Imagination, resilience and letting go

I recently had a 'fireside chat' for the National Digital Forum's AGM, which drew on many of the ideas I've been exploring this year - below is a summary of some of the things I touched on.

Based on the conversations I've had this year everyone working in digital and cultural work feels it - a sense of perpetual acceleration and uncertainty, and the growing tension between ambition, expectation and capacity. Exhaustion seems to be showing up in most conversations I'm having at the moment.

The philosopher Karl Popper once distinguished between clocks and clouds. Clocks can be fixed by fixing the mechanics - by tightening bolts, but clouds can't be fixed that way. Most of our most pressing current challenges are clouds, they're messy, cultural, and adaptive - but we seem to keep reaching for technical solutions. We buy new platforms and reorganise our teams, but the same problems keep drifting back into view.

It feels like we’re operating firmly in a moment where the traditional models of cultural leadership - those that are steady, certain, directive - no longer fit.

Margaret Heffernan recently wrote that once we accept we don’t know what the future holds, the only response is imagination. Strategy, she says, is not prediction, it’s creation. It is the act of "conceiving a world we don’t yet inhabit and designing multiple ways to create it".

That capacity for imagination isn’t just a leadership trait. It’s something everyone in an organisation can, and should, be trusted and empowered to exercise.

Imagination needs scaffolding

A few years ago, the Australian Centre for the Moving Image (ACMI) and the Australia Council ran a digitally-focused CEO mentoring programme that named digital "imagination" as a critical leadership attribute (I've spoken to Seb Chan, ACMI's CEO, about this on the podcast).

When I first encountered this term, I assumed it meant technological awareness and openness - things like staying curious, imagining possibilities, and tolerating uncertainty. But the research evaluation of that program revealed something more specific and complex. Effective 'digital imagination' as they defined it isn't just about 'having ideas', it's also about having the understanding to be able to make "confident and informed decisions" about those ideas.

Most participants on that ACMI programme described their digital mindsets as "developing" rather than well developed. They were confident in their ability to lead, but uncertain about making long-term technology choices, selecting providers, or understanding digital risks. One mentee described this, saying, "I don't know where the value resides" in digital work.

This matters because without that understanding, imagination has nowhere to take root. Cultural leaders on the programme were full of aspirations - about expanding access, serving new audiences, reimagining their missions - but struggled to translate those aspirations into informed action. They couldn't distinguish between what digital is versus what it could do for their specific organisational context. This is a challenge I have also seen emerge in the pilot cohort-based leadership programme I have helped The Space to deliver in the UK.

Digital imagination, then, is not just generic curiosity. It's sector-specific literacy developed through expert guidance. It's understanding the 'supply chain' and specific potential of digital work well enough to know which questions to ask and what might be possible. It's recognising that what digital offers a performing arts organisation fundamentally differs from what it offers a visual arts institution or a library.

And critically, the study showed, it requires conditions that many organisations don't have such as protected time to think; experts in-house, or as mentors, who understand cultural sector constraints; opportunities for peer learning with others grappling with similar challenges; and, perhaps most vitally, organisations stable enough that imagination doesn't feel like a dangerous distraction from survival.

When those conditions existed in the ACMI programme, the results were tangible and meaningful - participants developed effective digital strategies, reconsidered their operational models, and began asking fundamental questions about organisational purpose. When those conditions didn't exist - for example when participants were managing COVID disruptions, staff turnover, or simply trying to keep their organisations afloat - imagination stalled or failed to have any real impact.

The point is not that a focus on imagination is wrong, but that it's insufficient in and of itself. In healthy organisations, leadership behaviors like curiosity, initiative, and experimentation are allowed and encouraged to happen everywhere. But "allowed" is doing a lot of heavy lifting in that sentence - that permission requires power structures willing to distribute it, healthy culture requires cultivation, and imagination needs fertile ground to grow in.

One piece of that infrastructure is often invisible - the decision-making capacity itself. Most cultural organisations don't lack for ideas, what they lack is the attention and structures to be able to act on them.

Attention, like funding, is finite.

Good proposals queue up waiting for approval. Priorities blur across meetings and become confused. Projects lose momentum before they start. When leaders' attention is stretched too thin, imagination stalls not from lack of courage but from lack of oxygen.

Decisions are infrastructure too and, like any infrastructure, they need design.

Resilience through subtraction

Ed Rodley recently summed up something I’ve felt for years - cultural organisations are great at additive change, but terrible at subtractive change. We’re skilled at starting and adding new projects, platforms, and partnerships, but rarely do we stop to ask what we could remove or stop to make room for better thinking (for what it's worth, this is a humanity-wide issue).

Nassim Nicholas Taleb in his book Antifragile calls this via negativa - the road to robustness through subtraction, not addition. Every “no” creates a pocket of oxygen for imagination to happen in.

In the rush to build capacity and resilience, we often mistake busyness for strength. But resilience isn’t built by always doing more, it’s about knowing what (and when) to stop.

And this is where the idea of via negativa perhaps meets its limits in practice. I know from my conversations with cultural leaders this year, and the ACMI research also showed, that many cultural organisations aren't choosing between addition and subtraction. They're already stripped down to the essentials, with many unable to sustainably deliver on the absolute minimum levels of service. When you're in survival mode, saying "no" isn't thoughtful, strategic subtraction - it's triage.

The real challenge perhaps isn't that cultural organisations are bad at subtraction per se. It's that we're working within funding models that force us to keep saying "yes" to project-based work while our core capacity erodes. We outsource digital skills not because we haven't imagined bringing them in-house, but because we can't afford to. We pile on disconnected platforms and misaligned partnerships not from a lack of discipline, but from necessity in the moment.

