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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.

May 8, 2026 1 minute read

Doing Too Much

AIHumanLeadership

I’ve had 8 agents running at a time needing my attention.

I’ve used those agents to generate stacks of documentation, thousands of lines of code, dozens of ideas for solutions with prototypes, and hundreds of bulletized summaries that need to be read.

It’s too much.

Too much means you can’t pay attention to it all. Too much means you’ve lost track. Too much means your quality suffers.

Yes, AI makes it easy to do, but also easy to do too much.

The magic comes when we do the right work well, rather than simply more of it.

May 7, 2026 2 minute read

The Tickle in Your Throat

HumanThe250

It starts as a tickle at the back of your throat.

A little uncomfortable at first, but then it reaches the point where you must take some action. A sort of cough with your mouth closed. Not a full cough. Kind of under the covers and almost subconscious.

That works the first time, and the tension fades. Nobody really noticed. But it builds again, and you’ll have to deal with it again. Maybe that little throat-clearing works a few more times, and you’re still flying under the radar. The person next to you might be the only one who noticed. Maybe a little glance.

You know what’s coming, though.

Eventually, that little closed-mouth throat-clear doesn’t relieve the tension. You try to hold it off. A few more closed-mouth throat-clears, but the feeling builds. Maybe another person or two gives you the sideways glance.

You’re swallowing. Eyes are watering. Trying to do anything you can to relieve it.

But you have no choice. The existential reality requires you to succumb.

You must cough. Full-throated and probably a few times in a row. You can’t hide it anymore. You’re gonna make a ruckus.

Now they all know.

You’ve startled some. Annoyed some others. Some may be a little fearful.

But one other or, if you’re lucky, a few others think to themselves, “Thank God!” Because they too feel the same tickle. They, too, have been struggling to keep it under wraps, thinking to themselves, “can I get through this without anybody else knowing?”

Now they, too, can cough. You gave them permission to make their presence known. Relieve the tension that’s building in the back of their throat. So they do.

And now you’re a movement. Sometimes it just takes one.

Maybe that one is you.

May 6, 2026 1 minute read

Your Perfect Team

AIHumanLeadership

What kinds of people do you like to work with?

Are they friendly? Supportive? Maybe you like to work with highly capable people, regardless of their interpersonal skills. What about integrity and responsibility? Commitment to the mission?

Design your perfect team.

Then go ahead and write those personalities up as markdown files and hand them over to your agents.

It’s your team. You can design who they are.

May 5, 2026 1 minute read

Automating Scar Tissue

AIHumanTechnology

AI is great at reducing friction. It can take something tedious and make it tolerable.

But there is a trap there.

Pain is information.

Before you automate the status report, ask who reads it.
Before you automate the testing, ask what we are trying to learn.
Before you automate the meeting notes, ask whether the meeting is worth having.

If a process is painful, that pain may be telling you something. The outcomes may not be important. The ownership may be wrong. The system may be broken. The work itself may not matter.

Do we need more documentation? Do we need more review comments? Do we need more bullet points in the summary?

The answer to those might be “no.”

Take a good look at the friction before you automate around it.

May 4, 2026 1 minute read

Dividing the Room

AIHumanLeadership

Consensus builds comfort.

Consensus might be the right approach. You need people on board. You want them to feel safe. You want their status antennae tuned in to the connection.

But consensus might have to wait for phase 2 or phase 3.

Those people on that side of the room don’t want it. They understand today. They excel at today. The status hierarchy reflects today. Why would they want to flush their current position in the hierarchy?

The computer divided the room. The internet divided the room. The iPhone divided the room.

AI divides the room.

You might want to start phase 1 by dividing the room.

May 3, 2026 1 minute read

A Little Pride Goes A Long Way

HumanLeadershipThe250

Pride comes before the fall.

OK, sure, but let’s talk about your work. Something you’re making, or something you’re doing.

A little pride ensures you make it better. A little pride ensures you put more of yourself into it. A little pride ensures you care more before you say it’s complete.

A little pride goes a long way.

May 2, 2026 1 minute read

Were you there?

HumanThe250

We all have “were you there?” cultural moments.

Maybe a sporting or music event, a rally, a movement, or even a disaster.

These moments live in our memories specifically because of their cultural relevance. A collective experience. A shared experience with those who were there, yes, but also with those who cared, even if they weren’t.

It’s also possible that these moments gain momentum for you as time marches on. When it happened, maybe no big deal, or at least not as big of a deal as when you look back.

Memories are a funny thing.

And shared memories make everything bigger.

Be on the lookout for shared memories.

May 1, 2026 1 minute read

Two-Faced

HumanLeadershipThe250

We use two-faced as a slur.

But aren’t we all? Aren’t many-faced?

Don’t we each have many versions of ourselves? Each of these selves shows up at different times in different situations. Sometimes intentionally. Sometimes inopportunely.

Sometimes the situation calls for a different version of you.

Maybe we oughta lean into two-faced.

April 30, 2026 1 minute read

Throwing Tokens at the Problem

AILeadershipTechnology

Throw money at the problem.

Spend your way out. Possibly frivolously. More people, more services, more tools. Whatever’s necessary.

But spending more money requires an approval chain. Checks and balances. Is this a good idea? Do we have the budget? What if we don’t?

Now, tokens serve as a proxy for money, and engineers have direct access without the approval chain. Sure, someone pays the bill, and that person’s eyes may bulge when they get the bill. But not the engineer. The engineer can freely throw tokens at the problem. They’re building more, testing more, trying more, outputting more, documenting more, and failing more.

Since I built my own personal token tracker in the middle of February (entirely with AI tokens), I’ve spent almost 4 billion tokens myself. 4 billion with a “B.”

It’s coming, however. The approval chain and checks and balances for tokens.

Whether it’s an OpenAI or Anthropic IPO, or compute limitations, or someone in the token supply chain simply decides it’s time to cash in. Biggly.

Chuck ‘em now, before every prompt requires a purchase order.

April 29, 2026 1 minute read

“I Used AI to…”

AILeadershipTechnology

I see this a lot now. Also, “Here’s the AI summary of…”

There are two reasons why people at my company feel compelled to indicate they’ve used AI:

  1. It’s AI, so beware.
  2. You keep telling me you want me to use AI, so here you go.

In a way, it’s kinda like a, “So there!”

But, of course, we need to, and will get to the point where we just say, “I did this work…” and “Here’s my summary of…” AI will just become part of our workflow, not a novel or “because you said so” part of it. Part of our work.

Then, we’ll get back to the fact that work with our name on it is our work. No matter what tools we used.

It’s always been your choice about the quality of the work with your name on it.

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