10 Years as a Squarespace Website Designer: Stories, Lessons & What’s Next
After a decade of designing Squarespace websites and helping countless business owners, I have plenty to share! In this post, I’ll take you through my journey—how I started with no web design experience, the lessons I’ve learned along the way, and why Squarespace remains the perfect platform for entrepreneurs who want to grow their businesses without being afraid to touch their websites.
From life coach to website designer — how I got started.
Back in 2014, I was at a career crossroads. I had been working as a project manager at a tech startup, but I felt burnt out. I wanted a change—something more personal, where I could work one-on-one with clients and truly help them solve problems. After exploring different paths, I decided to become a life coach.
Of course, I needed a website. On a tight budget and with no web design experience, I discovered Squarespace. I was immediately impressed by how easy it was to use, and within a week, I had built and launched my first website.
Little did I know that creating my coaching website would prompt me to pivot my career (and life).
I quickly realized that my coaching skills were meant for me—they’re what I needed for my life rather than something I needed to build a career with.
After working with a few life coaching clients (who wanted to talk a lot about starting their own businesses), I decided to hang out my shingle as a Squarespace website designer. Was it scary? Kinda. Did I have the skills? Not yet. Did I go for it anyway? Yup.
Lesson Learned: Don’t be afraid to experiment or change.
Building my business with Squarespace.
Because Squarespace was fairly easy to use, I quickly updated my own website to reflect my new web design services. Before long, I found myself designing Squarespace websites for other life coaches and small business owners. My background as a project manager helped me streamline the process, and my life coaching skills made working with clients seamless.
When it comes to business and making money, my mindset is this: If I can make one dollar, I can make two.
This was over ten years ago, back when Instagram and Tik Tok didn’t make fake things look real and Pinterest wasn’t screaming at you to “Build Your Six Figure This!” or “Scale Your Six Figure That!” Of course, I was susceptible to compare and despair like anyone, and I felt really insecure about my lack of design skills. I bolstered myself by hiring a business coach and one day she said (after listening to me vent about not knowing enough), “Deana, you do NOT need to know the most. You just need to CARE the most.” Turns out, when you care the most, you learn what needs to be learned and do what must be done.
Caring the most about my clients shifted my focus to helping them with my whole heart.
And caring about every single client with my whole heart is what built my business. I won’t divulge numbers because my mom taught me it’s tacky to talk about how much you earn, but let’s just say, things snowballed month after month. One dollar became two. Two became four…you get the idea.Steve Farber
After a year, my husband Moses quit his full-time job and joined me as my business partner. Since then, we’ve built websites for all kinds of cool businesses all over the world.
Lesson Learned: As my client (and best-selling author) Steve Farber puts it, “Love is just damn good business.” He’s absolutely right.
Squarespace website design isn’t as easy as Squarespace wants you to think it is.
I love Squarespace — I do! But I meet a lot of people on my conference line frustrated up to their eyeballs with the hatchet-job of a Squarespace site they tried to DIY.
I feel for them.
When I decided to become a Squarespace designer I took thousands (seriously thousands) of dollars of trainings, workshops, and classes to acquire expert-level skills and certifications in:
Graphic design
Strategic User Experience
Conversion-driven copywriting
SEO
Online marketing
Google
Sure — you can drag and drop things around a Squarespace page until your eyes glaze over. You can fill your pages with words, words, and more words.
But if people can’t find your site on the internet ocean or if they DO get to your site and it looks like a 13-year-old built it (no offense 13-year-olds), all the time and energy you spent tinkering your site into being feels like defeat.
This is 2025 people. Design really does matter. For cripes sake, I won’t buy deodorant if the packaging looks rinky dink.
If a website looks crappy or it’s filled with a deluge of words no-one wants to sift through, you’re making a bad first impression and this is actually HURTING your business.
Lesson Learned: Your time is better spent in your genius zone. Let a pro in this field make you look like a pro in your field.
