How I Keep Repeating What I Thought I Had Mastered

I Thought I’d Learned This Lesson. I Hadn’t.

There are certain lessons in life that you believe you’ve mastered—lessons you’ve lived through, reflected on, even taught to others. You think you’ve sealed those chapters with hard-earned wisdom.

And then life humbles you.

Not by introducing something new, but by recycling your old blind spots and handing them back to you in a fresh package. Just when you think you’ve moved past them, they appear again—but on a different stage of life. Same mistake, different stage.

This is one of those stories.

It’s a story about grace. About mentoring, parenting, leadership—and how the temptation to control can follow us into every role if we’re not painfully self-aware. It’s about how the hardest leadership skill I’m still learning is not strategy, not clarity, not even vision—but the quiet courage to lead with grace.

And why, no matter how many times I think I’ve learned it, life keeps sending me the same invitation: to lay down control, and pick up grace instead.

When a Mentee (and your son) Becomes Your Mirror

The first time I truly learned the heart of mentorship was almost by accident.

It was August 2016. I had reluctantly agreed to attend a discipleship conference—more out of obligation than obedience. At that stage of life, I had little desire to serve others in that way. I was a new father, trying to balance my own family priorities, busy with work, and quite honestly, tired.

But my mentor insisted. He reminded me that part of my calling extended beyond my role as a father or businessman—that I was called to walk with others. Out of respect for him, I went.

During a Q&A session, someone asked a simple question that caught my attention: “How do you know when you’re ready to mentor someone?”

The speaker’s answer was equally simple: “You’ll know you’re ready when God sends you a mentee.”

That struck me.

In that moment, I offered a quiet, dangerous prayer: “If You send me a mentee, I will do my best.”

I didn’t know how quickly that prayer would be answered.

Later that very day, as I got back to my car to drive home, my phone rang. On the other end was a young man—heartbroken, sobbing after a painful breakup. He needed someone to talk to. Someone to walk with him.

Right there and then, I knew: This is the mentee You sent.

I hadn’t even unpacked my bags. He was already waiting outside my house. The timing was so divine I couldn’t ignore it.

That night, we sat in a cafe for hours. I had no grand plan, no agenda. The only thing I could offer was presence—and Scripture. So we began to memorize verses together. “Therefore, if anyone is in Christ, he is a new creation…”

It was raw. Unpolished. Human.

That season taught me something foundational: mentoring is not about fixing someone. It is about walking with them, at their pace. It is about creating space, not imposing outcomes.

Or so I thought I had learned.

The Mistake I Made—And Remade

For nearly a year, I walked closely with that mentee. But slowly, old patterns began to creep in.

As he began to find stability again, my own impatience surfaced. I wanted to see faster progress. I wanted him to “grow up” spiritually, emotionally, relationally. My tone shifted subtly. I started setting expectations. Applying pressure.

“You need to be teachable.”

“You need to progress faster.”

“You need to be more consistent.”

Without realizing it, I had crossed a line. I was no longer walking beside him. I was standing in front of him, pulling him forward.

Eventually, the inevitable happened. He withdrew. Avoided me. One painful conversation later, he finally admitted:

“I feel so pressured by you. I feel judged.”

Those words stung. Because they were true.

I had fallen into the classic leadership trap—confusing control for care. In my eagerness to “help,” I had unknowingly placed the weight of my expectations onto his shoulders.

It was a humbling realization.

I told myself: Never again. I’ve learned this now. I will never repeat this mistake.

But life has a way of testing your resolutions.

Yet even in that painful mentoring season, something good was planted. I didn’t walk away with just failure—I walked away with a deeper understanding of how to lead through presence, not perfection.

One practice that began in those mentoring sessions—starting with Scripture, letting the Word be the foundation, not my own wisdom—became a cornerstone of how I now parent my sons. Every morning, we begin our day with Scripture together. Not as a ritual to perform, but as a space to center ourselves in truth.

It was through mentoring that I first saw the power of leading through gentle repetition, through presence, through anchoring the heart—not through pushing the outcome. That lesson is now embedded in how I walk with my children.

And yet—even with that foundation—life has a way of testing whether I truly live by it.

Same Mistake. Different Stage.

Years later, I found myself in a new role—the most sacred leadership role of all: fatherhood.

