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.

August 3, 2025 1 minute read

Leading Like a Light Wave/Particle

Scientists have reconfirmed one of the most famous and vexing theories in physics — light is both a wave and a particle.

Which is it when? That depends on whether it’s being observed or not. 

If you measure it, it’s a particle. Precise and localized. Unobserved, it’s a wave. Fluid, adaptable, interfering with itself.

Effective leaders share this dual nature.

They’re decisive and clear when the team requires structure and certainty. They’re reflective and fluid when creativity and exploration are needed.

Great leaders recognize when to be each and can switch back and forth. 

Effective leadership isn’t about choosing a side. It’s observing, taking the pulse, and knowing the desired outcome. Tension isn’t a threat. It’s a signal. 

Which does your team need right now? 

August 2, 2025 1 minute read

The Town Water System Problem

Your town decides to build a centralized water system.

It helps many in the community. It’s more efficient. It provides standardized quality and access to that quality for more people. The generated revenue lessens individuals’ tax burden. 

But, you have a well, and it works fine. Water’s clean. Tastes great. You maintain it. Cheap. No need to change anything.

Now you’re being asked to pay for installation and then monthly for access to something that you think is probably worse than you currently have.

You didn’t ask for it. You don’t need it. 

That is the conundrum of the individual versus the collective and the present versus the future. The new system may not serve you better, at least not right now. 

But what about tomorrow, or five years from now? And what about your neighbor? 

August 1, 2025 1 minute read

Knowing Your Advantage (Centralized vs Distributed)

When you’re a centralized system, here are some of your advantages:

  • Speed – You can make decisions and engage machines or people quickly
  • Efficiency – You can spread and use resources with little waste
  • Communication – You can create a speedy and efficient communication system
  • Control – You set the standards, enforce consistency, and lead with impunity
  • Security – You can monitor and guard your systems more easily

When you’re a distributed system, here are some of your advantages:

  • Resilience – You can easily ensure no single point of failure
  • Self-sufficiency – Each part can operate independently, adapt locally, and take initiative
  • Scalability – You can grow organically, node by node, without a total overhaul
  • Flexibility – You can respond differently in different regions or contexts
  • Innovation – You can empower the constituents 

Coming to the table knowing your advantage is, in itself, an advantage. 

July 31, 2025 1 minute read

Knowing Your Advantage (Startups vs Enterprise)

When you’re a startup, here are some of your advantages:

  • Flexibility – You can say “yes” or “no” to anything
  • Decision-making – You can decide for yourself 
  • Speed – You can start, stop, finish, or change at any time
  • Attention – You can be razor-focused on whomever you want
  • Creativity – You have no box or boundaries
  • Upside – The upside is all yours

When you’re a multibillion-dollar enterprise, here are some of your advantages:

  • Budget – You can afford capacity, technology, teams, and systems
  • Access – You can access capacity, technology, teams, and systems
  • Systems – You can create, acquire, use, and polish systems
  • Risk – You can spread your risk
  • Emotions – You can flatten out the emotional rollercoaster
  • Downside – You can significantly reduce the downside

Coming to the table knowing your advantage is, in itself, an advantage. 

July 30, 2025 1 minute read

You Can’t Design for the Real 100-Year Flood

The 100-year flood, or for that matter, the 1000-year flood isn’t a real thing. 

It’s a set of statistical values used for engineering, insurance, and planning purposes. The engineers who design the burms, drainage, and pumps need a target. The actuaries need a target to price insurance policies. Community leaders need a target to put systems and policies in place. 

It’s a model, and nature doesn’t have to follow the model’s rules. 

Models are helpful for thinking through possibilities. For our business. For our retirement. For our health. 

But the real 100-year flood doesn’t know what year it is. It doesn’t know where it’s supposed to dump its water. It doesn’t know how much water. It doesn’t know which path it’s supposed to take. 

Plan all you want. And you should. But make room for chaos. Because it’s coming. 

The ones who thrive aren’t the ones whose model was better. They’re the ones who figured out how to float when the levee broke.

July 29, 2025 2 minute read

Resilience, Flexibility, and The Future

Do you know what your future looks like?

Have you planned it out? Do you know what you’ll be doing, where you’ll be living, and who you’ll be with? Can you picture it? 

You need a strategy, and I hope it works out.

But what if it doesn’t? 

What if there’s medical stuff? What if you miss on your market assumptions? What if your product doesn’t resonate? What if the kids move away? What if you have a financial inflection? What if you change your mind? What if the system changes? What if the world changes? 

All we know is today and history, but something, probably many things, will not look tomorrow like they do today or did last year.

Crazy will get crazier. The “can’t happen” will happen. The “never thought about” will become the focus.

However, there’s a solution — resilience and flexibility. Design resilience into your plans and foster mental and emotional flexibility. 

