We break down the biggest updates from Squarespace Circle Day, why this year felt different, and what matters for your client work. We cover Finish Layer in ProTools (animations, layers, grouping with Stacks, hide on mobile, copy and paste styles), the new custom fonts workflow, Circle dashboard upgrades that reduce Impact headaches, connected commerce and extensibility for stronger integrations, and Beacon AI, including SEO help for LLMs.
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AI is transforming everything, from how we work to how we build businesses. But what does that actually mean for entrepreneurs and creatives like us? Are we on the brink of losing our jobs… or stepping into a new era of possibilities?
In this episode of Somewhat Useful, Christy and Will have an honest, slightly nerdy, and surprisingly hopeful conversation about:
✅ How AI is already shifting our day-to-day workflows
✅ The tools we’re experimenting with (and the ones we avoid)
✅ Why we’re not panicking about job loss, and what we’re focusing on instead
✅ The mindset shifts that help us stay adaptable in a rapidly changing world
Whether you’re excited about AI, skeptical, or just trying to keep up, this episode will give you perspective (and maybe even a little peace of mind).
If you’re a web designer, freelancer, or someone exploring online business, you’ll get practical insights, career tips, and a sense of what’s ahead. Stick around for their stories, shoutouts from the live chat, and lightening round questions at the end.
Thank you to our sponsor SquareKicker. Get 15% off all SquareKicker products with code SOMEWHAT15 today: https://squarekicker.com/
Christy’s tutorial on SEOSpace
AI Tools Discussed:
In this episode, Will and Christy touch base about wrangling code updates, keeping up with Squarespace’s ongoing changes, and the debate between live and pre-recorded marketing. Then they bring in Kelsey Gilbert Kryling, founder of Week of the Website, to talk honestly about what it’s like running an agency and the day-to-day realities of digital business. Kelsey shares what it takes to balance work and family life, the practical realities of maternity leave, and her biggest lessons on team structure and workflow. If you’re weighing freelance vs. agency life or planning to step back for family or health, Kelsey’s open-book approach is both reassuring and eye-opening. They also take a few minutes to celebrate simple wins, like the joy of a good pastry!
Kelsey’s top tech stack:
Find Kelsey at https://www.weekofthewebsite.com/ or https://www.bykelseygk.com/
Sponsor: SquareKicker
What if you could have unlimited creativity on Squarespace? The SquareKicker Pro Extension gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.
In this episode, Will and Christy talk about everything from big Squarespace updates (especially around e-commerce), to taking real sick days (or not), and why it’s actually okay if your website isn’t the prettiest thing on the internet. We get into what dogs can teach us about web design, using loyalty and clear directions as guiding lights, and even where to find that “sunny spot” for your work and wellbeing. You’ll walk away with practical changes you can make to your Squarespace site, and a few reminders that taking care of yourself is just as important as impressing your clients. Oh, and we share a lot of love for pets, so if that’s your thing, stick around!
Sponsor: SquareKicker
What if you could have unlimited creativity on Squarespace? The SquareKicker Pro Extension gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.
Donald Miller book: https://storybrand.com/building-a-storybrand-book-new/
See the site Christy made about Beyla
Will’s Squarespace Designer Toolkit Chrome Extension
Christy’s Workflow.Design walkthrough
Where to find Kristine:
In this episode Christy and Will debrief the Kit conference and weigh the pros and cons of doing live and pre-recorded content. Then they bring on Hoyd Breton, principal product designer at Squarespace. They discuss the power of minimalism, story driven design, and the tools to support it. Hoyd shares his sources of inspiration as well as Squarespace’s most underrated feature. They also talk about working in person versus remotely and the effects on deep work and collaboration.
Will’s recent webinar: https://youtu.be/hRX0-LmhzWM
Eno documentary: https://www.hustwit.com/eno
Braiding Sweetgrass: https://www.penguin.co.uk/books/316088/braiding-sweetgrass-by-kimmerer-robin-wall/9780141991955
iA Writer: https://ia.net/writer
excalidraw: https://excalidraw.com/
Sponsor: SquareKicker
What if you could have unlimited creativity on Squarespace? The SquareKicker Pro Extension gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.
In this episode, Will and Christy review the tips from their last Circle Day talk, “7 Ways to Save Time as a Web Designer” and discuss which are still relevant. Then they talk with Liz Ellery about helping clients find their voice, bringing a sense of spirituality into her business, and what to look forward to in her next Summit. Liz emphasizes the importance of being intentional in your business and setting it up in the way that works best for your personality.
Christy’s Starter Template:
https://learn.christyprice.com/squarespace-starter-template-delivered
Short branded URLs tool:
Christy’s Breely review:
https://www.youtube.com/watch?v=cLiCEDySLPY
Automated tax rates in Squarespace:
https://www.youtube.com/watch?v=ltktp219RCQ
Where to find Liz:
Website: https://www.elizabethellery.com/
Instagram: https://www.instagram.com/elizabeth_ellery/
YouTube: https://www.youtube.com/@elizabethellery/
The Website Designer Summit: https://www.elizabethellery.com/summit
Sponsor: SquareKicker
What if you could have unlimited creativity on Squarespace? The SquareKicker Pro Extension gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.
