My NYC Adventure: Circle Day 2025 at Squarespace HQ

Sep 22

I've just spent two days at Squarespace HQ for Circle Day - their annual summit for pro designers - and my brain is still trying to process everything I learned.

But I had to share it with you while it's all still fresh, because what's coming to Squarespace is going to change everything for website owners (in the best possible way).

This Year Was Different

Last year's Circle Day felt more like a general celebration of Squarespace. This year it was laser-focused on us pro designers and how Squarespace can eliminate the need for custom code.

The rollouts they showed us are absolutely mind-blowing. We're talking animations, 3D effects, custom font uploads directly to your website, and enhanced AI tools that'll help with every element of your business - not just website support.

But here's what got me most excited: this means more freedom for you.

All those times you've wanted to update something on your website but thought "I'll need to ask Ruth to code that" - those days are numbered. You'll be able to make changes that previously required a designer or developer, all through Squarespace's interface.

It's taking us one step closer to websites that truly work as multi-purpose business tools, not just pretty digital brochures.

Beyond the Tech-y Stuff

This year also featured breakout sessions, which meant chatting with other designers in smaller groups instead of just sitting in a massive auditorium.

The first session I attended was with Nick from Squarekicker, all about finding your "why" in business. He asked us to really dig deep into what drives us beyond just "I build websites."

For me, the answer was crystal clear: I want to encourage possibility.

Yes, I'm a web designer and I can build you a lovely website. But why do I do it? Because I love helping people realise their dreams. I want to cheerlead others at the start of their business journey and help them believe in themselves through the power of a website.

That's why you'll only ever work with me throughout your entire project - because I genuinely LOVE this work and the transformations I get to witness.

The second session was hosted by Liz Ellery (also from the UK!) about intentional networking. I'd met Liz at a London meet-up previously, so it was lovely to see a familiar face across the pond.

Pushing Myself Out of My Comfort Zone

If I'm being honest, I was a bit shy at last year's event. This year, I made a conscious decision to push myself out of my comfort zone and actually talk to people.

Best decision ever! I made genuine connections with fellow designers Kessiah and Shannon, and we spent Thursday exploring NYC together. We walked the High Line, grabbed snacks by Madison Square Garden, and ended the day with drinks on my hotel's rooftop bar watching the Empire State Building light show.

There's something so uplifting about connecting with people who understand exactly what it's like to run a creative business. We swapped stories about difficult clients (we've all got them!), celebrated each other's wins, and shared practical tips that I'll definitely be implementing.

The Tourist Bits

Of course, I couldn't go to NYC without doing some proper exploring! Beyond the designer hangouts, I:

Walked the Brooklyn Bridge at sunrise (hence waking up at 5:30am every day - not by choice!)
Took a food tour of Chelsea Market (highly recommend if you're ever in the city)
Got a behind-the-scenes tour of Grand Central Station
Met up with old friends for dinner in Times Square

Every morning I'd wake up pinching myself that this was actually my life. A few years ago, I was worried about paying rent. Now I'm flying to New York for business summits and making friends with designers from around the world!

The entrepreneurial journey is wild, and sometimes you need these moments to pause and appreciate how far you've come.

What This Means for You

I won't lie - I feel a little overwhelmed by all the new features coming to Squarespace. They won't be publicly available for a few weeks yet, so I've got time to properly digest everything and figure out how to best use them.

But I do know they'll only enhance what I'm able to offer clients, and more importantly, they'll enhance how your website supports your business.

Imagine being able to add professional animations without touching a line of code. Or uploading your exact brand fonts instead of being limited to Squarespace's library. OR having AI tools that help you write better copy, optimise for SEO, and even suggest design improvements.

It's all coming, and it's going to be incredible.

The Bigger Picture

This trip reminded me why I love what I do so much. It's not just about building websites - it's about the ripple effect (if you read this post, you’ll know all about this!)

When someone finally has a website they're proud to share, everything changes. They show up differently in their business. They feel more confident. They attract better clients. They charge what they're worth.

That's the real magic, and that's why I'll keep flying across oceans to learn how to do it even better.

If you've been on the fence about getting your website sorted, know that the tools and possibilities are only getting better. But more importantly, remember that behind every great website is someone who believed in their business enough to invest in showing it off properly.

That someone should be you.