Eric Cheng

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Migrating from Wordpress to Squarespace

Last week, I made the mistake of asking the lazyweb about how to generate 301 redirects en masse during a theoretical migration from Wordpress to Squarespace. I was worried that I would lose Google search engine ranking because so many URLs could potentially change, orphaning content and disassociating it from hard-earned links at external sources. My readers did not like the idea of moving away from Wordpress, and they chose to voice their opinions instead of answering my request for information. 

I eventually just deleted the Facebook post because I wasn't interested in opinions about Wordpress vs. Squarespace. I really like Wordpress and would definitely run a business using it as infrastructure (in fact, I have, in the past), but I am just not interested in running Wordpress for a personal site that I really don't want to think about much. Social media outlets and fast-blogging sites like Tumblr have taken the vast majority of my content away from during the past 2.5 years; at some point, it became way too easy to write to an audience using Facebook, Instagram and Tumblr instead of logging into Wordpress and creating a post. Another reason I decided not to write at anymore was that I was embarrassed by the design of the site. The last revision of was done in 2002, and 13 years in web years is an eternity. I knew that I would have to redesign in order to want to start contributing content to it again, but I was always too busy to take on the project. Migrating so many years of content (from 1998 onward) was just too much of a burden to consider, especially because a great deal of it did not live in a CMS.

The loss of content ownership—not having my content on, a space I own—has been eating at me for a long time. So over the past week and a half, I migrated my site from Wordpress to Squarespace. Squarespace does feature automatically migration from Wordpress, and all of my journal entries made it over (over 2,000!). 

Some things worked really well:

  1. I use Disqus for comments, which uses the URL as a key for discussion threads. Luckily, I hosted my new journal at /journal, which is where the old journal lived, and Squarespace models URLs after Wordpress URLs. In theory, the vast majority of my journal content should have the same URLs. This is fantastic, because it means that most incoming links won't be broken, and all of my comment history has been preserved.
  2. Squarespace is ridiculously easy to use. I'm OK with the tradeoff of not having complete control in exchange for low posting friction.
  3. I'm also using Squarespace to run my new book website. E-commerce using Squarespace has also been extremely easy to configure and use.

There are some migration issues that I will need to address in the coming weeks:

  1. Much of my content is written in Markdown. Squarespace does have a Markdown block, but it doesn't automatically detect Markdown during migration, so I need to go back to those entries, manually create Markdown blocks, and move the content over.
  2. Many of my image galleries are embedded using static file includes (a horrible legacy). These need to be re-uploaded manually.
  3. Most of the Wordpress URLs are the same in Squarespace, but I found one that was not, which turned out to be because of a timezone issue. The old article was posted at 1:30am one day, and Squarespace imported it as being posted at 6:30pm the day before, which changed the post's URL. This obviously breaks both incoming links and Disqus comments. To solve this problem, I need to figure out which URLs on the old site no longer match URLs on the new site.
  4. I host a popular forum about Asians turning red when we drink alcohol. This was migrated to a standard server, and a 301 redirect has pointed the old URL to the new one. The new forum is a static copy, but that's OK because I really don't want to run the forum anymore.
  5. Almost all of my travel journals were not hosted in a CMS. These will need to be recreated manually. I'm currently at 2003!
  6. A bunch of other random hosting occurred in the old file structure. These are all dead now, and I think I'm OK with that.


I'll write more as I settle into Squarespace and get more and more of my content over. For now, I'm extremely happy with the situation, and am happy to have a refreshed website I no longer feel embarrassed to send people to!