I remember a mentor telling me this story, years ago, over a coffee. The moment and the taste have stayed with me.

A manufacturing plant had ground to a halt. A critical machine had failed, and the plant’s own engineers — good, capable people — couldn’t find the fault. Every idle hour cost thousands.

The plant manager called in someone with a reputation. The story goes that he walked the floor for ten minutes, listened, touched the pipes, said nothing.

Then he took a piece of chalk from his pocket and drew a cross on one specific section of the machine. Replace the part under this mark, he said. They did. The machine started.

A few days later the bill arrived: $10,000. Stunned, the manager asked for an itemised invoice.

It came back with two lines.

Making the chalk mark: one dollar. Knowing where to make it: nine thousand, nine hundred and ninety-nine.

The story is usually told with Henry Ford and the engineer Charles Steinmetz in the lead roles, at Ford’s River Rouge plant in the 1920s. Details get lost in often-told tales. But the lesson has outlived the argument over its facts, and that tells you something too.

My mentor wasn’t teaching me about generators. She was teaching me about worth. About value.

Our sector is changing shape. Fewer full-time roles, more contract work, more people setting themselves up as consultants and coaches because the old career ladder no longer holds. None of that is a problem in itself — there’s a lot of sharp thinking and deep experience among the people working this way now, by choice or necessity.

But it has made it remarkably easy to look like an expert without carrying the years that make one. Personal brand, a polished bio, a confident voice on LinkedIn — none of that is proof of the chalk mark. It’s proof of the way we tell a tale or a journey.

When expertise becomes harder to tell or believe in, the whole market for it gets cheaper. The people doing the hiring lose the ability to trust the real thing. The people selling themselves short learn that thinness sells almost as well as depth, provided the invoice is smaller.

There’s a second failure sitting right alongside it, and organisations like admitting to it even less. Sometimes the expert is real. The chalk mark is in exactly the right place. And still nothing changes — because paying for the diagnosis was never the same as doing the work it demanded.

I’ve sat in meetings where the argument was over a third page on a brochure, worried it might tip the fee past five hundred pounds, while a twenty-thousand-pound strategy sat waiting for sign-off three months later.

The cash worried people. The value didn’t. Our exchange rate seems lost.

Strategies get commissioned and quietly shelved. A five-figure diagnosis and framework for action gets filed next to last year’s, and the plant keeps grinding along at half its capacity — everyone quietly relieved that at least they tried.

Both failures come from a similar place: a market that has forgotten how to price the years behind the chalk, and a market that struggles to ask the right question to get answers it can trust. Ours is a sector full of good people doing good work. I’m not arguing otherwise.

If we keep treating expertise as a line item to negotiate down, and treating the fix as optional once it’s paid for, the plant stays idle.

That’s not bad luck. That’s someone’s choice.

So next time an invoice for someone else’s ten minutes of certainty lands on your desk and the number stings, it’s worth asking what you’re really objecting to.

Is it the size of the chalk mark? The real cost of knowing exactly where to draw it? Or the fear that, even when paid for, nothing would actually change?

Does this challenge resonate with you? What do you think? These and other posts are part of other hopefully helpful insights— Would love it if you’d subscribe - you’re welcome to join here.

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There comes a point in life when weddings start giving way to funerals.

You learn the rituals quickly enough — the awkward exchange in the car park, the song that greets you as you sit down, the person at the front doing their best to hold a room together, a shaking voice telling a story you never quite knew.

We’ve done this for thousands of years. Every culture has built something to help people gather, grieve, and make sense of a life that’s ended.

But there’s a newer ritual now, one that’s arrived quietly, without ceremony of its own. No announcement. You only really notice it once you’ve been to more than a few.

Or you have to do it for someone you have lost.

It’s the 25 photos.

At some point in the service, the lights may soften, a single chosen song begins, and a life is told back to the room in 25 photographs. Funeral directors, in very practical terms, ask a family for one song and roughly 25 photos spanning a person’s whole life.

The 25 isn’t arbitrary, either. Each photo gets six to eight seconds, which builds a three to four minute tribute — long enough to mean something, short enough to still fit inside a crematorium slot.

Twenty-five forces a choice.

It turns a life into a narrative arc instead of a complete archive, edited down under fluorescent chapel light while a room quietly tries to hold itself together.

Slot after slot, service after service — as familiar now as the coffin’s own entrance. Then one day it’s your own family’s turn. Mine, recently.

Sitting down with box loads of albums and a laptop, hunting through decades for the handful of pictures that would say, to a room full of people who all knew that person slightly differently, this is who they were. It is, though, a strange kind of honour — a genuine challenge, and one that stays with you.

Somehow, the constraint is the gift. It asks, gently but firmly, what actually mattered. A tiny act of legacy-making, long before the will and the paperwork that follows it — a compressed story that has to survive the room entirely on its own. A parcel of love.

None of this is new, of course. The Greeks and Romans placed a coin in the mouth of the dead, payment for the ferryman. Anglo-Saxon graves were furnished with jewellery, weapons and food, small deliberate statements of who someone had been.

In Tibet, a body is offered to the birds, impermanence made physical rather than spoken about. Every culture we’ve ever built has found its own way to carry a life across the gap it leaves behind.

Twenty-five photographs and a song have simply become ours — the digital version this age has landed on.

That’s the question that’s stayed with me since this experience and my curiosity. Why does a task this significant, this quietly powerful, only ever land on us once someone’s gone? The family sits with the albums when it’s too late to ask why that photo, or who took it, or what was happening just before or after the shutter clicked.

Wouldn’t it be something, if instead we sat down together and chose the 25 photos, and the song, while the person was still here to see it, laugh at the bad haircuts, and tell you what you’d got wrong.

This has become a modern ritual now, named and understood, and it carries real weight — a whole life condensed into 25 frames under a rented ceiling. The song is the light. It cuts you open. Then the images do their work.

Could you choose yours now? The photographs that matter. The story you’d want told.

The legacy you’d want left, on your terms, while you’re still the one telling it.

I’ll be exploring more of this in the weeks ahead — the small rituals we build around legacy, and what they teach us about living well before we ever get there. Plus lots of other hopefully helpful insights— Would love it if you’d subscribe - you’re welcome to join here.

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In 1978, Václav Havel in Czechoslovakia wrote an essay called The Power of the Powerless. In it, he tells the story of Communist rule through the lens of a greengrocer.

In their shop window, among the onions and carrots, there is a sign: Workers of the world, unite! The same sign is everywhere. Everyone has one. The greengrocer does not believe it. But that is the way things are, because not putting it up means you would be noticed.

A small daily compliance. A quiet pretence. The thing Havel called living within a lie.

Of course, rules are for order, stability, fairness, and compliance, so we can feel safe and flourish. Conventions and traditions are the glue that bind wisdom and evolution. But they need respect, tolerance, balance, and judgement.

The Power of the Powerless points to the pretence that can exist when you know you are living within a lie. It eats your soul. But the whole architecture of pretence starts to wobble when one person does not put the sign up. A simple act of change, born from an honest choice.

That is where courage actually lives.

How we find, decide and use that courage is what makes the difference.

Courage isn’t heroics. It’s choice.

When we think about courage, we reach for heroics. The hill. The flag. The rallying speech. The dramatic stand against impossible odds.

But that picture is a distraction. Heroic courage is rare and recognisable. Ordinary courage is constant and invisible. The world does not run on heroics. It runs on thousands of small daily choices that either uphold the order and freedom we strive for, or the pretence we know we are enduring.

But nothing moves until somebody chooses.

The choice is the engine for change.

The line between courage and recklessness

Here is the part that gets missed.

Courage and recklessness live close together. They are unusual bedfellows. Courage can look like recklessness in the moment. Recklessness can become courage over time. Both involve stepping forward when others will not.

The difference is emotional maturity. Wisdom. Knowing yourself before you speak. Confidence without performance. Fuelled by a reckoning with the past you bring, and by the direction and purpose you subscribe to. The discernment to know when this is the battle to fight, and when it is not. The discipline to seek wider counsel before lighting the touchpaper.

Two failure modes are equally dangerous. The first is paralysis-by-perfection. We will not move because we demand every detail, every assurance, every box ticked. We have forgotten the meaning of good enough. The second is the bull in the china shop — acting from gut alone because it just feels right, without the discipline of inquiry or judgement.

Courage sits in the narrow space between the two.

Decisive, but not impulsive. Honest, but not careless. Aligned to purpose, not to ego.

What courage needs to look like in our sector

What if we learnt to say these 12 words.

I’ll decide. I’ll carry it. If it goes wrong, I’ll own it.

That is not heroics. That is the daily job of leadership. It is the captain on the playing field, stepping forward to pick a team, knowing not everyone gets picked first. Uncomfortable. Necessary. The whole game stops without it.

