Why I Hosted a Squarespace Circle Day Watch Party in London
Circle Day is Squarespace's annual summit for Circle members, the professional designers who build client sites on the platform, held at their New York headquarters. I’ve been in person for the past two years. This year I couldn't make the trip, so rather than just watching it alone from my desk, I decided to bring the party to London instead.
Why a watch party made sense
Running a business on your own means most days are spent exactly where you'd expect, at a desk, with a cup of tea for company and very little in the way of other people in the room. The idea of spending a whole day surrounded by other designers who get genuinely excited about new website features was too good an opportunity to pass up, even if the actual summit was happening three thousand miles away.
So I hired a room in a pub in King's Cross, right above platform 9¾, and put the word out to the Squarespace Circle community. Sixteen members came together from across the UK, plus one who travelled all the way from Portugal, to watch the livestream and talk through it together as it happened.
This year's theme: Design Differently
Circle Day 2026's theme was Design Differently, with a lot of the day's conversation centred on AI and how it might shape the future of web design. Squarespace used the summit to announce Forma, their new AI based workspace, and we heard directly from the CEO about where that's headed.
What stood out most wasn't the announcement itself, but the range of reactions in the room. Some designers are already leaning heavily into AI in their own businesses. Others aren't using it at all. There didn't seem to be a right or wrong way to sit with that yet, which was oddly reassuring. For what it's worth, I think it'll be a while before AI becomes part of my own everyday process, and Forma is still in beta, so for now I'm happy to watch that space rather than rush to adopt anything.
One point that came up in our own discussion afterwards and doesn't get talked about enough: AI can help someone build a website, but it can't make that website secure. That's genuinely part of what a platform like Squarespace is doing behind the scenes as standard, and it's easy to overlook when the conversation is all about flashy new features.
On a smaller but practical note, one of the features I'm most excited about from this year's announcements is the ability to lock blocks in place once they're positioned correctly, so they can't be accidentally dragged or nudged out of place while editing the rest of a page. Small, but the kind of thing that makes an actual difference day to day.
The best part wasn't the announcements
As good as the content was, the best part of the day was simpler than any of it: being in a room with other designers, meeting new faces, catching up with familiar ones, and swapping stories about the genuine highs and lows of running a business. As a solo business owner, a day like that is good for the soul in a way that's hard to replicate from behind a laptop screen.
A big thank you to everyone who came along, especially Sandra who made the trip over from Portugal, and to Squarespace and Squarekicker for sending merch for everyone on the day. It made the whole thing feel that bit more special.
Why community matters, even in a solo business
It would have been easy to just watch the summit alone and move on with the day. Taking the time to organise a room full of people instead turned it into one of my favourite days of the year, and a good reminder that running a business solo doesn't have to mean doing everything in isolation.
If you're part of the Squarespace Circle community and fancy joining in next time, or if you just want to know more about what Circle Day covered this year, get in touch, I'd love to chat about it.
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