Pre-Colonial Fantasy Summits: Why Imagination Is Infrastructure For Possibility
Lesson 24 of 25 from podcast conversations with leaders who leave the world better than they found it
Devika Singh-Kohler did something remarkable for her birthday.
She hosted a pre-colonial summit between the Kingdom of Magadh (her home region in India) and the Kingdom of Luganda (Uganda). Complete with ocean-crossing caravans, full regalia, imagined diplomacy.
A total fantasy. A creative reimagining of what India-Africa relations could have looked like without colonialism's interruption.
"I'm tired of this mercantile relationship between India and Africa," she told me. "I want romance, I want culture, I want drama."
Most people would call this play.
I think it's strategic practice.
Because organizations that can't imagine radically different futures get stuck in incremental thinking. And incremental thinking doesn't create breakthrough impact.
The Incrementalism Trap
Most strategic planning is incremental:
We look at what we did last year. We ask how to do it 10% better. We identify small improvements. We optimize existing approaches.
This creates steady progress. It's safe. It's defensible to funders and boards.
But it rarely creates transformation.
Because transformation requires imagining something fundamentally different. Not "how do we improve our current model" but "what would we do if we could start from scratch?"
Organizations resist that kind of thinking:
It feels impractical: "We can't just throw out everything we've built."
It feels risky: "We know the current approach works, even if imperfectly."
It feels ungrateful: "We're dismissing all the work that got us here."
It feels impossible: "We have constraints—funding, capacity, regulations—that make radical change unrealistic."
So we stick with incrementalism. Small improvements to existing approach.
And we miss possibilities that would only be visible if we let ourselves imagine without constraints.
What Devika's Fantasy Teaches
Devika's pre-colonial summit wasn't meant to be real - it was an imaginative exercise.
But that exercise did something important: it created space to imagine relationships not defined by historical power dynamics.
What if India and Africa had connected through culture and romance instead of colonial extraction?
What if those relationships had been peer-to-peer instead of exploitative?
What if there was history and mythology to draw on beyond trauma?
This kind of speculative thinking doesn't erase real history. But it creates space to imagine different futures not constrained by past patterns.
And that's exactly what organizations need.
The Constraint-Free Exercise
Here's something most organizations never do:
Spend 30 minutes imagining your work if all current constraints disappeared.
Not realistic planning. Pure imagination.
No funding constraints. No regulatory limitations. No staffing challenges. No political obstacles.
If you could wave a magic wand and create exactly the impact you want to create, what would it look like?
Write it down. Draw it. Describe it in detail.
Then—and this is the critical step—look for elements that could actually be prototyped.
Most of what you imagine will be genuinely impossible given current constraints.
But usually there's something—a piece of the vision, a component of the approach—that's more possible than you initially thought.
That piece becomes your innovation.
Why Organizations Need Speculative Thinking
Speculative thinking—the kind Devika practiced with her fantasy summit—serves several strategic purposes:
It creates permission. Once you've imagined a radically different possibility, smaller innovations feel more achievable by comparison.
It reveals assumptions. When you imagine without constraints, you notice what you've been assuming is fixed that actually isn't.
It generates creative solutions. Breakthrough ideas rarely come from optimizing existing approaches. They come from imagining something fundamentally different.
It energizes. Incremental planning is exhausting. Imaginative thinking is energizing. Even if you can't implement the full vision, imagining it creates hope.
It attracts collaborators. People are drawn to bold visions, not incremental improvements. Speculative thinking helps you articulate the vision that attracts the partners you need.
When Speculation Becomes Strategy
I've watched organizations make this shift:
They start with fantasy: "What if we could completely reimagine how this community accesses resources?"
They don't dismiss it as impossible. They ask: "What would have to be true to make this possible?"
That question surfaces:
Assumptions that could be tested
Partnerships that could be formed
Policies that could be changed
Resources that could be mobilized
Technologies that could be leveraged
Not all at once. But piece by piece.
And five years later, they've built something that looked impossible at the start. Not exactly what they imagined—reality never matches fantasy. But fundamentally different from where they began.
That transformation started with permission to imagine freely.
The Questions That Enable Speculation
Most strategic planning asks:
What resources do we have?
What's realistic given our constraints?
How can we improve what we're already doing?
These are important questions. But they trap you in incrementalism.
Speculative strategic planning asks different questions:
"What impact would we create if we had no constraints?"
"What would this look like if we could start from scratch with everything we now know?"
"What becomes possible if we assume breakthrough rather than incremental progress?"
"What would competitors/peers think is impossible that we could actually do?"
"What would the world need from us ten years from now that doesn't exist yet?"
These questions create different thinking.
They don't replace practical planning. But they precede it.
You imagine freely first. Then you figure out what's possible given reality.
But if you start with reality, you never get to imagination.
Why This Feels Risky
Leadership teams resist speculative thinking for understandable reasons:
It might generate expectations you can't meet: "If we talk about this vision and can't deliver, people will be disappointed."
It might reveal dissatisfaction with the current approach: "If we imagine something radically different, does that mean we think current work isn't good enough?"
It might seem frivolous: "We have real problems to solve. We can't spend time on fantasy."
It might expose disagreement: "What if we don't share the same vision? Better not to surface that conflict."
All of these concerns are real. But they're also defenses against the discomfort of genuine strategic thinking.
Because real strategy sometimes requires acknowledging that incremental improvements to current approach won't get you where you need to go.
And that's uncomfortable.
From Fantasy To Prototype
Here's how to move from speculative thinking to strategic action:
Step 1: Imagine freely (30 minutes, no constraints, pure fantasy)
Step 2: Identify elements (What are the distinct components of this vision?)
Step 3: Test assumptions (What would have to be true for each element to be possible?)
Step 4: Find the possibles (Which elements are actually more achievable than they initially seemed?)
Step 5: Prototype (Choose one "possible" element and test it small-scale)
This process doesn't commit you to the full fantasy. But it creates space for innovation that wouldn't emerge from incremental planning.
What Devika's Imagination Creates
Devika's pre-colonial summit wasn't just personal indulgence. It was practice in imagining beyond constrained reality.
She's training herself to think speculatively. To create possibilities that don't exist in current frameworks.
And that capacity—to imagine beyond what is to what could be—is strategic leadership capacity.
Organizations need leaders who can do this. Who can hold both practical reality and imaginative possibility. Who can move between "here's what's achievable today" and "here's what we're building toward."
Imagination is infrastructure for possibility.
Next time you're in strategic planning, try this:
Before you dive into practical constraints, spend 30 minutes imagining freely.
What would you create if you could create anything?
Write it down. Don't edit for feasibility yet.
Then look at what you've imagined and ask: What piece of this is more possible than I initially thought?
That piece might be your next breakthrough.
Because organizations stuck in "how it's always been done" need permission to imagine radically different futures.
And strategy without speculation is just incrementalism.
This is lesson 24 in a 25-part series exploring insights from podcast conversations with leaders who leave the world better than they found it.
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