How to Prepare for Squarespace Circle Day (Live or Online)
If you’re a Squarespace designer or web design professional, Squarespace Circle Day is one of the best industry events of the year. It’s where the community comes together to learn, connect, and get inspired. This year will be my fourth Circle Day (I’ve attended every single one!), and each time I leave with fresh ideas and connections that shift how I run my business. And if you’ve been following me for a while, you’ll also know that this is my favorite work day of the year!
What Is Circle Day?
Circle Day is the annual conference for creators, agencies, and entrepreneurs who build websites using Squarespace. It's a one-day global event where Squarespace Circle community members and product experts come together to share insights on running a thriving web design business, mastering the platform, and staying ahead of what's next.
Here’s what you can expect:
Grow your skills — with sessions led by both Squarespace staff and seasoned peers.
See what’s next — early previews of new features (often part of Squarespace Refresh announcements).
Make connections — whether you're meeting people face-to-face in NYC or chatting live online.
Get inspired — through storytelling, real client showcases, and genuine community energy
In-person attendance is open to a limited number of Circle Gold and Platinum Partners at Squarespace HQ in New York City, while the online live stream and World Loop encore let global attendees participate from home. And yes, it’s all free.
👉 On social media, use #CircleDay2025 to connect with other Circle members as you plan for and enjoy Circle Day this year!
My First Circle Day (and How It’s Evolved)
My first Circle Day felt like walking into a roomful of friends I hadn’t met yet. Everyone was incredibly welcoming and inclusive. And true to the internet, people have waaaay different heights in real life than they look on Zoom!
One of the highlights was meeting the Squarespace Circle team in person. They do so much for the pro community AND they give amazing hugs. It’s great to connect IRL with the people we email all the time.
Each year, the format has evolved based on feedback. This year promises more opportunities for connection and networking, both in-person and online, and I can't wait. It’s a special kind of event where professional growth and genuine connection go hand in hand.
Here are some tips from me and other Squarespace Circle Members on how to make the most of your Circle Day.
Tips for Attending Squarespace Circle Day In Person
If you’re making the trip to New York City, here are the best tips I’ve gathered from experience:
Stay close to Squarespace HQ. Commuting eats up your energy. I’ve stayed at the Arlo SoHo, small and busy, but clean and close, plus it smells like vetiver and amber. Avoid the Four Points Sheraton, it did NOT smell good (and let’s leave it at that). This year, I’m trying the Washington Square Hotel. It was one of the few more affordable options within a 15-minute walk.
Skip the laptop. Squarespace always suggests it, but I’ve never needed mine. It’s just extra weight. Bring a tote or backpack instead, you’ll load it up with swag.
Come comfy. Dress comfortably and don’t worry about dressing up, unless that's your jam, in which case go for it! But, in general, we're a pretty casual bunch, so don't sweat trying to find the perfect outfit. Everyone will love you just as you are! (Tip from Kristine Neil, kristineneil.com)
Bring your own swag. Many designers bring stickers and branded goodies to exchange. It's a fun way to connect and leave a tangible reminder of the day.
Bring a battery pack. Taking notes on your device can often drain your battery more than you think. (Tip from Dave Hawkins, madebydave.org)
Take Breaks. You don't have to watch every session; feel free to relax away from the main stage with a fellow Squarespacer. (Tip from Will Myers, will-myers.com)
Say hi! If you recognize someone from online or admire their work, introduce yourself. And grab a selfie! It’s a keepsake and a great icebreaker.
Arrive early (and stay a bit after). I fly in a day or two ahead so I’m not rushed. I usually stay a couple of extra days afterward to explore and hang out in New York with other Circle members.
Book your hotel early. NYC prices climb fast, and this year they're especially high. Don’t wait.
Focus on connection. The conversations with fellow designers often leave me feeling just as inspired as the sessions.
Come to the after party (details here). Even if you are tired / jet lagged, you won’t regret it. (Tip from Dave Hawkins)
New for Circle Day 2025
Circle Day can feel overwhelming, especially if you’re introverted (and many of us are). Pause. Breathe. Re-center. If you’re attending in person, the Refresh Cafe is back, where you can grab a beverage, as well as a new Refresh & Watch space where you can decompress, watch online sessions, check email, work on an urgent client request, etc.
Part of the way Circle is expanding the networking opportunities is with dedicated breakout conversations. These feature a variety of topics (making bold business decisions, overcoming a scarcity mindset in creativity, streamlining your web design process, and more). My friend Liz Ellery is even leading one that's purely networking-focused! Each one will be led by a Circle member and is structured to spark meaningful connections. Plus, these sessions will happen twice during the day, so you can attend two, meet different folks in each, and move around Squarespace HQ.
Tips for Attending Squarespace Circle Day Online
If you’re joining virtually, the online version is supercharged to keep you connected:
Book the day out in your calendar. That way you can really immerse yourself in the learning rather than trying to juggle the presentations between client work. (Tip from Hannah Ippolito, squarekicker.com)
Plan your breaks strategically. Review the schedule so you know which sessions to attend live, and when to step away.
Dive into the chat. So much magic happens there. Be present. Ask questions. Say hi. Make friends!
Set up accountability. Text or Slack with friends attending online. Talk through sessions, swap notes, or even grab a virtual coffee.
Take breaks. Seeing everything is tempting, but taking time out helps you stay focused and present.
Watch replays afterward. Even if you attend live, the replays are full of gems you might have missed.
Focus on community and personal connections. I met some of my best business friends first over chat at Circle events, and then in person at Circle Day.
Plan for the future. Put a reminder in your calendar for a date 3 months or 6 months into the future called "Circle Day: Review Notes". On that day, look back at your notes to see if you have implemented your learning - and if not, remind yourself of what you learned and wanted to take forward. Too often we get super hyped around the event time and then life gets in the way of actually acting on our learning! (Tip from Miko Coffey, usingmyhead.com)
Don’t Miss the Aha Moments
Every Circle Day brings at least one idea that shifts how I work. One memorable moment for me was when Kristine Neil talked about running projects in phases and her system for that. It completely changed my process. Keep your ears tuned and you’ll find your own “aha,” too. More about that in 3 Lessons from Squarespace Circle Day 2023.
Bonus: A Meetup for My Students
Here’s a special bonus for The Web Designer’s Playbook™ students: The morning after Circle Day in NYC 2025, I’m hosting a casual student-only coffee meetup. We’ll debrief the day, chat about product updates straight from the team, and connect over what we learned. I think it will become a tradition, and I hope to keep doing it for years to come.
After Circle Day: Keep the Momentum Going
Good stuff happens even after the sessions end. My advice:
Pick one idea you learned and implement it right away. Keep it simple. Make it meaningful.
Share it. Post it on social media and tag who you learned from. This keeps you accountable and helps to inspire others.
Stay engaged in community. After building connections, I’ve felt more plugged into the Circle community than ever. We keep bumping into each other in chats and forums throughout the year, and it’s those relationships that keep me grounded in my business, even when things feel crazy.
Final Thoughts
Preparing for Squarespace Circle Day sets you up for not just day-of learning, but also growth, connection, and real transformation. Block your calendar, pack your bag (or your mindset), and get ready for a day that might just nudge your business (and your creative soul) forward in ways you can't predict.
