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.

March 27, 2025 1 minute read

When is the Weight Too Much?

When Carrying It Means You’re Standing Still
Because strength is useless if it keeps you from moving forward.
Maybe the bravest thing isn’t to carry more. Maybe it’s to set something down so you can take a step.

When It’s Not Even Yours
Because you might be shouldering someone else’s expectations, guilt, or fear.
We all do it. Parents, children, friends, colleagues. We take on burdens that don’t belong to us or we think helps another. The weight isn’t just heavy. It’s misplaced.

When It Costs You Everything With Nothing in Return
Because leadership isn’t martyrdom.
If the burden you’re bearing is helping no one but breaking you, it might be time to re-evaluate. Help and sacrifice aren’t the same thing.

When It’s Blocking the Light
Because the load on your back can also cast the shadow you’re stuck in.
Sometimes, the heaviness isn’t a badge of honor. It’s the thing keeping you from seeing clearly.

When You Can’t Ask for Help
Because isolation compounds pressure.
The weight becomes too much the moment you believe you’re not allowed to share it.

March 26, 2025 2 minute read

The Most Important Times to Keep Going

Right After the First Big Failure
Because you just learned something most people are too scared to confront.
You’ve lost. You’ve failed. Maybe even embarrassed yourself. But this moment, the one where shame and doubt creep in is where grit is born. The first failure is the gatekeeper. Keep going.

When the Applause Stops
Because external validation is fleeting.
Everyone loved your idea, and was very supportive. But that wore off. Now it’s just you, doing the work. Grinding. Thisis where real things are built. Keep going.

When You’re Being Ignored
Because silence isn’t the same as rejection.
You’re talking, sharing, offering, and trying to lead. And no one’s responding. It feels like shouting into a void. But silence often precedes breakthrough. Keep going.

When You’re Almost Done
Because quitting right before the finish line guarantees you never cross it.
The dip before the end is real. Fatigue shows up just as the breakthrough is near. Keep going.

When You’re No Longer Sure Why You Started
Because rediscovery only happens mid-journey.
You’ve outgrown the original reason. That’s normal. That’s evolution. Without evolution, there is no resilience or longevity. The only way to find the new reason is to keep going.

March 25, 2025 1 minute read

The Purpose of the Bow

A bow on a gift package is a useless adornment. It serves no functional purpose.

Yet, isn’t it nice to receive a gift package with a bow?

The purpose of the bow is intention. You’re special. This is special. You matter. This matters. I hope you enjoy this. I hope you feel loved.

Whatever change you’re trying to make in this world, make sure you wrap it in a bow.

March 24, 2025 2 minute read

Do You Need a New System?

I’ll never get the Wordle in less than 3 tries (well, once I got it on the 2nd, but I’ll explain later). Most of the time, it will be 4 or 5 tries.

The reason is my system. Here’s my system:

First word: S-N-A-R-E
Second word: P-I-L-O-T

Then, I look at what’s matched and go from there with intuition. However, if zero or only one of the letters from those first two match, or I just can’t catch an intuition, then I use:

Third word: F-U-D-G-Y

What’s my system?

Letter coverage. The first two words give me coverage of 10 oft-used letters, including the most used vowels. ChatGPT says that gives me about a 90% chance that two or more of those letters will be in the solution. If needed, the third word rounds out all possible vowels and adds another couple of common consonants. Now I’m at 15 and have raised my chances to 98% that at least two of the letters are in the solution and 100% that I know which vowels.

With a budget of 5 tries, I’m spending 2, sometimes 3 of them without regard to the actual solution. But I’m collecting valuable data.

I designed the system to produce a particular outcome — namely, maximize the chances of a solution within the constrained budget.

I did not design it to minimize the number of tries. 

We often get frustrated when outcomes don’t meet our goals or hopes. But is the system designed to meet those hopes? 

Systems do what they’re built to do. 

So, step one is to recognize the system. Step two is to ask yourself — do you need a new system?

P.S. The day I solved the Wordle on the 2nd try was when the word was “snake”.

March 23, 2025 2 minute read

Understanding Connectivity

Earth’s population currently sits at an estimated 8.2 billion.

Approximately 7.3 billion of those people have smartphones (Christopher Walken excluded, of course). That’s 89%. Let’s call the Blackberry the first smartphone. It came out in 2002. But we all know the first smartphone that went to the masses was the iPhone, and it came out in 2007. 

Let’s look at some other technologies and their penetration into the world’s population:

  • Running water: Practically available in the 1600’s. Currently, ~6.5 billion people have daily access. That’s 79%.
  • Clean/Safe water: Practically available in early 1800’s. Currently, ~6 billion people have daily access. That’s 73%.
  • Electricity: Practically available in late 1800’s. Currently, ~7.1 billion people have electricity in their homes. That’s 87%.
  • Car ownership: Practically available in early 1900’s. Currently, ~1.6 billion people own cars. That’s 20%.
  • Banking: Practically available in the 1400’s. Currently, ~6.4 billion people have bank accounts. That’s 78%. 

In approximately 20 years, the smartphone has out-penetrated all of these other technologies/services, some of which we could argue should be a basic right of every citizen of this planet (who desires it).

I’d be lying if I said I knew exactly what this all means.

Is it power? Economics? Geography? Maybe it’s choice. Like most complex problems, it’s probably some combination of many variables.