As a father, I adored my children. I wanted them to flourish, to grow strong, to thrive. And naturally, I wanted to give them every advantage.

But soon, that same old pattern crept back in.

One of my sons struggled in an area where I knew he had potential. At first, I encouraged him. Then I “encouraged” him harder.

“Why aren’t you practicing more?”

“You can do better.”

“Why are you avoiding this?”

I convinced myself it was love. But deep down, I knew what it was: my own anxiety masked as coaching. My own need for control disguised as concern.

The more I pushed, the more he withdrew.

And one day, it hit me like a punch to the gut: I was doing it again. Same mistake. Different stage.

This wasn’t about my mentee anymore. It was about my son. And once again, I was repeating the very pattern I thought I had outgrown.

The Grace I Never Knew I Needed

In one of our mentoring conversations, my own mentor Dato Peter shared a story that cut deep.

At the funeral of his old teacher, someone remarked in disbelief:

“I can’t believe you’ve become so successful. You were so slow in school. Always bullied.”

Dato Peter’s son bristled at the comment, but Dato Peter calmly said:

“I needed that. It reminds me that it was never my own strength. It was grace that brought me here.”

That one sentence stuck with me.

And it made me realize something I had missed: mentoring, parenting, leadership — all flow through the same S.T.A.G.E.

And at each stage, grace must lead the way:

• S — Self-awareness: Am I aware when I am pushing too hard?
• T — Trust: Do I truly trust this person to grow at their own pace?
• A — Acceptance: Can I accept that growth won’t always look like my vision?
• G — Grace: Am I leading with grace—not shame, not pressure?
• E — Example: Am I modeling the posture I hope they will one day carry?

Without grace, leadership becomes force.

With grace, leadership becomes love.

I saw it so clearly: I had failed at “T” and “G”—I had trusted outcomes, but not the person. I had withheld grace in the moments when it was needed most.

The Coaching Lesson That Endures

Later, when we brought Sol, a young believer, on a journey to KL, I saw once again how grace in leadership is not passive — it is profoundly intentional.

In just a few simple interactions, Dato Peter modeled the 4E framework that has quietly shaped so much of my own leadership philosophy:

• Evangelize: He welcomed her not as a project, but as family—“Welcome to the house of the Lord.”
• Establish: He gently began grounding her in faith and belonging, not rushing, but inviting her deeper.
• Equip: He spoke openly about her potential—not with pressure, but with hope.
• Extend: And he modeled what it looks like to extend leadership by raising not followers, but future laborers.

Watching him, I was reminded again: leadership is not about how fast you can move someone through a “process.” It is about how well you can walk with them through their own becoming.

And grace is what makes that possible. Without grace, the 4E collapses into a task list. With grace, it becomes a lifelong journey.

The Reverse That Redefines It All

One story that beautifully captures this truth is how legendary UCLA coach John Wooden led his players.

Wooden didn’t begin practice with advanced tactics or complex plays. He started each season by teaching players how to put on their socks without wrinkles—carefully, patiently.

Why? Because greatness isn’t built through force. It is built through a foundation of grace, patience, and presence.

When players made mistakes, Wooden didn’t shame or pressure them. He modeled grace under pressure.

His definition of success was simple:

“Peace of mind which is a direct result of self-satisfaction in knowing you made the effort to become the best that you are capable of becoming.”

Reading that, I saw myself clearly: I had not been offering that space to my mentee. I had not been offering it to my son.

Wooden had it right: grace is the soil where growth happens. Control is the weed that chokes it.

If there is one leadership paradox that life keeps sending me again and again, it is this:

• 👉 The more you force, the more you lose.
• 👉 The more you release, the more you lead.

Mentoring. Parenting. Leadership.

The roles may change. The titles may shift. But the invitation remains the same:

Lead with grace. Not control.

Because the opposite of leadership isn’t following.

It isn’t weakness.

It is control without grace.

And that is the trap I still have to watch for in every stage of life.

Legacy Question

In moments of reflection, one question anchors me:

“When my children and my mentees tell their stories one day—will they say I taught them?

Or will they say I loved them through their becoming?”

That is the only leadership legacy worth leaving.

And every day, I am learning to choose that path—again and again.