Inspired by the creation of this site, I declared on Twitter:
That led to a number of questions as to where one should create a blog; helpfully, I now have a blog where I can answer exactly these sorts of questions!
Before I get started, though, I need to give some necessary disclosure given the subject matter: I used to work at Automattic (the owner of the WordPress.com hosting service, and major contributor to the WordPress.org open source project), and Stratechery (and this site) runs on WordPress. On one hand, this is evidence that I follow my own advice; on the other, perhaps I am biased, but now you know why.
On to my advice:
Own your own domain
This matters far more than what service you use, because this is what allows you to switch between services in the future. If you have a Squarespace blog, but your domain is mysuperblog.net, you can switch to a WordPress blog and change where your domain points to (relatedly, you can also have an email address that is guaranteed to never change, even if you change email service providers). On the other hand, if you have a Medium handle, for example, you need to build your website’s identity from scratch when and if you want to move.
I would further suggest that you buy your domain independently from where you host your blog. Yes, Squarespace or WordPress or Wix all promise that you can point your domain elsewhere if you move your site (and of course you can always change your domain registrar), but part of what you are protecting yourself from is being too dependent on any one company.
In addition, don’t feel like you need a ‘.com’ domain; it is very hard to find one with a pronounceable name. The good news is that the huge expansion in generic top-level domain names means there are a lot of interesting names available, and most everything supports these names without an issue.
Have an open-source alternative
If your site is on Squarespace or Wix, but under your own domain, you can switch to another service like WordPress and still have the same address, but there is going to be a bit of pain involved if you want to keep your old content: you will need to export your content out of your old service and import it into the new one.
Moreover, there is no competition for Squarespace or Wix hosting: they are the only providers of Squarespace and Wix software, respectively. This is great as far as providing an integrated product goes, but in general it is not a good idea to be a customer of a monopoly (extremely narrowly defined, to be sure!), particularly for something you want to last your whole life.
Using a service that is built on open-source solves both of these problems: first, there is competitive hosting. Stratechery is currently hosted on WPEngine, but there are a host of competitors in the managed hosting space, and even more options when it comes to self-hosting. Moreover, you can run the entire service yourself on AWS, Digital Ocean, or even your personal computer.
This also means that if you are unsatisfied with your host it is easy to switch: not only can you change where your domain points, but it is far easier to seamlessly move content between servers, because they are all running the same software (this entire section, by the way, also applies to those who want to build their own CMS).
WordPress, I should note, is not the only option in this space: this post has a good overview of additional open-source CMSs, including Ghost, Drupal, Joomla, etc.
Consider optionality
If you are with me so far, we have established that the most important thing is to own your own domain (which rules out Medium and Substack, at least as far as a personal site is concerned), followed by using open-source software (which rules out Squarespace and Wix). To me that leaves two clear choices: WordPress and Ghost.
The fundamental premise of Ghost is that it is a drastically simplified and thus easier-to-use CMS for bloggers. WordPress runs all kinds of websites, and has the complexity that inevitably follows from so much capability; Ghost, by virtue of doing less, is easier to use, requires fewer resources, etc.
The problem — at least from my perspective — is that flexibility is optionality. If one day down the road you want your site to be something other than a blog, but you are using Ghost, you need to go through the same sort of transition process I described above. Sure, the reasons might be different, but the pain is the same!
That is why I have been and continue to be an advocate of using WordPress. Particularly with the Gutenberg Editor it is a pretty easy-to-use blogging set-up (yes, there is still a lot of cruft there), but you have the capability in place to do far more in the future. Moreover, the ecosystem of plugins and themes means the tools to do that future thing are probably already built. I’m no great shakes as a developer, but I was able to launch not just Stratechery but also the first version of the Daily Update thanks to this ecosystem of plugin developer and theme builders (today’s Stratechery theme was professionally developed, but that is another way of making a point about ecosystems — there are a lot of WordPress developers out there).
As to which WordPress host, WordPress.com is the best choice if you want long-term stability, but there are limitations as to what plugins you can install; paying for a managed service is a nice middle ground, and gets you out of the endless up-selling that can be endemic on “free” alternatives (Ghost also has a managed hosting option).
Again, I’m definitely biased about WordPress, but I think this combination of open-source and large ecosystem is really powerful. The entire point of having your own site is to be independent, but it is easier to be independent if you are one of many. At the same time, if you think an alternative is better, go right ahead — just get your own domain!