7 Questions Every Squarespace Designer Should Ask Themselves

If you’re a Squarespace designer, you’ve likely spent countless hours honing your craft. You can spot spacing errors from a mile away, create beautiful layouts in your sleep, and troubleshoot CSS quirks like a pro. Yet, despite your expertise, it’s easy to feel stuck in a loop—hustling for clients, juggling endless revisions, and wondering whether there’s a more sustainable way to grow.

Here’s the good news: your business already contains assets and opportunities you might not even see yet. And once you recognize them, you can unlock consistent income, better clients, and—most importantly—time and energy to focus on the creative work you love.

Below are 7 diagnostic questions that help you step back, take a fresh look at your business, and pinpoint exactly where you’re leaving money (and freedom) on the table.

1. What Does My Business Really Look Like Right Now?

Before you can scale, pivot, or optimize, you need a clear snapshot of how your current business operates. Often, we get so busy doing the work that we don’t notice what’s working—and what isn’t.

Ask Yourself

• How would I describe a typical client project from start to finish?

• What’s the single best experience I’ve had with a client—and what made it so great?

• How do my clients usually describe what I do for them?

• Where do my clients primarily come from—referrals, social media, or somewhere else?

Action Step
Write down your answers. Even if it feels obvious, seeing your processes and sources of new work on paper can reveal blind spots or hidden strengths you’ve been overlooking.

2. Which Relationships Do I Lean On Most—and How Am I Nurturing Them?

Strong client relationships, past collaborations, and professional connections can be a goldmine for new work, partnerships, or referrals. Yet most of us only reach out when we need something right now—missing the chance to cultivate relationships proactively.

Ask Yourself

• Who are the 2–3 most valuable connections I have (clients, colleagues, mentors)?

• How did these relationships start, and what opportunities have they opened for me?

• Do I keep in touch and add value to these connections regularly—or only when a project ends?

Action Step
Pick one high-value relationship and send a friendly check-in. Share an article or resource that might help them—even if you’re not pitching anything. Genuine, consistent communication helps keep you top-of-mind and can spark future collaborations.

3. Have I Clearly Identified My Core Process—or Is It All in My Head?

A repeatable, proven process is one of your greatest business assets. It sets clear client expectations and can be turned into packaged offers, templates, or even mini-courses.

Ask Yourself

• Do I have a defined step-by-step framework for every project (onboarding, discovery, design, launch)?

• Have clients ever shown surprise or delight at a step I take for granted (like a stellar briefing doc, a thorough revision checklist, or a unique consultation method)?

• Could I create a simple checklist or template out of the tasks I repeat for every Squarespace site?

Action Step
Document your process. You might discover that a standard “phase 1, phase 2, phase 3” approach becomes a blueprint you can package into a higher-value service—or even sell as a resource to other designers.

4. What Emotional Outcomes Do My Clients Actually Want—and Am I Selling Those?

People rarely buy “a Squarespace website” just for the surface level design. They’re actually buying confidence, peace of mind, professional credibility, and a sense of excitement about their brand. If you keep selling a website as a technical deliverable, you’re missing the chance to connect with what truly matters to your clients.

Ask Yourself

• When clients finish a project with me, what feelings do they describe—relief, clarity, excitement?

• Have I ever heard a client say something like, “This took a huge weight off my shoulders” or “Now I finally feel confident to market my business”?

• Do my proposals, website copy, and sales calls address these emotional outcomes directly?

Action Step
Go through your testimonials and highlight every time a client mentions a feeling: relief, certainty, excitement, ease. Next time you pitch or market, lead with those emotional benefits instead of just design features.

5. Where Am I Losing Time, Money, or Energy?

We often accept scope creep, underpricing, or disorganized proposals as “part of the job.” But these leaks eat away at your profit and sanity—leaving you with less bandwidth to optimize or innovate.

Ask Yourself

• Which parts of a project always seem to drag on longer than I estimated?

• Am I constantly lowering my rates or including extras for free because I’m afraid the client will walk away?

• Which tasks do I dread because they’re tedious or repetitive?

Action Step
Identify the biggest culprit—maybe it’s indefinite revision cycles or a chaotic proposal process. Draft a new boundary or system to fix it. You might, for example, create a standardized revision policy or a short “discovery session” that’s paid, ensuring both you and the client start the project aligned.

6. Am I Willing to Shift How I See My Value?

If you see your work purely as a skill, you’ll forever trade hours for dollars. Recognizing that your real value is the transformation and outcomes you deliver can completely change how you price, pitch, and package your services.

Ask Yourself

• Do I price based on hours worked or on the overall impact I create for a client’s business?

• Am I selling a “Squarespace website” or am I selling an easier, faster way for clients to stand out and build their brand online?

• What would it look like if I fully owned my expertise—and asked to be paid accordingly?

Action Step
Set a small experiment: quote your next project based on the outcome rather than hourly. Maybe a “brand refresh and launch system” at a flat rate that reflects the client’s future gains. See how it changes the conversation (and your income).

7. What’s My Next Best Step to Grow—Without Working More Hours?

Growth isn’t always about adding more projects to your plate. Often, it’s about finding ways to leverage what you already know or already do. That can mean higher-value offers, productizing your method, or scaling through partnerships.

Ask Yourself

• If I had absolute confidence in my method, what new service or product would I create?

• Is there an underutilized skill, template, or strategy I could brand and sell?

• How would my business change if I found just one new high-value offer that doubles my revenue per client?

Action Step
Choose one “lever” to pull. Maybe you turn a recurring request (like content migration or launch planning) into a fixed-price add-on. Or you create a mini-consulting offer that happens before every design project. Start with something small that doesn’t require a massive overhaul.

Ready to Dig Deeper? Let’s Talk.

If working through these questions has sparked new ideas—or uncovered gaps—you didn’t realize you had, you’re not alone. Most Squarespace designers are too busy delivering great work to see the goldmine hidden in their own business processes and expertise.

That’s where a fresh perspective can make all the difference. I specialize in helping designers uncover the hidden assets, offers, and systems that let them grow sustainably—without piling more work onto their plate.

If you’d like to identify your biggest untapped opportunity and map out next steps, I’d love to invite you to a Free Clarity Coaching Session. We’ll dig into your business, pinpoint exactly where you’re leaving money on the table, and plan a strategic path forward.