Most of the time, courage should look like this. A director choosing the harder strategy because it is the right one. A fundraiser sitting alongside a colleague who is losing their nerve. A chief executive saying no to a board favourite because we know it will not work. A manager, in week three of the wrong decision, saying out loud: we got this wrong, let’s stop.

Harvard Business Review published a piece last week called When Purpose Backfires. It names something worth holding onto: supported impact, the experience of being allowed to make the difference your role implies. Its opposite is thwarted impact: the slow corrosion of being prevented from doing the work that matters.

That is the toxic force many feel.

Environments that thwart impact also thwart courage.

They train people to comply, to defer, to put the sign in the window. This is personal. It is about you, there and then, in the moment, knowing that this is wrong, that another way is right, and yet saying nothing. That is a leadership moment.

The cultures we build either reward courage or punish it.

Why this closes the series

Across the last three pieces, I’ve circled the same challenge from three angles.

The case for an entrepreneurial spirit again. The case for simple, against the over-engineering and the jargon. The case against decision paralysis, the quiet death of the sector.

All three share a single solution. They are fixed by individuals, in real moments, choosing.

That is the whole thing.

It is what becomes true when enough people choose not to put the sign up. It is not the reckless nonsense of an ideological battle against authority. That is student immaturity. It is about adults who know this makes no sense. When enough of us decide, carry, and own.

The courage to lead is in those amplified small moments of choice.

But its impact and confidence come from the tailwinds of yesterday, and the compass of the future that guides you.

The greengrocer always has a choice.

So do you.

👉 This is the final short essay on non-profit leadership and impact reflections. Would love it if you’d subscribe - you’re welcome to join here.

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A fundraising director said something to me once that stayed with me.

“You can’t succeed in an organisation with zero tolerance for failure. You suffocate. You stop moving anything forward. Everyone’s terrified.”

I’ve thought that sentence hundreds of times. Because it isn’t really about failure.

It’s about what happens to people, teams and whole organisations when the cost of being wrong becomes greater than the cost of doing nothing. More than anything, I see this as is a disease the nonprofit sector is quietly drowning in.

In the first piece of this mini series I argued we’d lost our entrepreneurial spirit. In the second piece, I argued we’d stopped defending simplicity. Here’s where both failures actually live. In the Teams calls, the room, the meetings and emails.

In the moment when somebody needs to decide and nobody does.

The fear underneath everything

Strip back the language of strategy, governance, consultation, alignment, fundraising, campaigns, brands, marketing, stakeholder input — and what you find underneath is fear.

Fear of being wrong. Fear of being blamed. Fear of the inquiry, the email chain, the quiet reputational damage that follows anyone who commits to something that doesn’t quite work. So we don’t commit. We consult. We circulate. We copy everyone in. We open up another dimension just at the point of closure. We invent another perceived approval layer. We protect ourselves by ensuring no single person ever carries the weight of a single decision. Except the ones who should.

The meeting cycle isn’t about good governance.

It’s about distributed cowardice dressed up as collaboration. Hard to say I know.

The middle is suffocating

The people paying the highest price for this aren’t the boards. They’re the ones in the middle.

They have remit but vague authority. Targets but limited permission. Job descriptions that promise impact and reporting lines that deliver paralysis. They walk into rooms ready to act and walk out with another round of obfuscation. They are hired to solve problems and then prevented from solving them.

What is the point of their salary if the answer to every meaningful simple question that everyone can see the answer to is deferral, passing up, or silence.

I knew an organisation where commercial suppliers, by any standard outside the sector, would have been dismissed long ago. Instead the phrase used is it’s complicated, it takes time. It isn’t complicated. The supplier relationship is broken. The work isn’t being delivered. Everyone in the room knows it. Nobody decides.

That’s not complexity. That’s fear wearing complexity as a costume.

The drowning swimmer

There’s a useful test for whether a culture has lost its decision-making nerve.

Imagine somebody drowning in a pool. The right response is to jump in. The wrong response is to convene a working group on water safety protocols. We all know which is which when the stakes are visible.

But somewhere along the way, organisations have started behaving as if every decision is a health and safety check, and nothing is a drowning swimmer. Every choice gets the same treatment. Every action gets the same friction. There was a brief few months when Covid dialled it up. Oddly liberating. But now the urgency dial has been dialled back to normal or nothing or worse.

This is what happens when fear of getting it wrong replaces judgment about what matters.

The performers

There’s a subtler version of the problem worth naming. Not everyone in the indecision economy is paralysed. Some people perform decisiveness without ever actually deciding anything.

They have the language of action. The body language of authority. The image they’ve built of themselves as the person who cuts through.

But look at what they’ve actually delivered and the answer is not much. Their decisiveness is a posture. What they’re really doing is blocking, gatekeeping, frustrating, draining everyone else. Misplaced authority. They get away with it because they’ve trained the room to be afraid of them.

Why are they in the way? Can we go round them? Or better can we get them out of the way.

What it costs

This isn’t an abstract cultural failure. It costs people. Good ones.

The middle managers leave. The Directors leave. The life span is long enough but not long enough.

The fundraisers who could have built something worth building decide it isn’t worth the energy and go elsewhere. The directors who came in with mandates to change things give up trying.

Some manage to stay and break it, leaving a mess behind and then leave. And the mission — the actual reason any of this exists — slows to the speed of the most frightened person in the chain.

You cannot innovate in a place where failure isn’t allowed. You cannot grow in a place where every decision is by everyone. You cannot lead in a place where leadership has been quietly redefined as the management of risk away from oneself.

What it would take

Kamprad’s Testament from IKEA — the founding document I wrote about in my second piece — named complicated rules as paralysis. He understood, with brutal clarity, that an organisation that cannot decide cannot live.

Our sector needs to rediscover making day to day decisions.

Because when nobody decides, nothing lives. The fundraising doesn’t grow. The team doesn’t trust. The mission doesn’t move. And the people who came into this work to do something that mattered slowly stop believing it’s possible.

This isn’t a process problem. It’s a courage problem. And courage is where we go in my next piece.

👉 This is the third of four short essays on non-profit leadership and impact reflections. Lots more to come so would love it if you’d subscribe - you’re welcome to join here.

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Any trip to IKEA is an equal mix of fear, loathing and wonder.

You get sucked into the one-way system. You fill the basket with things you didn’t know you needed. You emerge the other side several hundred pounds the wrong side of what you thought you’d be spending, and you realise that somebody, somewhere, has built a very good business model.

There’s a simplicity to it. A formula. A repeatable thing that has anchored itself so deeply that you’re now eating a hot dog on the way out wondering what happened.

Staying in business at global scale, through decades of relentless change, is a tall order. It only happens when you pay attention to the things that actually matter — and refuse to pay attention to the things that don’t.

The letter Ingvar Kamprad, founder of IKEA, wrote to his own company

In 1976, Ingvar Kamprad stepped back from running IKEA day to day and wrote a short document called The Testament of a Furniture Dealer.

Some see it as strategy. Some see it as a manifesto. Read it properly and it’s something else: a warning letter from a founder to his own future organisation.

He names the enemy early. Not competitors. Not the economy. Complexity itself.

“Complicated rules paralyse. Historical baggage, fear and unwillingness to take responsibility are the breeding ground for bureaucracy. Indecisiveness generates more statistics, more studies, more committees, more bureaucracy.”

And the line that sits underneath everything IKEA does:

“Keep it simple. Complicated systems and rules are a form of paralysis.”

He didn’t wait for complexity to kill the company. He named it early, put it on paper, and built a culture around refusing it. The Testament has been preached inside IKEA like scripture for fifty years. It is woven into the DNA, the culture and the business practice.

That’s the point most people miss. Simplicity at IKEA isn’t a flat-pack aesthetic. It’s an operating discipline that a founder had the courage to write down and defend.

The letter the nonprofit sector never wrote

Our sector has no Testament. No founder’s warning letter. No scripture for simplicity.

There are plenty of strategy documents. Plenty of frameworks. Plenty of theories of change. But not that much that names complexity as the enemy and rallies the organisation to refuse it.

So the default wins, and its this: when friction shows up, we add.

We add a committee. We add a working group. We add a sign-off layer. We add a consultation phase. We add a new policy to cover a risk that has never once happened. We commission a review of the review. Not always wrong of course. But all of it is done by good, clever, well-intentioned people who genuinely believe they are making things better.

I sat with a Director recently who was proudly walking me through a new approval process. A fresh sign-off layer had been added to improve governance. Three extra reviewers. A fortnight added to every decision. The problem it was solving had occurred once, three years ago. And the cost — in speed, in energy, in the quiet demoralisation of the twenty talented people now waiting for permission to do obvious things — was invisible to them.

