Curious, Not Certain
What 2025 taught me and how 2026 will quietly change the rules
Curious, rather than certain. That’s my approach for 2026. Not because it’s fashionable, but because certainty is causing founder burnout, alongside anxiety, sleepless nights, and I’m convinced, discouraging new founders from embarking on their own journeys. Founders are burning out because they are playing the wrong game, and much of the advice they are receiving is just bad.
2025 was pretty awful all round, global macro pressures, local market changes and huge uncertainty, confidence was being tested from all angles. Making it harder than ever for entrepreneurs and founders to make progress.
Through Strive & Thrive, I’ve been talking a lot about learning, pattern-spotting, and understanding real lived entrepreneurial experiences. This hasn’t led to neatly stacked answers or “go-to” guides, instead it led to something messy but way more useful. By documenting the entrepreneurial journeys as they unfold in real time, not as we wished they did, I started to see how people actually walk them.
This is a reflection on that.
A reflection on the reflections of the founders.
My learning, shaped by learning alongside others.
What 2025 Made Hard to Ignore
When I step back and look at the bigger picture of 2025, a few things became very hard to unsee.
First, progress rarely came from moving faster. It came from seeing more clearly. The founders who made meaningful strides weren’t the loudest or most certain. They were the ones willing to sit with ambiguity long enough to reframe the problem.
One line I kept coming back to was:
“Clarity isn’t confidence. It’s context.”
The biggest take away for me is that it is clear that AI, tools, frameworks, playbooks helped. But only when grounded in human judgement. Where context was missing, automation and playbooks didn’t create clarity, it amplified confusion. That was a big takeaway for me. If AI is becoming ubiquitous, then the human bits become more valuable, not less. Judgement. Taste. Sense-making. Context. Narrative. The advantage no longer lies in access to information, but in the ability to interpret it well and turn it into meaningful next steps.
A lesson that I am still learning, is that many entrepreneurs don’t lack ideas, they are brimming with them. What they lack is an abundance of space; space to think, to sense check, to simplify. And often the real breakthroughs come not when we add more, but when we take something away.
And maybe the most revealing truth of all: confidence didn’t come from having the answer. It came from motion. Small, deliberate steps that created learning, not more plans, not another offsite, not another slide deck. Action created energy. Planning often drained it.
2025 reminded me that treating entrepreneurship as a straight-line problem is where a lot of the pain founders feel comes from.
Reflections as We Head Into 2026
So, if uncertainty is no longer a phase, but a permanent condition, then planning must give way to learning loops. Intentional cycles of sense, act, reflect. Not endless iteration for its own sake.
As well as this, the support systems of the entrepreneurial journey, including organisational systems, but also network, communities and even national approaches to entrepreneurship need to be able to adapt to the non-linear way in which entrepreneurship functions.
Because the exhaustion felt by founders is showing us that resilience isn’t about grit it's about design. How work is structured, how decisions are made and how the pressure that comes from that is distributed rather than absorbed by one person.
Signposting for 2026
Not predictions. Directions.
So, what does this point towards?
I’m less interested in forecasts and more interested in orientation. A few signposts that feel useful for entrepreneurs right now:
- A shift away from the hero-founder myth toward distributed capability. Less “hold it all together”, more “build systems that hold”. Organisations that can flex and adapt to constant headwinds.
- A move from rigid strategy toward adaptive intent. Knowing why you’re moving matters more than pretending to know exactly where you’ll land. The journey starts to matter more than the destination.
- A shift from scaling fast to scaling with consequence. Growth that compounds learning, not just workload. Progress is measured less by pace and optimisation, and more by insight gained.
None of this is radically new. But compounded, it makes you more adaptable. More anti-fragile entrepreneurship. Able to act decisively without pretending you know how the story ends.
“Most founders aren’t failing because they lack ideas or ambition. They’re failing because the systems around them are built for certainty in a world that no longer offers it.”
Writing this out made me realise something uncomfortable. I knew these things. But knowing isn’t the same as practising them, and that’s the real work for 2026.
Actionable Sets for 2026
What this looks like in practice
So what changes on Monday morning?
For me, and something I talk about a lot through Strive & Thrive, it’s about designing experiments that don’t destabilise your team. Fewer grand bets. More contained learning environments. Experiments over weeks or months are the way forward and should be implemented.
Build reflection into how you work. Not as an offsite luxury, but as a habit. A built-in organisational rhythm. Short pauses that prevent long detours; storytelling, capturing micro stories, learning from them will become a new must have tool in 2026.
And most importantly, treat entrepreneurship as a journey that evolves, not a puzzle to be solved once.
Create clarity without pretending certainty. Saying “this is what we’re trying to learn” instead of “this is the plan” subtly changes behaviour. It leads to different experiments, better signals, and less fear of being wrong.
How AI fits in, in 2026
AI is powerful, use it as a think partner. Personally, I use it a lot, it’s made a real difference to my work and business. But it’s not the answer or the solution. We need to be asking better questions, exploring scenarios, stress-testing assumptions all while keeping humans as the sense-makers. At Easol, we have started referring to this as the “AI handler”, someone who controls and manages AI, like a dog handler, it’s a change in thinking but its impact works.
In other words, as AI becomes ubiquitous, the uniquely human role becomes even more valuable, not less. Our judgment, taste, sense-making, and narrative skills are the true differentiators. The advantage no longer lies in simply accessing information, but in interpreting it meaningfully and turning it into actionable steps
AI isn’t reducing the need for humans. It’s exposing weak human thinking. Without judgement, technology just scales the problem. Try it yourself. You’ll see it quickly.
Why This Feels Different (and a Bit Uncomfortable)
This matters to me, to Strive & Thrive, and to how we work with founders, because it pushes back on some strong beliefs.
The market’s obsession with speed often covers shallow thinking. Moving fast in the wrong direction just wastes time.
“Fail fast” has quietly become “repeat the same mistake faster”, “ignore your own being” “do it properly” without the reflection needed to extract value. Stop the fail fast sentiment.
And a lot of what passes for innovation today is theatre. Real progress is about adoption and transformation. That means confronting identity, existing ways of working, personal roles, and wider uncertainty. That’s uncomfortable. So we avoid it.
In Conclusion
I’m not offering certainty, what I am doing is providing companionship, that thing most founders and entrepreneurs seek.
This comes from a year of lived experience alongside entrepreneurs, not abstract theory. That’s what we set out to do with Strive & Thrive is that as the world moves from linear to non-linear and quicker and quicker, support systems haven’t. Strive & Thrive is my attempt to close that gap.