Back in 2019, as Donald Trump was navigating the early days of his first term as President of the United States, countless articles dissected the new leadership of the free world – and what the British people thought of him. Among these analyses, one essay stood out, resonating far beyond the UK and becoming a viral sensation. Written by Nate White and featured in The London Economic, this masterfully witty critique not only pinpointed Trump’s personal shortcomings but also offered a window into the cultural clash that made those failings matter so much to the British psyche.
Fast-forward to 2025, and Trump is back in the Oval Office, making this essay feel as timely as ever – not just as a piece of satirical commentary, but as a reminder of how humour can illuminate deeper truths about leadership. At Humourology, we believe that humour has the power to reveal, connect, and shape perceptions of those in power. With Trump’s return to the global stage, we revisit Nate White’s essay in The London Economic to explore the psychology of humour, its role in leadership, and why the ability to laugh at oneself remains as vital as ever – and as quintessentially British as fish and chips.
For those unfamiliar with Nate White, he’s a seasoned advertising copywriter and creative thinker with a gift for wordplay. His essay didn’t just strike a chord; it struck an orchestra. But while it’s framed as a British critique of Trump, having spent significant time travelling across Europe, I can assure you this sentiment isn’t confined to the British Isles.
White’s opening salvo is a masterclass in sardonic wit
“Trump lacks certain qualities which the British traditionally esteem. For instance, he has no class, no charm, no coolness, no credibility, no compassion, no wit, no warmth, no wisdom, no subtlety, no sensitivity, no self-awareness, no humility, no honour, and no grace.”
It’s the kind of line that makes you wince, laugh, and then read it again just for the pleasure of the rhythm.
The British Humour Test
Humour is central to this critique—and, I’d argue, central to the divide between Trump and his British detractors. The British, as a nation, love to laugh. But more than that, they love a leader who can laugh at themselves. Self-deprecation is practically enshrined in the British psyche, and those who fail the “humour test” are viewed with deep suspicion.It’s not just about being funny—it’s about being in on the joke. Nate White highlights this cultural clash when he writes
“He [Trump] doesn’t even seem to grasp what a joke actually is—his idea of a joke is a crass comment, an illiterate insult, a casual act of cruelty.”
Now, while humourless leaders may survive in certain corners of the world, in Britain, they’re like tea without biscuits: awkward and just plain wrong.
The Psychology of Humour in Leadership
From a psychological perspective, humour – particularly the self-deprecating variety – builds trust, relatability, and connection. When a leader laughs at themselves, they signal humility, self-awareness, and humanity. It’s disarming in the best possible way.
On the flip side, humour that punches down, rather than elevates, can feel alienating or even hostile. Trump, however, has often been accused of punching down – or, as some might argue, punching in every direction. He punches everyone across the board: late-night hosts who roast him, grieving Gold Star families who question him, and, most notoriously, a disabled journalist. In fact, if humour is supposed to unite, Trump’s approach often feels more like a verbal WWE match – all body slams and no subtlety.
Three Tips for Leading with Humour
While it’s easy to chuckle at Nate White’s essay, there’s a deeper lesson here for leaders and professionals everywhere. Whether you’re addressing a boardroom or a ballroom, the way you use humour can have a profound impact on your ability to lead effectively. Here are three tips to help you harness the power of humour in your own leadership:
- Be the First to Laugh at Yourself
Leaders who poke fun at their own quirks and missteps show humility and relatability. It’s not about self-sabotage; it’s about showing that you’re human. As the old saying goes, “Blessed are we who can laugh at ourselves, for we shall never cease to be amused.” - Punch Up, Not Down
Great humour punches up at power, not down at vulnerability. When used thoughtfully, humour can challenge authority, highlight absurdity, and provoke thought – all without alienating your audience. Aim your jokes at the big issues, not the little people. - Know Your Audience
What lands in one culture might fall flat in another. The British love irony, subtlety, and dry wit, while Americans often appreciate boldness and energy. Tailor your humour to the room, and remember: laughter is universal, but the style of delivery isn’t.
A Universal Truth
Of course, Nate White’s essay is not without its critics, and it’s worth noting that while it’s undeniably funny, it also toes the line between clever critique and outright vitriol. As a proponent of Humourology, I believe humour should always aim to elevate, not alienate. While White’s takedown is a masterclass in wit, one could argue that it reflects the very polarisation it critiques. After all, the best humour doesn’t just mock – it makes us think.
Which brings me to my denouement (a word Trump may or may not pronounce correctly). If Trump were to read White’s essay, I’d like to think he’d defend White’s right to publish it in the name of free speech – before swiftly tweeting his own response in ALL CAPS.
But if there’s one thing we can all agree on, it’s this: humour, when wielded wisely, has the power to disarm, connect, and provoke thought. And whether you’re laughing with Trump, at Trump, or somewhere in between, we should all take a moment to appreciate the art of the well-crafted joke.
Because in the end, humour isn’t just about getting the last laugh. It’s about understanding the world – and ourselves – a little better.
See you next Tuesday.
Warmest,
Paul x