That is the sickness Kamprad named in 1976. Indecisiveness generating more statistics, more studies, more committees, more bureaucracy. Not the one or two right ones. The hundred not needed ones. Not from fifty years ago. But one meeting of many I was in this year.

The Agile that is isn’t Agile

I watched a charity try to adopt agile recently. Agile, by definition, means agile. This was about as agile as a turnip.

The implementation produced a bureaucratic monster. New ceremonies. New tiers of approval. A culture so afraid of building anything imperfect that nothing was built at all. The organisation tried to do the right thing. The evidence says it did the opposite.

The tragedy isn’t the failed rollout. The tragedy is the people inside it — capable, committed, tired — spending their days in meetings where no decision can be made because it requires another process. Soul-destroying. They deserve better.

What would the Testament of a Charity say?

Kamprad’s lesson is that simplicity doesn’t survive on its own. Complexity is the tide.

Somebody has to write the letter. Somebody has to name the enemy. Somebody has to defend simplicity out loud, on paper, often enough that it becomes how the organisation thinks.

So here’s my question and lesson.

What would it take for our sector to write its own Testament? A short, brave document naming the drift. Championing simple routines, faster decisions, proportionate checks, a higher tolerance for imperfect action, and the absence of fear that stops so many good people from delivering their best work.

Not a new framework. Not another strategy refresh. A letter. To ourselves. A rallying call.

Defending what we already know. Deciding what we should be doing. Or not doing.

Kamprad wrote his in 1976. The sector is fifty years late.

And if we do it well enough — maybe, just maybe, there’s a hot dog at the end.

👉 This is the second of four short essays on non-profit leadership and impact reflections. Lots more to come so would love it if you'd subscribe - you’re welcome to join here.

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I’ve always been a fan of Back to the Future.

The 80’s feel. The hoverboard. The flux capacitor.

But there’s a deeper fascination. The film holds past, present and future in a single frame. Like the moment someone shows you a photograph of yourself when you were young. Your view of yourself is how you’ve built the memory. A fresh view can change that.

I think about this when I look at the non-profit sector. And I fear for where we are going next.

I had a conversation recently with a leader in Eastern Europe — someone I met before the war in Ukraine and have stayed alongside ever since. An astonishing story, building civil society almost from scratch.

Entrepreneurial, purpose-driven, agile.

Listening to them describe how they operate made me realise just how far many established organisations have drifted from why they were created in the first place. The nonprofit sector seems stuck. Like a wrong turn.

Like Marty McFly seeing his future self if he’d taken a wrong turn.

We’ve built something heavy. Inward obsessed. And we’re quietly struggling to admit it.

For decades, the nonprofit world ran on a notion of value and prudence that translated into weak and poor investment. Value meant cheaper. Value stopped meaning effective.

Over time, like a creeping illness, we created a bubble. A swathe of cost with people pretending to create infrastructure. Perceived value and impact. Layer upon layer was added.

Much of it totally required in a modern world.

Yet much of it over engineered and indulged.

HR. Procurement. IT. Ethical policies. Governance frameworks. Data. Communications. Brand. Each one justified in isolation. Each one increasingly detached from purpose.

The fundamental problem has always been an assumption that the nonprofit world should operate cheaply, without understanding the real costs of building and scaling something that works.

And we have lost sight of the truth about what actually delivers. Ask anyone in any nonprofit these five questions:

1. Do you feel like you can get things done?

2. Are you waiting for others to do something else first — and don’t know why?

3. Is someone, anyone, making decisions?

4. Do you know or understand what value the thing you are asked to do or wait for adds?

5. Why does any of this matter to a donor, supporter or beneficiary?

We’ve become too complex. And complexity is the enemy of mission.

Talking to leaders In Eastern Europe and across younger civil society movements, I’m inspired by a fundamentally entrepreneurial model flourishing in some places. Distributed leadership. Purpose-driven action. Technology accelerators. Loosely constructed organisations where people come together to solve a problem — and then move on to the next one.

It’s closer to the original spirit of charity than most of us realise.

The 18th and 19th century model was essentially entrepreneurial. Someone identified a problem. They brought together a group of people to address it. They funded it. They delivered impact. It was simpler. It was driven by purpose and pragmatism, not bureaucracy and politics.

That spirit hasn’t disappeared. But in many established organisations, it’s been buried under decades of growing institutional weight.

Entrepreneurial energy without strategic grounding can burn hot and fast — and leave very little behind. Founder-led organisations can be brilliant at launch and fragile at scale. Agility without wisdom is just speed without direction.

So the answer isn’t to abandon what the old model built.

It’s to strip it back to what actually matters and rebuild with the entrepreneurial clarity that made nonprofits powerful in the first place.

Whether old or new, too many organisations, departments and staff have lost their connection with the people who fund them. Donors. Supporters. The people outside the building who want to help but are met with jargon, complexity, and institutional distance.

I’ve sat in enough rooms to know how this plays out. Internal language takes over. Quiet suffocation of initiative. Fear to make a decision. Internal pass the parcel. Strategy becomes a document nobody reads or understands (if there is one of course). Focus on the irrelevant. The voice of the donor — the person whose generosity makes everything possible — gets drowned out by the noise of internal process and inertia and smoke.

Many NGOs have also quietly lost influence because priorities drifted — away from mission and towards something more internal. They lost humility. They lost the trust that comes with it. And the public noticed before they did.

The reset is simpler than we think.

Give people inside clarity. Ruthless focus on mission. Purpose. Give them a role that they can execute. Solve problems not debate them. Reward initiative. Be free from the fear of failure. Embrace it. Remove obstacles with righteous fury. Connect staff and donors together emotionally, not transactionally. That’s what the best organisations have always done, whether they were founded in the 19th or 21st century.

The shift facing nonprofit leaders now is real. From managing stability to navigating constant change requires clarity on purpose. Resources and infrastructure must enable and deliver - or get out of the way. Collaborative, purpose-driven leadership that can actually get shit done.

We need an entrepreneur’s spirit again. We need honesty. Agility and speed. Leadership. We need a rediscovered founder’s spirit and purpose.

Marty McFly got to see where his wrong turn led. The question worth sitting with is simpler. Do we have the nerve to see ours — before it’s too late to turn back?

Because one path could build impact and legacy. The other could build missed opportunity and waste.

👉 This is the first of four short essays on non-profit leadership and impact reflections. Lots more to come so would love it if you'd subscribe - you’re welcome to join here.

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The great meal is never about a single ingredient.

We talk about the quality of the vegetables, the source of the meat, the freshness of the herbs. And those things matter.

But by themselves, they don’t quite cut through.

It’s the meal. The mix. The menu. The way it’s brought together.

So at 20 Legacy Lessons in, that’s where I’ve landed.

I read something recently about specialists and generalists. The specialist goes deep in a single lane. The generalist maps the lanes and brings them together.

I’ve always been a generalist.

I was a fundraiser and a fundraising leader for longer than I’ve been a legacy specialist. So when I came to legacies, I came with a set of ingredients — strategy, leadership, communications, brand, donor experience, team development — and I learnt to bring them together in a particular way.

For me that has shaped everything.

All too often, I see people picking away at a single ingredient by itself. Polishing a case for support. Refining a leaflet. Hunting for a better channel. Tweaking a welcome journey.

Each one important. Depth and focus. Layer upon layer of journey and understanding.

But for me work is the combination. The mix.

The strange thing about legacy fundraising is that it punishes single-ingredient thinking more than almost any other discipline.

You can’t out-creative a weak culture. You can’t out-message a misaligned strategy. You can’t out-measure an absent conversation. You can’t out-tactic a missing philosophy.

It’s genuinely a system - an eco system. A world. And systems reward people who can hold the whole thing in their head at once.

That’s the gift of stepping back and seeing where the dots join. Where the links are.

Where the power is.

Specialists give us the depth — and we need them. The behavioural scientist, the data analyst, the legal mind, the brand strategist. Without them, we would lose rigour. The part s under the bonnet that make an engine work.

But somebody has to map the lanes. Somebody has to hold the menu. Someone has to join the dots.

So here we are. 20 lessons, from 100’s of options, distill into these 4 ingredients that for me matter the most.

Emotional Connection, Culture and Behaviour. The philosophy. People-centred. The belief that legacies are about life, not death. About meaning, not mechanics. About who someone is, not what we ask them for. Without this, everything else turns transactional.

Ambition, Strategy, Principles and Methodology. The architecture. Without a system and a structure, you are improvising in a discipline that punishes improvisation. A system you could trust when instinct ran out and the team needed a map.

Practical Tools, Techniques and Measurable Systems. The toolbox. Definitions in english not academia. Future Value. The pipeline thinking that lets you see what you have and what you’re building. Tools that survive in the room when you’re not in it.

