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 26, 2025 1 minute read

AI — It’s a Mirror Not a Brain

AI doesn’t think. 

Not like we do. Not like our brain does.

It can spot patterns. It can synthesize. It can reframe, remix, and repackage. 

These can seem like thinking, much like it seems like we can fly with an airplane. But we can’t really fly. Not like a bird.

AI doesn’t feel. It doesn’t wrestle. It doesn’t wonder. It doesn’t push back. It doesn’t get fatigued. It doesn’t stress. It doesn’t wake up one morning and decide it doesn’t want to — or that it does want to. 

What it does really well is reflect. 

We gave it our libraries, galleries, feeds, opinions, and search histories. And now we ask it to tell us something about that. 

It’s very good at that. 

But it’s a mirror, not a brain.

And mirrors can be helpful. They show us what’s already there. They’re fluent in what’s already there. That helps us remember, see, and understand. 

However, let’s not confuse fluency with wisdom because we risk mistaking reflection for truth. 

And we’ll stop doing the hard part. The human part. 

May 25, 2025 1 minute read

AI — The Road from Personal to Organizational Productivity

We debate AI at the personal level. 

Is it OK to use AI to:

  • Help me do homework?
  • Help me code?
  • Help me script a speech?
  • Help me write a novel?
  • Help me find patterns in this data?
  • Help me determine the legal precedent?
  • Help me create music and video?

These are interesting conversations, and those who find the right answers will make themselves more valuable.

But make no mistake, these aren’t the questions “the system” is asking. The system is thinking about how to use AI for corporate and organizational productivity.

Personal AI productivity is step one. A necessary step, but organizations won’t scale through AI without true leadership. 

Nobody has the playbook. Not OpenAI. Not Microsoft. Not McKinsey. They can’t tell you how AI fits your company, team, or goals.

If you’re a leader, it’s your job now.

May 24, 2025 2 minute read

The Story We Tell Ourselves About Ourselves — Confessions of a Minivan Owner

I’m coming out of the closet. 

The best car we ever owned was a minivan. Specifically, a 2004 Toyota Sienna. Dark green. Tan interior. Stone-cold awesome.

We put 250,000 miles on that thing.

Three kids. Countless vacations. Thousands of sporting events, lake trips, and hardware store runs. It towed our jet skis, cruised the interstate, and swallowed everything we threw at it.

It was reliable. Comfortable. Easy to drive.

You might be thinking, “A minivan? Really?” Yeah. Really.

Why does a minivan trigger a little cringe?

Probably identity. And that identity has been shaped by the culture and the market. 

Minivans became shorthand for “settled-down.” People want vehicles that say “adventure.” Even if the closest you get to off-road is the garden section of Home Depot. 

Manufacturers know this, and they leaned in. Minivan margins are slim, and SUV margins are fat. Target the marketing dollars at the fat margins. 

And we followed. Not because SUVs and giant pickup trucks are better for our lifestyle. But because of story. The story we tell ourselves about the person we are or want to be. It’s a story of freedom and adventure.

I don’t, but I could

Whenever you’re making something for someone else, make sure you know the story they tell themselves about themselves. 

Because it’s the story they’re really buying. 

P.S. About 80-90% of the 30 million Jeeps, SUVs, and trucks with knobby tires, roll-bars, and lift-kits on the road today have never been, and will never go off-road. That’s about 24-27 million “I don’t, but I could.”

May 23, 2025 1 minute read

Disagreement as a Method

Disagreement feels like rejection. Agreement feels like validation.

Disagreement is discomfort. Agreement is comfort.

But if you’re a leader, agreement can be a trap because your idea isn’t always the best.

The best ideas, or maybe the best outcomes, come from creative tension. From friction. From someone brave enough to say, “That doesn’t make sense.”

Want better ideas? Invite your people to disagree. Create space where people don’t have to nod along.

If no one’s pushing back, you’re probably not leading. You’re just broadcasting.

May 22, 2025 1 minute read

More is Better?

More is many things.

We chase more because it looks like progress, value, and better.

More is easy to sell. It’s harder to maintain.

More meetings mean more overhead.
More stuff means more stuff to deal with.
More choices mean more decisions.
More features mean more bugs.
More success requires more success.

More is unstable. Because it requires more.

May 21, 2025 1 minute read

You’ve Got 3 Minutes

That’s about 450 words. What will you say?

It’s a hallway conversation. A coffee line moment. A surprise introduction or run-in at the grocery store.

That’s just enough time to either make someone lean in or check out. It isn’t long enough to say everything. But it’s more than enough to say something.

Will their eyes glaze over or flit about? Or will their pupils narrow just a bit as the muscles around them tighten slightly?

Start with the spark. Not the history. Not the digression. Not the explanation.

The spark.

What’s the essence of the story?

You’ve got 3 minutes. What will you say?

May 20, 2025 3 minute read

The Elevator Pitch (Get Ready for a Nightmare Ride)

The elevator pitch has several origin stories.

