Masterminding: Where Ideas Take Shape and Obstacles Lose Weight

02/02/2026

Masterminding: Where Ideas Take Shape and Obstacles Lose Weight

Why Small, Brave Circles Have Always Changed How Leaders Think

In a world that celebrates scale, speed and constant connection, it’s easy to slip into the idea that growth happens by adding more – more information, more opinions, more voices in the room. I mean, it’s what the word growth suggests, right?

Wrong.

Well… yes, it does mean that. But no – it doesn’t help.

The problem many of us face – especially in senior leadership roles – is losing sight of what actually matters. We stop seeing the wood for the trees and before you know it, you’re keeping everything and adding more “just in case”. Brilliant ideas, extra paragraphs in your copy, the emergency chairs in the loft that no backside has ever graced. You get the picture. 

We’re told, physically and intellectually, that stripping back brings rewards. Minimalism promises joy, liberation and a clearer sense of direction. Effective reductionism can – and often does – unlock something better.

The question is: where do you actually start?

The answer, thankfully, is achingly simple.
You find a masterminding group and get to work.

For well over a century, some of the most meaningful breakthroughs in leadership, business and personal development have happened in exactly this way. By stripping back to the bare bones and focusing on what really matters. Small, intentional groups of people meeting regularly to think well together.

This is the essence of masterminding.

At Lead Happy, we’re often asked what a mastermind actually is, where the idea came from, and why it works so powerfully – particularly for leaders who are thoughtful, experienced, and quietly carrying a lot.

That’s a long-winded way of saying that this article is an exploration of that. The origins of masterminding, how it has evolved, and why – when done well – it remains one of the most effective development formats available to us.

 

Before It Had a Name: Where Masterminding Really Began

Long before masterminding was coined as a phrase, it was already being practised in cafés, salons and shared thinking spaces where people gathered for one simple reason: to make sense of things together.

One of the most vivid examples comes from the coffee houses of Vienna in the late 19th and early 20th centuries. These weren’t casual drop-in cafés as we might imagine them today. They were intellectual homes – places where writers, psychologists, economists, philosophers and artists returned again and again, often to the same table, often with the same loosely gathered, informally committed gaggle of thinkers.

Ideas were aired, challenged, dismantled and rebuilt – not through formal presentations, but through conversation. Argument was expected. Curiosity was prized. Nobody pitched up with a slide deck, and nobody left with a neat resolution to all their ills.

Figures like Sigmund Freud, Alfred Adler, Karl Kraus and later Ludwig Wittgenstein were shaped not just by their individual brilliance, but by the company they kept and the thinking they did in these shared spaces. The coffee house offered something remarkably rare, even by today’s standards: time, permission and psychological safety to think out loud.

(You may also notice a striking lack of women in that list. That’s not an oversight – and it’s worth pausing on.)

Viennese coffee houses were culturally powerful, but they were also largely male spaces. Women were often excluded, or present only on the margins. And yet, while men were debating ideas over coffee, women elsewhere were doing something remarkably similar – often earlier, often more deliberately, and in ways that look uncannily like modern masterminding.

In 17th-century France, for example, women such as Madame de Rambouillet and Madame Geoffrin were hosting salons – regular, invitation-only gatherings in their homes where philosophers, writers, scientists and politicians met to think together. These weren’t polite social occasions. They were intellectually serious spaces, carefully curated and skilfully held.

The woman hosting wasn’t there to pour the wine and fade into the background. She shaped the conversation, balanced voices, managed egos and ensured the space remained one where ideas could be explored rather than performed. In today’s language, she was facilitating a mastermind.

And the roots go back even further. 

Long before salons became fashionable, women were sustaining rich correspondence circles – extended exchanges of letters where ideas about leadership, ethics, power and society were refined collaboratively over time. Christine de Pizan’s The Book of the City of Ladies, written in the early 15th century, is one of the earliest surviving examples of this kind of collective, dialogic thinking – a mastermind conducted by pen and paper.

So while the coffee houses of Vienna offer a vivid picture of shared thinking, they tell only part of the story.

And Vienna wasn’t alone – far from it. Across Europe and beyond, similar cultures were quietly doing the same work. Parisian salons. London’s 17th-century coffee houses (often referred to as “penny universities”). The clubs of the Scottish Enlightenment. Groups of people meeting regularly, on neutral ground, to wrestle with ideas that were too complex to carry alone.