Personal, Team and Career Growth. The capacity. Legacies are built by people, not platforms. And we don’t give nearly enough attention to growing the people who do the work — the careers, the confidence, the courage to have the conversations that matter.

These are the four foundations.

They are not a hierarchy. They are an eco system.

In practice, what do we end up doing though?

We obsess over the toolbox — the campaign, the message, the channel. We pay reasonable attention to strategy, though often after the campaign is already running. We pay lip service to culture and philosophy. To leadership. To the way we develop the the people doing the work.

That is single-ingredient thinking dressed up as a chef.

The best programmes I have seen — and the ones I’m proudest of having built or been part of — are the ones where all four foundations are alive at once. Where the philosophy informs the strategy, the strategy chooses the tools, and the people are growing inside all of it.

That’s the mix.

That’s the lesson. That’s the meal.

Methodology gives us a system. People give us its life. Tools give us its reach. Philosophy gives us its meaning.

It’s not one. It’s all four.

So here is my question.

Are you a single ingredient expert — or are you a chef making the best possible meal for your organisation and donors?

👉 This is Lesson 20 of 20. I’m pulling all twenty lessons together into a single PDF guide. If you’d like a copy when it’s ready, reply to this post or drop me a note. Lots more to come so would love it if you'd subscribe - you’re welcome to join here.

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We’re not really allowed to lead in legacies are we?

Programmes get run, administered, defended, reported on, picked at, focused on then ignored.

But rarely led.

Its a gap. Sometime wide, sometimes less so. Hot and cold. Rarely long term and strategic. Often short term and a regular crisis.

I was in a meeting recently with an organisation working through an infrastructure challenge. Tough thing to resolve. Idea after idea came in. Almost none of them bore any relationship to the situation they were actually in.

I remember saying: hang on a minute. This is like trying to build an extension on your kitchen when your house is on fire.

If I look back over legacies, it’s probably not quite as dramatic as that. But the pattern is familiar.

Nobody sees legacies as critical to the day or week they’re in. Until it’s not doing what they thought it would. Then they perk up. The rest of the time? Lots of goodwill. Positive thumbs up. And quiet focus on something more pressing.

It’s like walking through a beautiful wood. You can appreciate that someone, once, planted these trees. But you’re not really interested in planting your own.

So where is leadership going wrong in legacies?

It goes wrong at the top.

Boards turn up rarely understanding cause and effect in legacy fundraising. CEO’s spend their days balancing the unexpected — a shortfall, a reputational hit, an outlier gift that didn’t repeat. The long-term lever gets parked and at the bottom of the queue. Now is never the right time to think about legacies. Worse, no one gets it or understands whats possible and what isn’t. The search for certainty that doesn’t exist. The indifference to fix the roof when the sun shines.

It goes wrong in the middle.

A good fundraising director should be balancing three levers — short, medium, long term. But if the people above are pushing for short term, legacies quietly slip down. And the legacy lead? Often half a human perhaps. One leg in high value, one arm in legacies, one arm in direct marketing, one leg trying to remain standing. Pulled from pillar to post. Often inheriting the wrong programme on the wrong strategy. Limited authority. Leading from an inherited position and a promise of new, with confidence and ambition, is one of the hardest jobs in fundraising.

And it goes wrong at the edges.

Fundraising colleagues with their own targets, none of which mention legacies. So they help when they remember. And then everyone else in the organisation — paid by money generated by donors they have no relationship with. A fountain of income, detached from human connection.

Leadership is what holds all of that together.

Active, engaged, understanding leadership. From the role or position. From your place. From belief and understanding. From a moral compass and principles. From wherever you are.

Running a legacy programme should be one of the best jobs in fundraising. Genuinely. But it’s also the most frustrating — because so much of what determines its success sits with people who aren’t doing the legacy work themselves. Those who benefit but don’t engage.

So here’s my lesson and my question.

We’re not really allowed to lead in legacies are we? Its a promise only but a practice that remains flaky. Strategy. Belief. Appropriate attention. Investment. Culture. Guiding philosophy. Basic understanding.

So who is truly leading where you are? Not running it. Not reporting on it. Leading it.

Because the programmes that thrive are the ones where someone, somewhere, decided this mattered enough to truly lead towards an aspiration — and then did.

👉 This is Lesson 19 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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In 1950s Detroit, a young Berry Gordy worked the Ford production line.

He watched raw steel go in at one end and finished Lincolns roll out at the other. Every station had a job. Every job had a standard. Nobody reinvented the car each morning.

A few years later, he founded Motown. And he did something unlikely with what he had learned.

He built a hit factory.

Songwriting, recording, artist development, choreography, even etiquette — all brought in-house. Weekly quality control meetings, where teenagers off the street were sometimes pulled in to judge whether a record was any good. The whole thing mapped out on a single page of A4. A system. Hitsville.

It sounded like a contradiction. You cannot systemise creativity. You cannot put soul on a production line.

Except Gordy did. And the results speak for themselves.

He had not removed the artistry. He had built a container strong enough to hold it — so the talent could run loose inside the method, rather than having to invent the method every time.

Legacy fundraising methodology is a curious thing. Part US planned giving, part high value cultivation, part Direct Marketing, part behaviour science, part brand influence, part philosophy. Of course it’s all these and you find blended versions wherever you go.

But it’s the mix and application that’s the issue. Often bit of this, bit of that. Like someone has inherited a programme made from the Bumper Book of Legacy Fundraising 1976 and never changed a thing.

Now, I am no great fan of changing things for the sake of it. We are far too quick, as a sector, to rip up what works in pursuit of the next shiny thing. There is real wisdom in holding on to what has been proven — the universal truths that experience and time have handed us.

But there is a difference between honouring what works and being stuck.

And in legacies, we are often stuck and with the wrong mix.

We apply what we once thought worked in somewhere else and a different context, and assume that will carry us through our own context and changing world. The approach hardens. The thinking narrows. The programme stops truly learning.

I was in a best practice session once with a global charity.

The trouble with this best practice session was that most of it wasn’t best practice. It was a festival of perceived best practice. People arriving from all over the world, sharing clever things they had done, with no guiding framework or philosophy, no methodology underneath, no honest test of whether any of it actually worked. Nobody had the discipline — or the leadership courage — to stand up and say that is not the right way to do it.

Because a charity from a particular country had presented it, everyone assumed it must be sound. They wrote it down. They took it home. They applied it.

And the infection spread.

That is what happens when there is no method. No core appreciation of right and wrong. You do not get creativity. You get contagion.

Gordy understood this. His genius was not that he stifled creativity — it was that he refused to let sloppy thinking through the door. Every song got tested. Every record had to earn its place. The container held.

So here is my lesson and my question.

We already know more than enough, in legacies, to build a proper core methodology. The principles have been proven. The patterns are visible. The quality controls are there.

The question is whether we have the discipline to capture and champion a core engine of understood and wisely chosen methodology, our better defined container.

Strong enough to unleash our creativity, our curiosity, our artistry, our innovation.

And we might, just might, start producing the legacy equivalent of a number one hit.

Not once.

Not by accident.

Time after time after time.

That is what Hitsville really was. Not a production line. A promise — that the next song, and the one after that, would be worthy of the people who were going to hear it.

Our donors and our organisations deserve the same promise.

👉 This is Lesson 18 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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There is a small fly etched into a urinal at Amsterdam Airport.

Nobody told the men using it to aim better. Nobody put up a sign. Someone simply added a target, and spillage dropped by around eighty percent.

No rules. No lectures. Just a fly.

Any parent who has toilet-trained a small boy worked that one out long before Richard Thaler shared his famous story in his book Nudge. Give him something to aim at, and his attention goes exactly where you want it.

That is the thing about behavioural science. Most of it, we already knew.

We just didn’t have the words for it.

When we first set out to help make legacies normal, behavioural science was still new to most of us. Nudge had just been published. Social marketing was finding its feet — that clever blend of commercial marketing principles and behavioural insight starting to shift public health, environmental behaviour, and giving.

We didn’t use the language of choice architecture or defaults or friction. We called it drip drip marketing. We just knew, in our gut, that if you kept putting the right idea in front of the right people, in the right way, at the right moments, behaviour would move.

Then the science caught up.

And not surprisingly, it confirmed what our instincts had been telling us. Behaviour is shaped by context. By habits. By triggers. By environments we design, not just the arguments we make.

Every serious piece of research since has underlined it.

It’s our truth laid bare.

We are all about behaviour change.

We should understand behaviour change.

We should be applying behaviour change.

And yet in legacies, we are still stuck.

Look around the sector. There is a handful of people who have genuinely embraced behavioural science in fundraising — who understand the tools and can apply them with real craft.

Then there is the majority. And the reality.

A small number of specialists. A conference session here and there. No dedicated behavioural science capability for legacy fundraising. Frameworks once designed and barely revisited since.

