Thoughts on Squarespace’s Circle Day & In-Person Meetups

A few weeks ago I went to NYC to attend Squarespace’s first-ever Circle Day. It was an in-person event held at their headquarters in lower Manhattan, and it’s geared towards supporting Circle Members in the Squarespace community (us elite few… j/k, there are actually in the 10’s of thousands of Circle Members according to Squarespace). 

I assume a lot of you reading this, like me, work remotely at least some of the time — if not all the time. The web-dev community has always been largely remote, and thanks to that pesky little pandemic a few years ago now a lot of the world is as well (or at least can be). This was the first in-person work-related event I’ve been to in a long time, and I was curious to see how it went. 

High-level, I thought the event was great. The Squarespace offices are really cool, the speakers were solid, and the Squarespace team members were awesome and incredibly supportive of the “pro-user” community.

Moreover, there’s a special kind of fun that happens when you meet people you’ve only ever interacted with virtually. 3D! There’s an awkwardness at first, we’re all nerds at heart, but it quickly turns into a conversations-with-old-friends feeling. The community-building aspect was for sure my highlight of the event.

Will with Christy & Omari

Got to hang out with Christy and Omari, two long-time Squarespace friends.

 
 
Will, Ren, Nick & Rowan wearing ponchos

We went to see Blue Man Group with Nick and Rowan from the Squarekicker team, and clearly we had a blast.

I was reminded of the magic that happens when you get together with people in real life. I won’t make an argument that working in person is more “productive” than working remotely, but I will say that being with people in person creates these little sparks of opportunity and connection that would fizzle out over a virtual interaction. I left New York feeling inspired, motivated, and more connected to a community than I’ve felt in a long time. 

I think the world is still trying to figure out the role of in-person events in a largely-virtual work environment. It can be hard, especially as small business owners, to justify the cost of things like flights and hotels in Manhattan for an event with no measurable outcome. But people intentionally choosing to be in places together lays the groundwork for all kinds of cool things to happen, and personally, I think the cost of the trip was well worth it. I’m looking forward to attending again next year (hopefully we’ll see some of the Squarespace executive team show up in person next year too), and grabbing a beer with all my Squarespacer pals again. 

In the meantime, I’m currently based in Atlanta (which could change at any moment, my wife is a nomad at heart), and if you find yourself anywhere nearby, I’d love to get together in person and grab a coffee sometime. 

Keep Building,
Will

Will Myers

I support web designers and developers in Squarespace by providing resources to improve their skills. 

https://www.will-myers.com
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