Circle Day 2026: One of My Favorite Days of the Year
Last week, I headed to New York City for Squarespace Circle Day, one of my favorite days of the year! This was my third year attending in person, and each year just gets better.
Circle Day is an annual gathering of Squarespace designers, developers, and creative professionals at Squarespace headquarters in NYC. It's a chance to learn about what's coming to the platform, hear from fellow Circle members about their experiences and expertise, and connect with people who do the same kind of work I do. Squarespace founder and CEO Anthony Casalena also joins in to share his perspective on the company and where it's headed.
The Best Part? The People.
One of the things I appreciate most about being part of the Squarespace Circle community is how supportive everyone is of one another.
Most of us work independently or run small businesses, so having a network of people who understand what you do, are willing to share what they've learned, and genuinely want to see each other succeed is pretty special.
By my third Circle Day, I've made more connections than ever, and this year I had friends to meet up with both before and after the event. And, I always love meeting new people, too!
One fun addition this year was the option to be matched with another attendee for a virtual meet before Circle Day. I loved this idea! It's such a simple way to make an in-person event more welcoming, especially for someone attending for the first time.
And that's really what I love about this group. People are generous with their knowledge, genuinely interested in what others are working on, and always happy to connect.
A Look at What's Next for Squarespace
Circle Day is also about learning what's new, and this year there was a pretty big announcement.
Squarespace introduced Forma, a new AI-powered platform for building websites and applications through written prompts. It's a completely different approach from the way we currently build websites in Squarespace, and I'll admit, I'm not entirely sure how I feel about it yet.
I signed up for the beta waitlist because I want to understand what this means for the future of website design and for those of us who have built our businesses around Squarespace.
I also have mixed feelings about the rapid growth of AI in general, particularly when it comes to its environmental impact. The energy and water demands of AI infrastructure are real concerns for me, and I think they deserve more attention as these technologies become part of our everyday work.
I'm curious about the possibilities, but also apprehensive about the direction things are heading. There are still a lot of unknowns about Forma, and I'll be interested to see how it develops.
A Creative Pep Talk from Andy J. Pizza
Another highlight was hearing from Andy J. Pizza, an illustrator, author, and host of the Creative Pep Talk podcast. His keynote was called Creative Resilience: Unlock Your Creative Life Force in Challenging Times, and he was great!
Funny, animated, and full of personality. I think a lot of creative people can relate to the way his mind works, especially those of us whose brains seem to bounce between a dozen different ideas at once.
The Little Things (& the Rooftop Views!)
Squarespace always does a great job with the details. And having spent two decades planning events myself, I know how much work goes into making a day like this happen. From the programming and speakers to the food, logistics, and opportunities for people to connect, there's a tremendous amount of effort behind the scenes. I really recognize and appreciate it all.
And yes, there was swag! I was very happy to add another Circle Day tote and sweatshirt to my collection, along with an Owala water bottle and other fun little things. You know I've been a sticker collector since my elementary school days!
Another highlight is always the rooftop deck at Squarespace HQ! The views are amazing, but with Circle Day happening a month later this year, we got to enjoy a gorgeous October sunset and watch the NYC skyline light up as the evening went on.
And the fun didn't stop there! A bunch of us headed to Houston Hall, a bar around the corner, to keep the evening going.
Already Looking Forward to Next Year
I always come home from Circle Day feeling grateful to be part of this group of people.
Yes, I enjoy learning about new features and seeing where Squarespace is headed. But what keeps me coming back is the opportunity to spend time with other designers, share experiences, learn from each other, and continue building friendships.
When you work for yourself, having that kind of professional community means a lot.
Thanks to the Squarespace team for another wonderful Circle Day, and to all the people who made the trip so much fun. See you next year!
