Choosing a CMS for a creator site feels like deciding on a home: location, future-proofing, maintenance, and how much DIY you want to do matters more than the pretty façade. I’ve built portfolio sites, membership experiments, and small product shops over the years, and I’ve repeatedly seen the same trade-offs play out. In this piece I’ll walk you through the real questions to ask, show how those map to three common choices—headless, WordPress, and Squarespace—and give practical signals that tell you which route to take.
Start with the problem, not the platform
The single best piece of advice I give: define what you actually need before evaluating technology. Ask yourself:
- Who is my primary audience? (casual visitors, subscribers, clients)
- What content types will I publish? (longform articles, videos, products, courses)
- How often will I update content and how complex are the updates?
- Do I need custom UI or integrations (memberships, analytics, CRM)?
- How much time and money can I commit to maintenance?
Your honest answers will quickly eliminate options. If you want a low-friction, beautiful site up in an afternoon, forget headless for now. If you need a highly custom product experience and have dev resources, headless starts to make sense.
Quick mental map: headless, WordPress, Squarespace
Here’s a one-liner I use when advising creators:
- Squarespace — fastest path to a polished site with minimal upkeep. Great for portfolios, simple stores, and newsletters if you don’t need heavy customisation.
- WordPress — flexible and extendable. Good for blogs, community features, and moderate custom behaviour if you’re comfortable with plugins and maintenance.
- Headless — for creators who need custom frontends, multi-channel publishing, or scale/responsiveness that a monolith can’t provide. Requires developer time or using no-code headless builders.
How to match needs to choice
I break choices down across a few practical axes: speed to launch, customisation, ownership, performance and SEO, cost and maintenance, and extensibility.
| Squarespace | WordPress | Headless (e.g., Contentful, Strapi + Next.js) | |
|---|---|---|---|
| Speed to launch | Very fast — templates + built-in hosting | Fast with themes; slower if customising | Slow — requires setup of CMS, frontend, hosting |
| Customisation | Limited to template tweaks and built-in blocks | High with themes/plugins; can be messy | Very high — full control of frontend and architecture |
| Ownership & portability | Low — content export limited | Medium-High — you control DB and files | High — data in API, frontend portable |
| Maintenance | Low — platform handles updates | Medium — plugin and security maintenance required | High — you or your team update stack and infra |
| Cost | Predictable subscription | Variable — hosting + plugins/dev costs | Variable to high — hosting + developer hours |
Practical scenarios and what I’d pick
Here are common creator situations I’ve seen, and the choices that worked best.
- Just starting—portfolio + blog, no dev budget: Squarespace. You get clean templates, built-in SEO basics, and a simple editor. People often overestimate how much customization they need early on—get something live and iterate.
- Growing audience + need for newsletters and SEO: WordPress (managed host like WP Engine or Kinsta). WordPress gives you better ownership and SEO control (structured data, plugins like Yoast), and integrates with membership/newsletter tools like Mailchimp or ConvertKit.
- Selling digital products and memberships at scale: WordPress or headless. If your membership features are standard (subscriptions, gated posts), WordPress with MemberPress or Restrict Content Pro is faster. If you need a tightly integrated, custom checkout, or multi-platform delivery, headless + Stripe + a static frontend (Next.js) gives you scale and performance.
- Creator with a custom web-app or complex UX: Headless. If you're building an app-like experience—custom interactions, realtime updates, or a need to publish to web, mobile apps, and IoT—separating content (headless) is the cleanest path.
- Short-term campaign or event site: Squarespace or a hosted-static-site builder (Gatsby Cloud, Netlify with a headless CMS). If you need one-off microsites, speed and simplicity win.
SEO, performance and discoverability—what matters
People worry that headless is automatically better for performance or SEO. It depends.
- Squarespace: decent SEO baseline—fast to index, but limited control over advanced schema or asset optimisation.
- WordPress: excellent SEO potential with the right hosting and plugins; but it can be slow and messy if you overload it with plugins or cheap hosting.
- Headless: can deliver the best performance (static or server-side rendered frontends), and you control SEO details. But you'll need to implement meta tags, sitemaps, and structured data yourself—or use frameworks that handle SSR well (Next.js, Nuxt).
Costs and hidden maintenance
Think beyond the sticker price. With Squarespace your monthly cost is obvious. With WordPress you’ll add hosting, premium plugins, and occasional dev fixes. With headless you’re paying for the CMS, hosting, CDN, and developer time. I always budget an ongoing maintenance line—security updates, backups, A/B tests, and small improvements—especially for WordPress and headless setups.
Useful trade-off checklist before you decide
- How quickly do you need the site live? (If very fast, pick Squarespace)
- Will you need features beyond content pages—membership, e-commerce, custom search?
- Do you or your team have dev skills? If not, WordPress with a managed host is a middle ground.
- Is content portability and multi-channel publishing important? If yes, consider headless.
- What’s your acceptable monthly budget for hosting and tools?
Migration and future exit strategies
One pragmatic habit I recommend: design with portability in mind. Use standard content structures, keep a clean export of posts and assets, and avoid lock-in-only features where possible. If you start on Squarespace and later outgrow it, migrating content to WordPress or a headless CMS is common. It’s easier when your content model was simple to begin with.
Tools and combos I often recommend
- Squarespace for solo creators who value speed and polish.
- WordPress + Kinsta/WP Engine + Elementor/blocks for medium complexity with lower dev needs.
- Headless with Contentful or Strapi + Next.js + Vercel for high customisation, multi-channel publishing, and best-in-class performance.
- No-code headless alternatives: Webflow CMS (visual design with exportable code) or Sanity paired with a visual builder for teams without full-stack developers.
Picking a CMS will always involve compromises. The key is to align those compromises with your immediate goals and the resources you have. Start small, keep content portable, and prioritise two things I can’t overstate: clarity in your content model and a reliable workflow for publishing. Those two reduce friction no matter which platform you choose.