It’s simple, if not easy, to combat the unknown future with resilience and flexibility. Here are some ideas. 

For resilience: 

  • Assume it will break
  • Create margin, checks, guardrails, and failsafes
  • Abstract the interface from the implementation 
  • Have backups
  • Have a plan B, C, D (burn the ships is romantically overrated)
  • Watch what they do. Modify accordingly. 
  • Invest in a network

For flexibility:

  • Allow yourself to decide later
  • Play devil’s advocate
  • Instead of “What will happen?” try “What else could happen?”
  • Follow your curiosity
  • Challenge and reconfirm, or change, beliefs
  • Practice discomfort
  • Daydream about the what-if (not all the time, but occasionally)
  • Give yourself grace for past failures and poor decisions. The lesson learned should rarely be “I’ll never do that again.” Rather, it should usually be “This is what I’ll do different next time.” There are some important exceptions, of course. 

Preparing for the future isn’t about being right. It’s about being able to respond when you’re wrong. 

July 28, 2025 2 minute read

Front Door, Back Door, Third Door

Rule-followers (I’m one) take heed.

Paraphrased from The Third Door, by Alex Banayan.

  • Front Door: This is the main entrance for the ticket buyers. The people who follow the rules to see the show. It’s where 99 percent of the people wait in line, hoping to get in.
  • Back Door: This is the door for the people who have an “in”. Maybe they know somebody who can let them in, or introduce them to the right person. 
  • Third Door: This is the door that the truly successful person creates — out of thin air. It’s created by sheer force of will, effort, and creativity. It’s the entrance where you have to jump out of line, run down the alley, bang on the door a hundred times, crack open the window, and sneak through the kitchen.

People matter. Connections matter. Relationships matter. 

Creativity matters. Grit matters. Force of will matters. 

The rules don’t matter as much as you think they do. What the paper says doesn’t matter as much as you think it does. The sign on the front door doesn’t matter as much as you think it does.

If you can get in through the back door, do it. That’s a great way to get in. 

If you can’t get in the back, find the third door. It’s often the best door.

July 27, 2025 1 minute read

Nobody Reads Your Documentation

True for engineering deliveries. True for contracts. True for the rock band’s rider. True for packaging. True for the smart home water sensor you just ordered on Amazon.

There are exceptions, of course, but should you rely on the exception?

Nobody reads your documentation. 

Plan accordingly. 

July 26, 2025 1 minute read

Building Resilience

Childhood is the perfect time to teach and build resilience. It’s much harder as an adult. Maybe impossible.  

Resilience stems from emotional and physical recovery, as well as the confidence to overcome the challenges they face. 

Here are some things you can do to help your kids build resilience:

  • Enroll them in baseball or softball. 
  • Let them get the zero on the forgotten homework assignment.
  • Have them discuss the zero or failed test with the teacher themselves.
  • Don’t confuse embarrassment with bullying
  • Give accurate, if empathic, feedback. If you don’t like it, it’s OK for them to know. 
  • Encourage them to explore their curiosity.
  • Allow them to walk on the curb, climb the monkey bars, and play hockey in the street. 
  • Allow them to talk to strangers. 
  • If they don’t feel good, but want to continue, maybe let them. 
  • Encourage them to play with others.
  • Argue with them. Respectfully, of course. 
  • Fail in front of them (sometimes). 
  • Don’t get involved.
  • Sometimes, “Because I said so” is the perfect answer. 
  • Let them figure it out.

Life is full of disappointment, failure, and challenges. Let’s help kids build the skills to handle it.

July 25, 2025 2 minute read

The Difference Between Engineering and Marketing

My friend, one of the best engineers I’ve ever known, has a saying about how we should do good engineering:

“Requirements first, then principles, then feelings.”

This clearly and helpfully lays out the hierarchy of how we go about our engineering work individually and collectively. 

Requirements are the objective north star. Does it do what we’ve been asked to make it do? Requirements are worth arguing about to come to a consensus. They rule the decisions we make. 

When we lack a specific requirement, we rely on our engineering principles. The principles in play are worth discussing and arguing about, but consensus isn’t necessary. What should it do in this situation? What’s the “right way” to do this? 

Feelings are not only third, but the gap between principles and feelings is a chasm. We’re here to make this thing according to the provided requirements. In cases where we need to derive a requirement, we rely on solid engineering principles. Your feelings are irrelevant. 

Let’s contrast that with good product marketing.

It’s exactly the opposite. 

First, feelings. Then principles, and finally requirements. 

What’s the story around the product? How do we want our users to feel? What problem do they care about? 

What kind of person would use our product? What do they care about? What tribes do they belong to? What status do they want to achieve?

What are they trying to accomplish? Why would they use it? 

The engineer tries to build the thing right.
The marketer ensures it’s the right thing.

You need both. In tension. In conversation. With respect.

Because in the end, no one buys specs. They buy the story the specs create.

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