Will and Christy kick off this week’s episode talking about the fun industry events they recently attended. They share their top three feature requests for Squarespace as well as a couple Squarespace updates. Then they talk with Dreyah Bohlen-Harrington about how becoming a mom changed the way she runs her business, specifically around schedules, setting boundaries and delegating tasks. Dreyah explains how she’s using AI in her design work and her biggest challenge creating templates. She also shares the inspiration for the Designer Break Book - her coloring activity book designed by and for Squarespace designers.
Sponsor: SquareKicker
What if you could have unlimited creativity on Squarespace? The SquareKicker Pro Extension gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.
In this episode Christy and Will talk about their favorite chrome extensions and share the latest Squarespace update. They are joined by Jen Maher who discusses her ADHD diagnosis and how it impacts the way she runs her business. She gives her take on the common advice of charging your worth and encourages us to self evaluate and chart our own path as entrepreneurs.
Chrome extensions:
Will's Toolkit Extension / Code Curious Membership
Other tools:
Find Jen:
In this episode of Somewhat Useful, Will and Christy talk about how they are using AI in their workflows and share a couple platform updates from Squarespace. Then they chat with CSS expert Chris Schwartz-Edmisten about his journey from coding to photoshop mockups to helping clients customize their Squarespace websites. Chris shares insights on content marketing strategies, diversifying income streams, and balancing client work with educational content.
Sponsor: SquareKicker
What if you could have unlimited creativity on Squarespace? The SquareKicker Pro Extension gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.
Links:
In this episode, Will and Christy chat about the pros and cons of social media for their business and discuss how they manage their social media usage. They are then joined by Lex Roman, who talks about their journey from TV to web design, to growth and monetization, and now community building and virtual networking events. Lex discusses their “Legends” membership as well as their "Journalists Pay Themselves" newsletter for independent media professionals.
Notes:
In this episode, Christy and Will debrief Squarespace’s State of the Web Design Industry report, and share their thoughts on setting deadlines and shipping products. Then they talk with LaShonda Brown of Bootstrap Biz Advice about her YouTube channel growth strategies. She explains that fun is essential in creating an engaging learning environment. LaShonda shares the Pomodoro technique that helps her stay productive as well as her biggest learnings from creating an app. They also discuss how she uses brand-friendly content and affiliate marketing to secure brand deals.
Thanks to WEGLOT for sponsoring this season. Try Weglot for free for 10 days and enjoy a 15% discount on your first year of subscription with the code SOMEWHAT15 (offer valid for 12 months after subscription)
Industry report: https://pros.squarespace.com/squarespace-2024-industry-report
Framer: https://www.framer.com/
Uscreen: https://www.uscreen.tv/
LaShonda’s lofi playlists + timers: https://youtube.com/playlist?list=PLEqzDwLkhfMbjqdDoFfR87_PB4_twbxjS&si=P8xYnfic82pRMwd4
Where to find LaShonda:lashondabrown.comhttps://www.bootstrapbizadvice.com/ https://www.youtube.com/lashondambrown
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In this episode, Christy and Will chat about email marketing and how it fits into their business. Then they talk with Jeremy Schwartz, General Manager of Channel Partnerships at Squarespace. You’ll hear about the evolution of Squarespace over his 12 years there, including ongoing efforts to support us creative professionals. He takes us behind the scenes of Squarespace Circle and explains the reasoning behind the new tiers.
Notes:
CSS value “text-wrap: balance”
In this episode, Christy and Will talk about whether or not you need a website copyright and share their Somewhat Useful tips for your business. Then they talk with Kate Scott about her journey from WordPress book blogger to successful Squarespace educator and template creator. Kate discusses the advantages of Squarespace over WordPress and how she transitioned from client work to selling templates and courses. You’ll hear about her approach to productivity, strategies for growing a sustainable online business, and insights into hiring your first team member.
Follow Kate Scott on Instagram
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In this episode, Will and Christy discuss getting past perfectionism and give their Somewhat Useful tips. Then they talk with Weglot CMO Eugène Ernoult about the company’s innovative translation solution. You’ll hear about Eugène’s journey into marketing and his transition from being a founder to working at a startup. He shares Weglot’s business practices around employee wellbeing and the environment, as well as insights on revamping marketing strategies to better engage customers. He offers valuable advice for freelancers, stressing the importance of focusing on a niche and staying customer-focused. The discussion also touches on the role and limitations of AI in marketing and translation services. Links:
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In this episode, Will and Christy talk about the intersection of Google and AI. They share the big projects they’re currently working on and give some tips for your business. Then they talk with Becca Harpain of Inside the Square. Becca shares the challenges she faced with Google’s new algorithm and how it forced her to adapt and innovate in her business. You’ll hear about the launch of her exciting new project, Custom Codey, a custom chat GPT designed to assist users with Squarespace-specific queries. They also discuss the collaborative nature of the Squarespace community and how they’re using AI in their content creation and marketing strategies.
