Writing

At a previous org, I discovered a team had been using a standalone email platform to send communications to customers. Not the approved MAP. Not something IT had vetted. A completely separate tool, a relic of a long ago acquisition, with a single shared login, manually imported lists, and years of accumulated segments that existed nowhere else.

My first instinct was simple enough: migrate them to our actual platform. Consolidate the data. Get everyone on the same system. Easy.

It was not easy.

When you crack open one of these rogue platforms, it tells a story. Not a clean one. More like walking into someone’s garage workshop where everything is covered in sawdust but they swear they know exactly where the 10mm wrench is.

The list names alone were a journey. There were at least a few variations of “List Name_DO NOT USE” which, if you’ve been in this world long enough, you know means someone sent to the wrong list at least once. My personal favorite was a particular segment of customers that was apparently on its third iteration, helpfully identified with “_V2” at the end.

Growing up, I was the one in my family who wanted to know how things worked. Not just use them, but understand them. I built my first computer as a pre-teen and still remember the rush of watching it POST for the first time. I also remember when it caught on fire because I’d routed a wire too close to the GPU, but that’s a different story.

That curiosity shaped everything. I wanted to know how websites were made, so I learned. I wanted to understand how applications worked, so I tinkered. Technology wasn’t just a tool. It was a door to something bigger. The internet, especially, felt like an infinite library staffed entirely by weirdos who were happy to teach you things if you just showed up and asked.

I spent countless nights falling down rabbit holes. Learning about topics I didn’t know existed. Finding communities of people who cared deeply about obscure things. Playing games that let me wander through worlds someone else had imagined into existence. It was formative in a way that’s hard to overstate. The internet made me who I am.

And now I have kids. And I don’t know what to do with any of this.

It’s not that I think technology is bad now. That’s too simple, and honestly, kind of boring as a take. I still love building things. I’m writing this on a website I built myself. I have a 3D printer in my garage that is running constantly. I get genuine joy from making a small app that does one useful thing. Or a bunch of useless ones. The curiosity never left.

I’ve been evaluating, implementing, and occasionally ripping out marketing technology for over a decade now. CrowdStrike, Teradata, Coursera, and now Accruent. Different industries, different scales, same patterns.

After enough vendor calls, demos, and post-mortems, you start to notice things. Here are the red flags I watch for now.

Translation: you’ll be writing custom code forever.

A flexible API isn’t a feature. It’s an admission that the product doesn’t do what you need out of the box. Every “just hit the API” answer is future engineering work that doesn’t show up in the license cost.

Ask instead: What can I do without the API? What do most customers accomplish in the UI alone?

You know that feeling. You’re three hours into designing a solution. There are diagrams now. Maybe a spreadsheet mapping dependencies. You’ve considered edge cases that have a 0.3% chance of occurring. The voice in the back of your head is whispering something, but you’re not listening because you’re too busy adding another layer of abstraction.

The voice in the back of your head is saying: this is too much.

You ignore it. You keep building.

I’ve been there. Many times. So I built a quiz to externalize that voice.

Am I Overengineering This? is exactly what it sounds like. A few honest questions. An answer you probably already know but need externalized.

So the world is a lot right now. You’ve noticed. I’ve noticed. We’re all just… yeah.

Anyway, I made a website where you zoom infinitely into a potato. There’s another potato inside. And another. It’s potatoes all the way down. I don’t know what to tell you. You can also receive a random compliment from a very specific person. There is a Victorian ghost out there that really believes in you.

Weird Little Joy Machines is a collection of tiny, pointless joy machines. The whole point is there’s no point. You click around, maybe smile, close the tab, go back to your life. That’s it.

I wanted it to feel like the internet used to feel. Just weird stuff someone made because they wanted to.

A few years ago, I was knee-deep in a marketing tech stack migration when someone from IT pinged me: “Hey, did you update the SPF record for that new tool?”

I… had not.

Cue the frantic DNS lookup, the realization that we were one include: statement away from hitting the 10-lookup limit, and the growing suspicion that nobody actually knew if our DMARC was configured correctly. We patched it together, moved on, and I made a mental note: someone should build a simple tool for this.

That someone turned out to be me. Several years later.

SendReady is a free email deliverability checker I built to validate the stuff that breaks email delivery: SPF, DKIM, DMARC records, and the one-click unsubscribe headers that Gmail and Yahoo now require.

I’ll be the first to admit that doing quick calculations in my head has never been my strong suit.

So when I got my new french press (an Espro P3, if you’re curious) and the instructions threw out ratio suggestions based on roast level, I got a headache. I just wanted coffee. Instead I was staring at a bag of beans trying to do division.

So I built a calculator to do the math for me.

You pick your roast level, which sets a default ratio. Light roasts are denser and extract differently than dark roasts, so they need less water. A 1:15 ratio versus 1:17 for dark. I knew the basics, but building this sent me down a small rabbit hole confirming the details.