Alone With a Question

It is late evening. I am sitting alone, reflecting after a long day. The streets are quiet, the sky dim. In these moments of solitude, clarity often comes.

Tonight, one question stirs in me.

Can wisdom be taught?

It is a simple question, but layered. And today, of all days, feels like the perfect time to explore it.

What Once Killed You Now Feels Like Leisure

The morning began with our regular Parents Coffee Morning. These sessions are a space for parents to voice concerns, seek clarity, and help us align expectations. They sound simple, but in practice they are rarely easy.

Today, one parent was particularly vocal, upset that we had shortened some lesson times to allow students to practice for Sports Day marching. It was a small shift, intended to create an enriching experience for the children, yet it became the source of disproportionate frustration.

As I sat there listening, I noticed something within myself. Five years ago, a session like this would have consumed me with anxiety. I would have struggled to sleep the night before. I would have sat through the session tense, unsure, hoping to survive it. And afterward, I would have been drained.

But today, I smiled inwardly. I was calm. Present. Even amused at moments. After the session, I shared with a new team member that back in the early days, I could not sleep before these sessions. Now, I have trouble waking up for them. It was a light way of saying something much deeper had changed.

The situation had not changed. The challenges had not gone away. What had changed was my own capacity.

Photography, Preschool, and Perspective

This pattern is not new to me. Back in 2013, I worked as a photographer taking on paid client shoots. At the time, editing wedding photos was a source of deep stress. I would edit each image one by one in Photoshop, unaware that there were better tools like Lightroom or batch editing. Each project consumed endless hours and mental energy.

Then came 2016, when we launched Stellar Preschool. Overnight, my world expanded. Suddenly, I had to think about operations, finances, parent expectations, staff morale, and the day-to-day running of a school. The complexity of my responsibilities multiplied.

And something unexpected happened. The photography editing, which once stressed me out, became something I did to relax. During staff meetings, I would edit photos quietly in the background. The very same task that had once overwhelmed me had become my leisure.

The lesson was clear. Stress does not disappear. We grow to carry it differently.

The Ancient Body Still Needs the Gym

Later that day, I went to the gym with Samuel and Ryan. For the past five years, our gym sessions have been a ritual. They are not about body image. They are about discipline, clarity, and community.

As we trained, another parallel became clear. In a world of technological advancement, why do we still need to exercise?

Because our bodies remain ancient. Shaped over millennia, our physiology expects physical exertion. Without it, we deteriorate. No AI or machine can replace this biological need.

Wisdom is the same. It cannot be downloaded. It must be built, like muscle, through tension and resistance.

The Spelling Test That Breaks the Heart

That evening, I saw another example through my children.

My boys were preparing for a spelling test. What seemed like a small task to me felt overwhelming to them. There were tears, anxiety, sleeplessness.

To me, it was tempting to say, it is just spelling. How hard can it be?

But I stopped myself. Developmentally, their prefrontal cortex is not fully formed. To them, this experience was real, stressful, and deeply emotional.

As a father, I must honor that experience. To them, this is their current version of heavy weights.

Leadership Patience: Meeting Others Where They Are

The same applies in leadership.

How often do I see team members struggling with tasks that now feel obvious to me? It is tempting to say, just do it this way.

But their stress is real. Their wisdom is still forming. What feels like common sense to me is not yet obvious to them.

Here lies one of the most delicate leadership disciplines. Knowing when to coach, when to challenge, and when to simply let life teach.

As a visionary, I often see five steps ahead. But wisdom in leadership means meeting others where they are, not where I wish they were.

Wisdom Is Not Knowledge. It Is Capacity Earned.

And so the question returns. Can wisdom be taught?

Knowledge can be taught. Frameworks can be taught. Skills can be taught. But wisdom is different.

Wisdom is the capacity to navigate uncertainty. To hold paradox. To discern when to act and when to wait. To carry heavier weights without crumbling.

This cannot be transferred through a classroom or a book. It must be forged through lived experience.

Just as physical capacity is built through progressive overload, so wisdom is built through life’s stresses and tensions.

The Origins of School: Why Wisdom Was Never Meant to Be Taught

The very origins of schooling reflect this truth.

Before institutions, education was deeply human. Rooted in family, community, and shared life. Children learned through stories, rituals, and lived experience.

Formal schools arose to transmit knowledge. Initially to prepare scribes, then citizens. But wisdom remained the domain of life itself.

Even today, the deepest lessons often happen not in textbooks, but in the moments that test us. The failures. The paradoxes. The tensions we cannot avoid.

We must remember this as AI reshapes education.

Why AI Can Never Replace Lived Wisdom

AI can transfer knowledge faster than ever. But wisdom? That is something else entirely.

Wisdom requires pattern recognition across time. Emotional resilience. Judgment born from loss, failure, joy, and perseverance.

No algorithm can replace the formation that life demands.

A gym membership cannot build muscle without lifting. A leadership framework cannot create wisdom without experience.

In this, humanity retains its unique role.

Designing Experiences, Not Shortcuts

So what is our role as leaders, as parents, as builders of the future?

Not to teach wisdom as if it were a module to be completed. Our role is to design experiences. To create safe, challenging environments where others can earn wisdom.

In the gym, you cannot carry another’s weights. You can spot them. Encourage them. Model the right form. But they must lift.

In leadership, it is the same. We must model wisdom. Hold space for growth. Resist the temptation to shortcut hard lessons.

The Growth You Cannot Shortcut

And here lies the paradox. If you could fully teach wisdom, you would rob others of it.

You would deny them the very experiences that form resilience and capacity. You would create fragile followers, not independent leaders.

As a father, I remind myself of this when my children face their spelling tests. As a leader, I remind myself of this when my team struggles with tasks that now seem obvious to me.

Wisdom must be earned, not downloaded.

A Question for Your Own Leadership

So I leave you with this.

Where in your leadership or parenting are you rushing to teach wisdom, when you should be holding space for others to earn it?

Slow down. Let life do its work.

Be present. Be patient. Be ready when they seek your insight.

But never rob them of their right to grow wise through their own journey.

Good night.