Less Hustle, More Calm: My Takeaways from Squarespace Circle Day 2025

I’ve been making my way through my notes from Squarespace Circle Day 2025 (you can watch the replays here), and as always, it’s a mix of inspiration, new tools, and big-picture reminders about how we build our businesses. There were plenty of product updates and clever ideas, but the thread that stood out to me most was this: we don’t have to keep hustling at a frantic pace. There is another way — one that feels calmer, more grounded, and ultimately more sustainable.

Here are five takeaways that stayed with me:

01. Lead with strategy, not just design

Connie Holen’s session (Connie runs Pixality Design) reminded me how easy it is to fall into the role of “just the designer” — when actually, the value we bring is so much bigger. Clients aren’t only paying for pages on a website; they’re paying for our experience, insights, and ability to guide them. That means leading conversations around their goals and marketing, and weaving strategy into our process from the very beginning.

It also made me reflect on how I present myself. Am I communicating that strategic value clearly enough? Or underselling it by packaging it as “extra”? A good reminder for me (and maybe you too) that expertise belongs upfront, not hidden at the edges.

02. Redefine success in calmer terms

Marya Nguyen’s (from Yangu Web Studio) talk hit me right where I needed it. She asked: “What does success even mean to you?” and honestly, I had to pause the recording and sit with that for a while. Too often, I catch myself managing my business like it’s a series of small crises — rushing through, pushing past my limits, trying to prove I’m keeping up.

Her invitation to realign instead of push through was exactly what I needed. What if success didn’t look like constant motion, but instead felt like breathing room? What if I trusted that creating from rest could actually lead to better results than forcing myself forward in urgency?

03. Choose tools that lighten the load

Of course, Circle Day came with a stack of shiny product updates — the new Circle Dashboard, expanded payment options, Beacon AI, and more. There were also third-party tools like SEO Space and Tiny Currency that promise to make our work easier.

But the truth is, I don’t need them all. The temptation is always to try everything at once, but the calmer path is to choose what genuinely supports my workflow and reduces stress. For me, that means starting small: testing one tool at a time and letting it earn its place, instead of piling on more complexity.

04. Remember that clarity is everything

One phrase that stuck with me was: “Clarity is for sale.” And it’s so true. Clients are often overwhelmed with decisions, content, and tech. When we step in with a structured process — project briefs, checklists, even simple content workbooks — we’re not “over-delivering,” we’re giving them something they will happily pay for: peace of mind.

This was a gentle nudge to notice where I’m already doing this informally, and to stop treating it as a free extra. Instead, I can lean into it and package it more intentionally, so that both my clients and I feel aligned.

05. Make one shift at a time

The sheer volume of ideas I scribbled down from Circle Day could easily tip me back into hustle mode. Starter templates! Live-feedback sessions! New discovery call questions! Refined services! Pricing experiments! The list goes on.

But one piece of advice really grounded me: don’t do it all at once. Choose one shift you can make this month. That’s it. I love this because it creates a sense of movement without the overwhelm. For me, I’m leaning toward refining my discovery call questions first, and letting that be enough for now.

Final thoughts

Squarespace Circle Day 2025 reminded me that building a business doesn’t have to feel like constant scrambling. Less hustle, more calm. Success isn’t just about growth charts or endless output — it’s about creating in a way that honours our values, our capacity, and the kind of life we actually want.

I’d love to hear from you — if you were at Circle Day (or have been catching the recordings), what’s one idea you’re taking forward in a way that feels less like hustle, and more like calm?