What linked all of these spaces wasn’t expertise or hierarchy. It was relationship. The understanding that thinking improves in company, and that insight often emerges not from certainty, but from conversation sustained over time.

Seen through this lens, masterminding isn’t a modern innovation at all. It’s a continuation of something deeply human: our instinct to gather in small circles, to test our thinking against others’, and to let ideas grow legs by walking them around together.

The phrase came later, the practice came first.

 

When the Practice Was Finally Given a Name

It wasn’t until the early 20th century that this way of thinking together was finally given a label.

The term mastermind is most commonly attributed to Napoleon Hill, a journalist and researcher who spent years studying influential business leaders of his time, including Andrew Carnegie, Henry Ford and Thomas Edison. Hill wasn’t interested in tactics or tricks. He was trying to understand how these people thought – and, crucially, who they thought with.

What he noticed was strikingly familiar.

Time and again, the people he studied were not making their most important decisions in isolation. They were surrounding themselves with small, trusted groups of peers – people who could challenge their assumptions, offer perspective, and hold them to account without threat or hierarchy.

Hill described the Mastermind as:

“The coordination of knowledge and effort, in a spirit of harmony, between two or more people, for the attainment of a definite purpose.”

In many ways, Hill simply put words around something that had been happening for centuries. He took an organic, relational practice and translated it into a concept that could be recognised, replicated and – eventually – taught.

But in doing so, something subtle evolved, as things generally do.

Hill’s framing leaned heavily towards achievement and outcomes. Purpose became “definite”. Harmony was often interpreted as alignment rather than difference. And as the idea of masterminding moved into business culture, it slowly edged away from the salons, coffee houses and correspondence circles it had grown from.

What had once been about sense-making became, in some spaces, about optimisation. What had once welcomed uncertainty was sometimes repackaged as certainty-sharing.

And yet, even in its most transactional forms, the core insight remained intact.

People think better together than they do alone.

That insight is what has allowed masterminding to endure – quietly resurfacing whenever leaders find themselves overloaded, isolated, or stuck inside their own thinking.

Modern masterminding, at its best, isn’t a return to Napoleon Hill. It’s a return to the roots he was observing: small, intentional circles where trust, curiosity and challenge coexist – and where ideas are allowed to evolve rather than perform.

At Lead Happy, this is precisely what we advocate for, promote and celebrate.  The return to the intentional circles.

Which brings us neatly to the question that really matters now.

Why is this way of working more necessary than ever?

 

Why This Way of Working Feels More Necessary Than Ever

On the face of it, never has it been easier to access other people’s thinking.

We’re surrounded by opinions, frameworks, podcasts, think-pieces, hot takes and post-it-note-sized wisdom for every conceivable challenge, and yet, how much useful insight do you actually get? In 2026, the word insight often feels conflated with opinion – and much of what gets billed as insight is nothing of the sort.

What’s quietly missing for leaders – especially those carrying a lot – is usually space.

Space to:

• slow their thinking down rather than speed it up
• say “I’m not sure yet” without needing to land somewhere decisive
• explore complexity without immediately translating it into action

For those in senior or visible roles, this gap can feel particularly pronounced. The more responsibility you carry, the fewer places there are where unfinished thoughts are welcome. At some point – we’re not always sure when – uncertainty stops feeling like something you can bring into the room.

What happens then is an important shift, ambiguity gets handled elsewhere. More often than not, it gets handled alone. Squeezed into the margins between meetings, messages and expectations – or, depending on your neurotype, buried completely or obsessed over.  Whichever way it is, internaisling only more questions is never going to end well. 

At the same time as all this is going on, many of the informal thinking spaces that once supported leaders have quietly disappeared. Fewer corridor conversations, less time spent sitting with peers without an agenda. Fewer moments where ideas are allowed to wander before being put to work. (The reasons for this are beyond the scope of this article — but it’s an important side note.)

The result strikes me as a strange paradox: all the connection, and very little depth.

And just like everything else, the response is often to add more. More conversations. More voices. More touchpoints – just in case, of course. Connection, much like wine, and almost everything else, isn’t helpful in unlimited supply. We don’t need everyone, all of the time. We need some of the right people, at the right moment.