The real power of behavioural science is not in understanding people. It is designing the environments, systems and communications that make the better choice the easier one. The one we all want.

I gave a presentation once at a conference in Canada, on how to apply behavioural science to legacy fundraising. I was genuinely energised by it — the theory, the logic, the possibilities. And I watched the room as I always do.

The gap between this energy and the possibility of the session, was the reality of what they needed to change. For most of them, it was just too big. The model they were working inside was just too fixed. The hill, just a little too steep.

That has stayed with me.

Because it isn’t the science that is failing us. The science is solid. Its proven.

It is us. It’s the gap we must close.

Our habits. Our systems. Our leadership. The comfort of the model we already know.

Nobody else is coming to bring behavioural change into legacy fundraising unless we do.

It takes time. Focus. Energy. Curiosity. A willingness to hold our own practice up to the light and ask whether the environment we have built for donors is really making their meaningful choice easier - or it remains a theory on a book shelf or a conference keynote.

And, as is always the way in these places, it takes a little bit of courage.

The fly in the urinal was not clever. It was humble. Someone noticed the real behaviour happening in the real world, and gently redesigned the context around it.

So here is my lesson and my question.

Because the science has caught up. The question is whether we have the courage to catch up with it.

We could do with a few more flies.

👉 This is Lesson 17 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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There’s a moment in every good night out that you remember.

The first drink. The one chosen carefully. Ordered, not grabbed. It has a taste you actually notice. Something worth sitting with.

Then comes the second. And the third. And somewhere between the third and whatever came after, the drink stops tasting the way it did at the beginning. The quality has gone.

What’s left is volume.

We’ve all done it. And it’s the perfect analogy for one of the oldest arguments in fundraising.

Quality versus quantity. Value versus volume. The debate that never quite goes away.

In legacies, it gets particularly interesting. Because on the surface, volume and value look like the same thing. They both arrive as money. They both push the totals up. They both feel like progress.

But they are not the same. And confusing them can quietly mislead an entire programme.

Let me ask you a simple question.

Would you rather have one legacy gift of £1 million, or 50 gifts of £20,000?

Both, obviously. But bear with me.

50 gifts of £20,000 tells you something profound. A platform. A base. A rhythm. Risk lower. Income more predictable. The variables smooth themselves out. You are managing a programme with real confidence.

A single gift of £1 million is extraordinary. Life-changing for a cause. But also random. Unpredictable. A moment, not a movement.

Both are valuable. Both are legacies. Both can happen together. Both are sought after. But strategically, each is at opposite ends of the same table.

I remember looking at a very impressive graph with a charity. Legacy income, year on year, climbing beautifully upwards. Comforting, reassuring, right place and very nice to see.

The number of people leaving gifts had actually gone down. The income growth was being driven by one or two high-value gifts landing in a good year. The warm glow of success was masking a programme of quiet decline.

A simple trap

It’s easy to fall in love with the line on the graph. What’s really driving it though?

And it doesn’t stop at income. The same trap shows up in how we market.

We count hand-raisers. Enquirers. Interest and commitments. The lovely volume metric that tells us the campaign might be working. (And we underplay the volume who don’t respond - that’s another juicy subject).

But what if we’ve effectively offered people a free car or cruise to the Bahamas to raise their hand? What if half those enquirers have no real interest in a gift in their will, and are simply enticed by the offer?

The metric looks intoxicating. The reality is thinner than we think. The volume is lying to us.

The truth is that most legacy gifts come from a relatively small number of people with real money. That’s the top of the triangle.

Volume at the base matters enormously. It creates the social norm. It gives legacy giving its cultural weight and its trajectory.

But value at the top is where transformation happens.

Lose sight of either and the whole triangle wobbles.

So here’s the lesson and my question..

Wisdom in legacy fundraising is balance. Not either/or. Not volume over value. Not value over volume. Both — and knowing which one you’re actually looking at in any given moment.

Look under the bonnet. Clarity and understanding. Always.

But perhaps more importantly its about quality.

Ask the awkward second question after the headline. How many gifts this year versus last? What does the curve look like if you strip out the one-offs? What’s the true quality of the people coming into your pipeline?

Because the drink you remember from a good night isn’t the fourth or fifth one.

It’s the first one you noticed. The one that you remember.

It’s the quality that matters.

👉 This is Lesson 16 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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Burt Bacharach wrote a song about the look of love.

You know the one. That moment between two people where something passes without a single word. A glance. A small signal that carries more weight than a whole conversation could.

I’ve been thinking about that lately.

Because it has more to do with legacy fundraising than most of us realise.

In 1992, Gary Chapman wrote The Five Love Languages. Words of affirmation. Quality time. Gifts. Acts of service. Physical touch. The book’s claims have been picked apart by researchers ever since, and that’s not what I’m here to defend. What I am here for is the idea underneath it.

That love has more than one language. That people give and receive it in different ways. And that if you don’t understand which language someone is speaking, you can stand right next to them and still miss each other entirely.

Sit with that for a moment. Because this is exactly what’s happening in legacy fundraising.

We know the research.

Dr Russell James has spent years showing us that legacy language matters — that simple, emotional, identity-driven words outperform legal and technical ones every single time. Family words. Lasting impact. Stories over structures. Emotion before logistics. A message that feels like a conversation with your grandmother, not a meeting with your solicitor.

Its a philosophy I’ve believed in and practised for over twenty years. That conversations are the engine of legacy giving. I believe that more than ever.

But a conversation about love? That’s a tougher place to explore.

And I think that’s where many of us quietly stall.

I’m writing this sitting outside a café.

At the table next to me is an elderly lady in a wheelchair. She’s recovering from a stroke — I can see it in the way her hand rests on her lap. Her husband sits beside her with his arm around her shoulders. Two teenage grandchildren are opposite, helping her with a slice of lemon drizzle and a cup of tea that’s gone a little cold.

Nobody is saying very much.

And yet the entire table is speaking a language of love so loud I can hear it over the traffic.

Simple but beautiful.

This is the world our donors live in.

This is what we are, at our best, an extension of. Not the case for support. Not the tax relief. Not the pledge or the brochure.

This. The hand on the shoulder. The cake cut into smaller pieces. The life being honoured while it’s still being lived.

And here’s what troubles me.

I’ve read a lot of brand books and legacy strategies in my time. Most of them don’t come anywhere near this. They don’t even try to. They sit in a different room altogether — safer, tidier, more measurable — and they wonder why the conversation feels flat.

So here’s the lesson and the question.

A charity that doesn’t try to understand where it fits in a moment like the one at that café table doesn’t really deserve its place in it.

The language of legacy love isn’t a tone of voice. It isn’t a phrase guide. It isn’t a clever swap of bequest for gift in your will, useful as that is.

It’s a practice. It’s a way of showing up. It’s the difference between speaking at someone about death and assets, and sitting alongside them in one of the most tender moments of their life.

We have a duty — and it is a duty — to understand the whole language. To practise it. To believe in it. To demonstrate it in how our organisations behave when no one is watching, and especially in later life.

Because we should be an extension of a donor’s love.

We need to behave like it.

Respond like it.

Be it.

And here’s the question I’d leave you with: if a donor could listen to your organisation the way I listened to that family at the café table — would they hear the same language of love being spoken back?

👉 This is Lesson 15 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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Every leader says legacy matters. Not enough protect it.

I’ve watched it happen so many times now that I’ve stopped being surprised. A CEO stands up, declares legacy giving a strategic priority. Passionate. Articulate. Convincing. Everyone nods. The head of fundraising feels hopeful.

Then the budget review arrives. Income is down. A major donor campaign needs more resource. There’s a restructure. And that strategic priority gets squeezed — quietly, efficiently, without ceremony.

Legacy falls to the bottom of the list. Again.

It’s not that leaders don’t believe in legacies. Most do. They understand the lifetime value, the strategic importance, the transformational potential. But belief doesn’t protect investment when short-term pressure arrives. And short-term pressure always arrives.

I remember one mid-sized charity I worked with that had approved a solid legacy growth plan. Dedicated staff. Training. Supporter research. New proposition. Integrated campaigns. The board was behind it.

Eighteen months in, other income dipped. Not catastrophically — but enough to trigger reactive cuts. The legacy programme lost half its resource overnight. The rationale? Legacy income takes years to materialise.

We need results now.

The irony? That decision guaranteed they’d be having the exact same crisis down the road. They’d just killed the engine that was supposed to solve it.

I spent years being perplexed by this. Intellectually, everyone gets it. So why can’t leadership follow through in practice?

I was trying to explain it for a board one day. I pictured the three hand pumps at my local pub - an ongoing source of inspiration.

Three levers. That’s all it is.

The first lever is short term. The monster. The one that drives every decision, every day. The next week, the next quarter, the next budget cycle. It dominates everything. It has to — survival depends on it.

