Circle Day 2026:The Trip, the Talk and the People
I built my first Squarespace site in 2014. In October I walked into their New York head office to speak on the main stage at Circle Day. Here's everything that happened, everything they announced, and what I'm still thinking about.
Will Myers, Becca Harpain and Dave Hawkins
Gate A17, 08:15
Out of the windowLanded at JFK
We'd left the cold, wet rain of London behind, and walked out of the terminal into beautiful sunny New York skies. It was really refreshing. After a great trip over, it felt like the perfect way to start.
The AirTrain
From the terminal, the AirTrain to Jamaica.
The Long Island Rail Road
From Jamaica, across Queens towards Penn Station.
Into Penn Station
Under the river and into Manhattan.
The 1 to Houston St
I'd never used the subway before. I've always gone for Citi Bike, so I thought I'd give it a chance. I got on the wrong side and had to work out which way was downtown and which was uptown. An interesting moment. Then down to Houston St, and up out of the subway right by Varick Street.
Base camp in Chinatown
I wanted to be within a short walk of Squarespace HQ. It's always nice to be around.
Rehearsals at Squarespace
Then over to Squarespace HQ for the first time, to rehearse ahead of the big day.
Dinner in the West Village
Dinner for the speakers and community leaders, the night before the big day. We had pizza and a great time. We met loads of people, and it was great to catch up and do community, just chatting over food.
Blank Street, on my own
Just around the corner from HQ. Very, very surreal. I sat there thinking about the day ahead, while messages came in from people in London commuting in for the London meetup. That was really fun to see.
A pinch me moment
Getting the invitation to speak at Circle Day, I genuinely didn't think it was going to happen.
Then I walked into the foyer of the head office, and there was a screen showing the names of everyone speaking and presenting. I'll be honest, I welled up a bit.
Twelve years of building websites, and here I was, at the company whose platform I've built my whole working life around.
The day itself
- 01Intro from PunoOur host
- 02Opening keynoteThe Squarespace team
- 03Breakout conversations10:20 AM
- 04Vibe coding: hype, risk, and where it actually fits11:25 ET. That was us.
- 05Lunch
- 06Anthony CasalenaCEO and founder of Squarespace
- 07Breakout conversations2 PM, a repeat of the morning
- 08Building products in the Squarespace ecosystemNick Ippolito and Will Myers
- 09Product deep diveThe Squarespace team, on the new platform they've made with AI
- 10Andy J. PizzaCreative resilience: unlocking your creative life force in challenging times
- 11Happy hourRefreshments, then up onto the roof
Vibe coding: hype, risk, and where it actually fits
Me, Becca Harpain and Will Myers on the Circle Day stage. All three of our businesses have changed in the last twelve months, so we talked about where each of us draws the line. Here are the lines that stuck.
Watch the talk
On stage
With Becca and Will, talking about how AI changed all three of our businesses this year.
Will: don't be a tool
Will's graph of how good AI is at our work. His point: wherever you put the dots, they're all moving in the same direction. Scroll and watch them move.
Would anyone care if a person did this?
Will splits the job into tool work you can hand off and human work you shouldn't. Try it yourself, then see what we said.
Drag the ticket, or tap a pile
Me: to vibe or not to vibe
I think we're living through our generation's printing press moment. It didn't make writers redundant. AI doesn't replace the designer. It adds to the craft. So the real question isn't whether to vibe. It's how we use it, and when it matters.
Pages in one brief
A clearly AI-written brief. Two pages in, I was out. So my AI talked to their AI, I got it down to one page, priced it, and sent a quick prototype as a Site Viewer link I could switch off. My job wasn't to read 56 pages. It was to be the consultant.
Skim-read email
AI pulled the facts together, I skim read it and sent it. Then: "Did you write this? It felt really cold." I hadn't. People can't always name it, but they can feel it.
Free work for this client
I gave AI a proposal to draft and it wrote that the client was basically going to do a whole load of things for free. I told it off like it was a real person.
What AI gets
The intern jobs. The boring, rinse-and-repeat stuff.
