johnmaconline chain logo johnmaconline / The250
Daily one-pagers about AI, leadership, technology, and being human.

johnmaconline

I'm writing to think, learn, and remember in public. I'll be here everyday.

April 19, 2025 1 minute read

What Kind of Work Do We Want to Do?

AIThe250

One of the hopes for AI is that it can help us do more of the work we want to do and less of the work we don’t want to do.

The question is: What kind of work do we want to do?

It’s easy to answer with clichés. Work that’s creative. Work that’s meaningful. Work that’s fun.

What’s meaningful? Fun for who?

AI doesn’t care. AI will take on whatever we give it. Boring? Repetitive? Beneath us?

Sure, but if we’re not careful, we’ll discover that sometimes the boring parts are the parts that keep us engaged in life. The routine that shaped us. The repetition that made us better.

The work we say we want is often messier than we remember.

So, what kind of work do we want to do?

April 18, 2025 1 minute read

Maybe AI Should Replace the CEOs

AIThe250

Here’s a cool little experiment that the people at The Hustle did: they used AI to replace the CEOs at several companies and compared what AI would do to what they actually did.

Same company. Same data. Same market conditions.

It’s a fun read. Spoiler alert: some of the decisions are the same, some are different.

AI is really good at patterns. It’s good at bounded problems. It’s good at history. 

Part of being a CEO is all those things.

However, part of being a CEO is also leadership. Leadership isn’t just making decisions given all the facts. Leadership is about having a vision for the future.

AI has no vision for the future. Just incentives.

If you’re a CEO, you should be using AI.

But also, you should be asking, “What kind of company do we want to be?”

April 17, 2025 2 minute read

Verbosity (Core Dump)

AIThe250

I’m wordy. Especially when I’m thinking and talking at the same time. That’s a recipe for disaster.

So I ramble. And I can see the eyes glazing over.

I’m much better when I can dump it all out of my head, roll it around, experiment, and edit the snot out of it. It’s one of the reasons — actually the main reason — why I keep these posts to less than 250 words. 

Less is more.

But in software development, my tendency towards verbosity pays dividends.  

The more explicit, the better. Dump a million messages to the console so that if you have to analyze what happened after the failure, you’ll have a complete step-by-step map — the core dump. Future me (or future someone else) will thank you. 

And AI loves verbosity.

It doesn’t care if I’m rambling. It doesn’t care if I repeat myself three different ways. It doesn’t care if I’m even coherent.

AI just eats it up. The more I feed it, the more it gives me back. Round and round. AI doesn’t know what to leave out. It doesn’t know what’s important. It doesn’t know when to stop.

That’s still my job. Cut. Tighten. Refine.

Say less.

Make it mean more.

April 16, 2025 1 minute read

Should We Bring Back the Direwolf?

The250

De-extinction. Should we be doing this?

We’ve brought dire wolves back to life. What’s next? Wolly mammoths and saber tooth tigers? 

Soon, it’s Jurassic Park.

Science and technology are wonderful engines that move us forward. On one hand, science and technology exist to solve problems. We generally agree on what those problems are. Not many people (although some, for sure) would rather have lived in 1225 than in 2025. Life was much harder in 1225. 

Thank you, science and technology. 

On the other hand, science and technology move forward through passion and excitement. Passion and excitement aren’t necessarily tied to objective or even subjective problem-solving. 

Sometimes, we just wanna try stuff that we think is cool. Because we can. 

Just because we can doesn’t mean we should. 

The juxtaposition of capability and incentives and ethics. How do we resolve it?

We might not need to slow down, but we definitely need to look up.

April 15, 2025 1 minute read

Good at Mechanics, Bad at Why

AIThe250

AI is probably better at grammar than you but has no idea what to write about.
AI is probably better at Python syntax than you but has no idea what the application should do.
AI is probably better at Excel formulas than you but has no idea why it needs a spreadsheet.
AI is probably better at generating CSS than you but has no idea what the website should feel like.

Until you tell it.

AI is good at the mechanics, but bad at the why.

April 14, 2025 1 minute read

Remember Alex Tew’s Million Dollar Homepage?

The250

Here it is.

