Squarespace… Squarespace always changes.

Those of you who frequent the post-apocalyptic world of Fallout might have quietly winced at the title above. No need to reach for your Pip-Boy, though. This article does not talk about bottle caps or Super Mutants. It is all about building on shifting ground. Squarespace keeps moving, always with a helpful smile, always offering new features… and always dropping just enough “this has changed” surprises to keep us all on our toes.

For anyone who's ever poured a cup of tea, sat down to film a training video, and then had Squarespace shimmy its interface the very next week, you’ll know this story. If you’re an educator or a creator managing a growing library of web tutorials, the feeling might be less ‘cozy productivity,’ more ‘painting the Forth Bridge with a wet brush:’ by the time you get to the end, it’s time to start again.

And yet, we come back. Why? Progress is better than standing still, and, let’s be honest, we like new toys.

Why This Matters

Let’s cut past the cheery marketing: when Squarespace updates, it causes more than just a fun, shiny progress bar for website owners. For those of us building resources, creating online courses, or managing business sites, it’s a logistical minefield. Modules that took months to script and record are suddenly obsolete. The ‘How to use Summary Blocks’ video now has an interface that exists only in museum exhibits. That might seem like progress or chaos, but either way, the cost is real.

Here’s what’s at stake:

• Wasted time: You might spend weeks assembling clear training materials, only to have them invalidated overnight. Re-recording is never as simple as swapping in a screenshot or two.
• Money lost: Staff hours, freelance rates, and time sunk into work that’s swiftly marked ‘outdated’ equal budget black holes.
• Frustration: Your learners (and customers) will always find the one part you didn’t have time to update before they needed it most.

At Pixelhaze Academy, we’ve rebuilt Squarepspace courses more times than I care to remember. You could set your watch to the cycle: release, enjoy a brief moment of calm, then suddenly, new feature leads to new upheaval. Most recently, we’ve had to dismantle entire chapters to make way for Squarespace 7.1’s latest batch of interface changes.

This impacts more than just educators. If you’re running your own site, it costs you time and revenue to keep up with new workflows, never mind learning how to actually use the shiny new options appearing in your dashboard.

In summary: Squarespace’s constant updates keep us sharp, and they also regularly send us back to the editing suite or the drawing board. If you’re tired of feeling one update behind, you’re in good company.

Common Pitfalls

If I had a fiver for every time a student or client told me, “But the video looks nothing like my screen,” I could probably retire in a small Welsh valley and live contentedly off grid. There are a few classic blunders almost everyone stumbles into at first.

1. Treating Squarespace courses as ‘set and forget’: Many folks put hours into creating beautiful walkthroughs, believing it’ll serve indefinitely. A few months later, an update arrives and the tutorial becomes a trip down memory lane.

2. Trying to learn (or teach) everything at once: The minute you approach Squarespace as a monolith, you’re setting yourself up for an overwhelm session worthy of a Netflix binge. Updates replace panels, buttons move, names change. The big picture is hard to keep up with.

3. Ignoring small UI changes (“I’ll update it later!”): Delay it too long, and suddenly you’re ten features behind, with a jumble of old and new screenshots, and left wondering why your students or colleagues keep sending frantic emails.

4. Neglecting feedback from real users: “It worked for me!” isn’t the same as “My clients/students can follow it.” You’ll always miss something from inside your own echo chamber.

5. Skipping the underlying “why”: When features change, so does best practice. You need more than “do this”—you need to know and explain the thinking behind it, or you're training people to memorise, not adapt.

If one of those sounds like your day-to-day, you’re in good company.

Step-by-Step Fix

Here’s how we at Pixelhaze manage the Squarespace octopus and keep our courses and content useful without burning ourselves out. Use these tips to make your own process easier.

Step 1: Chop the Course into Modules

Before you record a marathon series, stop. Imagine your course is a giant block of cheese. Now slice it up.

When Squarespace changes their Font Picker, it doesn’t affect every nook and cranny of your course. By dividing training into discrete chunks such as ‘Getting Started,’ ‘Page Building,’ ‘Summary Blocks,’ and so on, we only need to re-shoot the impacted modules when the inevitable update lands. We do this as a tactical survival strategy.

