When to Hire a Squarespace Expert (And When to DIY):A Brutally Honest Guide
What working with a Squarespace web designer can look like for solopreneurs & small business owners
As a solopreneur or business owner, your to-do list never ends. It's a living, breathing monster that grows two new tasks every time you cross one off.
And somewhere on that monster of a list? "Build new website" or "Update website that hasn't been touched since 2017."
Many business owners eventually find themselves wondering if they should hire a Squarespace expert rather than continuing to struggle through the process alone.
Building a website on your own is absolutely doable with platforms like Squarespace – that's why they exist! But sometimes, bringing in a professional might make sense depending on your situation, timeline, and goals.
Your website represents your business online 24/7, and deciding whether to DIY or hire help is a personal choice that depends on several factors.
Pssst hi it's me, Janessa! 👋 I'm a web designer and I design exclusively in Squarespace, so that's what I write about. But this can be true for any design platform - WordPress, Showit, Wix, etc. So if you're reading this and on a different platform, all the below still holds true.
Here are five honest considerations about when working with a Squarespace web designer might make sense:
01. Time: It’s Always a Tradeoff
Let's be realistic about website projects - they generally take longer than expected.
When I talk with business owners who've gone the DIY route, they often share that what they thought would take a weekend ended up taking weeks or months of evenings and weekends. Between learning the platform, researching, making design decisions, writing copy, optimizing images, and troubleshooting unexpected issues, the hours add up quickly.
This is exactly why so many busy entrepreneurs eventually decide to hire a Squarespace expert – they realize their time is literally money.
If you're in a season of business where your time is better spent elsewhere (like, actually making money!), working with a Squarespace designer could be a practical decision. On the other hand, if you're just starting out and have more time than budget, diving in yourself might make perfect sense. After all, ramen-fueled late nights building your website are practically an entrepreneurial rite of passage.
The question isn't whether you can build your own site (you absolutely can), but whether it's the best use of your limited time right now.
02. Expertise
Squarespace is designed to be user-friendly, and many business owners successfully create their own beautiful websites.
That said, there's still a learning curve.
Professional Squarespace web designers work with the platform daily and have experience with hundreds of different site configurations. They know the latest feature releases, have a stash of their favorite code plugins, how to troubleshoot common issues, and often have efficient workflows that come from repetition.
When you hire a Squarespace expert, you're not just paying for a website – you're paying for the hundreds of hours they've already invested in mastering the platform so you don't have to.
If you're someone who enjoys learning new platforms and has an eye for design, you might find building your own site rewarding.
If technical details make you want to throw your computer out the window (and maybe follow it yourself), working with someone who already climbed the learning curve could save your sanity, your laptop, and possibly your neighbors from witnessing a meltdown.
Something worth noting: if you work with a Squarespace Circle Member (like me 🙋♀️), you'll receive a 20% discount on your first annual plan, which can offset some of the design cost.
Building your site yourself? Grab this freE Squarespace launch checklist to make sure you tick all those boxes 👇
03. Customization
Squarespace offers some templates that are swoon-worthy right out of the box. Many businesses find a template, fall head over heels, and call it a day with minimal tweaking.
But here's the thing no one tells you when you're caught up in template love: looking hot and performing well are completely different ballgames. (And yes, that's true in more areas of life than just websites, but I digress...)
Those fun & lovely templates often come with structural nightmares hiding behind their pretty faces. I've seen templates with FIVE H1 headings on a single page (massive SEO & accessibility facepalm), missing alt text for images (hello, accessibility problems), heading structures that make Google cry, and color contrast that would make some visitors squint harder than trying to read a menu in a dimly lit restaurant.
Where designers like me add serious value is by fixing both the stuff you can see AND the stuff you can't:
SEO Optimization: Making sure your site follows actual search engine standards so you can be found online
Accessibility Standards: Fixing heading hierarchies and structures so everyone can use your site
Custom Code Plugins: Special effects and glow up features that make your site stand out
Brand Flexibility: More options with your brand colors while maintaining readability
Strategic Layouts: Custom page designs specifically built to convert visitors
Focused Navigation (Conversion Gold): Landing pages with intentional pathways that keep people from bouncing
Portfolio Enhancement: Specialized displays that showcase your work effectively
Tech Integration: Connecting your site with tools that save you tons of manual work
A lot of Squarespace designers know how to work magic within the platform's limits without diving into complex code (though many of us can go there when needed and in fact love to go there!). We make your site not just "ooh that's pretty" but "holy smokes, this is actually bringing me clients."
