Little to no Experience

You’ll hear this a lot in blockchain circles now.

“Smart but young.”

“They don’t have much blockchain or tech experience.”

“Their background isn’t impressive.”

“They haven’t worked for an all-star company.”

“Nobody important has invested in them.”

I used to hear the same when I started working with WordPress, which just had its birthday, 15 years ago. Before I became a certified, legit, Automattic engineer and an untouchable, I worked for over a decade pushing through this Little to no Experience tag.

If you’re new to a technology ignore anyone who tells you that you’re too new and lack experience. It’s their way of making themselves feel better about the things they’ve done or may have also missed out on.

Everyone’s green. Everyone. Embrace the feeling of insecurity and hunger before you become just another jaded professional.

Nothing Is Sacred

There is not a single piece of software—all technology, in fact—that cannot be disrupted or forgotten.

Apache used to dominate web servers. Nginx said, “Hold my beer.”

Bitcoin was at near 95% market share dominance in 2013. Altcoins and other communities entered the space, and now Bitcoin is at 44% market dominance.

WordPress continues to grow. It’s over 60% of total CMS market share and 30% of the web. Joomla and Drupal are dwindling. Shopify and Squarespace are growing. Someone, somewhere, is working on something better than all of these.

Facebook matters today, so much that it’s jeopardizing democracies. It didn’t exist before 2004, and it may not endure in 2034.

These are broad, somewhat abstract ideas. I’ll go smaller.

Look around you. Pick something. I’ll pick my glass cup. It’s not that interesting at all; it holds water and ice and isn’t great on my wooden table during the summer time. It sweats and leaves traces of condensation around my phone and bedstand items.

There is someone right now in this world figuring out a way to make a better glass cup. One that doesn’t easily sweat. One that’s beautiful and fits with the aesthetics of almost any interior. One that stays cold and stays hot. One that doesn’t slip or chip. Someone is attempting to make the perfect glass cup when so many exist already.

Think of this whenever you marry yourself to an idea. You may love WordPress or Bitcoin. Nginx may be your jam. You may feel lost without the auto-sync between your MacBook, iPhone, iPad, and Apple Watch.

You may never imagine a future in which your favorite social network or current reality does not exist but that day will come. It will.

Your parents will die and so too will the roses you toss on their graves.

Stratechery 4.0: Not Just Another WordPress Site

Many moons ago I refactored Stratechery 3.0. I use “I” only because it’s convenient. Usually, when you do work with someone like Ben Thompson, it’s collaborative. At the time the bulk of the work was centered around gutting the old Stratechery codebase and making room for a new _s-based theme, new membership software, a better mobile experience, and more exposure for Daily Updates, Ben’s highly sought after and substantial analysis of the tech news of the day.

This time around, for 4.0, it was all about content discoverability. This meant, in short:

  • creating new content taxonomies;
  • integrating better search;
  • avoiding the disruption of Ben’s revenue stream while allowing paid content to selectively be shared freely;
  • exposing featured insights in the lesser noticed areas;
  • and improving the readability of Stratechery’s content.

The actual list of work done was much, much longer than this, but it shouldn’t always be the goal of a developer to expose everything but the kitchen sink. What the Stratechery reader sees on the front end is the tip. My job was making sure that it appears exactly as it should but, more importantly, ensuring that Ben is able to interact with the rest of the data management from the control panel of his site. The part that people will never see was the most difficult.

Working on Stratechery, or a site like it should be a requirement for anyone in WordPress or web publishing development that thinks he knows it all. Sometimes we create solutions we believe real, serious writers need, only to find out that everything we thought about publishing was wrong. Add in a revenue component, and our shortsightedness becomes even more apparent.

When I think about someone like Ben, who makes his living by writing independent, high-quality, fierce, uncompromising analysis of modern technology and all that it entails, I don’t know if WordPress alone could ever meet the mark. There are so many holes in the software’s publishing experience that it’s almost a certainty that themes and plugins as we know them—both custom and premium—will always be around to play patchwork.

We were promised that premium solutions (themes, plugins, you name it) would die back in 2008 and I’m still selling them in 2018.

Toss in Gutenburg, sure. Throw in style packs on themes if you like. Do what you will with content blocks or Jetpack or this or that, and it still won’t address a vast majority of issues that are faced by writers who depend on a predictable, controllable, unbreakable publishing experience.

If I had to recreate Ben’s website using WordPress and only WordPress, I wouldn’t be able to. We tried it. God knows I would have loved to make it happen, but it just wasn’t possible. Stratechery is the perfect example of a website that with WordPress should just work but doesn’t, and it’s also a perfect example of a business website that doesn’t look the part.

Stratechery is what I would show anyone who thinks that WordPress is just for blogs (it’s not) and also anyone who says that Jetpack-powered WordPress is enough to run a real business (it’s not). What’s my point here?

It’s mostly that I don’t know what WordPress is supposed to be anymore but I don’t mind where it’s at. It’s been shuffled into the category of my “must-haves” for site building but taken out of the category of quick-and-easy solutions for the average business owner.

What would I suggest now? I don’t know. There’s a void that can still be filled. WordPress powers a massive portion of the internet and will continue to do so, but it’s not immune to losing market share. We’ll see how things play out in the next decade. I hope that WordPress is still around. It’s how I spend the majority of my waking hours. I’d be lying, though, if I said that I didn’t think it could be completely disrupted by something better.

I wanted to write a post-mortem on the Stratechery 4.0 launch yesterday but I was too busy buying the dip.


The cycle is always the same. Work happens in a fury. Things quiet down for a while. A project appears finished. And just before launch, it seems as though no work was done. The fury picks up again, launch happens, and tomorrow all is forgotten. We move on to the next thing.

Pre-launch jitters or coffee jitters. I’m not sure which I’d choose as a chronic illness.

The Problem with Important, not Urgent Emails

At this point, at least 90% of the email I receive is purely automated or transactional. Purchase confirmations; newsletters for both research and consumption; 2FA links, you name it.

The other 10% is incredibly important.

Of that 10%, only 2% is urgent. Email is not where I go for urgency. It’s a chore. I have to block time out for it. The thought of writing responses is brutal.

In my starred folder—which means “pretty important, but not urgent”—around 50 or 60 emails have piled up that I haven’t had time to give myself to.

I’d love for there to be a way to automate responses that go something like this:

I promise to get back to you because this is important, but it’s not urgent, and I think we can both agree that whether or not I respond now or in 3 months won’t change much.

That’s impossible to do now, and I’m probably not going to manually can those responses.

I don’t think email’s broken. This part of it is, though.