I went to Squarespace Circle Day 2026 ready to hear what was next for the platform. I came away thinking just as much about what’s next for my own business.
Between the product previews, conversations about AI, and smaller roundtable discussions, the day kept bringing me back to the same question: how do we keep growing without losing the parts of our work that make it ours? For me, that meant thinking about creative judgment, the clients I want to work with, and the kind of business I actually want to run.
A first look at what’s next for Squarespace
The opening keynote offered a sneak peek at Squarespace Forma and an invitation to join the waitlist. If you’re curious, you can explore the preview and sign up for Forma early access.
Later, the conversation with Squarespace founder and CEO Anthony Casalena returned to Forma and how AI could reshape our workflows. Across the day, I was especially interested in the possibilities around AI-assisted building inside the editor and protecting custom work during client handoff.
My takeaway wasn’t that every new feature needs to become part of my process immediately. It was that staying curious matters, while still being thoughtful about what will genuinely improve a client’s website and experience.
Brand Therapy starts with the business behind the brand
One of the most useful sessions I attended was “Brand Therapy: Identity and Clarity for the Business You’re Building,” with Asia David of Die Free Studios. We explored what happens when the business you’ve built no longer quite reflects your vision.
Asia’s Brand Therapy methodology made space for questions that are easy to skip when you’re busy delivering client work. Who am I now? How do I work best? What boundaries would help my business support that?
Sometimes the answer is practical: clients don’t need weekend access to you. Sometimes it means adjusting an offering because the way you enjoy working has changed.
One exercise I’m taking with me is to review every service and package I’ve delivered over the last three, six, nine, and twelve months. Which projects did I enjoy? Which ones would I rather not repeat? That’s useful information for deciding what comes next.
We also discussed beta offerings: a clearly scoped way to learn a new service while being paid, with a lower-budget client receiving a testing-stage offer and contributing feedback, an honest testimonial, and a case study. The bigger lesson was to build a strong foundation first, so future changes become decisions you can work through rather than emergencies.
AI doesn’t remove the need for expertise
The panel “Vibe Coding: Hype, Risk, and Where It Actually Fits” brought together Becca Harpain of Inside the Square, Dave Hawkins of Made by Dave, and Will Myers. The conversation addressed a question many designers are navigating: what happens to the value of our work when AI can help produce it faster?
What stayed with me was the importance of knowing what to ask. Generating a layout isn’t the same as understanding whether it supports a visitor’s journey, makes the next step clear, or serves the business.
Even the less glamorous details came up, like remembering to account for an appropriate privacy policy. A site can look finished while still missing something important.
For me, that reinforced why design fees shouldn’t be reduced to time spent moving things around a page. Clients are also investing in judgment, direction, and the ability to notice what’s missing.
Staying human means staying involved
In “Human by Design: Staying Original and Trusting Your Creative Instincts in the Age of AI,” Clarissa Burton of Clarissa’s Creative Consulting guided a conversation about our changing roles.
We talked about remaining the creative director or project lead, rather than handing over the thinking along with the task. There were honest concerns about trusting AI-generated results and the attention needed to catch inaccuracies.
One participant described us as becoming “curators.” I liked that framing, provided it still means actively shaping the work: choosing, questioning, refining, and making sure the result fits the client.
I don’t want a faster process at the expense of originality. I want tools that leave more room for thoughtful decisions, without taking my responsibility for those decisions away.
A different workflow doesn’t mean starting from zero
That perspective continued in “Building Products in the Squarespace Ecosystem,” with Nick Ippolito of SquareKicker and Will Myers. My takeaway was reassuring: the underlying language of development hasn’t disappeared just because the way we work with it is changing.
I heard that as encouragement to build on what I already know. Experience still helps me ask better questions, evaluate an unfamiliar solution, and recognize when something isn’t right.
Looking at my own brand with fresh eyes
During a brand consultation with Patricia Johnson of Cultivation Studio, we reviewed my homepage and target audience. We discussed how I could expand into more industries while keeping hospitality as an important part of my positioning.
The useful shift was to think beyond industry labels. Who are the people I want to keep working with? What stage is their business in? What are they ready to change?
That conversation helped me think about hospitality as a foundation, rather than a limit. I’m interested in working with people whose businesses have grown and whose brands or websites need to catch up. A website refresh might be the future for me.
Permission to keep creating
Andy J. Pizza’s keynote, “Creative Resilience: Unlock Your Creative Life Force in Challenging Times,” brought the day back to the creative process itself. His discussion of failure reminded me that style and direction develop through making, learning, and trying again.
I left with ideas to explore, questions to sit with, and permission not to have every answer yet. The next chapter doesn’t need to abandon what came before it.
If your business is evolving and your brand no longer feels like the right fit, you don’t need to have the whole solution mapped out. Let’s talk about what’s changed and where you want to go next.