Resilience through subtraction requires having something to subtract from. For many organisations, especially small to mid-scale ones, the question isn't "what should we stop?" but "what can we possibly sustain?"

This doesn't mean the idea of via negativa is useless - it means that applying it requires first securing the baseline from which strategic choices become possible. Saying no to overcommitment, legacy processes that drain resources without delivering value, and to decisions made primarily to avoid upsetting existing arrangements, is indeed a form of leadership. But it's a form that becomes available only after the structural question is answered - does this organisation have enough resources to make that choice meaningful?

At the same time, for organisations already operating below that baseline - the ones asking stark questions about survival, not strategy - imagination might actually be the only deployable resource left. When money, time and headcount are fixed or falling, the ability to think differently, to prototype in tiny ways, to borrow ideas from adjacent organisations are the bits that no funder can cut. In those contexts, imagination isn’t a nice-to-have, it’s a low-cost act of refusal - a way of saying “we won’t let scarcity define what’s possible here”.

Learning through small bets

Pragmatic and flexible resilience - or antifragility - is discovered in the relationship between an organisation’s core and its edge - between what must endure and what needs to evolve.

The core is the work that sustains you - your mission, audiences, and craft. It needs consistency and care.

The edge is where you explore through small, time-boxed experiments that test ideas, reveal new needs, and feed learning back into the core.

The healthiest organisations connect the two. They protect the core while allowing the edge to evolve.

When I visited the Museum für Gestaltung Zürich earlier this year, their Museum of the Future exhibition turned part of the building into a space for genuine experimentation. Seventeen digital experiments explored how their collections could reach people differently. It wasn’t performative 'innovation theatre' - it was structured practice and learning in public.

As Nick Sherrard put it when we spoke on the Digital Works Podcast, “in the commercial world, innovation is how you manage the risk of change and find the opportunities in it. In the cultural sector, it’s often treated as a reputational risk. But the real risk is doing things exactly the way you always have. That’s how you become the next Blockbuster Video”.

Small bets (experiments) matter because they stop 'innovation' being a grand, empty, or high-stakes gesture, it instead becomes a low-cost, ongoing way of learning in public. Tiny experiments reduce the risk and potential downside while increasing your surface area for opportunity. They create a controlled edge where teams can safely test, adapt, and feed insight back into the core.

Maybe the cultural organisation of the future isn’t the one with perfect answers, it’s the one that’s comfortable learning in (and with the) public.

Letting go: collective imagination in action

The Oodi Library in Helsinki remains one of my favourite examples of imaginative leadership. It wasn’t the product of a single architect or committee, but the outcome of over 3,000 citizens co-designing their library after two decades of meaningful ongoing engagement.

That process required a remarkable act of trust. Helsinki’s leaders didn’t cling to control, they distributed authorship, it was a true example of co-creation. Citizens voted on priorities, allocated budgets, and shaped the vision of the new library collectively.

One librarian put it beautifully: “It wasn’t us professional librarians deciding to create this. It belongs to them”.

But what often goes unsaid when we celebrate examples like Oodi is that Helsinki's leaders didn't just "let go" and trust. They invested two decades and substantial resources in the scaffolding that made this collective imagination possible. They built frameworks, facilitated thousands of conversations, maintained momentum across political cycles, and funded the infrastructure that could hold distributed authorship.

Oodi is 'antifragile' and the result of collective imagination not because imagination itself is inherently resilient, but because it's backed by sustained civic investment and institutional stability. The ACMI programme research observed what happens when you try collective imagination without that foundation - three participants left their organisations mid-programme. Organisations struggled to transfer individual learning back into institutional practice. Even with expert mentoring, transformation stalled because the structural conditions - stable staffing, adequate funding, protected time to think - weren't in place.

This isn't a criticism of collective imagination. It's recognition that imagination requires supporting conditions. When we point to Oodi without acknowledging the decades of investment that made it possible, we risk suggesting that what cultural organisations lack is vision, when what they actually lack is stability.

The courage to imagine

From Heffernan's "crisis of imagination" to ACMI's findings about digital imagination, and from Taleb's antifragility to Oodi's collective authorship, there's a thread here.

Imagination matters, and organisations can build resilience through adaptability - through simplifying to strengthen, through delegating and experimenting, and through accepting uncertainty. Digital maturity is enmeshed with imaginative maturity.

Imagination at its best is a shared muscle that strengthens every time someone is trusted to think differently.

But imagination without conditions is aspiration without traction.

The cultural organisations that will thrive aren't just those with imaginative leaders - they're those operating in spaces and contexts that have invested in the scaffolding that imagination requires. Scaffolding that includes expert guidance, shared infrastructure, funding models that allow strategic choice rather than perpetual crisis response, and policy choices that put digital transformation at the centre rather than the margins.

That scaffolding starts with honest reflection. What conditions exist, and what needs to change? How do we make digital work sustainable through intentional structures and rhythm rather than heroics? Where are we going, how will we get there, and what are we learning along the way? These aren't rhetorical questions - they're examples of the diagnostic practice that will turn imagination into infrastructure.

The future won't reward certainty. But it won't reward curiosity alone either. It will reward sectors that had the courage to build the structures in which curiosity could lead to capacity, where imagination could help define infrastructure, where individual insight could accrue and compound into collective transformation.

The question for all of us is are we building those conditions, or are we just asking people to imagine harder?