16×16 is 256: Lessons from a Middle School Classroom

The Overhead Projector

"16×16 is 256."

I was standing behind my middle school math teacher, Mr. Heidepriem. I would later learn that his first name was Donald and his wife, Phyllis, was an elementary school teacher in the area. But in that moment, twenty years after I'd last seen him, in the middle of JJ's supermarket, all I could think about was the overhead projector.

Every day, Mr. Heidepriem started class the same way. An overhead projector displaying a 10×10 grid of multiplication problems. One hundred problems. Five minutes. Every minute, he'd rotate the grid.

Complete all the answers correctly in five minutes, and you could move on to something new. Fail, and you'd repeat the exercise tomorrow. And the day after. And the day after that.

Most students never made it through.

I was reluctant at first. Resentful, even. Why did this matter? When would I ever need to know 16×16 without a calculator?

But then something shifted. I caught on. Not because I was naturally gifted at math, but because I was too stubborn to keep failing. By the end of the year, I was the second or third student in the class to complete the task. Maybe five or six of us total made it.

Mr. Heidepriem was a stoic man. Strict. I don't recall him smiling much, if at all. But that day, standing in the grocery store aisle, looking into his eyes two decades later, an amazing smile came across his face.

I said, "Thank you."

He knew what I meant. And I think, in that moment, he felt it, the connection between a teacher who planted a seed and a student who carried it forward into a career, a life, a way of thinking about hard problems.

Looking back at his obituary, he must have died within a few years of that encounter. I'm grateful I got the chance to say thank you.

Standing on the Shoulders of Giants

There's a phrase, often attributed to Isaac Newton: "If I have seen further, it is by standing on the shoulders of giants."

In Star Wars, this is the relationship between master and apprentice. Qui-Gon teaches Obi-Wan. Obi-Wan teaches Anakin, and later, Luke. Yoda teaches generations of Jedi, each one carrying forward the knowledge, wisdom, and discipline of those who came before.

The Jedi Order understood something essential: knowledge is not just information. It is the discipline to use it, the wisdom to apply it at the right moment, and the perseverance to master it even when it is hard.

Mr. Heidepriem didn't just teach me multiplication. He taught me that effort compounds. That struggling today makes tomorrow easier. That mastery is not about being the fastest or the smartest, it's about showing up, every single day, and doing the work.

And when I stood in that supermarket aisle, I realized: I was standing on his shoulders. Everything I'd accomplished, the security career, the leadership roles, the ability to break down complex problems into manageable pieces, all of it traced back to lessons learned in that middle school classroom.

He smiled because he saw it too. The student had become the professional. The seeds he planted had grown.

The Age of AI: Knowledge vs. Questions

Now, we live in an age where AI can solve 16×16 in microseconds. It can write code, analyze data, generate reports, and answer questions that would have taken me hours to research twenty years ago.

So the natural question arises: Does knowledge even matter anymore?

If AI can answer any question instantly, why bother learning? Why memorize? Why struggle through the 10×10 grid when ChatGPT can do it for you?

Here's what I've learned: AI hasn't made knowledge less important. It's made the right question more important than ever.

The Jedi Training Paradox

In The Empire Strikes Back, Luke trains with Yoda on Dagobah. Yoda doesn't give Luke a manual on how to use the Force. He doesn't provide step-by-step instructions. Instead, he teaches Luke to feel, to sense, to trust his instincts.

When Luke's X-wing sinks into the swamp, he tries to lift it with the Force and fails. He says, "I don't believe it."

Yoda responds: "That is why you fail."

The lesson isn't about raw power. It's about understanding what question to ask. Luke was asking, "Can I do this?" when he should have been asking, "What am I not seeing?"

AI works the same way.

You can ask an AI, "How do I secure my cloud infrastructure?" and get a generic, 10-page answer that may or may not apply to your specific situation.

Or you can ask, "Given our multi-cloud deployment across AWS and Azure, with microservices architecture and a distributed development team, what are the top three identity and access management risks we should prioritize this quarter?"

Same tool. Radically different outcomes. The difference? The quality of the question.

Perseverance in a World of Instant Answers

Mr. Heidepriem's 10×10 grid taught me something AI can't replicate: perseverance.

The struggle to get faster, to memorize the patterns, to push through frustration when the answer didn't come immediately, that struggle built something in me. It taught me that hard problems are solved through sustained effort, not one-time brilliance.

In the AI age, this lesson is more valuable than ever.

Because AI gives you instant answers, but it doesn't give you perseverance. It doesn't teach you to sit with a problem for hours, days, or weeks until you truly understand it. It doesn't force you to struggle, and in that struggle, build the mental muscles that make you capable of tackling the next hard problem.

The Myth of Effortless Mastery

There's a dangerous myth emerging: that AI makes expertise obsolete. That anyone, with the right prompts, can be an expert in anything.

This is like saying that because lightsabers exist, anyone can be a Jedi. The weapon is not the skill. The tool is not the mastery.

A Jedi spends years training, not because they need to memorize forms, but because mastery is internalized through repetition, struggle, and reflection. When the moment comes, in battle, there's no time to consult a manual. You act, instinctively, because the knowledge is part of you.

