It’s where I record the kind of advice that finds you rather than you finding it. A line overheard in conversation. Something a colleague said that stopped me mid-sentence. A quote I’d read before, but one day actually heard for the first time. I’ve been carrying some version of this book for a long time now. The current one is suitably battered and frayed, which I think is entirely the point.
What strikes me every time I page through it is not how much has changed but how much hasn’t. Particularly when it comes to leadership. The world looks very different in 2026 than it did when some of these entries were first written. AI is reshaping industries faster than most organisations can track. The post-pandemic reconfiguration of work is still unsettled. Geopolitical uncertainty has become a permanent feature of the landscape rather than an occasional interruption. Leaders are under more pressure than ever to have answers, to act decisively, to project confidence, often simultaneously and always immediately.
And yet here I am, paging through this battered little book and finding that the most important things are still the same three things they’ve always been.
So think of this as a hitchhiker’s offering. These ideas didn’t arrive in any particular order or by any particular design. They showed up, as the best things tend to, when I wasn’t especially looking for them. I’ve simply written them down, and I’m passing them on. Take what’s useful. Leave what isn’t. And if something here finds you at the right moment, well, that’s exactly how it’s supposed to work.
Meg Wheatley once said, “Thinking is the place where all intelligent action starts.” I visited Meg at her home in the Sundance Valley outside Salt Lake City years ago, not long after her book Leadership and the New Sciences had properly derailed my thinking in the best possible way. That line has stayed with me ever since.
Here’s what I observe in 2026: leaders are busier than ever, and thinking, real, unhurried, reflective thinking, is the first casualty. The always-on culture didn’t slow down. It accelerated. AI tools have added capability, but also added noise. The expectation to respond, react and produce has never been higher. And somewhere in all of that, the habit of pausing to actually think has become not just neglected but almost apologised for, as if it were a luxury rather than a necessity.
It isn’t a luxury. It is, in fact, the work.
Leaders who don’t protect time to think will eventually stop leading and start just reacting. There’s a difference and those around you feel it even when you can’t see it yourself. Confucius identified three methods by which we learn wisdom: by experience, which is the bitterest; by imitation, which is the easiest; by reflection, which is the noblest. Reflection requires time. Time requires a decision. That decision starts with you.
Here’s the quiet incentive too: when you model the habit of thinking, visibly and intentionally, you give everyone watching permission to do the same. And in most organisations right now, that permission is badly needed.
Years ago, I watched a film called The Music Within. There’s a scene where a student has just delivered a speech to his coach in an empty theatre. After a long pause, the coach asks, “You like it up there?”
“Better than anything,” says the student.
“Why?”
“I don’t know.”
“That,” says the coach, “is the first honest thing you’ve said.”
He then sends the student away with words I’ve never forgotten:
“Go live your life. Fill yourself up. Find out what’s important. Earn a point of view. Then come back when you have something to say.”
In 2026, the pressure to have answers has intensified in ways that feel almost absurd. Generative AI can produce a confident-sounding answer to almost any question in seconds. Which means the ability to say “I don’t know”, genuinely, without performance, without immediately pivoting to a deflection, has become rarer and I’d argue more valuable than ever.
There is something deeply human about a leader who can sit with not knowing. It builds trust in a way that polished certainty never quite manages. It creates space for the people around you to think rather than simply wait for instructions. And it models the intellectual honesty that most teams are desperate for but rarely see from the top.
“I don’t know” is not a weakness. In the current climate, it might be one of the more courageous things a leader can say.
Try it. See what happens.
Mark Twain said, “It’s not what we don’t know that gets us into trouble, but what we know for sure that just ain’t so.”
Certainty kills curiosity. I keep coming back to that. Ready answers stifle budding questions. Black and white thinking strips out the grey, and the grey is exactly where paradox and ambiguity live.
If there is one defining feature of the leadership landscape right now, it is this: the leaders who are struggling most are not the ones who lack information. They are the ones who are clinging to assumptions that no longer hold. Assumptions about how organisations work, about what employees want, about where value is created, about what leadership itself is supposed to look like. These assumptions feel like solid ground. They are not.
The instinct when facing uncertainty is to resolve it, to find the answer, create the plan, project the confidence of someone who knows where they’re going. I understand that instinct. But I’ve come to believe it’s exactly the wrong response to the world we’re currently in.
Uncertainty and paradox are not problems to be solved. They are the terrain. And the leaders who learn to operate within them, who can hold competing truths without collapsing, who stay curious when the ground shifts, who resist the temptation to oversimplify, those are the leaders whose organisations will still be standing when the dust settles.
Playwright Robert Ardrey once said, “Not in our powers but in our paradoxes shall we search for the essence of man.” He could have been speaking directly to leaders today.
Befriend the uncertainty. It will demand more of you than comfort ever did. But it will also reveal things about your leadership that calm waters never could.
I’ll close with a traditional Hawaiian blessing I’ve carried in the book for as long as I can remember: E mālama pono. Take care. Be strong. Stay integrated.
In 2026, that feels like exactly the right instruction.
This is the thinking Keith brings to leadership workshops around the world. Not tidy frameworks or packaged answers, but the kind of real, honest conversation that helps leaders think better and lead well in a world that isn’t slowing down.
If that’s a conversation worth having, we’d love to hear from you.
Keith is based in South Africa, but presents globally, with recent travel including working throughout the UK, the USA, Saudi Arabia, Dubai, Abu Dhabi, Germany, Switzerland, Singapore, and, of course, South Africa.