It’s about Legacy, Stupid.

In just over a week, I’m performing the first Work-In-Progress version of my forthcoming comedy special at a pretty unusual venue:

The Crypt of St Paul’s Cathedral.

The sheer prominence of the Cathedral in British Public Life is daunting. I remember as a child watching (on TV) Diana and Charles’ marriage there, along with the rest of my country. In the Crypt itself are the tombs and tributes to a few better known creatives than me: Blake, Turner and Wren, to name just three.

No pressure, right?

I feel incredibly lucky to perform there, and it’s deeply fitting. Because the show, “Meek Inheritance”, is all about Legacy.

I won’t lie: I’m worried about the world that my kids (and the rest of their generation) are growing into. The political madness, the instability, the divisiveness - and most of all the lack of role models. In the past days yet more Tech Bros have come out claiming an impending white collar jobs bloodbath from the next generation of AI LLMs.

We seem to be in a world where we are creating new things at pace, but with no clear sense of what or who we are creating it for.

And I (and perhaps I am also speaking for my generation of educated elites?) feel pretty complicit in creating this world. Occasionally through our direct actions as leaders, parents and citizens. But more often through our inaction - sleepwalking through all this: by not asking enough critical questions of the Leaders around us, and not pushing back enough.

I used to think that History was created by the Legacy of a small number of Leaders. I think that still holds, but to create a better, enduring future, I think we need to ensure that everyone who can and wants to, needs to create their version of legacy now. We need to democratise the concept of legacy itself, and start it much earlier in our lives and careers.

That can only be done if we work with others - and particularly the next generations - to define that legacy and create new common ground. And to think about legacy at four distinct levels: as individuals, in our families and communities, in our organisations, and in society at large.

It won’t be easy. It will take a lot of unpicking some of the mental models that have gotten us here. The ability to question what has motivated us to date, and perhaps turning that motivational dial inwards; the ability to see the world with fresh eyes and the difference it can make.

But for me, the days of waiting for that heroic national or global leader - whether or not they ever come - are gone.

I’m increasingly seeing my own legacy ‘north star’ as helping others define theirs intentionally, boldly and authentically. Whatever their stage of life or position. And while the bulk of my time will continue helping leaders define bold new north stars for their organisations, I also want to increasingly find ways to engage with individuals who deeply care about this. The comedy show is just the start.

The rub is, we have to engage on this Legacy discussion NOW. Even if you half believe the tech bros (and I do usually only half belief them), some of the biggest shifts in AI are just years - not decades - away. I’m frankly at a point in my life where I have a level of economic security, but I know I am one of the fortunate ones, and that’s definitely not true of my kids’ generation.

Legacy is not a new concept, but it needs to be defined: not as just what we leave behind when we pass (that’s too far away), but also how we show and live from now, each day and every day.

The key is to make our definition of legacy deeply intentional. And to do it with the fierce urgency of now.

Please come on the journey with me if you can, through this Substack and beyond.

PS - I am developing some exciting retreats and experiences to engage individuals around this topic of legacy, with some wonderful co-collaborators. If you are interested in learning more - or in the upcoming comedy tour - please drop me a line!

Pic from a recent exploration of the rich legacy of Malta.