AI can give you the answer. But it can't give you the instinct to know when the answer is wrong, when to dig deeper, when to ask a different question, or when to trust your gut over the data.

That comes from experience. From perseverance. From doing the hard work, over and over, until it becomes second nature.

The Right Question at the Right Moment

Here's where Mr. Heidepriem's lesson and the AI age intersect:

In a world where knowledge is abundant, the ability to ask the right question at the right moment is the ultimate competitive advantage.

Why This Matters in Security

I've spent decades in cybersecurity. I've seen countless incidents where the information was available, but the question wasn't asked.

• Logs showed unusual access patterns, but no one asked, "Why is this service account active at 3 AM?"
• Vulnerability scanners flagged a critical CVE, but no one asked, "Is this actually exploitable in our environment?"
• An employee reported a phishing email, but no one asked, "Who else received this, and did anyone click?"

AI can surface all of this information. It can flag anomalies, highlight risks, and generate reports. But it can't replace the human who looks at the data and asks, "What am I missing? What does this mean? What should we do about it?"

That intuition, that ability to see patterns, to ask the question no one else is asking, that comes from experience. From perseverance. From years of struggling through problems until you develop a sixth sense for what matters.

Why This Matters in Leadership

Leadership is not about having all the answers. It's about asking the questions that unlock progress.

• "What is the real problem we're trying to solve?"
• "What are we optimizing for, speed or quality?"
• "What assumptions are we making that might be wrong?"
• "What would success look like six months from now?"

AI can help you execute faster. But it can't tell you what to execute. That requires judgment, context, and the wisdom to ask the right question when it matters most.

What AI Teaches Us About Learning

AI hasn't made learning obsolete. It's changed what we need to learn.

The Old Model: Memorization

For centuries, education was about memorization. Knowing facts, formulas, dates, names. The more you could recall, the more valuable you were.

Mr. Heidepriem's multiplication grid was part of this model. But here's the thing: it wasn't just about memorizing 16×16. It was about building mental endurance, pattern recognition, and the confidence that comes from mastery.

The New Model: Curation and Application

In the AI age, the bottleneck is not access to information. It's:

• Curating the right information from an ocean of noise
• Applying that information to the specific problem you're solving
• Synthesizing insights from multiple domains
• Judging when the AI is right, and when it's confidently wrong

This requires deep foundational knowledge. Not because you need to recall every fact, but because you need to know what questions to ask and how to evaluate the answers.

The Yoda Principle

Yoda's teaching method was not, "Here are the answers, memorize them." It was, "Here are the principles. Now struggle, fail, learn, and internalize them until they are part of you."

AI is a tool, like the Force. Powerful, but only in the hands of someone who understands how to wield it.

And that understanding comes from perseverance. From doing the hard work. From standing on the shoulders of giants like Mr. Heidepriem, who taught us that mastery is earned through struggle, not shortcuts.

The Smile in the Supermarket

When Mr. Heidepriem smiled at me in JJ's supermarket, I think he saw something I didn't fully understand at the time.

He saw that the lesson had taken root. That the seventh grader who struggled through the 10×10 grid had grown into someone who could tackle complex problems, lead teams, and navigate ambiguity.

He saw that what he taught me wasn't multiplication. It was perseverance.

And perseverance, I've learned, is the one thing AI can't give you. It can make you faster. It can make you smarter. But it can't make you persistent. It can't teach you to sit with a hard problem until you break through. It can't instill the confidence that comes from knowing you've done difficult things before, and you can do them again.

That comes from teachers like Mr. Heidepriem. From mentors who push you, even when you don't understand why. From leaders who believe in you before you believe in yourself.

And it comes from you, choosing to show up, day after day, even when it's hard.

What Matters Now

So, does knowledge matter in the age of AI?

Yes. But not the way it used to.

What matters now:

• Asking the right question at the right moment
• Knowing when to trust the AI, and when to challenge it
• Building deep foundational knowledge so you can evaluate answers critically
• Persevering through hard problems until you truly understand them
• Standing on the shoulders of those who came before, learning from their wisdom, and carrying it forward

AI is a tool. A powerful one. But like the Force, it amplifies what you bring to it. If you bring curiosity, discipline, and perseverance, AI makes you exponentially more capable.

If you bring shallow thinking and shortcut-seeking, AI will give you shallow answers.

The choice is yours.

Standing on Shoulders

I think about Mr. Heidepriem often. About that smile. About the moment when teacher and student reconnected, two decades later, and both understood what had been passed down.

He stood on the shoulders of his own teachers. And now, I stand on his.

The lesson he taught me, perseverance, discipline, the value of doing hard things, is the same lesson I try to pass on to the teams I lead, the companies I advise, and anyone willing to listen.

Because in the end, the tools change. The technology evolves. AI will get smarter, faster, more capable.

But the human elements, curiosity, perseverance, the ability to ask the right question at the right moment, those remain constant.

16×16 is 256.

I still remember.

Not because I need to. But because it reminds me that the struggle was worth it. That the hard work built something in me that no AI can replicate.

And when the moment comes, when the question needs to be asked, when the decision needs to be made, when perseverance is the only thing standing between success and failure, I'll be ready.

Because Mr. Heidepriem taught me how.

Thank you, Mr. Heidepriem.