This post was written in paid partnership with Squarespace. All views and experiences are my own.
A week in New York, built around Circle Day
For the third year running, I built a week in New York around Circle Day. The first year I attended as a regular attendee. Last year I was invited to lead two breakout sessions on growing your own team. This year I was invited to offer brand consultations to three conference attendees who signed up in advance. The conference at Squarespace HQ was in the middle of the week, and around it I met with clients in person, both active projects and projects we completed in the last year or two.
AI, images and Forma
I will be honest about one thing, and I know it is a little paradoxical. AI image creation is a service we offer our clients, it has come in handy many times, and it is good that Squarespace offers it. As a placeholder to get a site launched, it is fine. But I am a little concerned about how it will turn out in everybody’s hands. The tool already exists, so the question is how it gets used in practice. If you are trying to build a trust-based relationship with a client, I think AI imagery removes an element of trust. It can read as if you did not care enough to do a photo shoot or select the right pictures. I am like that as a consumer myself. I would not buy from a company whose site is only AI images presented as real people and real places. Nobody likes to be deceived. If the imagery is clearly AI and that is part of the creative idea, why not. But the eye is getting trained to recognize these images, and poorly executed AI imagery, the AI slop we are all starting to see everywhere, can damage a business more than it helps. More broadly, it is pushing us toward a more uniform visual world, and that worries me as much as the broken trust.
As for Forma, the Squarespace team described it as a way to build, run and connect like never before, and that is the promise. I received early access this week and I have joined the community for it, but I have not yet found the right project to test it on. There is so much it can do that I want a really good idea before I start, so that I am not thinking of it as starting another website but asking how I work with a completely new tool that can, in a way, do almost anything.
The opportunity I see is in business automation and integration combined with a very cohesive look and feel: a high-touch, customized experience for the visitor that is at the same time much simpler for the small business owner, so they can focus on their business. The right clients for it exist.
I do have two open questions. One is what happens to clients who are not very tech forward and may still prefer 7.1? The other is about designers, who are fundamentally visual people, now expressing themselves through words and a chat interface instead of the blocks and raw material that make Squarespace so unique to build with. I am curious to see whether creatives enjoy working this way, and whether clients find the back end approachable or intimidating.
What I’m taking home
There is a tension in all of this that I kept noticing during the week. Work is accelerating toward the automated and the remote, and at the same time we get to decide what we do with the time that frees up. I chose to spend it in person, making connections and getting creative. Getting our time back is, I think, going to be one of the greatest opportunities AI gives us. It clears brain space and capacity, and that is what enables creativity. But we have to be very intentional about how we use that time, whether it goes to our business, to creative pursuits, to parenting, or to the other things that make us human and better people.
The new business tools announced this year (SMS Campaigns stuck in my brain) will matter a great deal to e-commerce businesses, and I do not do a lot of e-commerce, so it is not my place to speak on them. My clients are not the most marketing-oriented people, simply because of their profile. We always want best practices in place, but for them it is less about the highest conversion rate or how many inquiries come in per week, and more about confirmation. Their visitors already want to work with them, whether that is a doctor, a dermatologist, an interior designer or a photographer. They are basically ready to book. What they need from the website is confirmation that this person is indeed who they appear to be, that they are professional, and that they take care of their own online presence and invest in it. The way you do one thing is the way you do everything. That is why so much care goes into each site. My clients want websites that are beautiful, that function well, that are fun to interact with, and that do not make you exhale a sigh of frustration every time you need to change something on the back end. Squarespace achieves exactly that.
Thank you
Thank you to the Squarespace and Circle teams for another year, and to my own team at September Design Studio. This year we also went through our own rebrand and launched a new website, and I believe that website is what earned us the invitation to consult. It is an honor to be invited back, and I am already looking forward to next year.
Looking back at Circle Day 2025
Circle Day 25 Squarespace Headquarters
