Personal Tech Debt & Rediscovering Jetpack

We’re deep into summer here, but I’m in the mood for spring cleaning. Half a year into my role at WooCommerce, and I’m starting to shed some of the habits from my agency and freelancer days: I’m cleaning out old software subscriptions that I’d been hoarding or managing for others.

You ever get hit with a random annual software license and think “I still have a BrowserStack account?!” You set a calendar event to cancel it next year and hope you actually pay attention to it. Well, not this time. I’m cancelling as much as possible right now.

One the one hand, I feel kind of bad about it. I like spending my money supporting software, much of it coming from small WordPress and indieweb development shops. But I’ve got kids to feed, and many of these licenses are only cost effective when you’re using them across dozens of sites. For my small stable of personal sites, I just don’t need them. I’m dropping page builders, form plugins, analytics suites, transactional email servers… I’m even dropping the perfectly good platform powering this newsletter ((Convert)Kit).

So where am I going? That’s been the most shocking part- for a lot of these tools, I’m consolidating via the Jetpack plugin. If you’d have told me that a few years back, I’d have politely scoffed at you. Jetpack has a lot of features, but each feature functions a bit like an MVP. It offers a limited and opinionated way to accomplish something specific. That used to bother me, but these days I appreciate the simplicity. Now that I work for the same company, I may as well dogfood the product.

It started with contact forms. I’m a big fan of the team at Gravity Forms, but I’m just not using any of the advanced features or managing a bunch of websites for other people who are. Mike McAlister turned me on to how great Jetpack’s block editor integration is, and I have to agree. The fields are easy to style and they conform to your theme seamlessly. My only concern was how good Akismet would be compared to Recaptcha/Turnstile, but so far so good.

After forms, I realized Jetpack could solve more of my minimal use cases, like basic analytics, SEO, and maybe even this email newsletter. Previously, I was writing my posts as a custom post type and manually pasting them into Kit, but if you look at my email template, it already looked exactly like the Jetpack email templates. I’m migrating to Jetpack, and once complete, there’ll be no more copy/pasting across platforms. Plus Jetpack has a slick email preview tool built into the block editor.

The only thing I can’t do with Jetpack is my dripped email course. (You don’t see this in other newsletter platforms like Substack or Ghost, either.) I would love to see email sequences in the plugin, but since they don’t exist, I may have to drop mine. Maybe I’ll add Sensei LMS, Mailpoet, or Jetpack’s CRM feature to accomplish this, but I’d rather not. Instead, I’m thinking it’s time to retire it (though the downside is that it’s a big driver of new subscriptions).

Overall, it feels like a full-circle moment. When I enabled Jetpack on my site last week, it showed me old contact form entries from the last time I had Jetpack enabled – almost ten years ago. Talk about backward compatibility. Jetpack was one of the first plugins I used when I started with WordPress, so it feels almost nostalgic to bring it back.

I have some concerns migrating existing subscribers to Jetpack, because they automatically get a WordPress.com account to manage their subscription. This felt controversial when it launched, but it’s exactly the way Substack works- one central account to manage all of your subscriptions. Again, a full-circle moment. WordPress ahead of its time. My main concern is whether or not to auto-migrate all of my subscribers, or have them opt-in.

I think it’s all worth it, because ultimately this is a personal newsletter, not a media brand. I want to lower the barrier between my thoughts and publication, and this seems like the right approach. Maybe I’ll get to post more frequently, or experiment with smaller micro-blog style posts, which I enjoy from writers like Simon Willison. Or maybe I’ll separate out my link roundups from my longer-form writing. With the WordPress.com integration, subscribers have the option to manage email frequency, and I can publish posts without sending them to email. (Don’t worry, RSS is still a thing.)

The next frontier for me will be my web hosting. I’m running a Digital Ocean server with Spinup WP (and AWS for backups) and honestly, I’m not sure I’m happy with it. I’m paying around $50/month to host a few small sites, but I have to keep cranking the server up. At Woo I’m working on big sites hosted on VIP and Pressable, meanwhile this DO server still feels sluggish.

I’m building a Woo store for my wife, and it definitely won’t be able to live here. I feel like good WordPress hosting (and you need good hosting) is still too pricey for hobby/low-income sites. I’d love to see something like Netlify for WordPress, free tiny sites you can experiment with, like WordPress.com but open to developers. (I’m excited about the idea of WordPress.com expanding their cheaper plans to allow plugins and appeal to developers and tinkerers, and I hope it’s something feasible long-term.) Where are you hosting?

Oh, and next year, I just know I’ll be doing a spring cleaning of all of my AI subscriptions- heads up Cursor!

Aside: I’ll be at WordCamp US in less than two weeks. My time will be split between connecting with old friends, making new ones, working at the Woo booth, and helping to host the Woo Community Meetup (RSVP now!). I’ll also be speaking at WordCamp Canada later this year. Let’s meet IRL!

Reading List

• Paul Ford had a great write-up about the weird product decisions happening at OpenAI and ChatGPTs inability to let you do the things it’s actually good at.
• Ryan Welcher helped me out tremendously by pushing some updates to the wordpress/create-block package. I want to see this become the de facto scaffolding tool for WordPress.
• WordPress Studio is working on Blueprint.json support. This came to Woo recently and I want to see more adoption of this new standard.
• Speaking of Playground Blueprints, I built myself a tool to spin up demo Woo stores with fake products, customers, orders, and more. All on WordPress Playground. Plus you can have it load betas and nightly versions of Woo.
• It’s been wild watching the team at Woo completely re-haul the complex plugin release process, leaning into automations, GitHub actions, and more robust testing.
• Last month I hosted a live event for Woo’s developer community to let Woo’s marketing team share all the ways they’ve ramped up marketing the platform. Rae had a great write-up at The Repository.
• OllieWP launched Menu Designer – a plugin to build mega menus and custom mobile menus inside block themes. I’ve been beta testing it and it’s solving a huge pain point. I still believe the navigation block situation is one of three top blockers for block theme adoption.
• Dries Buytaert (Drupal’s founder) has been writing some bangers recently, and this piece about digital agencies in the age of AI is no exception.

That’s all folks. If you’re heading to WCUS, let me know so I can keep an eye out for you!