Recently, I went through one of the worst setbacks in my professional life. We were bidding for a major tender—a supply contract that would have secured business for the next two to three years. We had run the numbers, factored in historical data, and made what I believed to be a calculated pricing strategy.
But we were wrong.
We underestimated the moves of our competitors. We overestimated how the market would play out. And we misread the weight of a few critical decisions. We lost the tender.
It wasn’t just a missed opportunity. It was a blow that could reshape the company’s financial outlook for the next few years. When you’re leading a business, mistakes like this don’t just stay on the spreadsheet—they ripple through your people, your plans, and your confidence.
When Leadership Feels Lonely
When something like this happens, it’s natural to look for blame. But when you’re at the top, that spotlight often turns inward. And that’s both the burden—and the privilege—of leadership.
I had to face my own discomfort. The questions I asked myself weren’t just about numbers. They were about judgment, process, and foresight. What did I miss? What could I have done better? Who did I fail to listen to?
Leadership often feels lonely not because we lack support, but because we carry the weight of the decisions we make—for our people, our business, and the path ahead.
I struggled silently for more than a month. I carried the burden quietly and went through a difficult time. It was seriously, quite bad.
But here’s the thing: leadership is not about never failing. It’s about what you do after.
Lesson One: Challenge Your Assumptions, Constantly
One of the biggest takeaways from this episode is how dangerous it can be to rely on outdated thinking. I had used historical tender data as an anchor for our pricing strategy. But the industry has changed. Margins have tightened. Players have grown bolder. Customers have shifted their priorities.
In fast-moving environments, assumptions must be treated like perishable goods—they expire quickly. This applies not just in pricing, but in every corner of business: strategy, people management, market positioning, even customer loyalty.
What worked yesterday may no longer apply today. Leaders must build in mechanisms to challenge their own thinking regularly—not only when something goes wrong.
Lesson Two: Build a Culture Where You Can Be Wrong
If there’s anything harder than making a bad call, it’s creating a culture where people feel safe to challenge your thinking before that call is made.
In hindsight, I wish we had debated harder. I wish my team—and even I—had pushed back on our assumptions more forcefully. Sometimes, in leadership, you don’t need more certainty. You need more dissent.
This experience reminded me to keep encouraging open dialogue in the organisation, especially in high-stakes decisions. It’s not enough to have a smart team. You need to create space for uncomfortable truths to surface.
Lesson Three: Own the Outcome, Lead the Recovery
Once the result was in, there was no point dwelling in disappointment. The only way forward was through ownership. I addressed the setback with my team transparently—not just to explain what went wrong, but to share what we were going to do about it.
We are now more careful in our pricing strategy. We’re working harder to gather better market intelligence. And we’ve added internal checkpoints to avoid overconfidence in future tenders.
In business, losing hurts. But losing without learning—that’s what truly destroys momentum.
The Personal Parallel: The Other Decision I’m Questioning
This business loss also triggered a more personal reflection—one that’s even harder to sit with.
Last year, my wife and I made the decision to send our son to Singapore for secondary school. We believed it would offer him a better learning environment, a chance to grow in independence, and exposure to a more competitive academic setting. On paper, it made perfect sense.
But now, I’m not so sure.
He’s struggling. With his grades, with focus, with being away from home. And the hardest part is this: he’s trying to self-regulate during a season of life when most teenagers still need guidance and presence—not distance.
I thought I was setting him up for success. But I may have overestimated his readiness. Or underestimated how much a child—any child—still needs the steady presence of their parents to grow well.
The truth is, leadership at home is no different from leadership at work. You make decisions based on the information and intentions you have. But you don’t always get it right. And when you don’t, the only way forward is humility, honesty, and change.
Lesson Four: There’s No Perfect Decision, Only the Willingness to Adjust
Whether in business or parenting, we often search for the “right” choice. But the truth is, there’s rarely a perfectly right decision—only the best one you can make with the wisdom you currently have.
The real test of leadership—at work or at home—is how willing you are to reassess that decision when the outcome doesn’t match your expectations.
Do you double down in pride? Or do you pivot in humility?
I don’t have all the answers yet when it comes to my son. But I’ve started showing up more, even if it means making the commute. I’ve made a conscious effort to be present when he needs me. To talk, listen, and remind both him—and myself—that success isn’t about always making the right moves. It’s about being willing to grow through the wrong ones.
Forward, Wiser
This season has been humbling. But also, clarifying.
I still dread setbacks. I still replay what I could have done differently. But I no longer see failure as something to avoid at all costs. In fact, some of the most meaningful growth in my life has come from the places where I stumbled.
To anyone going through a season of doubt, disappointment, or decision fatigue—whether in business or in life—know this:
You’re not alone. The pain of getting it wrong is real. But the power of learning from it, and leading forward with courage, is even greater.
In the end, we are not defined by our perfect decisions. We are defined by how we rise after the imperfect ones.