It was a weird, interesting, and ultimately successful (for him) idea — sell 1 million pixels of advertising on a webpage for $1 a piece. 

Rake in $1 million dollars. Done.

Alex put this up in 2006. If you go to the page now, it seems largely, possibly completely, unchanged from its initial inception. It’s kind of a cool snapshot of one side of the internet in 2006. There are lots of gambling ads, a bunch of “free” promises, companionship, some ads pointed at the fringes, and several promising to help you make money or get traffic. 

If you click on the pixels/ads, you’ll find that most are broken or redirect to something different than the original. 

It’s weird colors and images and is very clunky. It strikes me as Donkey Kong crossed with AOL. Nothing stands out (OK, I do see Thomas the Tank Engine). It’s a sea of 8-bit colors. The very opposite of useful advertising. 

Who could have possibly extracted the value supposedly provided by this page?

Nobody, of course.

Except Alex.

April 13, 2025 1 minute read

Managing Versus Leading

The250

The manager looks for the right time.
The leader makes it the right time.

The manager sticks up for the process.
The leader sticks up for the endpoint.

The manager creates safety.
The leader creates tension.

The manager saves it for tomorrow.
The leader does it today.

The manager has authority.
The leader takes responsibility.

The manager waits for permission.
The leader acts regardless.

The manager has a good system for tracking and reporting status.
The leader turns reports into decisions.

The manager has an effective defensive posture.
The leader gets punched in the face.

The manager proceeds knowing it will work.
The leader proceeds knowing it might not work.

Good management is necessary in a well-functioning organization. The systems we all depend on daily need good management.

But let’s not confuse management with leadership.

Leaders are in short supply. Will you be one?

April 12, 2025 1 minute read

Systems are Designed to Be Followed

The250

I recently detailed my system for Wordle.

I went on and on about how my system isn’t designed to solve the Wordle in a minimum number of tries. It’s designed to solve it within 6. There I was on my high horse about expectations and systems, wagging my proverbial finger, “Don’t expect an outcome it’s not designed for! If you don’t like the outcome, design a new system!”

And then it happened. I’d seen something similar one other time, as I mentioned, and I nailed it. I got excited. 

My first word:

Wow! Opportunity! I got this in 2! Screw the system!

And then, womp, womp, womp…

I went off script, and it sucked me into the Wordle quicksand. The seemingly easy but actually tricky one-letter problem. Which is it?

If I’d stayed with the system, I’da had it in three. 

Systems are designed to be followed. If you don’t like the outcome of your system, design a new system.

April 11, 2025 1 minute read

Why Not Today?

The250

Let’s assume you’ve gotten out of bed (or maybe you’re reading this in bed, but definitely will get out of bed).

That means today can be the day.

Today can be the day you make the call.
Today can be the day you say “Hello.”
Today can be the day you clean it out.
Today can be the day you decide.
Today can be the day you cut it off.
Today can be the day you build it.
Today can be the day you get excited.
Today can be the day you learn it.
Today can be the day you cross it off the list.
Today can be the day you say it.
Today can be the day you stop.
Today can be the day you start.

So why not today?

April 10, 2025 1 minute read

Humans Cooperate, AI’s Interface

AIThe250

We’re built to cooperate. Heck, you learned it in kindergarten, but let’s face it, you didn’t need to learn it. You already knew it.

We comunicate, coordinate, and generally work together towards some cooperative goal. Even when we are singular and working by ourselves.

We journey through community. Community happens through cooperation. We like doing what other people are doing. We like doing the things that people like us are doing. Even when we are not cooperating on purpose, it’s because we’re cooperating with a different community.

AI has no desire to cooperate. Well, AI has no desire. Just capability and incentives. AI doesn’t give one shit about what another AI is doing. We, as humans, can incentivize AI’s to work together, but it’s not cooperation. It’s interfacing.

This one to that one, each with its own incentives and APIs. Pass the bits back and forth. Even if the AI is provided a collective incentive, it’s not cooperation. It’s mathematical interfacing.

Cooperation requires “I” and “we.” It requires desire. A will. A soul. Whatever you want to call it.

Humans cooperate. AIs interface.

Pin It on Pinterest