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 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. 

September 12, 2025 1 minute read

Gaming the Algorithm

First, there was SEO (Search Engine Optimization). 

If you were clever, you could figure out how Google ranked websites in its search results. Once you knew that, you could game the system. Once you could game the system, you could sell your services to others. 

Then, Google became more sophisticated and outpaced the gamers. Then the gamers caught up. And then SEO became YouTube and social media algorithms. 

And so on. Round and round.  

Is this the game you want to play?

You can chase the algorithm, but they have the control, and they’re trying to keep out the gamers. 

But there is a different and deeper algorithm. One that hasn’t changed in 1000 years. 

The human one.

It’s built on curiosity, trust, relevance, usefulness, and impact. 

The “you should see this” impulse and it spreads around dinner tables, break rooms, and group texts. It’s shared not because it was optimized for the algorithm, but because it hit something real. 

You can choose. You can play for the click, or you can play for the conversation. 

The real algorithm is still human. 

September 11, 2025 1 minute read

Desires and Needs

Hunger is physical. 

Our body needs food. Our physical state drives physical hunger.

Hunger is also emotional.

We desire particular tastes, forms, and food experiences. The stories we’ve experienced, we tell, and we hear drive emotional hunger. 

One keeps you alive. The other makes you feel alive.

We need food. But we want tacos. We want the corner booth, the smell of lime and cilantro, the basket of chips before the meal. The margarita. 

We want the feeling.

Needs keep the system running. Desires shape the experience.

This isn’t just about food. It’s how we build products. Lead teams. Raise our kids. Choose careers.

Desires and needs don’t always align. Sometimes they conflict. Sometimes they trick. 

Our job isn’t to eliminate desire or shame it. It’s to see both. To design for both. To build stories around both. 

A life that meets only needs is starvation. 

September 10, 2025 1 minute read

Showing Up

A friend of mine has an amazing little trick she uses with her kids. 

Well, it’s not a trick. To call it so is to undervalue its brilliance and the truth it uncovers. It’s psychology at its most powerful. 

Two photos:

  1. Very happy and excited
  2. Sad, upset, crying, or angry

In the moment (whatever moment that is), you simply show them each of these pictures of themself and say, “Both of these are you. You get to decide which one of them you want to show up. It’s up to you.”

How you show up is a choice. 

At the table. At work. For your partner. For your family. For your community. 

You are all those people in the pictures. 

How do you want to show up for this? 

September 9, 2025 2 minute read

Starting Your Story

Have you seen the (brilliant) Miller Lite 50th anniversary commercials? 

Christopher Walken voicing over, “Legendary stories start with a Lite.” 

It taps into something powerful about human nature (as does most good advertising) — life is all about stories. 

And the start is magic. You’re staring at the fork in the road. You can go either way. Which way? Well, where do you want to go? You don’t know? Then it doesn’t matter. Just go. 

Yet, starting is sometimes the hardest part.

We don’t like unknown. We like guaranteed. We want to know the ending before we commit to the beginning. 

If this, then that. Go this way, you’ll end up here. 

We obsess over perfection. Over what they’ll say. Over how we’ll look. Over losing what we have. Over never making it to the destination.

So we stay put. We stay in our lane. We keep sipping the green juice. We keep funneling the 6% into our 401k. 

But that’s not how legendary stories are made. 

Legendary stories start with an unknown ending and a host of possibilities. 

They start with a desire and a little risk. A little curiosity. A little stupid. A little brave.

They start before the plan is ready. They start with motion.

So go ahead. 

Crack one open and take that first step. 

Start your story.

September 8, 2025 1 minute read

Open to Changing Your Mind

In Season 5, episode 2 of Downton Abbey (IYKYK), Carson and Mrs Hughes face a disagreement. 

He and she are on different sides of an issue he feels strongly about, and he’s uncomfortable. He doesn’t like it when they’re not on the same side. 

But also, he’s convicted. He believes he’s right. She’s wrong. He can’t simply go along to get along. He’s too principled for that. 

However, he remains open. He admits that he’s willing to be convinced. All he needs is someone to convince him. 

And eventually, a simple conversation does the trick. He’s been convinced. 

That’s what we need more of. More openness without tossing our principles to the wind. 

Open to new data, new arguments, new feelings. Open to changing needs, changing perspectives, and changing culture. Open to changing one’s mind. Open to being convinced. 

Open.

Changing your mind isn’t a weakness. It doesn’t mean you don’t have principles. 

Openness is the bridge between conviction and wisdom. Without it, all you have is stubbornness.

September 7, 2025 1 minute read

Another Trip Around

Today is my birthday.

Thanks. No big deal.

Yet, it is a big deal. Not because it’s me, or it’s a milestone, or there’s some need to celebrate. 

It’s a big deal because a) there aren’t that many left, and yet b) there are many left. 

What will I do with them? 

I plan to keep the “I will be” list long and inspiring. 
I plan to express my gratitude.
I plan to keep learning.
I plan to ensure those around me know I love them.
I plan to get better.
I plan to take it as it comes.

I plan to get started. 

September 6, 2025 2 minute read

PhDs

I stood in front of potential investors, giving my pitch, and was asked the following:

“Are you all working full-time in the business?”
“Yes”
“Oh, good, we like our founders to be PhDs.”

A little confused, I said, “PhDs??”

“Poor. Hungry. And desperate.”

Oof.

When you see movies about startups or hear founders talk on Guy Raz’s show, you get a lot of this. Couch surfing. Living in a barely running sub-compact (that you park around the corner so nobody sees). Skinny and scrounging. Two different shoes or homemade clothes. Lots of kindness from family, friends, and sometimes strangers. 

Poor. Hungry. Desperate. It makes a good origin story. 

You have two things when you are in this state:

  1. Nothing to lose. 
  2. No power.

That’s right where they want you.

Nothing to lose means you should have the fire to do whatever it takes. Yet, no power means you’re desperate for the money/resources. Which means if they give it to you, they have the power.

The magic here is hungry.

You don’t need to be poor or desperate to be hungry. Hungry can come from vision, hope, and desire — a deep inner need to make a difference. 

So the question isn’t just, “Are you hungry?” The real question is, “Who holds the power when you are?”

Because with hunger as the fuel, power is the steering wheel. If you hand off the steering wheel, then someone else is in control of your destination. 

September 5, 2025 1 minute read

What to Avoid Today

Maybe avoid one or some of these today:

  • Hitting snooze
  • Sitting all day
  • Taking what’s yours
  • Looking past the person talking to you
  • Talking over someone else
  • Checking your phone in the middle of a conversation
  • Getting upset about gas prices
  • Taking revenge
  • Skipping a lunch break
  • Staying comfortable
  • Overexplaining
  • Overpromising
  • Underdelivering
  • Staying in your lane
  • Sugar substitutes
  • Doing the easy thing
  • Busyness
  • Filling the silence
  • Focusing on what you can’t control
  • Doomscrolling
  • Saying “I can’t”
  • Reacting to a post
  • Waiting for permission
  • Multitasking
  • Gossip
  • Quicksand
  • The News

If you need something to do, here are some ideas. 

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