Thanks to WEGLOT for sponsoring this season. Try Weglot for free for 10 days and enjoy a 15% discount on your first year of subscription with the code SOMEWHAT15 (offer valid for 12 months after subscription)
Links:
• toolkit.will-myers.com
• Becca:
◦ tutorials.squarespace.com
◦ insidethesquare.co
◦ https://www.youtube.com/@InsideTheSquare
◦ https://www.instagram.com/thinkinsidethesquare
◦ AI Optimization: https://www.youtube.com/watch?v=6_eHaU17bJQ
◦ Custom Codey: customcodey.com
• https://claude.ai/
• Adobe enhance audio feature: podcasts.adobe.com
• Day Trading Attention book: https://garyvaynerchuk.com/attention/
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In this episode, Christy and Will share their words for the New Year and tips for your business. Then they talk with Omari Harebin about his journey from a struggling freelancer to a successful entrepreneur and coach. Omari shares his thoughts on adapting to changes in the web design landscape, particularly with the rise of AI. He discusses the therapeutic nature of storytelling and the role Squarespace has played in his creative process. You’ll hear about his memoir, 'The Corporate Dropout', which encapsulates his experiences and insights on creating a life aligned with one's deeper purpose. In speaking about his coaching practice, Omari emphasizes the importance of finding one's lane and the challenges of monetizing natural talents. He also introduces his concept of mindset plugins, which aim to help individuals navigate their mental landscapes.
Thanks to WEGLOT for sponsoring this season. Try Weglot for free for 10 days and enjoy a 15% discount on your first year of subscription with the code SOMEWHAT15 (offer valid for 12 months after subscription)
Show notes • Verve chair • mindset plugin (coming soon) • The Corporate Dropout
In this episode of "Somewhat Useful," we get to speak with special guests Sarah Greisdorf, team lead for Squarespace Circle, and Sam Zelitch, Squarespace senior community events manager.
Our conversation centers around Circle Day, now in its third year, which celebrates the work of professional Squarespace website designers. Sam and Sarah share some updates for this year's event, including a new "world loop" feature that will broadcast the event across multiple time zones and languages.
We discuss:
Episode Links:
Special thanks to Termageddon for sponsoring this season of Somewhat Useful. Termageddon is the only Privacy Policy Generator founded by an actual attorney. Their generator asks you questions about your business, finds out which privacy laws apply to you, and then generators the policies specific to your website’s needs. Follow this link to learn more and get a special offer for web designers.
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In this episode of "Somewhat Useful," we dive into the world of Squarespace plugins and digital entrepreneurship with Cody Juhnke, the founder of Ghost Plugins. Cody shares his journey from freelance web designer to creator of the largest resource for Squarespace websites, offering over 500 free plugins and a suite of premium tools. We explore:
The origin story of Ghost Plugins and how it evolved to meet the needs of the Squarespace community
Insights into running multiple successful businesses, including Pluto and Ghost Marketplace
The challenges of maintaining plugins with Squarespace's evolving platform
Cody's unique approach to template design with "paper templates"
Tips for balancing multiple projects and avoiding burnout as an entrepreneur
The future of Ghost Plugins
Episode Links:
Special thanks to Termageddon for sponsoring this season of Somewhat Useful. Termageddon is the only Privacy Policy Generator founded by an actual attorney. Their generator asks you questions about your business, finds out which privacy laws apply to you, and then generators the policies specific to your website’s needs. Follow this link to learn more and get a special offer for web designers.
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In this episode of Somewhat Useful, we get to pick the brain of Tony Howell, a personal brand strategist and web designer for award-winning artists. Join us as we discuss:
Whether you're a web designer looking to level up your process, an entrepreneur considering the digital nomad lifestyle, or just curious about the intersection of technology and the arts, this episode is packed with actionable advice and candid discussions about the realities of running a creative business in today's digital landscape.
Don't miss Tony's thoughts on creating timeless designs, future-proofing client websites, and why Bali has become a hub for digital entrepreneurs. Plus, get a peek into how he structures his work week to maximize creativity and maintain work-life balance in paradise.
Episode Links:
Special thanks to Termageddon for sponsoring this season of Somewhat Useful. Termageddon is the only Privacy Policy Generator founded by an actual attorney. Their generator asks you questions about your business, finds out which privacy laws apply to you, and then generators the policies specific to your website’s needs. Follow this link to learn more and get a special offer for web designers.
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Ready to dive into the world of AI, personal branding, and digital nomad life? In this episode, we're joined by the wonderful Phil Pallen, a brand strategist, speaker, Adobe ambassador, author, and just all around great guy.
Phil shares with his:
Whether you're a solopreneur looking to level up your personal brand, a content creator navigating the world of sponsorships, or just curious about the intersection of AI and creativity, this episode is packed with actionable insights and candid discussions about the ever-evolving digital landscape.
Episode Links:
Special thanks to Termageddon for sponsoring this season of Somewhat Useful. Termageddon is the only Privacy Policy Generator founded by an actual attorney. Their generator asks you questions about your business, finds out which privacy laws apply to you, and then generators the policies specific to your website’s needs. Follow this link to learn more and get a special offer for web designers.
Follow:
Follow Christy on Instagram