Want a middle ground?
I offer a “strategically boring” Squarespace template for a fraction of the cost of hiring a designer. It's SEO-optimized, accessibility-friendly, and conversion-focused without the template pitfalls—perfect if you want something that performs well but aren't ready for full custom design yet.
The One That Doesn’t Take Your Breath Away
The Boring Template is designed to give you the framework to get your site up and running & complete with your own creative genius. Perfect for service providers, freelancers, creators and solopreneurs who want to get their venture started on the right foot.
If your business needs are straightforward and you're willing to geek out on learning the technical best practices (YouTube rabbit hole, anyone?), a standard template might do the trick.
But if you want something that actually performs as good as it looks, a designer can save you from the template traps that most DIYers fall into headfirst.
04. Technical Know-How
One of the most common scenarios I see is when a business owner starts their site but hits a technical roadblock. This is when A LOT of people start looking for help from a Squarespace expert.
Maybe they're stuck figuring out:
How to connect domain settings properly
Setting up email marketing integrations
Organizing complex product collections
Making sure the site looks good on all devices
Setting up SEO correctly across the site
While these challenges aren't insurmountable, they can be frustrating if you're already stretched thinner than dollar-store paper towels. Forums and YouTube tutorials are helpful resources, but sometimes having someone handle the technical aspects directly saves you from the special kind of 2 AM existential crisis that comes from watching your sixteenth "how to fix your Squarespace header" tutorial in a row.
Some Squarespace designers (myself included) offer post-launch support and training to help you manage your site independently after the initial build, which can be a nice middle ground.
05. Branding and Messaging
Creating an effective, optimized, strategic, gorgoues website involves more than assembling some pages together and throwing in some ChatGPT-generated copy – it's about creating a cohesive, smooth experience that guides visitors toward specific actions. Working with someone who specializes in Squarespace design can make a BIG difference in this area.
Sometimes the biggest challenge isn't the platform itself, but clarity around your brand messaging and user pathways. An experienced web designer often brings a strategic perspective to how information is organized and presented.
For my clients, I provide content planning tools with prompts and examples to help clarify their message before we even start designing. This step alone often provides clarity that makes the whole process smoother, whether you build the site yourself or work with a designer.
A thoughtful site structure that aligns with your business goals can make a significant difference in how effectively your website converts visitors.
The Reality Check: When DIY Makes Sense
To be completely transparent (and I might be shooting myself in the foot here as a Squarespace designer), there are definitely situations where DIY is the better choice:
You're just starting out and working with minimal budget
You have the time and interest to learn Squarespace
Your website needs are relatively simple
You enjoy design and want control over every detail
You want to DIY but with some expert guidance (consider hiring a Squarespace expert for a consultation or Power Hour)
Lots of successful businesses start with owner-built websites and later transition to professional design as they grow. There's no one-size-fits-all answer. If you decide to DIY and want a Squarespace expert for an hour to answer all your ‘but what about THIS?” questions, schedule a Power Hour with me. I’m happy to help!
When Professional Help Makes Sense
On the flip side, bringing in professional Squarespace help might be worth considering when:
Your time is limited and valuable elsewhere in your business
You have specific design needs or wants beyond basic templates
Technical aspects of websites cause you stress
You want strategic input on user experience and conversion
You're rebranding or making a significant pivot
Your current site isn't performing as well as you'd like
At the end of the day, your website should serve your business goals without becoming a source of stress. Whether you build it yourself or collaborate with a designer, what matters most is that it effectively represents your business online.
Interested in getting your website off the ground?
I can help. Whether you need full-service design or just want to hire a Squarespace expert for a few hours of troubleshooting, investing in professional help often pays for itself through better results and saved time.
Shoot me an email or schedule a free consult with me.
