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/⁠

Circle Day

SEOSpace

Christy’s tutorial on SEOSpace

Podia

AI Tools Discussed:

ChatGPT

Midjourney

Manus

RightBlogger

OpusClip

Cursor

Claude

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: 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.

⁠⁠⁠⁠⁠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: 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.

⁠⁠⁠⁠Learn More

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

Workflow.Design

Christy’s Workflow.Design walkthrough

Where 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-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.

⁠⁠⁠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-delivered

Short 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: 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.

⁠⁠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 Templates

Designer Break Book

Instagram

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.

⁠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 Finder

GoFullPage

Lorem Ipsum Generator

Window Resizer

WhatFont

Eye Dropper

Will's Toolkit Extension / Code Curious Membership

Other tools:

Loom

Find Jen:

Website

Instagram

YouTube

The Mighty Fer

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.

⁠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: 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.

Learn More

Links:

Chris' website

Custom Layouts in Squarespace course

⁠CSS Course⁠

Chris' YouTube Channel

Generative Fill Tutorial