Here’s one I like:

In 1854, Elisha Otis dramatically demonstrated his safety elevator at the New York World’s Fair by cutting the support rope on a hoisted platform on which he was standing. The platform safely stopped mid-air.

Here’s another:

In early Hollywood, screenwriters used elevator rides to pitch ideas to busy executives, prompting the creation of brief, persuasive pitches that required clarity and efficiency.

So what is it? Here is an elevator pitch for an elevator pitch:

“An elevator pitch is a powerful, concise summary of your idea, product, or value proposition that you can deliver in the time it takes to ride an elevator.”

Elevator pitches are very difficult for someone who rambles, tends towards overexplaining, uses too many words, includes too many details, digresses, inexplicably feels the need to explain tangential concepts, is secretly afraid that the audience thinks he doesn’t know what he’s talking about, and really and truly just wants to ensure that everyone, everywhere gets the point.

That’s me. And that’s a terrible explanation, like most of mine.

Now, here’s the elevator pitch version of the previous (from ChatGPT):

I ramble, overexplain, and occasionally give TED Talks on side topics, which is why delivering an elevator pitch feels like a personal nightmare.

Or, here’s another (from ChatGPT):

Elevator pitches are hard when your brain writes a novel, your mouth reads the footnotes, and the elevator only goes up three floors.

This post is proof. I set out to write an elevator pitch but ended up walking you around the entire building, door by door, floor by floor. We went to the basement to see the plumbing and electrical infrastructure. We went to the roof to see the antennas. I told you about our contract with AT&T and Verizon to lease antenna space. I probably pulled out the documentation. I showed you the custodian’s closet. I explained the lighting strategies and provided some wonderful (ly boring) anecdotes about the automation features. Did you know that the floors use a new compound that not only meets the green requirements for this building, but have actually saved us almost 5% compared to the alternative?

I’m sorry for that. I can’t help it. That’s why this blog is called The250.

Here’s the elevator pitch for this post:

Elevator pitches are simple, but not easy, especially when your instinct is to explain the elevator before you ride it.

May 19, 2025 1 minute read

What You Get Paid For

Contractually, you might get paid for hours or milestones. At least according to the terms and conditions. 

But you’ll get paid much more for value.

(Thank you, Seth)

May 18, 2025 3 minute read

Proverbs for the Professional

I’ve written a few proverb lists over the years. Here’s a curation of those, plus some new ones that apply to the professional. No matter where you are, what you do, and what role you have, these are for you. 

  1. The same old mistakes form the walls of your prison. New mistakes pave the highway forward.
  2. Multitasking is a myth. 
  3. You don’t have a time management problem. You have a time priority problem.
  4. Avoid hanging out at the corner of bitch and moan. 
  5. Be willing to get punched in the face. 
  6. The one who gets ahead is the one who takes responsibility. Especially for the failures.
  7. Compete.
  8. Follow the money, power, and status, but learn to navigate all three without becoming owned by any.
  9. Color outside the lines. Walk on the curb. Run with scissors. Not all the time, but sometimes.
  10. Creative tension is how great teams get better. Embrace the disagreement.
  11. Always assume the other person doesn’t mean harm and that you misunderstood.
  12. Consensus does not equal truth.
  13. Curiosity and the desire to explore keep you young and make you more valuable.
  14. Bring your passion with you. 
  15. Value doesn’t necessarily mean hours or KPIs. Be valuable. 
  16. Legacy isn’t a name on a building. It’s the effect you’ve had on the people around you.
  17. You are a work in progress. So is everyone else. Remember that before casting the first stone.
  18. Learning how to recognize, confer, and use status is a superpower.
  19. Don’t be snowed by credentials. Respect everyone. 
  20. The best method for learning is to teach someone else.
  21. Do things that make you feel like an impostor. That feeling means you’re growing.
  22. Inspiration shows up more often in the middle of the work than in the middle of the night.
  23. It’s OK, maybe encouraged, to geek out on tools.
  24. You don’t have to start in the mail room, but pay attention to those who have. Their perspective is likely a magnetic pole to which you should be attracted or repelled.
  25. Leave your colleagues feeling, “I want to work with this person.” That’s not the same as, “I’d love to hang out with this person.”
  26. Once you learn how work works, you’ll never worry about machines taking your job.
  27. Professionals play hurt.
  28. Professionals show up when it counts.
  29. The leader isn’t necessarily the name in the box at the top of the chart. Be a leader. At the very least, lead yourself.
  30. Teach others to do your job.
May 17, 2025 1 minute read

The Control Dilemma

Stuff you can’t control directly:

If someone else says “yes.”
What politicians decide.
The price of gas.

Stuff you can:

How many conversations you have.
Who you vote for.
What you buy, where you go, how you get there.

It’s important to both recognize and remember what you can control directly.

Not just intellectually, but emotionally.

Although it’s useful to discuss and debate the things over which you have no direct control, it’s not useful to lose sleep over them.

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