Step 2: Build a Flexible Update Workflow

Trying to rebuild your whole course at each update leads to frustration and long nights. Instead, make a checklist for each module: what’s changed, what stayed, which screenshots are now ancient relics. We keep a ‘change log’ for each tutorial, listing Squarespace releases and their ripple effects.

Step 3: Involve Your Audience Early

You won’t be able to spot every change yourself, but your learners will (often at the least convenient moment). Set up a simple feedback channel: a form, a private email, or even a post-course survey. Ask specific questions (“Did anything look different for you in the latest update?”), and log all confusion. Over time, those emails are golden clues on where your next bite-sized update is most urgent.

Step 4: Prioritise Big Changes Over Cosmetic Tweaks

Not every Squarespace update requires urgent action. When they add a completely new panel, overhaul the Page Editor, or change how blocks are added, you should update the relevant modules as soon as possible. If it’s just new button styling or minor colour options, stay calm and update on your regular schedule.

Step 5: Create Advanced Modules for Experienced Users

Some students want to push past Squarespace’s training wheels. Rather than include advanced code injection tips in your standard intro modules, create a ‘Stretching Squarespace’ (or another advanced module) section. This section is ideal for using Chrome’s Property Inspector, custom CSS, workarounds for limitations, and so on. It gives advanced learners the details they need without overwhelming your beginners.

Step 6: Keep Improving Production Quality

Learning about professional web design is much harder when distracted by poor audio. We started with a kitchen table and a basic microphone. Now, after student nudges (read: polite memes), we’ve built a purpose-made sound booth and upgraded our audio kit. If you’re serious about web teaching, invest in basic upgrades such as a pop filter, room dampening, and proper lighting. Your learners’ ears will thank you.

What Most People Miss

Textbook guides and YouTube creators rarely share this: when you use Squarespace, you’re really learning how to adapt and learn as the platform changes. The product keeps evolving. If you approach it with a fixed mindset, confusion and chaos are almost guaranteed.

It’s easy to get stuck in the loop of “I’ve learned the current setup, job done.” That sense of completion is always temporary. If you expect and design for change from the beginning, you can respond effectively and with confidence every time the “What’s New” banner flashes across your dashboard.

You gain an advantage by tying your expertise—and your course videos—to the underlying principles rather than just this week’s UI. Explain why Squarespace moved that feature and what problem it solves. That way, when things shift in the future, you and your students aren’t starting from scratch. You’re simply applying your understanding in a new context.

The Bigger Picture

Learning a platform like Squarespace is more like a dance marathon than a sprint. Once you accept the rule changes mid-step, you begin to see true value in adapting your process. By working with regular updates and making change part of your method, you get:

• Massive time savings – you avoid course-wide rewrites each quarter and need only targeted updates.
• Stronger reputation – when your training matches the current version, people trust you and come back.
• Less waste – your resources adapt instead of being discarded. Course content lasts longer.
• Happier learners – nothing frustrates a student more than following a tutorial and hitting an “outdated” wall.

And, perhaps most important in our corner of online teaching: you stay ahead, not behind. Treat it as surfing the update wave rather than trying to outrun a flood.

Wrap-Up

Squarespace will keep changing. That’s good: new tricks and features benefit users and deliver moments of genuine excitement when something just works. It is also a challenge. By breaking material into modules, treating updates as part of the process, and paying attention to feedback from real users, you will spend less time scrambling and more time creating.

If you want ongoing practical systems and the occasional developer’s experience, join Pixelhaze Academy for free at https://www.pixelhaze.academy/membership.

We've done more than our fair share of Forth-Bridge-style repainting so you don’t have to. Let’s keep building and rebuilding with better results.

Related Posts and Extra Credit Reading:

• Combining Canva with Squarespace – Part One: Why integrate Canva graphics, and how do you get started? Real-world examples inside.
• Unlock Your Web Design Potential with our Squarespace Box of Tricks Course: The box is open, the tricks are new. See what’s changed for 2023 and save hours in your workflow.
• Three ways to display images in Squarespace 7.1: If you want that magazine look, Elwyn walks through three practical layouts with step-by-step guidance.
• Hyperdrive video tutorials: Lightning tutorials for daily Squarespace fixes. These guides help you solve problems efficiently.

Want more? That membership link above is your golden ticket.