Self-hosting gave me control. WordPress.com gave me peace of mind — and I didn’t lose any of the flexibility I cared about.
For years, my site lived happily on SiteGround. I managed the SSLs, the CDN, the updates — all the knobs and switches that come with running your own WordPress installation. It worked, but it also pulled focus away from what I actually wanted to do: write.
At some point, I realized that maintaining my own infrastructure was solving a problem I didn’t have anymore. I wanted a space that just worked — one login, one dashboard, zero maintenance. That’s when I moved everything to WordPress.com.
It wasn’t a professional decision because I work at Automattic. It was a personal one, shaped by the same instinct I wrote about in Do You Trust Your Instincts? Making Smart WordPress Choices. Sometimes, the best move is simply choosing ease over control.
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All in One Place
Running multiple sites across different providers sounds harmless until you have to manage them all: SSL renewals, CDN configurations, backups, and plugin updates.
I like things to stay organized and self-sustaining. But when I was hosting on SiteGround, I used MaxCDN for performance and Let’s Encrypt for SSL. Every three months, the SSL certificates expired. And every three months, I would tell myself, “I’ll renew that later.”
You can guess how that went.
When I switched to WordPress.com, all that maintenance vanished. SSL renews automatically through Let’s Encrypt. Jetpack CDN handles media delivery globally without setup. Backups happen in the background.
I still have all the performance benefits (and even more), just without the constant reminder emails and fear that something would break without me noticing. Everything’s in one place, and I spend less time maintaining, more time creating.
Freedom with Custom Themes and Plugins
A few years ago, one reason I didn’t host on WordPress.com was the inability to upload custom themes or plugins. That’s long gone.
Now, on the Business plan and above, you can upload your themes and plugins — just like a self-hosted site. You get the same PHP flexibility, SFTP and SSH access, GitHub deployments, and even staging sites if you want them.
That meant I could keep using Enfold, the theme I was previously using on this site, along with my small custom plugins and the usual stack from WordPress.org. No compromises, no feature loss.
This shift also says something bigger about how WordPress.com has evolved. It’s not a “limited” version of WordPress anymore. It’s the same core software — just managed, optimized, and monitored by people who know exactly how it works and how to manage it.
Ease of Use That Actually Scales
If you’ve managed WordPress sites before, you know the update cycle: make a backup, create a staging site, test, then push live.
On WordPress.com, that entire workflow collapses into a single click. I update everything directly from the dashboard. There’s no anxiety attached to that “Update all” button because I know there are hourly backups and one-click restores behind it.
“I used to treat updates like a chore. Now they’re instant and safe — I just click ‘Update all’ knowing I can roll back if anything breaks.”
Add to that automated SSLs, caching, and Jetpack CDN, and you’ve got a system that runs itself. I don’t babysit my site anymore; it just works. That’s time I can put into things that actually move forward — like writing or experimenting with new tools.
If you’re curious about how I balance plugins now, you might like Top 5 Essential WordPress Plugins I Always Install and Why. Most of my must-haves work seamlessly on WordPress.com.
The Real Value: Less Maintenance, More Focus
Moving my site wasn’t about performance or pricing. It was about mental bandwidth.
Self-hosting gave me flexibility, but it also meant spending time on tasks that weren’t part of my core goal. With WordPress.com, I get the same control where it matters — code, design, content — and automation everywhere else.
I log in, write, publish, and move on. The platform takes care of the rest. And that simplicity compounds.
If you’re considering a platform switch, ask yourself what you actually want from hosting: control or calm? For many creators and developers, the sweet spot is somewhere in between — and WordPress.com now lives right there.
The Bigger Picture
WordPress.com today isn’t the same platform it was five years ago or even last year. It’s faster, more open, and more flexible. You can bring your stack, your design, and your workflow.
It’s also evolving in ways that align with where the web is heading — toward more automation, smarter publishing tools, and AI-assisted workflows. That’s something I’ve written about before in AI and ChatGPT in WordPress: A Year of Transformation.
For me, the move was part of a larger shift: less time on infrastructure, more time on creation.
Should You Move to WordPress.com Too?
Hosting choices are trade-offs. For some, self-hosting will always be the right fit. But if your goal is to create more and maintain less, WordPress.com has matured into a platform that gives you both freedom and focus.
I didn’t move because I had to — I moved because it made sense. And I haven’t looked back since.
Are you self-hosting or using WordPress.com? What made you choose one over the other? Let me know — I’m genuinely curious how others think about this balance.
And speaking of curiosity and WordPress, my friend at Iterative Wonders wrote about how it all started as a blog fix.
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