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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.

November 13, 2026 1 minute read

AI Writing Slop

AIHumanTechnology

AI stinks at writing, and we’re already getting used to it.

I’m not talking about emails or Slack messages, because generally, who cares? The usual purpose of emails and Slack messages is to convey a short, succinct piece of information. AI gets that pretty good and honestly, we don’t care if it reads a bit AI-y.

I’m talking about actual writing. The kind that comes from your brain and out your fingers. The conveyance of thoughts and ideas via prose. Whitepapers. Essays. Reports. Books.

You know what I mean. You’ve seen it. You’ve shaken your head at it.

Be careful what you let yourself get used to, because the last thing we need is for the AI slop to become the norm.

AI will get better, but only if we demand it. So let’s do that.

Hmmm. Now wait a minute.

Isn’t this what English teachers show up every day trying to do with us?

Hats off to the English teachers. Thank you for what you do.

Please help.

November 12, 2026 1 minute read

Accidental Bad Boss

LeadershipThe250

It’s the boss’s job to create the conditions for their team’s success.

First, it’s worth defining what success looks like. Both for the collective and the individuals.

Those conditions can be built intentionally or “just happen.” Both approaches can yield success or failure. You might be a bad (or good) boss intentionally or accidentally.

If you’ve accidentally created the conditions for success, take notes so you can do it intentionally next time. If you’ve accidentally created the conditions for no success, take notes so you can figure out what to do next time.

Either way, you’re trying to become an intentional good boss next time.

November 11, 2026 1 minute read

Feeling Invincible

AIHumanTechnology

I admit that in some ways, I feel invincible right now.

It’s AI’s fault. Or rather, it’s my fault because I have AI.

Or is “fault” even the right word?

Because could it be true? Could I actually do anything because I have AI at my fingertips?

Want a web page? Hang on a minute. Need a change to the firmware? I’ll have it in a half hour. Should we refactor the middleware? I don’t know, but I’ll do some experiments. Need to add some user accounts? What are the names? Wish you had an iPhone app for this? I’ll have the prototype in an hour.

I’ve done all of these things. Because I have AI at my fingertips.

Feeling invincible lets you move forward on things that would normally hold you back. As long as that doesn’t mean running off the cliff like Wile E Coyote, its probably helpful.

There’s a catch, of course, because feeling invincible isn’t being invincible.

The trick is to notice whether you’re standing on the ground or in mid-air.

November 10, 2026 1 minute read

The Curve

AIHumanTechnology

Maybe some day with AI’s help, we’ll be able to build deterministic models for all of the systems in our world. The weather. Biology. Politics. Financials. You get the point.

I don’t think so, but I’m also willing to admit that maybe I’m wrong.

More and better AI, which means more compute power, can and will solve problems of scale. But I don’t think solving some of these systems in our world is a scale problem. I think an inherent source of non-determinism exists. That source goes by many names, but I call it God, and at the human level, I call it a soul.

Our world is probabilistic. Not deterministic.

I don’t think AI will change that. Even if it does someday, it won’t be in my lifetime.

So probabilities. The curve. What could be. What might be.

All beautiful and messy, and scary, and full of possibilities.

Don’t turn the curve into a toggle switch.

November 9, 2026 1 minute read

Just Do It

LeadershipThe250

“Just do it” is a terrible management approach.

Yet, it’s tempting. Especially in the moment.

Instead, side-by-side might work better.

Here’s how I do it. Here’s how you can do it. What would you need to do it? How can I help you do it?

Similar, but all more effective.

November 8, 2026 1 minute read

Take Your Hands Off the Wheel

AIHumanTechnology

Have you tried it?

Whether its full self-driving, or maybe just parking assist.

It’s hard. It’s scary.

It’s a trust thing.

The same is true for code. It’s time to think about taking your hands off the wheel. You don’t need to see the code anymore.

But you do need to understand the new paradigm of ensuring that the code does what you want it to.

This is engineering. This is the new world of engineering, which looks a lot like the old world of engineering, just at hyperspeed.

What does taking your hands off the wheel look like?

November 7, 2026 1 minute read

Looking Where They Want You To

HumanThe250

Like all nerds, I went through a magic phase as a preteen.

Of course, this was the 80s. No internet. No YouTube. But my neighbor was a basement magician. He and my Dad would sit around and drink beer, and I’d get the benefit of watching and learning some basic magic. So I soaked it up, and he taught me some stuff. I wasn’t very good, and then, you know, girls caused me to lose interest.

You’ve probably seen a good magician work their art.

It really seems magical, although you know intellectually that you’re just really looking where they want you to. It’s an illusion. Sleight of hand. Not real magic.

But if you want to enjoy it for the art it is, you suspend your intellectual knowledge, and you simply look where they want you too.

Be careful, though, when it’s not a magic show.

November 6, 2026 1 minute read

But That’s What I Do

AIHumanLeadership

I told you the story about Bill and why his attitude of “But that’s what I do!” left an important impression on me and ultimately led to his demise at the company.

Author’s Note: Wow. Now, with several years of writing these anecdotes under my belt, I would tell that story quite differently. But that’s part of what we’re doing here. We’re progressing in public.

Whether it’s a younger colleague in your office, offshoring, or now AI, if you find yourself thinking or saying out loud, “But that’s what I do,” it’s probably time to start thinking differently.

What is the moat you’ve built around your role?

Generate ideas. See bottlenecks. Strive for better. Help others. Try new ways. Change roles. Orchestrate and coordinate. Understand why. Create value. Be human.

In the age of AI, these are good moats.

November 5, 2026 2 minute read

Whales in a School of Fish

AITechnologyThe250

“In the 20th century, we were trained to be whales—massive, slow-moving, centralized, dominant. In the 21st, power has shifted to the school of fish: agile, decentralized, coordinated in real time.”
– Lisa Gansky

At this point, it’s a cliche to say “AI changes the game.”

It’s true, of course. I’ve been working through that here and taking you along in my daily existence as I wrestle with AI each day. It’s energizing. It’s exhausting. It’s fun. It’s scary. But make no mistake, you better figure out how to get AI working for you, or you will be working for AI.

As soon as I hooked into ChatGPT around Thanksgiving of 2022, I recognized it as the game changer. I didn’t yet know exactly what it would look like, but I knew. I first started talking about using it versus it using you here.

Which brings us to fish and whales.

You’re a fish. Institutions, big companies, and governments are the whales.

Consider Microsoft.

Microsoft already has/had the equivalent of 10s of thousands of software engineers that they could throw at any problem or project. Nothing really changes for them.

The magic of generative AI is for you. The fish. It allows you, the indivual, or a small team, to do amazing things. It gives you the ability, which in some ways, gives you the power. It gives you access to an elastic army of superworkers.

What can you do with an elastic army of superworkers?

AI rewards people with ideas.

November 4, 2026 1 minute read

Frivolous Tokens

AIHumanTechnology

I wonder how many tokens were spent this year on some form of this prompt:

“Help me decide what to be for Halloween.”

That, of course, is not the only frivolous way to spend tokens. I’m not sure where the line is. What’s a good use of tokens? What’s a frivolous use of tokens? What can we spend tokens on? What should we spend tokens on?

In fact, is using AI to help you decide what to be for Halloween frivolous? Because who am I to decide?

Just because you can doesn’t mean you should, but sometimes you should.

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