The second lever is medium term. Three to five years. The things you do today that move you to a more stable platform. It makes the short term easier to manage. It builds capacity. Gravitates you away from short term.

The third lever is long term. The things you invest in today that yield income over years, sometimes decades. This is where legacies live. A forest you will never see.

Three levers. Not complicated. But they have to be pulled deliberately, constantly, in balance.

The problem is that in practice, almost everyone over-pulls the first and ignores the other two.

Boards do it. Chief executives do it. And fundraising directors, I’m afraid, do it too.

We live hand to mouth. We think legacies come in anyway, that we don’t need to do anything. That it’s expendable — because you probably won’t be in the organisation long enough to see the return. Everyone will have left. So why bother?

The here and now is what will see you survive.

So you focus on it. And the long term gets sacrificed.

The truth is that most of us are scrabbling to generate legacy income because the people before us didn’t take those long-term decisions either. They kicked it down the road. And here we are, picking it up.

The best time to invest in legacies was yesterday. The second best time is now.

But it takes courage. It takes leadership. Maturity and wisdom. It takes the ability to articulate what three levers looks like and why you’re pulling all of them. At the same time.

The leaders who understand this — who look after a fundraising portfolio and recognise that what they do today is what they leave behind for the people who come after them — those are the ones building something. Its their legacy.

The ones who only pull the short-term lever drive everyone to the cliff edge. And then we spend years firefighting. Exhausted. Going nowhere.

So here’s my lesson and my question.

If you lead a fundraising programme, which levers are you actually pulling? All three — or just the one that screams loudest? What are you doing to do the right thing, not the expedient thing.

Because legacy isn’t a channel to be funded when times are good. It’s a leadership decision for the long haul. And the organisations that treat it that way are the ones that will still be thriving when the short-term noise has long since faded.

👉 This is Lesson 14 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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We love a funnel.

Awareness, Interest, Desire, Action. Start wide, narrow down, convert. Perfectly logical. Beautifully linear.

And almost entirely wrong for legacies.

I remember sitting with the agencies at Remember A Charity when we were trying to map what a legacy journey actually looked like. We’d been through the classic marketing models. AIDA. Sales funnels. Conversion pipelines. They made sense on a whiteboard. They made sense for selling products.

But they didn’t make sense for what we were trying to describe.

Because legacy giving isn’t a purchase. It’s a life decision wrapped in mortality, identity, family, love, and fear — and it rarely moves in a straight line.

That’s when someone showed us Prochaska’s change model. Pre-contemplation to contemplation. Contemplation to preparation. Preparation to action. Action to maintenance.

It came from social change programmes, not sales. And its behavioural roots were so aligned with what we were seeing in legacy giving that the room went quiet.

Not the quiet of confusion. The quiet of recognition.

Here was a model that understood something most marketing funnels don’t: people don’t move through stages because you push them. They move because something shifts inside.

The problem with traditional funnels is that they have an inherent objective to convert. Prospect to customer. Lead to sale. Entry point to exit point. And in legacy fundraising, much of the sector has been stuck at that action stage for years — over-indexing on free will services, chasing the pledge, trying to force a decision that hasn’t been made yet.

But trying to sell a product to someone who doesn’t know they need the solution, let alone understand the problem, is counterintuitive at best.

Conversion in legacy is an outcome. Attention on conversion doesn’t convert. It pushes people away.

So what does the real journey look like?

It’s messy. It’s human. And if I’m honest, it looks something like this:

I don’t know about this consciously, but it’s there. Somewhere in the background. A passing ad. A mention at a funeral. A thought that hasn’t formed yet.

I’ve seen it now. I’m open to it. You’ve drawn attention to something. It registers.

I need to act on this. Life has changed. A parent has died. A grandchild has arrived. Something has shifted.

I’ll consider it. It makes sense. I’m willing to think about it.

I’ll do it, but not yet. Understood and accepted — but parked. Life gets in the way.

Done. Will written. Gift included. I might tell you. I probably won’t.

Stay with me. Because if the connection fades, so might the commitment.

Something’s changed. Circumstances shift. Relationships alter. Priorities move.

Do I still want to do this? A question that gets revisited more than we acknowledge.

Too late.

That’s not a funnel. That’s a life.

And for shorthand, most legacy programmes already work with a simpler version of this — I’m thinking about it, I’m going to do it, I’ve done it. Whether they tell you is another story entirely.

The maps we use for legacies are not linear. They do have a logic to them. They do have a messy human sense of order. And if we understand and pay attention to the complexity of it, we stand a much better chance of being alongside supporters at every stage — in their hearts, not just on their database.

It requires attention to all of those moments. Not just the ones we can measure.

So here’s my lesson and my question.

If your legacy programme is built around a conversion funnel, what are you missing in logic v reality? The quiet life moments where someone is considering, reconsidering, hesitating, returning or have moved on to a new reality that doesn’t now involve you?

Because the true legacy funnel isn’t a funnel at all. It’s a human journey. And the organisations that understand that will be the ones people choose to remember.

👉 This is Lesson 13 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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There has never been a better time to be in legacy fundraising. And yet…

Here’s the part that you should really understand - there has never been a worse time to be ignoring it.

Right now, in this decade, six forces are converging. Not gently. Not gradually. They are arriving together, at pace, and they are creating an opportunity that we most likely wont see again. I’ve watched it over the years and its at the heart of my lessons.

Organisations that recognise this and act will look back on this moment as the turning point. The ones that don’t? They’ll be left wondering how they missed it.

So let me walk you through all six. Because once you see them together, the case isn’t just compelling. It’s undeniable.

1. The Demographic Dividend

The Baby Boomers — born between 1946 and 1963 — are beginning to turn 70. Think about that for a moment. This is the generation that changed everything. Politics. Culture. Social norms. The very face of voluntary giving. They rewrote the rules of how we live, and they’re about to reshape how we give.

For the first time in human history, people aged 65 and over outnumber children under five. The UK population is projected to reach 74.3 million by 2039, with the 65+ age group alone hitting 16.9 million by 2035. More people. Living longer. And with that comes an inevitable rise in the death rate over the next three decades.

In its simplest, most human form: more legacies are coming.

The question is whether your organisation will be there to receive them. Whether you’ll have done the work — the emotional work, the cultural work, the strategic work — to be in people’s hearts and minds when the moment comes.

2. The Greatest Wealth Transfer in History

This isn’t just the largest generation. It’s the wealthiest generation in human history.

Baby Boomer wealth in the US alone is estimated at $64 trillion. In the UK, PwC estimated that 36% of total liquid wealth — roughly £1.7 trillion — will be in the hands of retirees over the next ten years. Men and women over 50 hold 80% of the UK’s private wealth. Those over 60 contribute more than half of all charitable giving.

Now, much of this wealth will pass to family. That is right and proper — family first, charity second, always. But a small share, thoughtfully invited, wisely positioned, could be transformational for the causes people love. Not extracted. Not pressured. Invited.

The intergenerational transfer has already begun. The invitation from charities must follow.

3. Digital Access Has Opened the Door

A generation ago, reaching older supporters at scale was costly and slow. That world is gone.

Internet use among people aged 65 and over grew by 150% between 2009 and 2011 — the fastest growth of any demographic group. Today, one in four over-65s uses social media. 71% of older people who go online do so daily. The Telegraph famously dubbed them “instagrans” — and they weren’t wrong.

This is not a niche audience on the margins of digital life. They are active. They are connected. And they are increasingly open to conversations about meaning, contribution, and legacy.

Integrated campaigns — combining TV, print, digital, storytelling — can now reach them in ways that simply weren’t possible a decade ago. The door is wide open. We just need to walk through it.

4. The Human Need to Be Remembered

Here’s something that never changes, and it’s the thing we come back to again and again.

The desire to matter.

As people move into later life, a powerful psychological shift takes place. Symbolic Immortality — the deep, ancient human need to leave something of yourself behind. To live on in the difference you’ve made. I think about this every time I picture those tiny engravings on the banisters of Southwold pier — stories of family, holidays, pets, loved ones. Beautiful, quiet expressions of the same truth: we want to be remembered.

Baby Boomers, more than any previous generation, are asking: what will I leave?

Research by Age Wave and Merrill Lynch found that retirees are expected to donate $6.6 trillion in cash and $1.4 trillion in volunteer time over the next 20 years. They are 49% more likely than their parents to research how a charity uses money before they give — and 44% want to direct how their gift is used.

A gift in a will is the perfect response to this motivation. It’s personal. It’s purposeful. It’s lasting. It’s not about death — it’s about the life someone wants to keep living after they’re gone.

This is legacy fundraising at its most human. And it’s where the real power lies.

