ThinkInsideTheSquare

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AI can write our emails, help us design websites, automate repetitive tasks, and solve problems in seconds. But is all that efficiency making us more creative, or just giving us new ways to avoid doing the creative work?

After Squarespace Circle Day in New York City, I sat down with six creative professionals to talk about AI, creativity, and the pressure to produce more.

And wow, did they have some thoughts.

We're talking about the temptation to automate everything, what happens when we outsource our creative thinking, and how to protect the unique perspectives that make our work worth sharing.

From AI-powered editing tools that create more work to the surprisingly relatable experience of spending hours automating a task that takes minutes, these conversations are full of reminders that being more efficient doesn't always mean being more creative.

In this episode, you'll hear:

• Why AI-powered efficiency doesn't always save time
• How relying on AI for content creation can affect your creative process
• Why your personal voice matters more than perfectly polished content
• How to recognize when automation becomes procrastination
• Where creative professionals are drawing their own boundaries with AI
• Why human creativity is still the most important ingredient in great design

I love using AI to help bring creative ideas to life. But I don't think we need to fill every minute we save with more things to produce.

Sometimes, the best thing we can do with that extra time is simply make something because we want to.

Episode Chapters

00:00 AI, creativity, and efficiency after Squarespace Circle Day

01:33 Christy: AI content creation and finding your authentic voice

03:39 Aaron: When AI productivity tools make us less efficient

05:51 Monica: Can AI make creative writing harder?

07:46 Will: When AI automation becomes procrastination

09:19 Kristine: Why human creativity still matters in web design

10:29 Sam: Using AI for research without losing your creative voice

12:15 Becca: Making more time for creativity in an AI-powered world

Meet the Guests

Christy — Squarespace Designer
https://christyprice.com/

Aaron — Sueño & Co.
https://www.suenoandco.com/

Monica — Hold Space Creative
https://www.holdspacecreative.com/

Will — Squarespace Developer & Educator
https://www.will-myers.com/

Kristine — Squarespace Designer & Strategist
https://kristineneil.com/

Sam — Culture Boy
https://cultureboy.substack.com/

More From Inside the Square

Explore more episodes of Think Inside the Square:
https://www.insidethesquare.co/podcast

Visit Inside the Square:
https://www.insidethesquare.co/

I'd love to hear your thoughts! Has AI helped you become more creative, or have you noticed yourself spending more time working with AI than getting things done?

Let me know in the comments or email me at [email protected].

And as always, have fun with your Squarespace website!

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

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I redesigned my website.

Again.

Yes, this is the second time this year. Apparently some people buy sports cars during a midlife crisis; I apparently rebuild websites.

But this time, I went much further than swapping a font and moving a few sections around. I changed the structure of Inside the Square, retired hundreds of old pages, created new content, changed what I want the site to be known for, and rebuilt the entire thing around where the business is going next.

And while the new design is a lot more fun to look at, this episode isn't about the design.

It's about everything I did behind the scenes so Google wouldn't wake up one morning wondering where my entire website went.

In this episode, I'm talking about the difference between a website refresh and a true redesign, what to check before you launch, what needs to happen immediately afterward, and why your work isn't quite finished when the new site goes live.

And yes, the new Inside the Square is officially live.

It's weird. It's handmade. There are doodles I drew on my kitchen counter, crumpled pieces of paper I photographed, strange little animations, and considerably more personality than the last version.

Maybe considerably more personality than any version I've made before.

Go explore the new site at insidethesquare.co.

And if this redesign has you thinking about what you could do differently with your own Squarespace projects, enrollment for Beyond the Basics is officially open too.

Beyond the Basics is where I teach Squarespace designers how to take the ideas that don't fit neatly into the standard settings and turn them into working solutions with AI — using your Squarespace expertise to direct the process instead of hoping AI magically figures it out.

Use the tools. Trust your judgment. And most importantly, have fun with your Squarespcae website.

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

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Some of the worst website design decisions start with perfectly good advice.

Keep everything above the fold. Make your content scannable. Keep your layouts consistent. Make your buttons stand out. Add more interactivity.

Sound familiar?

In episode 105 of Think Inside the Square, Becca takes a closer look at five common design principles that can make a website less effective when they're treated like rules instead of guidelines.

From overcrowded hero sections to repetitive layouts and animations that compete with the content, we're talking about why context matters more than following every so-called best practice.

In this episode:

• Why everything important doesn't need to fit above the fold
• The difference between scannable content and content that's too short
• Why consistency doesn't have to mean repetition
• How too many calls to action can create confusion
• When website animations become distractions instead of enhancements

Good design isn't about memorizing more rules. It's about knowing which decisions make sense for the website you're creating.

