Like many of my compatriots, I’ve recently ended a (relatively) short, torrid love affair with Squarespace and am now back to running this site on WordPress.I doubt anybody reading this really gives a crap why I’ve done this, but I’m going to cite my reasons here, if only to give myself some closure or something.
(What makes this especially awkward is that Squarespace has been sponsoring my podcast for the past few months. I’m not so conceited as to think that my own departure will be what ends that particular relationship, but I guess we’ll see. And, you can consider those last two sentences my “disclosure” or whatever.)
Now, then – let’s get on with the reasons why I left Squarespace.
Cost
I don’t have a problem with Squarespace’s cost per se, but my issue is more with the cost relative to what I was doing with my site. Essentially, it’s a simple site with a few static pages and a blog. I wasn’t taking advantage of any of the really spiffy Squarespace features that ship with the plan I had (the $20/month jobbie, if you’re curious).
I simply didn’t need all of the bells and whistles that were included in the admission price. Please realize that this isn’t a knock against Squarespace. I just bought a nice sedan when all I really needed was a skateboard.
Publishing Pain
I do the vast majority of my personal writing on my iPad (that’s where I’m writing this now, in fact). My normal writing workflow looks like this:
- Look through entries in Drafts for post ideas I’d jotted down recently.
- Find one I like and start typing in Drafts (using Markdown).
- Once I’m reasonably sure the article won’t be garbage when/if I finish it, I move it to Byword and finish it.
- Take the finished article text, export it as HTML.
- Open the iOS app that corresponds to the blog where the article will be published (Squarespace for this site, WordPress for nerdgap.com).
- Add any images or formatting I’d need, verify it looked alright and either publish it or schedule it to be published.
Like I said: all of this is on the iPad. Frankly, Squarespace’s iPad app hasn’t been functional in awhile. This would have been less of a problem if I’d been able to publish to my site via Mobile Safari, but that never worked right. At the end of the day I was, in effect, unable to publish anything to my site using my iPad. That quickly went from a slight nuisance to a deal-breaker for me.
I know that Squarespace’s engineering staff is super busy. The new version 6 of their platform looks like it was a mountain of work and I can completely understand why something like the iOS app would get a bit less attention than they would have liked. But, I needed it to work and it didn’t.
Fiddling Fiddlesticks
This is definitely a deficiency of mine and not with Squarespace, but I found the admin site to be a fiddler’s playground. As somebody who has spent more than his fair share of time dorking around with various apps and their preference panes, I couldn’t go near my Squarespace site without tweaking something. That got annoying.
Familiarity
I’ve been using WordPress since around 2004. I know it well, including how to properly configure it, administer it and develop for it. I’d be lying if I said that I didn’t miss the comfort and confidence of using a publishing platform that I’ve spent years and years getting to know (despite the quirks).
Squarespace-version 6 in particular-is extremely powerful, but I didn’t find many of the customizations to be super intuitive. I could usually figure out how to do what I wanted to do, but it was rarely quick.
I can’t objectively say one is better than the other: you’d have to pluck somebody out of gen-pop, plop them down with both platforms and ask them. I just know WordPress better (like, far better).
Why You Should Probably Ignore What I’m Saying
Other than the iOS app thing (which, according to a post on their blog today, they’ll be addressing soon), my reasons for leaving are more personal preference things than straight-up indictments against Squarespace. If you’re not a nerdy type and just want a website that won’t go down and you don’t need to get all fiddly with it, then I’d still recommend Squarespace quite highly.
We just weren’t the right fit, I think. And that’s ok.
Going Forward
My real blog is the one I take seriously. This site is sorta like my playground and I won’t be super apologetic about reinventing, migrating or otherwise gutting it from time to time. If you’re cool with that, then we’re going to get along just fine, you and me.
Oh, and I’ve decided to enable comments on this site. So… leave a comment if you want. Or don’t.
Incidentally, this post represents my kicking the tires of an iOS app called Poster. So far, I’m digging it. If you have a WordPress blog and you publish to it from iOS, definitely give ‘er a look as she’s a great deal more nerd-friendly than the goofy official WordPress app (which is a big turd, if you want to know the truth).

You don’t know how hard it is to resist posting FIRST!!111eleven or something else really childish here.
So I’ll post this half-childish comment instead.
Glad to see you calling a spade a spade though
Childish behavior is part of what makes all this narcissistic nonsense bearable. Next time, don’t hold back.
I went through the exact same thoughts last year. Squarespace is a great platform but their iOS apps consistently borked my content and their customizations usually left me wanting more freedom, keep in mind I’m also a massive tinkerer.
I’m glad your sponsorship didn’t stop you from publishing your feelings. You got integrity.
Thank GOD they’re finally going to update the mobile apps. That’s been an annoyance of mine since I signed up for Squarespace, and it only got worse when I switched over to v6.
I couldn’t agree more. I gave them a shot and it wasn’t a good fit for me. I tried it on a client project and it backfired. I prefer the nuts and bolts of WordPress. I know Squarespace has their audience and they do it really well.
Squarespace is the biggest tech con-game to ever hit the market. I admit, being creative rich and tech dumb, I was sucked right into the slick, Apple-esque marketing ploy where less costs much, much more. I wanted to love it.
However, once you get past the initial dazzle of their almost hypnotic marketing wizardry, you have the reality of it to deal with.
It is NOT easy to use as they imply. The learning curve is steep. Yes, they offer 14 days of free trial but it will take every day of that to sort of get it figured out. Even then, without programming, designing or developer knowledge you are hopelessly trying to make something “exceptional” out of templates that just scream “GENERIC” “LISTLESS” LIFELESS” and “DULL” There is no way any “award winning” developers created these awful templates. They look as though a couple of eager young grads spent two weeks with their pimply faces pressed up against the cold glass of every minimalist art gallery and furniture store in Soho (Same hood as their ultra hip n’ cool offices) and were told to “make something elegant–and fast!”
If all of that were not bad enough you have this tiny, light gray font which is very hard to see. And it is all down hill from there. There are no 3rd party blogging plug-ins to optimize your postings, no editing, no nothing.
But, clearly, these arrogant Frat boys don’t really care whether you go or stay because they just conned some funding out of a bunch of clueless money bags who havent quite figured out that this is a house of cards destined to come tumbling down hard.