The night I nearly blew my career at a football match

Not every fail is a failure, writes James Chisholm.

17 November 1999. Brazil versus Australia at the MCG. The crowd was excited by the rare opportunity of some of the greatest world footballers in their backyard as a young short short-haired Ronaldinho was weaving his magic alongside Aussies Viduka with Bosnich in goals.

It was a night I should have remembered for the football. But for me, it marked a very different turning point.

It was the night I nearly torpedoed my career.

At 27, I was a newly appointed team leader at global technology and manufacturing company Honeywell in the Melbourne office. I was eager, ambitious, and like many young professionals, still learning the unspoken rules of diplomacy.

At a post-match event, I was introduced to a senior consultant who had ties to several of my colleagues. Trying to make an impression, or perhaps just feeling too comfortable, I cracked a joke, “Ah yes, I’ve heard about the dodgy deals you do!”

It was meant as a lighthearted quip, but his reaction was instant and ice-cold. What I thought was banter landed like a lead balloon. I had unknowingly offended someone important to the business and, by extension, risked damaging the relationships and credibility of senior colleagues I respected.

The gravity of it hit me like a freight train.

By morning, the embarrassment had hardened into a knot in my chest, and I felt like a liability. Worse, I feared I had let down people who had placed early trust in me, so I did what felt honourable. I wrote a resignation letter.

I figured if I was going to be fired, I would at least own the mistake, and although I hoped my manager wouldn’t accept it, I felt it was the right thing to offer him the option. Thankfully, he didn’t accept it.

In fact, he told me something I’ve never forgotten: “Doug (the big boss in Sydney), knows what happened. But he has no intention of firing you over something silly you said.”

That boss, Doug, never mentioned the incident to me again, and for over two decades, we never spoke about it.

However, we caught up recently and finally debriefed on that awkward night from 1999. The conversation was warm, honest, and deeply affirming. It reminded me that leadership isn’t forged in flawless moments, it is shaped through stumbles, accountability, and grace.

Reflecting on that experience, there are three lessons I believe are just as relevant to emerging leaders today as they were back then.

1. Own the mistakes, don’t run from them

By taking responsibility for the fallout, even overcompensating by offering to resign, I gave others permission to be generous in return. When people see you are accountable, they are more inclined to offer support than punishment. Ownership disarms defensiveness.

2. Lead with intent, not perfection

As Doug told me recently, “I don’t believe in ending careers over someone saying something silly.” He looked at the intent behind my actions, not just the impact.

That decision changed the trajectory of my life. I’ve carried that ethos with me ever since. Everyone you lead will make mistakes. Your job is to ask: “What was their intent? What’s the learning?”

3. Context is everything. Get briefed, and brief others

One of the most avoidable parts of that night was my lack of awareness. I didn’t know who the consultant was, or how critical he was to our team. Had I been briefed, or asked for a briefing, I may have adjusted my approach.

These days, I am hyperaware of the importance of context and make it my job to equip others with it too.

I ended up spending 16 years at Honeywell, growing in responsibility, confidence, and capability. But it could easily have ended in the first 90 days over a clumsy joke in a moment of poor judgement. That’s the fragility of early leadership. The stakes feel high, the learning curve is steep, and the safety nets aren’t always visible.

I’m sharing this story to demonstrate that not every fail is a failure. We don’t talk enough about the early missteps, the moments we cringe at years later, or the leaders who backed us when they didn’t have to.

If you’re a new manager, know this. Setbacks will come. You will say or do the wrong thing. You’ll feel out of your depth. But if you own it, learn from it, and surround yourself with leaders who see your potential, not just your performance, you’ll grow faster than you imagined.

And if you are that leader, the “Doug” in someone’s story, never underestimate the ripple effect of grace in a tough moment.

It might just shape a career.

James Chisholm is the co-founder of Peeplcoach.