What I keep
- Tiny jobs like hex colours
- Tone of voice
- Pricing
- Scoping
- The big creative idea
Your clients are paying for your judgment, not your keystrokes. You're the brick wall before anything goes out the door.
Becca: when AI has to guess, you end up with a mess
Becca met someone at an AI event with a paid app and over a hundred beta users. It was built with AI, and this is what it didn't have. AI can build the thing. It can't answer the questions clients don't know to ask.
- Terms and conditions
- A privacy policy
- Submitted to Google
- A 404 error page
Her fix for made-up code is to stop letting it guess: pull the real source code out of the section you're editing and hand it over.
Our hopes for the future
Will
Less stuck in front of a computer, and more time connecting with people.
Becca
Now efficiency is easy, authenticity is worth more than ever. She hand-drew her new site's details with a giant Sharpie at the kitchen counter.
Me
I get to be the driver. I tell the system what I want in plain English and it takes care of the clicking. I still get my hands on it. Creativity stays with us. We just get to do more of it, quicker.
That's why so many of us are in this room. We've learned from each other, and we're here to cheer each other on.
The Q&A, in short
What tools are you all on?
Claude, pretty much across the board. Canva does way more than people think, too.
What about clients sending over their AI chats?
Ask for it on one page, in their own words. Often they just want to feel heard, so a quick call goes a long way.
What can you finally fix now?
Old sites held together with string and glue. Rescuing AI builds that went wrong is turning into a proper service too.
Are digital products done for?
Honestly, nobody knows yet. Things are shifting towards community, people and teaching confidence.
Do you tell clients you use AI?
You're paying for expertise, not keystrokes. And if AI is touching client details, tell them.
And off we came.
Coming off stage at Squarespace HQ, in front of a packed room.
Forma
The upcoming AI-native platform for building the custom software and workflows that power your business.
With 2026 very much being the year of AI, you can see why Squarespace built a brand new product to meet that moment. Forma was the big announcement of the day, and we saw more of it in the product deep dive.
It's early days, and I'm looking forward to getting stuck in. Want to be among the first to try it? Sign up to the waitlist and you'll get an email as soon as you have access.
Join the Forma waitlistExplore the releases
It's the people who make Circle Day so much more than an event.
Happy hour on the roof. The views are stunning, but it's this lot you remember.
Circle Day in pictures
The morning after
I was super jet lagged and knew I'd be up early anyway.
A bike ride to Williamsburg
So I took a bike from the hotel over to the Williamsburg waterfront, met a friend and went to the gym. Not strictly part of Circle Day, but a good way to explore the city.
Breakfast
Then back over the river to Greenwich Village, where the guys at SquareKicker and Eventually Ticketing put on a lovely little breakfast. After a big day, it was a slower moment to properly connect, and catch up with people you'd only managed a quick hello with the day before.
The food tour
From breakfast, a group of about 12 friends walked up to Chelsea Market. Mostly an excuse to eat, and eating is very important. We had pizza, coffees and all sorts, and it was a chance to walk, talk and reflect on everything we'd just been part of.
The waterfront and the High Line
We wandered around Chelsea Market, down to the waterfront, then up onto the High Line. We could see all the way out to the Statue of Liberty.
Exploring Dumbo
I'd never seen Dumbo, or that part of the city, and I really wanted to explore it. So I took a bike over one bridge, came back over the other, and just pinged my way around.
Back to the hotel
A bit more walking around and exploring, then I picked up my things and headed back to the subway.
Lost in the station
I took the train back the same way, from Grand Street towards Penn Station. My phone signal dropped in the station, I got a little lost, and I had to get out and walk a bit. Which is how I ended up walking past Macy's and seeing their Christmas decorations out.
Flying home
Then the AirTrain back to JFK, the same way I came, and home.
One square. My first Squarespace site.
All the Squarespace City Leads got together during the event.
The websites were never really the point. It's always been the people.
Some of you I'd only ever known as a little head in a Slack group. It would have been a very different trip without you, and a lot less fun.