Resources

Explore more Squarespace design resources and find the episode transcript at https://insidethesquare.co/podcast

About Think Inside the Square

Think Inside the Square is a podcast about thoughtful website design, creative possibilities, and making Squarespace uniquely yours.

Hosted by Becca from Inside the Square.

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

In this episode of Think Inside the Square, I’m talking about one of the biggest shifts in the way I approach Squarespace projects: start with what the website needs to do, then decide how it should look.

We’ll look at why the names Squarespace gives its features don’t have to determine how you use them, how collections can become surprisingly flexible content systems, and why starting with the platform’s existing structure can save you from hundreds of unnecessary lines of custom JavaScript.

I’ll also share a real project where a portfolio’s SEO description became part of the visible page design with a little AI-assisted coding. Because sometimes the clever workaround is absolutely worth it. And sometimes the smartest thing you can do is use Squarespace exactly the way it was built.

Show notes: insidethesquare.co/podast/104

CHAPTERS

00:00 Building a staff directory in Squarespace
01:55 Start with function, not design
03:06 Why a blog works for more than blogging
05:08 Avoid unnecessary custom code
08:29 How to choose the right Squarespace feature
09:32 A creative portfolio + AI coding workaround
11:35 When to get clever — and when not to

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

AI has become an essential part of my workflow as a Squarespace designer. So when I came back from maternity leave, I added a new question to every potential client call: How comfortable are you with me using AI as part of this project?

In this episode of Think Inside the Square, we're talking about the awkward part of using AI professionally: disclosure. What should your Squarespace clients know? Do you need to tell them every time AI helps you write CSS or troubleshoot JavaScript? And what happens when a potential client says they don't want AI involved at all?

CHAPTERS
00:00 How I Disclose AI to Clients
01:44 AI in the Squarespace Workflow
04:17 AI Tools vs. Designer Expertise
06:04 When Clients Don't Want AI
07:50 AI, Client Data & Transparency
09:18 Why Your Expertise Still Matters
13:18 Setting AI Boundaries With Clients

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

Your next web design client might already have an AI-built website.

AI can help someone get surprisingly far into a website project. They can create layouts, generate copy, choose images, and build something they're genuinely excited about.

And then they hit the part where the website actually has to work.

In this episode of Think Inside the Square, I'm talking about what I think is an emerging service opportunity for web designers: taking an AI-built website and getting it across the finish line.

Because the real problem isn't necessarily that an AI-generated website looks like AI. The bigger opportunity is improving the parts AI hasn't finished: functionality, accessibility, responsiveness, maintainability, design judgment, brand personality, and the overall structure of the website.

For Squarespace designers especially, this may mean entering the project much later than we're used to. The client has already started;  our job is to finish it.

In this episode:

• Why making a website “look less like AI” shouldn't be the main goal
• Why familiar AI design patterns aren't necessarily the biggest problem
• How clients are starting website projects differently
• What it means to finish an AI-built website
• Why designers may start entering projects at the 60–80% mark
• How Squarespace can simplify an unnecessarily complicated AI-built setup
• Where accessibility, usability, branding, and design judgment still matter
• Why this work starts to look more like consulting than traditional website design

If clients are starting to bring AI-built websites into your inbox, I'd love to hear what you're seeing. Email me anytime at [email protected].

Full episode transcript & resources: insidethesquare.co/podcast

Hire me to build your AI design on Squarespace: insidethesquare.co/hireme

Questions or something interesting happening in your own Squarespace business? [email protected]


The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with or endorsed by Squarespace, Inc.

#SquarespaceDesigner #AIWebDesign #WebDesignBusiness

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

I built a Squarespace membership site, even though I’m definitely not a fan of Squarespace Member Areas. 😂

In this episode, I’m sharing why Squarespace was still the right choice for this particular project, plus the parts of the member experience that continue to drive me bananas: the avalanche of signup emails, the limited control over the account interface, and the surprising lack of search for paywalled content.

We’ll also talk about the bigger question I think matters more than Can Squarespace do this?

That question is: Should you use Squarespace to do this?

Because the best platform isn’t always the one with the longest feature list. It’s the one that gives your specific project what it actually needs.

In this episode:

• Why I chose Squarespace Member Areas for The Archive
• Where the signup and account experience falls short
• Why I had to create my own search workaround
• When Squarespace can be a great fit for membership content
• When you should probably use a dedicated membership platform instead

Mentioned in this episode:
The Inside the Square Archive: tutorials.squarespace.com

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

For years, Inside the Square was built around answers.

