Are You Unlucky? Or Just Unprepared?

Gary Player, controversial as he is, is a legend. And he has one line that has aged remarkably well: “The more I practice, the luckier I get.” It sounds like something you’d expect from a man who hit more balls before breakfast than most of us have in a lifetime, but there’s something deeper sitting underneath it. We like to romanticise luck as this mystical force: some people have it, others don’t. Yet if you sit with it long enough, you realise luck is far less random than we pretend. As Lucius Seneca put it:  Luck is when preparation meets opportunity. 

I am reminded of that every day, when I stand in front of audiences and help them grow their capability – my life’s work.  

In 2019, I experienced a meaningful acceleration in doing the work that truly made me happy. On paper, it looked like I was simply in the right place at the right time. An opportunity came my way to train for the global network of EO Accelerator. And in many ways, that’s exactly what it was. I now realise how lucky I was. That specific opportunity hasn’t come around again in the same way in the seven years since. It was rare, almost a one-off alignment of timing, network, and context. And it set me on a path that has led to significant traction and impact today. And… I almost missed it! The good thing is, I didn’t, and it’s because I had spent years quietly putting myself into the frame where that kind of opportunity could even see me.

This was how: My travel business had grown to a meaningful size and ran quite autonomously, freeing me up for other pursuits. But before I started that business, I had wanted to do the teaching and training work that I do today. Only, the timing was off. In 2008, I didn’t have the network, skills or credibility to enter the space. But that changed over time. By 2019, I had started my own teaching NGO working with kids from disadvantaged communities, and was enthusiastically coaching and serving business leaders in EO. None of these activities made immediate commercial sense, but they made me happy. I had attended events I could easily have skipped, and one of those conversations… just one… shifted the trajectory. It nudged me toward the path that made that 2019 moment possible. So yes, it was luck. But it was also engineered luck. It was the result of showing up often enough, long enough, and prepared enough that when the train arrived, I wasn’t scrambling for a ticket. I was already on the platform.

That’s where Jim Collins reframes the conversation in a way I’ve found incredibly useful. He doesn’t ask whether you are lucky or unlucky. He asks something far more uncomfortable: what is your return on luck? Because if you study great companies or great careers, you find something surprising. They don’t necessarily experience more luck than others. What they do is convert it better. 

Think about it through three lenses.

The first is what Collins calls "who luck": the idea that sometimes a person enters your world and changes your trajectory. In a South African context, you see this constantly. Take the Springboks. Rassie Erasmus didn’t just stumble into success; he assembled the right people around him at the right time, from Siya Kolisi’s leadership to Jacques Nienaber’s defensive systems. Those weren’t random encounters. They were cultivated relationships, years in the making. When the moment came, the right people were already in the room. That’s not luck in isolation. That’s return on luck.

The second is "event luck", and here, South African business gives us plenty of examples. Consider how companies like Checkers 60/60 navigated the pandemic. COVID was, by any definition, a massive external shock luck, if you want to call it that, albeit the kind none of us would have ordered. But Checkers had built capability, flexibility, and decision-making speed, and swept the market with its delivery services, converting that disruption into acceleration. Others, facing the exact same event, simply survived or even regressed. Same luck event. Very different return.

The third is what Collins describes as "bad luck turning into good", which is often where the real story lies. Current events are full of these moments. Load shedding, for example, has been a structural constraint on the South African economy, yet it has also forced innovation in energy, logistics, and operational resilience. Entire industries have emerged because of it. The question is never whether the event was good or bad. The question is whether you had the mindset and the capability to extract something useful from it.

This is where the thinking connects neatly into broader leadership frameworks. In Atomic Habits, James Clear talks about the power of small, consistent actions — essentially the practice behind Player’s quote. In The 7 Habits of Highly Effective People, Stephen Covey pushes us to be proactive rather than reactive, to operate in the space where we actually have control. And Collins himself, across Good to Great and Great by Choice, keeps returning to the same theme: disciplined people, disciplined thought, disciplined action.

When you overlay those ideas, a pattern emerges. Luck is not the variable you manage. The system you build around it is. Which brings us to what to actually do with this… 

PG’s Pro Tip:

If you want to improve your return on luck, you don’t need a philosophical breakthrough. You need a practical system.

The first is to deliberately increase your surface area to attract luck. This means saying yes to the meeting, attending the event, and making the call you’ve been postponing. Not recklessly, but intentionally. Most people miss out on luck not because it never arrives, but because they never put themselves in its path. I do annual, monthly, and daily planning. It helps. And I try to focus on gratitude, and I pick up the phone to let people know what they did for me and how grateful I am. It’s something I’ve picked up from observing Tatjana Smith, our Olympic champion. Acknowledge your village!

The second is to build readiness before the moment arrives. Skill, reputation, relationships… these are your encodings. When the opportunity shows up, you don’t have time to prepare. You either are, or you aren’t. The quiet work you do when nothing is happening is what determines what you can do when everything is happening.

The third is to create slack in your system. If your calendar, energy, and finances are maxed out, you physically cannot respond to opportunity. You’ll watch it pass by while telling yourself you’re too busy. High performers often miss this. They optimise for efficiency, inadvertently destroying their ability to be opportunistic. 

ChatGPT Prompt:

And if you want to operationalise this with a bit of help, try this prompt:

“Act as a strategic advisor. Based on my current business and network, identify three specific ways I can increase my exposure to high-quality opportunities over the next 90 days, and three constraints I should remove to improve my ability to act on them.”

Because in the end, Gary Player had it right. It just turns out that “practice” isn’t only about hitting golf balls. It’s about designing a life where luck has somewhere to land, and something to work with when it does.

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