems I’ve encountered over the last few years while running my own site. My site was “defaced” via an exploit in an out of date version of WordPress, was unable to connect to Jetpack services, and needed to be re-installed one too many times. This iteration was the last straw. I needed to switch from site maintenance mode and get back to blogging.

Self Hosting

There’s a lot you need to keep up with when running your own WordPress install. I enjoyed learning all the details over the years of running my site. Finding the pieces and putting them all together was fun and made for fulfilling work when the site decided to play along. Although, when something went wrong, managing this workflow and disjoint accounts brought my progress writing posts to a complete halt.

Here are many of the pieces required to run a WordPress site (all of which WordPress.com will handle for you):

Hosting

Your site needs to live somewhere (search for “WordPress hosting” to find a few options)

Domain Name

A site needs a url, so you have to ensure your domain name registration is up to date every year, AND linked to the WordPress install. The latter is a constant source of struggle. (Namecheap, Google, GoDaddy, Hover, etc)

Certs

Want that green lock on your site? You’ll need an SSL certificate. Site certificates let people connect securely and communicate privately with your blog, so it’s important that your has the correct certs. (Let’s Encrypt, Comodo, Namecheap, etc)

Backup

Site backups are crucial in case anything every goes wrong (which through my experience seems common), but they are costly, unintuitive, and require manual configuration.

Updates

WordPress must be kept up to date, with a self-hosted site, you need check for updates. It requires active engagement. I try to write posts on a weekly cadence, but sometimes there would be long stretches of time I didn’t go on the site. You can configure auto-updates to the WordPress core, but there are many caveats. In either case, it’s another task you need to keep in the back of your mind, using up resources I could allocate elsewhere.

Customization

Do you spend way too much time setting up your video game character, even before starting the game? You’ll do the same with WordPress site customization. While seemingly a differentiator, a site’s look is not nearly as important as it’s content. (Ironically, switching from a highly customized theme to the default Twenty Seventeen theme kicked off this whole ordeal)

In then end, all this mental overhead was cutting into my time and creativity. Running the technology distracted from what I wanted to do with my site. And with that, I handed over the keys to WordPress.com.

Going Forward with WordPress.com

Note, this is not a review of WordPress.com. I’ve only used the service a couple days, so I’m still deciding if it’s the right fit. However, I had five accounts to manage everything related to my website, and now I have one.

Blog spectrum of User customization and control to One experience fits all (Doing my best Stratechery impression)

WordPress.com sits in the middle of the blogging platform spectrum of user control and one experience fits all. I can still modify my the site to make it feel like my own, but I don’t have the same level of configuration as a self-hosted site. It’s a good first step to building a focus on writing, because I don’t want bells and whistles anymore. I want to write and develop something new.

Technology works best when it’s invisible. I am optimistic that getting the site administration work out of the way will free up headspace to think and give me time to create more.

My site has a history on WordPress, so there is some lock in to the technology. As I searched for a platform that just lets me write, switching to WordPress.com was an easy first option to explore. Since it’s easy to transfer WordPress data from one hosting service to the next, I brought all my posts with me to WordPress.com.

With that said, I am going to keep iterating, with new formats, platforms, and mediums. I am now a customer of WordPress.com. If I decide their services improve my ability to create, I will stick with them. Otherwise, as WordPress.com says in their own words “You own your data – take it anywhere”.

Medium.com leans further towards the one experience fits all side of the blogging platform spectrum. On Medium, you get a title, and a story. That’s it, but it’s amazing. The focus is on the content of the words on the page, not the theme of the website.

I have a Medium account with zero posts (until know). Starting today I will be cross posting longer form thoughts like this under the Medium Partner Program (and I checked, this is allowed by the Medium Content Guidelines). All my posts will still be on my site, but I want to experiment with Medium to learn how the different communities interact.

So let’s see how this goes. The content of my blog has changed over the years from small ideas (Seth Godin-style), to connecting things I read/hear/watch, weekly reviews, back to connections, and now a news feed. I can already tell this latest iteration is working well. It’s easier to get back to writing and integration with email updates, social media, and reader feedback is better overall. There’s less in the way of getting things done, and I’m hopeful this new format will keep my momentum going strong.

Be on the lookout for a future post explaining “Why I’m Staying with WordPress.com” or perhaps “Why I Switched to Medium”.

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