Somewhat Useful

If we had to start over today, with no audience, no email list, and no reputation, what would we actually do?In this episode, we break down what still works for building a web design business, what we'd skip completely, and where we'd focus if we had to rebuild from scratch in 2026. We also talk about SEO, YouTube, AI search, email lists, Instagram, digital products, client work, and the slow reality of growing something that lasts.Plus, Christy shares the story of winning $5,000 at Sponsor Games, and Will talks about how he's in his Claude era.Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.Mentioned in the episode:Sponsor Magnet by Justin MooreAtomic Habits by James ClearKit ConferenceWeb Designer's PlaybookWill's ToolkitWill's email listChristy's email list

In this episode, Christy and Will discuss recent and upcoming conferences, Squarespace updates, and Will’s evolving opinion on OpenClaw. Then they chat with Gavin Zuchlinski, founder of some of the best scheduling tools on the market, including this season’s sponsor, Breely! You'll hear about how he created Acuity as a side hustle, the Squarespace acquisition, and why he wanted to build yet another scheduling platform. Mentioned in the episode:Will’s article about OpenClawFinal Surge appDie with Zero bookThank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

AI tools are moving fast, client work gets messy, and some days, business feels heavier than it should. In this episode, we talk honestly about what makes entrepreneurship feel miserable, how AI is adding new anxiety (hello, OpenClaw), and the boundaries that actually help.You'll also hear a few timely Squarespace updates (and bugs), plus what the next year might look like for Squarespace designers and developers as AI keeps changing the workflow.Mentioned in the Episode:Squarespace CircleThe Web Designer Summit (March 5)Thanks to our sponsor Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

We start this episode by reviewing what’s new with Squarespace, including the retirement of the Amazon block and our thoughts on search functionality. We also discuss Squarespace’s recent Super Bowl ad. Then we’re joined by author and writing coach Jacq Fisch to talk about: Writing in 2026 and how to stand out in a sea of noise and AI-written contentWays to use AI without selling your soulFind Jacq at:https://theintuitivewritingschool.com/https://jacquelinefisch.com/https://jacquelinefisch.substack.com/https://www.instagram.com/theintuitivewritingschool/Mentioned in the episode:Monacle searchVoxerOtterThank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

In this episode we chat about what 2026 looks like for web designers and developers. We'll share what we're leaning into this year and what we're leaving behind.Mentioned in the episode:Kit conferenceSponsor GamesChristy's YouTube Growth LabSponsor:Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.Follow:⁠⁠Follow Christy on Instagram⁠⁠⁠⁠Follow Will on Instagram⁠⁠⁠⁠Sign up for Will's Newsletter⁠⁠⁠⁠Sign up for Christy's Newsletter⁠

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.Follow:⁠⁠Follow Christy on Instagram⁠⁠⁠⁠Follow Will on Instagram⁠⁠⁠⁠Sign up for Will's Newsletter⁠⁠⁠⁠Sign up for Christy's Newsletter⁠

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 worldWhether 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/⁠Circle DaySEOSpaceChristy’s tutorial on SEOSpacePodia AI Tools Discussed:ChatGPTMidjourneyManusRightBloggerOpusClipCursorClaude

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:Slack [https://slack.com/]Pipedrive [https://www.pipedrive.com/]EOS/90.io [https://www.90.io/] (Entrepreneurial Operating System organizing tool)Find Kelsey at https://www.weekofthewebsite.com/ or https://www.bykelseygk.com/ Sponsor: SquareKickerWhat 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.⁠⁠⁠⁠⁠Learn More

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: SquareKickerWhat 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.⁠⁠⁠⁠Learn MoreDonald Miller book: https://storybrand.com/building-a-storybrand-book-new/See the site Christy made about BeylaWill’s Squarespace Designer Toolkit Chrome ExtensionWorkflow.DesignChristy’s Workflow.Design walkthroughWhere to find Kristine:https://kristineneil.com/https://www.linkedin.com/in/kristineneil/https://www.youtube.com/@kristineneil 

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-LmhzWMEno 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/writerexcalidraw: https://excalidraw.com/ Sponsor: SquareKickerWhat 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.⁠⁠⁠Learn More

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-deliveredShort branded URLs tool:https://www.rebrandly.com/ 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: SquareKickerWhat 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.⁠⁠Learn More

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. SquareKicker TemplatesDesigner Break BookInstagramSponsor: SquareKickerWhat 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.⁠Learn More

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:Squarespace ID FinderGoFullPageLorem Ipsum GeneratorWindow ResizerWhatFont Eye DropperWill's Toolkit Extension / Code Curious MembershipOther tools:LoomFind Jen:WebsiteInstagramYouTubeThe Mighty FerSponsor: SquareKickerWhat 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.⁠Learn More

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: SquareKickerWhat 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.Learn MoreLinks: Chris' websiteCustom Layouts in Squarespace course⁠CSS Course⁠Chris' YouTube ChannelGenerative Fill Tutorial

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:Clearspace app: https://www.getclearspace.com/AI voicenotes app: https://voicenotes.com/Beehiiv: https://www.beehiiv.com/Ghost: https://ghost.org/Legends: https://lexroman.com/legendsJournalists Pay Themselves: https://journalistspaythemselves.com/

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 Follow:Follow Christy on Instagram⁠⁠⁠⁠⁠⁠⁠Sign up for Christy's Newsletter⁠⁠⁠⁠⁠⁠Follow Will on Instagram⁠⁠⁠Sign up for Will's Newsletter⁠⁠⁠

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:Aeron ChairVerve ChairWill's Computer StandCSS 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 InstagramLaunch Out LoudFollow: ⁠⁠Follow Christy on Instagram⁠⁠ Follow Will on Instagram⁠⁠ Sign up for Will's Newsletter⁠⁠ Sign up for Christy's Newsletter⁠

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: The Profitable Web Designer podcast: https://webdesigneracademy.com/profitable-web-designer-podcast/ ahrefs: https://ahrefs.com/  Follow: ⁠⁠Follow Christy on Instagram⁠⁠ ⁠⁠Follow Will on Instagram⁠⁠ ⁠⁠Sign up for Will's Newsletter⁠⁠ ⁠⁠Sign up for Christy's Newsletter⁠

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/  Follow: ⁠⁠Follow Christy on Instagram⁠⁠ ⁠⁠Follow Will on Instagram⁠⁠ ⁠⁠Sign up for Will's Newsletter⁠⁠ ⁠⁠Sign up for Christy's Newsletter⁠