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Daily one-pagers about AI, leadership, technology, and being human.

johnmaconline

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April 28, 2026 1 minute read

So You Wanna Be a Gambler?

HumanThe250

The Monty Hall problem.

You’ve got 3 doors to choose from.

One has a new car, the other 2, goats. So you pick one, but don’t open it yet. The host, who knows what’s behind each door, opens one of the 2 you didn’t pick, and it has a goat. Now you have 2 doors to choose from, the original one you picked and the other.

He then asks you if you’d like to switch your answer.

What do you do?

Most people look at it and say, “Well, 50/50, why would I change? It doesn’t matter.”

But its not 50/50. It’s 2/3 to 1/3. You should change. Every time.

If you do, you will win 66% of the time. I won’t explain it here, but you should look it up. I prefer the YouTube explanations. The answer includes probability, foreknowledge, and problem definition.

If you wanna be a gambler, stock trader, or even an NFL draft picker, you should get very clear on why it’s not 50/50.

Experts do their homework.

April 27, 2026 1 minute read

New Versus Used

AITechnologyThe250

I’ve purchased 16 cars over my adult life.

Twelve of them have been used. I like to buy used cars. For me, I feel like I get most of the new stuff for that model at a better price. I miss out on the latest and greatest, of course, but that’s the tradeoff I make.

Opus-4.7 and GPT-5.5 just hit.

All of a sudden, I feel like 4.6 and 5.4 are useless.

But they’re not, of course. Just like used cars. 4.6 and 5.4 were new until about yesterday. They were serving me well.

And now they’re gonna get cheaper.

I suspect that new versus used models will be one of the variables we all use when token cost becomes the limiting factor.

April 26, 2026 2 minute read

Film and Vinyl

AITechnologyThe250

Vinyl has made somewhat of a comeback, and film’s been popping its head up as well.

By the way, neither is “better” than their digital counterparts. Not objectively, anyway. You may think so, and that’s either equipment, nostalgia, “people like me,” or confirmation bias. It’s preference, and preference makes this world an amazing place. Lean into your preferences.

Regardless of their comeback, neither vinyl nor film will re-overtake their digital counterparts across the market. Digital is simply too convenient. Use whatever cliche you’d like — can’t put the toothpaste back in the tube, cat’s out of the bag, etc. Digital’s here to stay.

Technology has a way of making what used to be done by experts convenient and accessible for normies. The form once served as a fence. Keep the experts and artists in, and the regular people out.

While the content of art can be connected to the form of the art, making the form easier for the masses exponentially ramps up the amount of content produced.

Some of it good, some of it terrible, and most of it mediocre at best. The content itself matters.

AI now makes forms such as coding, accounting, financial planning, and consulting easily accessible to just about anyone.

But just because you can vibecode an app idea, doesn’t mean it’s gonna be a good app. Just because you can build out a financial plan in a few minutes doesn’t mean it’s a good financial plan.

The content still matters.

Let’s stop complaining about AI taking over the form and stay focused on content.

April 25, 2026 1 minute read

Should You Even Become That Person?

HumanLeadershipThe250

We are all becoming.

We are becoming at work and at home, and likely they are intertwined, whether you want them to be or not. One affects the other. Linked by the fact that although you can play roles, you can’t disconnect your being.

The question is, who are you becoming? Your habits, learning, feelings, and experiences (intentional and unintentional) all play a role as change agents.

Look at those above you. You might want their title and benefits, but do you want their job?

Look at those around you. You might want their lifestyle, but do you want to do the work?

You are becoming somebody, but should you even become that person?

April 24, 2026 1 minute read

The Objectives Trap

HumanLeadershipThe250

The people selling life plans tell you that you need to set objectives.

Your boss, shareholders, or HR department tells you that you need to set objectives.

And then, of course, you gotta measure yourself against these objectives.

What happens if you meet all of your objectives? What if you change your mind? What if you don’t meet some or any of those objectives?

Maybe you’ll get an attaboy. Maybe you’ll get your hand slapped. Maybe you’ll get fired. Maybe you’ll find yourself down some road or at the bottom of some gully that you never, just because someone else told you you needed objectives.

What do you want to do? Deep in your soul.

Do that.

April 23, 2026 2 minute read

The Dark Grey Cloud

HumanLeadershipThe250

I can see most storms coming my way.

I look out my window, to the west, across the farm field, and see the grey cloud. Gathering darkness as it creeps closer to the hill on the other side of that field. It’s over there. Not here.

I see one now. Impending.

The cloud changes when it gets to the hill. It morphs from a dark, sharp wall into a lighter, amorphous blob. Hard to see where it begins. As it envelopes the hill, the sheets of rain begin to obscure the dark green with a haze like a sheer curtain flowing in a breeze.

The trees and bushes in my yard start to rustle, at first, and then wave violently as if they know what’s coming and they’re doing their best to get away. Yet, they are handcuffed to the trunks that anchor them to the ground.

And that billowing, sheer curtain walks across the field. Slow but deliberate. It knows we can’t go anywhere.

When the curtain reaches my yard, it’s almost tentative. A few drops at first. You can count them on the front walk. Individuals sent out either to test the ground or to announce what’s coming. Maybe both.

But then, quickly, a deluge. No longer individuals. Too many. Too fast. Too wet.

You can see those dark grey clouds coming, but you can’t always get away.

So what will you do?

April 22, 2026 1 minute read

The Day is Young

HumanLeadershipThe250

Normally, you hear, “The night is young!”

A mantra to keep the party going. We don’t know what might happen, and this could be the best night of your life (if you’re willing to keep the party going).

Fine, but why not the day?

Work happens during the day. Responsibilities happen during the day. Regular stuff happens during the day.

Exactly. And that’s the life you make.

The day is young.

What will you do with it?

April 21, 2026 1 minute read

Running in CRisis Mode

HumanLeadershipThe250

We all can run in crisis mode for a time, and it can be fruitful.

But it can’t last forever. If crisis mode just becomes “our mode,” a few things happen.

We forget how to work on important things. We forget how to plan out what the important things are. We forget how to prioritize and what our priorities should be.

If all work gets prioritized by the crisis of the day, we can’t possibly know when we’ll be done with the important things.

Crisis mode can be a tool, but it can’t be a way of life.

April 20, 2026 1 minute read

It’s New Model Day!

AILeadershipTechnology

Opus 4.7 hit the planet yesterday.

For engineers, new model day has become like Christmas Day for an 8-year old. “What great new stuff can I do with this?!”

Maybe new model day should have it’s own named holiday.

I’ve already got it in my agent configs and have moved about 200M tokens through it.

Each model update, so far, has been tangibly better than the last. Each one moves us closer to “now it can do my job.”

Either figure out how to get AI working for you, or you’ll work for AI.

April 19, 2026 1 minute read

Trust Stories

AIHumanTechnology
  1. Evidence. Data.
  2. Hypotheses. Findings. Conclusions. “This is what this means.”

The first should be objective (assuming proper instruments, methods, and measurements) and hopefully complete. That’s the truth.

The second is the story about the first. Human interpretation.

If the humans do their job correctly, and the evidence and data are complete, the second should also be truth. We want them to be truth. The pursuit of science.

But trust comes to the table here. Do you trust the humans drawing the conclusions? Do you trust their methods, motivations, and perspectives? Do you think their data is complete? Do you believe their stories?

Because if you don’t, or your tribe doesn’t, you might not trust their answers.

Maybe AI will help us here. I think it can, but also, AI only knows what we know. Plus there’s the whole question of “how is this AI incentivized?”

So we’re back to trust. Which is a story.

Humans lean more on trust than they do evidence.

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