5. We Now Know How to Have the Conversation

For years — decades, really — legacy fundraising was held back by a quiet kind of paralysis. Organisations didn’t know how to ask. Supporters didn’t know how to respond. And so the conversation simply didn’t happen. We tiptoed around it. We coughed nervously. We talked about death and taxes when we should have been talking about meaning and memory.

That has changed.

We now have a remarkable body of behavioural insight — drawn from psychology, social research, and decades of legacy marketing experience — that helps us understand exactly how and why people decide to leave a gift. We understand the barriers. We understand the language that opens rather than closes. We understand that the best conversations about legacy giving aren’t really about money at all. They’re about connection. About identity. About what someone values most.

Organisations that use these insights — building supporter journeys grounded in empathy, not just asks — are seeing real, measurable results. The science of the conversation has finally caught up with the art of it.

We don’t need to be afraid of this conversation any more. We need to be brave enough to start it.

6. The Momentum Is Building

Legacy giving is no longer a niche activity. It is becoming a social norm.

In 2007, 35% of UK adults said they would consider leaving a gift in their will after family. Today that figure has risen to 40%. Attitudes are shifting. Visibility is increasing. And as more people leave legacy gifts, more people talk about legacy gifts — creating a virtuous cycle of normalisation that is still only in its early stages.

This is the drip drip effect in action. Every campaign, every conversation, every story shared is making legacy giving more visible, more normal, more human. We are building something here. And we are nowhere near the ceiling.

I’m proud to have played a part in helping build that momentum.

We are not at the end of this story. So much more to do.

So Where Does This Leave You?

Six forces. One conclusion.

Legacy fundraising is not a nice-to-have. It is not a bolt-on programme or a quiet footnote in the fundraising strategy. It is — right now, in this moment — the most strategically important investment any charitable organisation can make.

The demographic window is open. The wealth is there. The motivation is real. The tools exist. The conversation is more possible than it has ever been. And the momentum is with us.

But here’s the thing I’ve learned over 30 years in this work: the opportunity doesn’t wait. Windows open and windows close. The organisations that acted and the ones acting now — with clarity, with courage, with a genuine belief in the human power of legacy — are the ones that transform their futures.

The only question is: are you really, truly, honestly seizing this moment?

👉 This is Lesson 12 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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There is one sin I have come to fear above all others.

Certainty.

I heard that line and stopped.

Not because it was surprising. Because it was true. True in religion, perhaps. But also — uncomfortably, precisely — true in legacy fundraising.

It’s from Ralph Fiennes playing Cardinal Lawrence in the film Conclave, addressing the cardinals gathered to elect a new Pope. His argument: that certainty is the enemy of unity. That doubt is not weakness — it is what keeps faith alive.

I am not drawing a religious parallel here. I am drawing a human one.

Because in legacy fundraising, we have a certainty problem.

We are often driven by people who need to see clarity, precision, and detail in absolutely everything. So much energy is directed at that pursuit that we lose sight of the real picture. The manageable one. In chasing ever-more granular measurement, we risk misleading colleagues into believing that everything is knowable. That everything is controllable.

It isn’t. Uncertainty is the landscape. Our job is to navigate it, not pretend otherwise.

Ashley Rowthorn from Legacy Futures wrote about this recently and got it exactly right. His analogy: we know the seasons are coming. We don’t know what happens on each individual day. But we trust the pattern. We act on it. We plan around it.

That’s the relationship legacy fundraising needs to have with measurement.

What I’ve come to believe is missing — what I’ve looked for throughout my career and rarely found — is a clear narrative model. Something that explains what’s measurable, what isn’t, what’s worth pursuing and what to let go of. Over time, these are what I use to guide these conversations.

Here are my six rules.

1. Breadth

We start wide. The dimensions of why someone leaves a legacy gift are vast — human, emotional, cultural, behavioural, statistical, rational and deeply irrational. If we begin by narrowing too quickly, we miss the truth before we’ve even looked for it. Breadth is a mindset. Curiosity as a starting point. Go wider first, before you go deeper.

2. Data

Data is multiple points of light. Collected deliberately, from as early as possible, across past, present and future. Lead indicators and lag indicators — what predicts outcomes, and what confirms them. Data alone isn’t knowledge. But data, gathered with intention and kept faithfully, gives us something to work with. Something to see.

3. Pattern

With breadth and data, you begin to see. Patterns show you trends. Trends tell you what’s more likely — and what carries risk. Like the seasons. You won’t know every day’s weather, but you know winter is coming and spring will follow. Pattern is a torch in darkness. It doesn’t illuminate everything. But it’s enough to move forward.

4. Interpretation

Much of what we see will not land with certainty. We can trust the anchors: people age, they die, and some will choose to give. But the meaning between those anchors — that requires interpretation. It is sense-making, not false precision. It takes experience, diversity of perspective, and the intellectual honesty to say: I don’t know exactly, but here is what I think this means. That takes confidence. Real confidence — not certainty.

5. Focus

Focus is the choice of what to pay attention to. The 20% that drives 80% of the outcomes. The measures and actions that are both meaningful and within our influence. This is perhaps the most important rule for those of us educating colleagues and boards — because without focus, we create the illusion that everything matters equally. It doesn’t. Some things are worth knowing but impossible to change. Focus on what you can move.

6. Faith

And then, finally, faith.

Some things guide action even when certainty is impossible. Principles. Philosophy. A belief that this work matters, that the model holds, that the direction is right — even when the data is incomplete and the outcome unclear. Faith is never certainty. If it were certain, it would have no value. As Cardinal Lawrence put it: if there was only certainty and no doubt, there would be no mystery — and therefore no need for faith.

For legacy fundraising, that is not a theological statement. It is a professional one.

So here is my challenge.

The problem isn’t that you don’t know enough. It’s that some think you do.

Certainty closes things down. It stops questions. It misleads people. It creates unrealistic expectations that eventually undermine trust in the whole enterprise of measurement.

We can make this so much better — more honest, more credible, more useful — if we take the time to build a narrative first, rather than react and improvise. If we explain what we can know and what we can’t. If we can hold space for discovery yet focus on what matters. If we hold the line on good enough being genuinely good enough.

The best legacy leaders aren’t the most certain.

They’re the most curious.

👉 This is Lesson 11 of 20. Get the full series delivered to your inbox — you’re welcome to join here.

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Legacies are the true DNA of a brand.

But in most charities, they’re treated like distant cousins.

I remember sitting in a room with a brand team who had lost their story.

Not lost it exactly. They’d polished it into something unrecognisable. A proposition full of clever language, beautifully designed, professionally presented — and completely disconnected from what the organisation had actually been created to do or actually did.

More importantly it was detached from true purpose and clarity.

The only way back was to go to the beginning.

We went back to the founding moment. The original purpose. The reason the organisation existed before anyone worried about positioning or messaging or brand architecture. And when we found it — when we read the words written before any of the current leadership were even in the room — something happened.

That’s us.

A revelation. Not from an agency or brand specialist.

It came from a legacy conversation.

Here’s the thing about brand that gets missed in most organisations.

Brand at its best is not a communications strategy. It is not a visual identity. It is not a set of values on a wall. Brand, at its deepest level, is an organisation’s identity — who it is, what it stands for, why it exists — expressed consistently over time.

And identity, consistently expressed over time, does something remarkable.

It finds its way into people. Their DNA.

Not all people of course. Not quickly either. Not through any single campaign or clever idea. But over months and years and decades of consistent presence, repetition with cut through — your brand, the real one, the one rooted in purpose — begins to feel to certain people like a mirror.

They look at what you do and see something that reflects who they are. What they believe. What they care about.

They see themselves in you.

Many if not most legacy gifts come from people you have never met. Not recruited by a legacy fundraiser. No legacy event. No brochure. They left a gift because, over time, your brand became part of their identity. Your purpose and their purpose bonded. The line between the two began to blur.

It is belonging. It is depth. It is trust. Sometimes it is, quite simply, love.

And when someone sits down to write their will, you are there — because you had built something they didn’t want to see disappear.

That is the most enduring measure of whether a brand is working.

Brand gets overcomplicated. Too clever. Too focused on edge and differentiation and visual. Too political and functional. Not enough emotion. It loses its connection to the fundamental question: who are we, and do the people who matter truly understand that?

And so the connection between brand identity and fundraising becomes fractured. A tense stand off. Forces competing. We’ve all been there.

I have two defined aims for brand. The first is to ensure the mission is delivered. The second is to enable fundraising to pay for it.

Legacies are an outcome of brand. But all too often its treated as an unexpected bonus rather than a strategic lever.

That is the secret weapon most organisations don’t know they have.

So here’s the lesson for me and the question I would sit with.

Do the people responsible for your brand truly understand what brand actually is? Do they understand that its true power is much more simple than often practiced. Do they understand how legacies are woven through everything?