Squarespace has come a long way, baby.
When I first started using Squarespace in 2014, it was a solid platform but had limited functionality. You picked a template (probably Brine), added your content, and set up a basic e-commerce shop for your products and services. That was about it.
With Wix, WordPress, Showit, Webflow, and Shopify nipping at their heels, Squarespace has stepped it up with integrations and improvements.
Design & Customization
Fluid Engine: A game-changing drag-and-drop editor for more flexible layouts.
Enhanced Styling Options: Greater control over fonts, colors, animations, and branding.
Mobile Customization: Ability to design mobile views separately from desktop layouts.
E-Commerce Enhancements
Expanded Product Management: Up to 10,000 products with advanced categorization.
More Payment Options: Flexible checkout experiences with integrations like Afterpay.
Improved Cart Customization: More ways to optimize the user experience.
SEO & Marketing Tools
Advanced SEO Settings: Enhanced schema markup and integrations with marketing platforms.
Member Areas: Ability to create exclusive content for paying subscribers.
Acuity Scheduling Integration: Seamless appointment booking.
After 10 years in the biz, this is my list of Squarespace website must-haves:
1. A SIMPLE USER EXPERIENCE
A beautiful website is useless if finding your way around is hard. Prioritize simple, clear layouts and double-check how things look on mobile (Squarespace makes this easy with their independent mobile editing tools).
2. AN SEO STRATEGY
Your website needs to be found! Optimize for search engines by using the right keywords, improving site speed (compress those images), and structuring content properly (H1, H2, H3, etc).
3. A CLEAR & COHESIVE MESSAGE
I could say a lot on this topic, but I’ll save my breath for another post. To sum it up, don’t use a bunch of words talking about things no one really cares about or answering questions no one is asking.
4. TOOLS TO STREAMLINE YOUR BUSINESS
You have enough on your plate. You shouldn’t be fumbling on the backend of your business trying to set up meetings through email tag, sending invoices manually through Paypal, or wondering what the heck those steps were to publish an SEO-rich blog post. Your website can and should be set up with the right integrations for your business goals and business owner lifestyle dreams.
5. ADAPTABILITY
My clients range from seasoned pros to absolute newcomers. What do they ALL have in common? Overwhelm about things like how to package their services, how to communicate on a sales page, how to seem legit when they’ve yet to build a track record, and how to pivot in a new direction after years of being known for something else. The pressure to get their website * perfect * is bone-crushing. The thing is, clarity comes from taking action. You need a great website that positions you as a credible professional (with a personality) in your field. One that makes taking action feel less scary. Only by taking action will you understand what’s working so you can adapt and do MORE of it! All that to say — a website you feel comfortable updating along the way as your business goes from one chapter to the next is a must-have.
Looking ahead…
Keeping up with the pace of online business feels like catching an ocean in a teacup these days. Some mornings I wake up and wonder if AI will eventually render my skills, experience, and desire to do good work in the world completely irrelevent. Do you wonder about this, too? If so, let’s have a pep-talk:
Humans need humans. Artificial intelligence should really be called artificial assistance — it can be a good helper who’s there for you to bounce ideas around or do a little (questionable) research, but it’s a terrible substitute for a human who deeply listens, truly cares, thoughtfully connects the dots, or has spidey senses around BPT’d * facts * that are robo-hallucinations.
Just like I did 10 years ago, I’m reminding myself to focus on caring the most and helping people with my whole heart. The rest will sort itself out.
So, as I look ahead, I see amazing humans with fun projects on my project calendar. Want to be one of them?
About the author:
Deana Ward is an experienced Squarespace website designer and professional copywriter. Over the past decade, she’s helped thousands of business owners ditch the DIY hellscape so they can stop tinkering and start taking action. Want to shine up your brand so you feel proud? Overhaul your message so you say the right words instead of all the words? Or soup up the SEO engine under the hood of your website? You’re in the right place!
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