Becoming Yourself: Leadership in the Messy Middle. Share this with a leader in process. We don’t need more heroes. We need more humans becoming whole.
It’s not often I do a reflection while standing still. Usually, I walk. I think better when my body is in motion. But tonight, something different called for something deeper. Maybe it was the conversation with Dr. Goh, or maybe it was the stillness of a Tuesday night well spent.
Either way—this one’s worth sitting with.
A Meeting That Meant Something
We met Dr. Goh, the CEO of HELP University, to seek his insight on campus expansion planning. What struck me wasn’t his position, or his portfolio. It was how present he was.
He didn’t speak to impress. He spoke to help.
He wasn’t perfunctory. He was intentional.
And in a world where so many meetings feel like checkbox exercises, that meant something. He gave us his best thinking—on traffic flow, campus accessibility, prime location design, and parent expectations—not because he had to, but because he cared.
He reminded me: real leaders don’t just give answers. They give themselves.
From Be Yourself to Become Yourself
Later that day, during our leadership development session—the 30th session we’ve done—we were presented with a deceptively simple reflection:
“Should you be yourself… or become yourself?”
At first, it sounds motivational. Just be yourself, right? But the more I sat with it, the more I realized: “be yourself” is passive. It’s static. It’s a snapshot of who you are now.
But “become yourself”—that’s active. That’s transformation. That’s leadership.
Being yourself is declaring who you are. Becoming yourself is discovering who you’re called to be.
And that discovery? That’s a life’s work.
Analogy: The Sculptor and the Stone
Being yourself is like standing in front of a block of marble and admiring its shape.
Becoming yourself is picking up the chisel.
It’s messy. You get it wrong. You make chips in places you shouldn’t. But slowly, painfully, beautifully—you reveal what’s inside. The shape of purpose. The image of leadership. The version of you that was always there… just buried beneath comfort, fear, and ego.
Three Dilemmas of Becoming
The discussion gave us three powerful leadership dilemmas:
1. My Dream or Someone Else’s?
Should I become who I want to be—or who others expect me to be?
The story of Al Gore hit me. His father wanted him to be president. And he tried. He served. He campaigned. He even won—technically.
But deep down, it wasn’t his dream.
When he finally stepped away from politics and focused on environmental activism, he found his voice. His passion. His legacy. And he won a Nobel Peace Prize—not for following someone else’s map, but for finally choosing his own.
Sometimes, the loudest voices in your life don’t come from enemies. They come from those who love you… but see you through their own lens.
Leadership isn’t echoing expectation. It’s clarifying conviction.
2. Result vs Principle
Should I become someone who gets results—or someone who upholds values?
We’ve all faced this.
You can sell more by exaggerating.
You can close faster by cutting corners.
You can rise quicker by staying silent.
But at what cost?
A person who steals because he’s desperate will stop once his needs are met.
A person who never steals because it’s wrong… never starts.
One is result-based. The other is principle-based.
And while both may lead to the same short-term behaviour, only one builds character that lasts.
As leaders, we need both logic tracks. But when they clash—choose principle over profit. Because reputation can buy success, but only character can sustain it.
3. Which Principle When?
What happens when values collide?
Do you report your father for stealing, or do you protect him out of loyalty?
Do you uphold honesty—or family?
Confucius once faced that very dilemma. And today, many leaders face the same—just in modern form: fairness vs loyalty, honesty vs unity, transparency vs discretion.
The mature leader doesn’t choose one value over the other. He integrates.
He searches for wisdom, not convenience.
Because true leadership isn’t picking sides—it’s elevating truth.
Joseph: Leadership in the Middle
That morning, we also had our weekly leadership devotion. We reflected on the life of Joseph in Genesis.
From dream to fulfilment, 22 years passed.
He was betrayed, sold, imprisoned, forgotten. And yet… he didn’t give up.
Why?
Because he held on to three things:
Patience.
Humility.
Gratitude.
When his breakthrough came, he didn’t boast. He said, “I cannot do it, but God can.”
When he named his sons, he didn’t name them after pain. He named them after healing.
One meant “God made me forget my trouble.”
The other, “God made me fruitful in suffering.”
That’s the mark of a leader in process—not bitter, but better.
The Messy Middle: Where Most of Us Quit
Reading this, I was reminded of Scott Belsky’s The Messy Middle—a manual for those in the tough middle stretch of any big journey.
That’s where leaders are made or broken—not at the start, not at the finish, but in the middle.
A few takeaways stood out:
- Endurance is a Skill
Startups, school reform, leadership culture—it’s not the bold start or grand finish that counts. It’s showing up when there’s no applause.
- Optimise What Works
Before chasing new ideas, double down on what’s already producing fruit.
In our leadership programme, we kept refining the same framework—because depth matters more than novelty.
- Kill Your Darlings
That programme you love? It might no longer serve your purpose.
We’ve sunsetted beloved initiatives at Stellar—because clarity is kinder than comfort.
- Self-Talk Shapes Strategy
What you say to yourself leaks into how you lead others.
I reflect nightly. It’s not therapy—it’s calibration. Leaders must curate their inner voice.
- Don’t Let Chaos Distract from Craft
It’s easy to be busy. It’s harder to be excellent.
At Stellar, we build leadership not by adding, but by refining. Coaching. Tight feedback loops. Relentless alignment.
Reverse Insight: Becoming is the Braver Choice
The world tells you to “be yourself.”
But maybe… that’s a trap.
Because if “being yourself” means staying safe, small, or stuck—then it’s not authenticity. It’s avoidance.
The real courage?
Becoming.
Becoming someone your children respect.
Becoming someone your team trusts.
Becoming someone who carries weight—not with words, but with presence.
Be yourself is a comfort zone.
Become yourself is a calling.
And the world needs fewer performers—and more people in process.
Final Reflection: The Walk That Never Ends
After a full day—meeting wise mentors, coaching leaders, swimming, walking with my wife and children, doing reflection in the garden—I felt full.
Not because I had accomplished much.
But because I had aligned deeply.
With who I’m becoming.
With what matters.
With how I want to lead.
“Becoming yourself” is not a slogan. It’s a sacred responsibility.
So tonight, I ask you what I ask myself:
Who are you becoming?
And if the answer feels uncertain… good.
That means you’re still in process.
Still chipping at the marble.
Still walking the messy middle.
And still… choosing to become.
