Thoughts on Legacy: Does Defining Your Legacy Make You a Better Leader?

If you asked most people when they start thinking about legacy, they’d point to something for people who already have one foot in their “after” story, not those still firmly in their leadership years – maybe retirement age, estate planning, or grandparents deciding what to leave behind. Legacy feels like a later-in-life topic.

But here’s a drop of wisdom I’d like to share with leaders: legacy isn’t something you think about at the end, it ought to be something you think about at the start, and then intentionally build in the middle.

Back when I was in my corporate life, I didn’t have the language for that yet. In my twenties and thirties, the idea of legacy felt like the domain of the wealthy and the elderly. I pictured antique-filled rooms with older relatives debating wills and memorial plans. Legacy was about assets, monuments, and stuff, not necessarily anything with deeper meaning. It felt entitled – transactional even – and very far away from the busy, high-stakes world of leadership and organisational impact that I lived in.

It wasn’t until much later that I realised legacy has very little to do with being remembered and everything to do with what continues because of you.

The question nobody asks until later

When I was nearing the end of my first career, I did finally start thinking about legacy, but the frame was still narrow. I wanted my leadership, my thoughtfulness, my way of problem-solving to live on. I wanted others to learn from me, emulate the best of what I brought, and ultimately make it their own.

That was, if I’m honest, two things at once. Part of it was ego: wanting to be personally impactful. But the more generous part of me understood that the true legacy would never be traceable back to me at all. It would be in other people’s choices, behaviours and ways of leading long after I disappeared from the organisation.

The funny (and brutally humbling) truth about corporate life is this: organisations move on fast. Within just a few weeks of you leaving, someone else occupies your office, your calendar, and your seat at the table. The business adapts to the gap you leave. It has to.

It’s safe to say that legacy doesn’t live in the plaque on the wall or the succession document. It lives in other humans.

And that’s when this question arises: If what lasts is what lives on in other people, then what exactly am I leaving behind?

The part that isn’t neat and tidy

Of course, the moment you start asking that question, you’re also confronted with everything you’re not proud of, the compromises you’ve made, and the values you’ve bent in the name of being a “team player”.

I had a period in my career when I felt the legacy being created through my leadership team wasn’t the one I wanted to leave. I didn’t agree with the approach, I didn’t align with the values, and I had misgivings about decisions being made. I wanted to be a change agent from within, but if I’m honest, at that particular point in my career, the system shaped me more than I reshaped the system.

Should I have been more courageous? Yes, I think so. But I wasn’t. And it has taken time to make peace with that. Many leaders never tell the truth about the cost of staying or the complexity of leaving. We make trade-offs we hope we’ll be able to justify later, and we make them without the certainty of knowing whether they’re “right”.

The uncomfortable reality is that legacy is shaped just as often by the compromises we make as by the triumphs we celebrate.

We’re not as significant as we like to imagine

The next major shift in my understanding of legacy didn’t come from a leadership book or a strategic framework. It came from a museum in Johannesburg.

During the South Africa Leadership Retreat last November, our group toured the Origins Centre, where the story of humankind, from its earliest incarnations in Southern Africa, is described and contextualized. One exhibit contained three tall glass columns filled with stratified sediment representing different geological periods. The remnants of early humans appeared right at the very top – just a whisper at the end of billions of years.

I remember standing there with this visceral, humbling awareness: in the scale of time, we are specks.

Whatever legacy I leave will be no match whatsoever for a stone tool that survives millennia. No LinkedIn achievement or annual report accolade will make it into a glass column for future generations to consider.

Oddly enough, that experience didn’t depress me. It freed me.

Once you stop imagining legacy as a monument, you can start imagining it as a transmission. Not what outlasts time, but what expands life.

A question for you as a leader

If legacy isn’t what people remember, but what continues because of you, then the question becomes both simpler and more intimate:

What do you want to 'transmit' while you’re still in the room? What do you want to be known for when you’re not in the room?

Not someday. Not at the end. Not once the estate lawyer arrives. But now. Because legacy is not for grandparents, legacy is for leaders. And, trust me on this, it starts long before you leave the room.

You don’t need to have all the answers yet but I’m here if you’re curious about what this might open up for you. 

One final note, if the anecdote from the Origins Center struck a chord with you, the 2026 South Africa Leadership Retreat – an all-inclusive, 8-day/7-night experience from 7-14 November focused on your personal and leadership development – is now open for enrollment.