This is where masterminding re-enters the picture.

The counterbalancing force.

It promotes what our working lives often feel designed to forbid:

• deliberately slowing down
• returning to conversation over consumption
• treating thinking as an activity in its own right, not just a means to an end

In times of complexity, the instinct is often to reach for certainty. But history (and Rory Sutherland*) tells us something different. When the world becomes harder to interpret, the people who navigate it most effectively tend to do one thing consistently.

They think together.

*“The opposite of certainty is not uncertainty. It’s curiosity.” – Rory Sutherland

 

How Masterminding Differs from the Things It’s Often Confused With

In the spirit of this article as an introduction to Masterminding, let’s look at what it’s not. Part of the reason masterminding can feel hard to pin down is that it doesn’t sit neatly in the boxes we’re used to.

It isn’t coaching – though coaching skills may be present.
It isn’t therapy – though it can be deeply reflective.
It isn’t mentoring – no one is there to pass wisdom down.
..And it isn’t networking – outcomes aren’t transactional.

What distinguishes masterminding is its relational symmetry.

Everyone brings something, everyone receives something and no one is positioned as “the expert”.

Advice may surface, but it isn’t the currency. We trade in enquiry (or inquiry!). Questions matter more than answers and listening matters more than speaking. Also let’s not forget silence – something many professional spaces rush to fill – silence does happen. It can be – and often is – where the most useful thinking happens.

For people used to performing competence, this can feel really quite unfamiliar at first. There’s nothing to prove, no role to play and no expectation on destination. 

And, you guessed it – That’s precisely why it works!

 

Who This Tends to Work Best For (and Who It Might Not)

Masterminding isn’t universally enjoyable. It can be, it’s just that not everyone is always in the right place for it to be useful to them.

It tends to suit who are in a place where they:

• value reflection as much as action
• are comfortable not knowing straight away
• are curious about how they think, not just what they think
• appreciate challenge offered with care

It regularly resonates most with people who are outwardly successful but inwardly carrying complexity – responsibility, ambiguity, or decisions that don’t fit neatly into existing frameworks.

Equally, it may feel frustrating for those who:

• want quick answers or clear instructions
• are looking for validation rather than exploration
• find uncertainty intolerable
• prefer to think alone and then present conclusions

Neither stance is right or wrong. They’re just different needs at different moments.

Understanding this tends to be reassuring. Masterminding is a particular kind of space, suited to a particular kind of readiness. It’s not a universal remedy.

 

Why Time, Continuity and Small Numbers Matter

One-off conversations can be useful. But do they really change how we think?  In isolation, rarely. 

What makes masterminding distinctive is the continuity it provides. Seeing the same people regularly and returning to ideas after they’ve been lived with. Letting insights (there’s that word again) mature rather than forcing them into action straight away.  Trust builds quietly, through consistency, reliability, and the experience of being listened to without interruption or agenda, and as it does, the quality of thinking deepens as individuals lean into vulnerability and perceived risk.  They speak more honestly. Any vestige of performance by this time has been swapped for exploration. 

Small numbers matter for the same reason – they reduce noise and soften hierarchy, while making it easier to be seen and heard as a whole person rather than a role.

Over time, something else happens too. You start carrying each other’s thinking between sessions. Ideas resurface unexpectedly. Questions start to have an echo. While walking, driving, or staring out of a window, that’s often when the real connections start to grow. 

…and that’s usually a sign the work is doing what it’s meant to.

 

A Quiet Closing Thought

Masterminding has endured because it honours something deeply human: our need to make sense of the world with others. It really is that simple when it comes down to it. 

In an age of acceleration and constant ‘growth’ chat, it slows us down.
In a culture where certainty is dangerously over-valued, it gives uncertainty somewhere to breathe.
In a landscape crowded with opinions masquerading as expert insight, it offers space for actual insight to emerge.

You don’t need a mastermind all the time, it’s not a permanent seat. You need it when the questions you’re holding start to feel heavier than the answers you’re finding.  It’s a steady place to set them down.

If you want to explore being part of a masterminding group, and want to talk, arrange a chat here about the next available cohort of our masterminding series: The Leadership Lab.  Limited numbers, one sector only, expertly facilitated.

Or you can head straight to the Masterminding page and find out more about the structure, pricing and availability.