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.

September 22, 2025 1 minute read

Giving Up

All the inspirational posters talk about not giving up.

But they’re wrong. Sometimes you should give up.

But not because it’s hard, or uncomfortable, or you can’t yet find a solution. 

You should give up when it’s wrong — the wrong path, outcome, or the ends don’t justify the means.

Giving up is the best approach when it’s wrong. 

September 21, 2025 1 minute read

Pointing

Sometimes it’s, “Hey, look at that over there.”

A spectator. Observer. Unengaged. 

Sometimes it’s, “Hey, let’s go over there. Let’s go that way. Let’s get there. Come with me.”

Sometimes it helps to point. 

September 20, 2025 1 minute read

Renting Versus Owning

I’ve been a renter. College, just out of college, and many vacations over the years in many locations.

I’ve been an owner of rental properties. College apartments and single-family homes. 

As a renter, I just showed up, kept the place nice, paid my bills, and called the landlord when there was a problem that needed fixing. 

As the owner, I cared. Deeply. About everything. Even things I didn’t cause. The pipes. The paint. The neighbors. The future value of the place. I couldn’t just show up.

Same thing happens with work.

You can rent your role. Check the boxes. Wait to be told. Clock in, clock out.

Or you can own it.

Solve problems that might not be technically your problem. Put yourself on the hook. Show up like your name is on the building.

You can tell who’s renting and who owns it.

AI won’t ever take the job of the owners. 

September 19, 2025 1 minute read

The First Draft Lie

You call it a “first draft” for a reason.

It’s the raw footage, not the edited version. It’s the napkin, not the document. It’s some tiles laid out on floor in front of you, not the cut and glued pattern on the wall. 

You don’t have to make your first draft the final plan. It’s a starting point. A vehicle to get your thoughts down. A catalyst to help you think about it and see where it might go. 

Write the garbage version. Say it badly. Build the barely-functional prototype. 

The first draft allows you to play. You can rethink it. You can change directions. You can change your mind. 

You don’t have to show the public.

But you gotta start laying bricks. 

September 18, 2025 1 minute read

Dead Air

If you’re a broadcaster, you never want dead air. 

Dead air indicates a problem. Something technical, procedural, or even human. The producer panics. The talker scrambles. The audience wonders. 

That silence screams loudly — what’s wrong?

But in your life, dead air is a signal.

Dead air gives you a chance to listen, breathe, think, feel, and allow the next thing to rise. 

Embrace the dead air. 

September 17, 2025 2 minute read

The Cutback

The cutback, sometimes called putting his foot in the ground by announcers searching for new descriptions, is a fundamental tool of the running back.

Everybody and everything is flowing to the right — the lineman blocking, the running back following,  defenders pursuing. The play unfolding like a river flowing. 

And then BLAM. 

He plants his right foot. Defies inertia. Cuts hard left. Against the flowing water. 

If he’s picked the right moment and executed it correctly, the defenders don’t have a chance against the river that’s already flowing. 

Because now it’s chaos. Defenders legs and bodies still moving right as they reach back to the left. The blockers keep them flowing. The angles collapse. 

The cutback wasn’t part of the plan. 

But he saw something and made a split-second decision. An opening. An opportunity. Or maybe he saw that the plan was going to fail miserably. It was going nowhere. A loss of yards. 

And he had the guts to cut back.

Sometimes you gotta take that opportunity. Even if it doesn’t score. 

Trust your eyes. Trust your knowledge. Trust your people. Trust yourself. 

Keep your eyes open for the cutback opportunity. 

September 16, 2025 1 minute read

Having It Your Way

You can probably have it your way. 

It might even feel good or comfortable in the moment, or make you feel like you’ve accomplished whatever you set out to do. 

It’s also usually easy to say, “This is how I want it.”

But what would it take to have it our way? Or making it possible for them to have it their way?

You can build something — a business, an organization, a family, a marriage — around that. 

September 15, 2025 1 minute read

Can’t Afford It

We do it all the time, especially as parents.

We say we can’t afford it. Whatever it is. Could be money. Could be time. 

We say it because it’s irrefutable. It’s a get of out jail free card. But it’s usually not quite true. 

What we really mean is we don’t want to prioritize the money or time. We’d rather spend it on something else. 

It’s healthy to occasionally rethink our priorities. 

September 14, 2025 2 minute read

The AI Plateau

Everyone’s using AI now.

We use it to draft emails, frame out contracts, identify plants, translate to English, tailor resumes, develop code, write marketing copy, analyze data, TL;DR stuff, plan dinners, build spreadsheets, and find analogies. Or, at least, that’s how I use it. But I suspect you and your colleagues are similar. 

And we’re getting pretty good at it. I mean, who even “Googles” things anymore?

AI is an amazing personal helper. A power saw rather than a hand saw. Personal automation. 

But companies? We’ve hit a plateau. 

Small business adoption is stalling. Mid-size companies are backing off. Enterprises are stuck in pilot mode — testing, pausing, hesitating.

Why?

Because personal use is simple. 

Organizational use is messy. Hard to grasp. Is AI another worker or is it still a tool? 

It affects systems, roles, trust, and risk. It requires change. It requires forward-thinking. It requires trying stuff that might not work. 

Most leaders haven’t figured out how to cross that chasm. 

But that’s the opportunity. 

Right now, AI work is mostly a side hustle. Quiet. Individual.

That’s not transformation. That’s personal productivity (although that is a worthy goal for workers themselves).

If you’re the leader who can figure out how to build AI into your operations, not just your inbox, you can win.

And then the magic happens — you can free up your people to do the work that actually matters.

Because AI isn’t the goal. It’s the amplifier. It’s the power saw. 

We want to use AI — not work for it.

September 13, 2025 2 minute read

But Will it Make Money?

From one or even several perspectives, this is the first and only question that matters.

Will somebody pay you for what you made?
Or, will somebody pay you for what you do?

This is what the market asks. Investors, bosses, even friends and family. We’ve normalized getting paid as a measure of what it’s — and you’re — worth. If you’re “in business,” then this is the question at the top of your mind.

And fair enough. Our system is built upon the exchange of money.

It’s an important question, but is it the most important? 

Here are some other important questions that need to be asked:

Will it make a difference?
Will it build trust?
Will it help someone?
Will it teach me something?
Will it get me in the room I want to be in?
Will it make me proud five months or years from now?
Will it attract the kind of people I want to work with?
Will it challenge the status quo?
Will it create a new system?
Will it make me better?
Will it make someone else better?
Will it make the system better?
Will it get me out of my comfort zone?
Will it make others want to talk about it?
Will it build community?

These questions get at the heart of the matter — what’s your signal? The signal is your work. Your impact. The dent you make in the world.

Profit isn’t the signal itself, but it rides on top of it. It modulates it. Amplifies it. Distorts it. Sometimes overtakes it.

But the signal is still yours to send. It’s the heart of the matter.

So yeah, we should ask, “Will it make money?”

Just don’t stop there because snake oil makes money if you know how to sell it.

But it poisons the well. 

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