What we do know, however, is that connectivity is king. Connectivity, in whatever form it takes, is a fundamental human need. 

If you’re trying to make a difference in this world, focus on connectivity.

March 22, 2025 1 minute read

Who are you Trying to Serve?

Let’s talk about choo choos.

Passenger rail is an systemically efficient method for moving people around. I was recently in Germany, and it’s a wonderfully practical and pleasant method of getting from somewhere to somewhere else.

As long as you’re near a station. And the place you are going is near a station. And you don’t want to go anywhere the train doesn’t go. The cost to create new rail infrastructure to new places is very high.

Roads with automobiles are also an effective method for moving people around, but systemically much less efficient. However, the cost to add new infrastructure to new places is relatively inexpensive.

Roads are less efficient as a system but optimize for individual flexibility. Trains are the opposite — efficient as a system but rigid for individuals.

We see this trade-off everywhere. Healthcare. Education. Business processes. Even relationships.

When you’re making something, do you design for the system or for the individual? The answer depends on who you’re trying to serve.

Step one is to get clear about who you’re trying to serve.

March 21, 2025 2 minute read

Let’s Waste Some Time

When I was in 4th and 5th grades, I got in trouble sometimes for Daydreaming. Standard stuff. My mind was off on an adventure (outer space, likely), the teacher called on me, and then I was embarrassed in front of the class.

I don’t know how often, but it happened enough times that I can recall a few. So, I guess often enough to have left an impression. Or, at least, the story of a memory.

The point the teacher was trying to drill into me was, “Daydreaming is bad. Quit wasting time.”

Today’s hustle culture drills the same thing into your head, “Do more! Schedule every minute of your day! Follow the script! Be productive!” Hustle culture sells the idea that attention should always be optimized—focused, productive, goal-oriented.

And sure, unconscious distraction by The World — mindlessly scrolling according to the algorithm’s desires — is a problem. Both for productivity and for your mental well-being.

But sometimes, don’t we need to explore?

Time isn’t just for crossing off items on your list. It’s about seeing new connections, letting your brain breathe, and allowing creativity to emerge. Some of your best ideas will come when you’re wasting time.

Get bored. Daydream. Walk without headphones. Look around. Read something you find entertaining. Let your mind stretch.

Maybe waste some time.

March 20, 2025 1 minute read

Trust as Currency

Trust is fuel.
Trust is a bridge
Trust is a contract.
Trust is a foundation.

And trust is a currency.

You can trade it, spend it, and invest it. Like with money, you can track your spending and ROI.

Some people say you must earn trust, but what if you choose to freely give it first?

Starting from a position of trust doesn’t mean you’re naive. It means that you recognize that most relationships, businesses, and institutions function best when trust is the default. Trust accelerates collaboration, fuels relationships, and builds stronger communities.

Starting with trust creates momentum. Withholding it creates barriers.

Of course, not everyone will provide a positive ROI. Some will take advantage or not rise to the occasion. That’s why you should freely give it, but not blindly keep it.

Trust left unspent is like sticking money under your mattress. It won’t grow, and it’ll lose value. You have to spend it for it to work.

Like money, trust is only valuable where you put it.

March 19, 2025 2 minute read

The Paradox of Problem Recognition

Before automobiles, people spent a lot of time and energy dealing with horse manure. 

They probably complained, but they also recognized it just was. It wasn’t a problem that had a solution. Therefore, whole cottage industries built up around dealing with horse manure. Street cleaning. Resellers. City-center stables and stable hands. 

Along comes the car.

At first, many resisted. Not because they liked horse manure but because they couldn’t imagine a world without it. The entire system was built around horses. 

Why question something so fundamental?

That’s the paradox of problem recognition. If people can’t envision an alternative, they don’t see a problem at all. The mess in the streets wasn’t ideal, but it wasn’t avoidable, either.

Then, as cars became practical, something shifted. The problem had always existed, but only after a better way emerged did people truly recognize it as a problem. 

People defend inefficiency, struggle, even frustration. It’s not because they love it, but because they don’t believe there’sanother way. 

Until there is. If you’re designing a better way, the most important part, and probably the hardest part, is to help people understand that the problem has a solution.

That’s messaging. 

March 18, 2025 2 minute read

The Trust Puzzle

How do you pick your expert? The person you’ll hire to diagnose your illness, fix your plumbing, or lead the town.

If you’re like most people, you start with trust. Who you know and who the people you know know. Personal trust is a powerful selector.

If you don’t know somebody, you’ll probably use credentials. Credentials serve as a surrogate for personal trust.

How else do we build either real or surrogate trust? It’s a puzzle.

We trust signals. Small cues that feel like expertise. A doctor in a white coat, a confident politician, a loud voice. But signals can be misleading.

We trust consensus. If enough people believe someone is an expert, we assume they must be. But crowds can be wrong, and reputations can be built on perception, not reality.

We trust teams. Which team are they on? But teams are built upon ideology, loyalty, and compromise. All of which may have ulterior motives.

So, how do you solve the trust puzzle? You test it.

Ask questions. Look for explanations, not just answers. The best experts have something behind the white coat, confidence, and which team’s shirt they wear.

And be wary of those who avoid the questions.

Real expertise can withstand scrutiny. Real expertise knows it’s limitations. Real experts aren’t afraid of your questions. Real experts pass the test.

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