Someone had a specific Squarespace problem. They searched for a solution. I made a tutorial that helped them solve it.

That model worked incredibly well, until the way people found those answers started to change.

Squarespace can now handle many customizations that once required code. AI can generate code, layouts, copy, ideas, and technical answers in seconds. But just because the answer is easier to get doesn't mean the decision is easier to make.

And that's the shift I'm exploring in episode 100.

The problem I built my business around hasn't disappeared. People still want more control over their Squarespace websites. But the way they solve that problem is changing — which means the way I help solve it needs to change too.

In this episode, I'm sharing what that realization means for the future of Inside the Square, why I think value is shifting from knowing the answer to knowing what to do with the answer, and how you can use the same idea to think differently about your own work.

In this episode:

• How one tiny CSS tutorial accidentally became Inside the Square
• Why the business model that worked in 2019 doesn't make as much sense today
• The difference between the problem you solve and the method you use to solve it
• Why easier access to answers doesn't automatically lead to better decisions
• Where experience, judgment, taste, and perspective become more valuable
• What the next chapter of Think Inside the Square will focus on
• Three questions to ask when technology starts changing your industry

AI is already showing up in Squarespace client projects in some pretty unexpected ways. My new resource, Now What? walks through six real situations I've encountered — from AI-generated code and mockups to questionable copy and complicated client expectations — and how I'm thinking through my response.

→ insidethesquare.co/nowwhat

Have a weird AI/client situation of your own? Send it my way at [email protected].

Most importantly, have fun with your Squarespace website.

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

Will Google penalize your Squarespace website because you used AI to write your content or code? Not automatically, but what you actually publish still matters. In this episode of Think Inside the Square, I’m breaking down what Google currently says about AI-generated content, how to review AI-written copy before adding it to your Squarespace site, and why AI-generated CSS and JavaScript deserve an extra layer of scrutiny. We’ll also talk about the SEO features Squarespace already handles for you, AI-powered search, llms.txt, and the three questions I ask before publishing anything AI helped create.

Important Chapter Timestamps
00:00 Does AI-Generated Content Hurt SEO?
02:07 What Google Actually Says About AI Content
04:19 What to Check Before Publishing AI Content
05:24 Is Your AI Content Original Enough?
06:52 Does Your Content Actually Answer the Question?
07:50 AI-Generated Code on Squarespace
10:05 What Does the Website Visitor Experience?
11:15 Does Squarespace Already Have a Solution?
12:32 Squarespace SEO in the Age of AI Search
14:10 llms.txt + My Final Answer

For a full transcript, resource links, and summary, visit insidethesquare.co/podcast/99

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast

Send a message to InsidetheSquare

If I teach people about Squarespace, why don't I sell my digital products on Squarespace? It's a fair question — especially considering digital products have been at the center of my business for years.

I actually did start on Squarespace. In this episode, I walk through why I eventually moved my digital products somewhere else: the customer experience after purchase, the amount of support and follow-up the system created, and the costs that started adding up as my sales volume grew.

We'll talk about expired download links, the three-email membership experience, and why something can technically work while still not work well for your business.

I also cover where I think Squarespace is a great choice for selling, including physical products, services, limited releases, and simpler digital downloads. And if you're deciding where to sell your own product — or helping a client make that decision — I'll give you the three questions I think you should ask before choosing a platform: What are you selling? What's your volume? And what happens after the sale?

Plus, in the show notes you'll find three alternative platforms worth exploring for digital products: Flodesk (my personal favorite), SendOwl, and Payhip.

Full show notes, transcript, & resource links: insidethesquare.co/podcast/98

Timestamps

00:00 Why I don't sell my digital products on Squarespace
01:00 The 34-page PDF that started it all
02:20 Expiring download links and the support problem
03:38 When something technically works but creates a bad customer experience
05:21 Follow-up emails and digital product delivery
06:20 The Squarespace membership experience
08:03 The hidden cost of a system that requires constant effort
08:42 When fees started changing the equation
09:25 Squarespace can still be a great selling platform
09:47 New Squarespace tools for limited releases
10:53 When Squarespace might still be the right choice
11:14 Three questions to ask before choosing a selling platform
11:28 Question 1: What are you selling?
11:48 Question 2: What's your sales volume?
13:05 Question 3: What happens after the sale?
13:49 Retiring the digital product that started it all

Support the show

The term "Squarespace" is a trademark of Squarespace, Inc. This content is not affiliated with Squarespace, Inc.

 For a transcript of this episode, along with the links to any resources mentioned, visit insidethesquare.co/podcast