The Paradox of Progress

There are seasons in life when growth feels like regression. You keep moving, but it seems like you are losing ground. You give your best, yet feel more lost than before. Somewhere between knowing who you were and becoming who you are meant to be, you lose yourself.

I used to think that once I reached stability, whether financial, emotional, or spiritual, life would finally slow down. That clarity would settle, and peace would come naturally. But I was wrong. Life does not reward mastery with rest. It rewards mastery with a harder test. The moment we think we have arrived, life upgrades the level.

It is the same design in games my son plays. Early levels are easy. You earn experience points fast. But the higher you go, the more each level demands. What used to take minutes now takes days. Progress slows, but the growth deepens. The more capable you become, the more life stretches you. The paradox is this: as we become wiser, the game requires more of us.

In leadership, parenting, and purpose, the pattern is the same. The very things that once gave meaning, such as success, position, or even identity, start to feel like weights. But that does not mean you have failed. It means you are evolving.

Growth does not always feel like winning. Most of the time, it feels like losing who you once were.

Throughline: Growth feels like losing until you realise you are leveling up.

Story and Struggle

When I look back, life’s rhythm has always followed that same loop: find yourself, lose yourself, find yourself again.

In preschool, life was simple. I still remember the pride of seeing a five-star stamp on my paper. The teacher’s “Good job” felt like a medal. Progress was linear. You do good work, you get praise. Then came primary school, and the game changed. I entered the first class, surrounded by students sharper, faster, more disciplined. Suddenly, being good was not enough. To move from twentieth to nineteenth place could mean scoring three marks higher, but to lose one mark could send me four ranks down.

At twelve, I experienced my first taste of relative failure. I had not regressed; I had simply met a higher standard. Yet it felt like falling behind.

The same thing happened again at every life transition. Secondary school. University. Work. Leadership. Fatherhood. Every time I thought I had found my purpose, the next phase demanded a new version of me.

In my early career, leadership felt exciting. I was driven by achievement, not yet by meaning. But as I rose higher, the weight of responsibility grew heavier. I was no longer just managing outcomes; I was shaping culture and stewarding souls. When Stellar began expanding, I thought I had finally found the “why” that anchored everything. But over time, even that certainty began to shift. The structure that once empowered others began to feel limiting. What used to fit perfectly started to feel tight.

That was when I realised something vital. Purpose, like identity, is seasonal. You do not lose it because it is wrong. You lose it because you have outgrown it.

Even education mirrors this truth. Preschool children thrive on repetition and affirmation. But by adolescence, repetition becomes boredom. By adulthood, affirmation turns into pressure. The same systems that once nurtured you must eventually be restructured, or they will hold you back.

Losing yourself is not failure. It is the shedding of a form that no longer fits the next season.

The Truth Beneath the Tension

John Maxwell once said, “Leadership develops daily, not in a day.” That sentence has shaped how I view every chapter of life. Growth is not a straight road. It is a spiral staircase. Each turn brings you back to familiar questions, but from a higher altitude.

Every new level of leadership exposes a new lid. In The 21 Irrefutable Laws of Leadership, Maxwell called it the Law of the Lid: your leadership ability is the lid on your effectiveness. When your capacity plateaus, life raises the difficulty to stretch your ceiling. You cannot reach new impact without outgrowing old habits.

It is the same principle I see in educators who stop learning after ten years of teaching. They master techniques but lose freshness. The classroom changes, but they do not. Their lid becomes the school’s limit.

It is also visible in leaders who cling to what once worked. When the system starts failing, they double down instead of evolving. They confuse loyalty to a method with loyalty to a mission. True stewardship requires detachment. The Purposebility Vocab Bank says it clearly: leadership is stewardship, not ownership. We hold things lightly to serve greatly.

Growth demands detachment. Every breakthrough begins with a letting go.

In the Southeast Asian context, especially in Malaysia, this is a tension many leaders face. Cultural loyalty often prizes stability over evolution. But leadership, by nature, disrupts comfort. To raise purpose-driven schools, or to reform education, means to question old norms, to lose the identity that once defined success.

When we built Stellar’s foundation, we were defining not just a school but a way of living. Our PVMC: Purpose, Vision, Mission, Core Values, anchored us. But I have learned that even purpose must be renewed. Purpose is not a destination. It is a compass that needs recalibration every time we outgrow the map.

And recalibration hurts. It costs clarity. It tests security.

But that is the true work of leadership: facing yourself without losing yourself.

Psychologists call it identity reformation. Spiritually, it is surrender. Strategically, it is reinvention. Every name describes the same reality. Growth always requires a small death. You lose the old self so the new one can emerge.

So when life feels confusing, remember this: confusion is not chaos. It is the sound of construction.

Making Peace with the Process

How then do we live within this cycle without burning out?

First, by making peace with it. Growth is not meant to feel comfortable. Every version of you is built at the cost of the previous one. That is the cost of commitment. Dreams come with receipts. Legacy is not just what you build. It is what you are willing to exchange for it.

Second, by anchoring rhythm. The simplest way to avoid burnout is not to slow down. It is to find rhythm between pressure and pause. During one of our leadership training sessions, Uncle Tao Boon reminded us to check in with our mental, emotional, physical, spiritual, and relational health. That rhythm is not luxury; it is leadership hygiene.

Because when leaders neglect inner balance, society normalises dysfunction. We start seeing it in schools, in families, and in politics. We confuse achievement with maturity. But success without self-awareness always collapses under its own weight.

Third, by redefining mastery. Mastery is not perfection. It is repetition with awareness. In Purposebility’s words, “Repetition is the bridge between intention and transformation.” Growth compounds quietly, like Anne Scheiber’s story in The 21 Laws: the woman who invested $5,000 and built $22 million over fifty years, one disciplined decision at a time. That is how leadership works too. The returns are invisible until they multiply.

Finally, by remembering this truth: you never truly find yourself once and for all. You rediscover yourself again and again through service, struggle, and reflection. Each loss makes you lighter for the climb ahead.

The real question is not “Who am I becoming?” but “What am I outgrowing?”

If we can learn to hold our roles lightly, to see success and failure as feedback, and to walk humbly with each version of ourselves, then losing ourselves becomes sacred work. Because every time you lose who you were, you make space for who you are meant to become.

The Reverse Insight

You do not truly find yourself by holding on.

You find yourself by letting go of who you no longer need to be.