There are 3 questions a brand needs to ask to always drive impact:

1. Do you know who we are?

2. Do you understand what we do?

3. Would you consider giving?

Focus on this consistently anchors itself in purpose. Its not an accident. Its the consistent accumulation of trust — the kind that shows up, years later, in a legacy gift from someone you never knew.

But even more than that.

Its a strategic lever that requires action. It places legacies as core, not on the edge and not connected. Its at the heart of everything you do. It runs through every positioning, campaign, and message and if legacies are to truly find their place and be embraced — this is where it starts, where true change happens.

Not in the legacy team.

In trust. In leadership.

In the bonding of identity.

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Busy is the enemy of culture.

In most nonprofits, that’s not a criticism. It’s just the truth.

And in legacy fundraising, it costs more than people realise.

I’ve watched organisations nod at culture for years. They know it matters. They say it matters. Then the week fills up, the inbox takes over, and culture becomes one more thing on the list — the thing you know instinctively you need to do something about, but don’t know where to start.

So it never gets driven to the top of the pile. Always busy though.

Everyone says culture eats strategy for breakfast.

Fine. But when culture becomes the strategy, you know you’re beginning to get somewhere. That’s the shift most organisations haven’t made yet.

Culture is the most underused, underutilised tool in any organisation.

In the nonprofit world, people talk a good game. But the gap between talking about it and actually building it is where most programmes quietly stall - especially in legacies.

Because behaviour — and all the signals that result in behaviour — are what make legacies work. What people do, what they say, how they respond when a supporter mentions their will: all of it is shaped by the culture they’re living inside. If the culture doesn’t support legacy thinking, the conversations don’t happen. And if the conversations don’t happen, everything else fades.

Without culture, three things start to go wrong.

First: most of the people in your organisation don’t know what to do, or why. Yet they are the gatekeepers. Your community team. Your events volunteers. Your frontline staff. They have access to audiences, relationships, and moments that a legacy fundraiser simply can’t reach alone. If they’re not actively on your side — if they don’t understand what to do or how to be part of your legacy quest — they can’t contribute. They’re one of your most underutilised assets.

Second: culture is a signal. It tells the people you’re trying to reach something important about who you are. That legacy giving isn’t a transaction — it’s a relationship, an identity. That the people who leave a gift to you are genuinely special. That you’d love and value others to feel the same. Supporters can feel the difference between an organisation where legacy lives and one where it’s bolted on.

Third — and this is the one that matters most — culture requires deliberate. It doesn’t drift in. Think of the brands you love most. The ones where the experience stays with you. Where the person you spoke to seemed genuinely invested. That stems from something: from the culture instilled when people joined, the behaviours that were rewarded, the sense that everyone is part of a tribe, part of a quest, making something worth coming back for.

Legacy culture works the same way.

It has to be built. It has to be taught. It has to be tended.

The organisations I’ve seen that build exceptional legacy programmes all do something similar. They make legacies visible and vibrant. They help people have the conversations. They give everyone — from the CEO to the volunteer at the welcome desk — a clearly understood role to play and the training to support. They share stories. They celebrate.

They make it something you want to be part of.

And the cultures that thrive deliver great legacy connections.

If legacies are one of your most important long-term income streams — and for most charities, they are — are you building the culture that makes that possible?

Or are you looking at it longingly from the outside, hoping it will somehow take care of itself?

Because culture doesn’t wait. And neither do your supporters.

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The 1% ask sounds simple, sensible, and easy to say.

And it’s wrong.

Let me be clear about what’s happening. In some quarters, a case is being made for asking people to leave 1% of their estate to charity. The logic is understandable: make it easy, reduce friction, give people a number they can grasp. Make the ask accessible.

No one disputes that conceptually, simplicity matters.

But here’s the problem. Simplicity isn’t the same as wisdom. And in this case, we’ve simplified ourselves into a corner.

I remember sitting behind the double screen in a focus group in Brighton. We’d prepped the facilitator with questions around percentages. 1%, 5%, 10% — what would people like? What would make sense?

The group was clear.

They understood the direction we were going. They got it. But they didn’t want a specific number. They felt it would interfere with their own thinking. Almost an overreach.

When the facilitator suggested “a small share” instead, the room shifted.

They liked it. It wasn’t judgmental. It didn’t dictate. But it did what we needed it to do — it made the concept accessible without boxing people in.

From that moment, we rooted our methodology in that phrase. A small share.

Tried and tested. A wiser simplicity.

Later, others tried specific percentages. The results varied. I remained unconvinced.

And now, the 1% ask is making the rounds. Capturing headlines. Sounding easy.

Here’s why I think it’s a mistake.

First, we’re trying to position legacy giving as something simple, easy, relatively small. Friends and family first, then a share for charity. That makes sense. But the interpretation matters.

Specifying 1% is very low. Yes, it makes it easy. But we’re also undermining the likelihood that donors might leave more if we guide them differently.

Second, it sounds like a tax. A commission. A service charge.

Third, there’s no reason to say it. We’ve dumbed it down to the point where we’ve minimised the opportunity, experience and logic. Like it doesn’t matter, so long as you say yes.

And fourth, we’re not learning from any behavioural science at all.

I’ve learnt a different way.

Build on the phrase “a small share.” It illustrates what we want, what’s needed, what might work. But it doesn’t dictate to the donor. It doesn’t alienate them or make them feel like they’re hearing a commission rate.

A small share, positioned as a slice of something after friends and family, illustrates the sequence we’re looking for. It’s residuary. It’s inflation-proof. It makes sense.

And then, in conversation or presentation, we use behavioural science to anchor around a reasonable figure.

We are fundraisers. Remember sponsor forms at school? The one with the higher starting figure always raised more. The one with the lower figure anchored everyone down. Anchoring.

A simple conversation if you can, or position that talks about what most people do. That some do more. And some do less. Guidance.

What does a small share look like for them?

That’s anchoring. That’s choice. That’s autonomy.

And critically, we answer the question that actually matters: why would someone consider leaving a gift in the first place?

Boxing it into a tiny figure doesn’t answer that.

It just makes us feel better about having something simple to say.

So here’s the lesson and the question.

If you want to reduce friction and make legacy giving easier, are you making it easier for the donor — or just easier for yourself?

Because one builds trust and potential. The other just sounds like a service charge.

👉 This is Lesson 8 of 20. Get the full series delivered to your inbox —You’re welcome to join here.

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Last week I wrote about how organisations quietly lose wisdom — not because people leave, but because their experience becomes invisible. You can read the full piece here Modern Elders and the Window Tribe: The Untapped Power in Your Organisation

Many readers asked a simple, practical question:

“So what can we actually do about it?”

You don’t need large budgets, new departments, or complex systems. You need a shift in how you see experience — and how intentionally you make space for it.

Here are ten practical ways to begin.

1. Create mentoring pairs — and give them real time

Not informal “check-ins”, but structured time where younger staff can learn how experienced colleagues think, not just what they know.

Wisdom transfers through conversation, not documentation.

2. Run wisdom sessions before people leave

Exit interviews capture feelings.

Wisdom sessions capture judgement.

Before someone retires or moves on, ask:

What do you know now that you wish you’d known earlier?

3. Treat long service as a resource, not a risk

In many organisations, experience becomes associated with resistance to change.

Often it is actually the opposite — it is what allows change to happen without repeating old mistakes.

4. Invite elders into key decision conversations

Not to decide.

But to add perspective.

A single sentence from someone who has “seen this before” can prevent months of wasted effort.

5. Capture stories, not just processes

Processes tell you what to do.

Stories tell you why.

Build a simple library of lessons, turning points, and hard-won insights.

This is how organisational memory survives.

6. Make reflection part of leadership practice

Experienced professionals carry judgement shaped by decades of pattern recognition.

Create regular spaces where leaders can share what they are noticing — before it becomes a crisis.

7. Signal respect publicly

Recognition is not about praise.

It is about visibility.

When organisations visibly value experience, younger staff learn that wisdom matters — not just speed and novelty.

8. Build intergenerational teams deliberately

Most teams mix ages accidentally.

But when experience and fresh perspective are intentionally paired, decisions become both wiser and more adaptive.

9. Create pathways for “semi-retirement contribution”

Many experienced professionals don’t want to stop contributing.

They want to contribute differently.

Part-time advisory roles, mentoring programmes, and project-based involvement allow organisations to retain decades of insight.

10. Define your own “Window Tribe”

Every organisation needs a clear pathway for its elders to remain active contributors, not ceremonial figures.

Not everyone will want to take it.

But those who do will shape the organisation long after they leave.

None of these are really about budget. They require something more demanding:

A change in mindset. From seeing experience as cost… to seeing it as one of the organisation’s most valuable assets.

Because when wisdom is lost, organisations don’t just lose knowledge.

They lose judgement.

And judgement is what protects the future.

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