Building for Reality, Not the 3%

I am mapping out several scenarios for how I want to build the community that will shape the development of my conversational role-playing game. At the center of that work is a tension I keep running into.

The tools and resources flooding the nonprofit market reflect a deep misunderstanding of the practical reality most fundraisers live in.

You can see it clearly in online spaces. LinkedIn threads. Reddit conversations. Message boards. It becomes obvious very quickly who actually works inside a nonprofit and who is speaking from a vantage point that is disconnected from day-to-day operational life in the United States and Canada.

This disconnect is not accidental. It is structural.

The business of nonprofits has been shaped by product development and market research norms that optimize for roughly 3% of organizations, those making more than $5 million in annual revenue. Most tools, certifications, conferences, and buying frameworks assume that level of resourcing as the baseline.

Even that framing is too generous. After nearly two decades in the sector, what I have seen consistently is that development shops, especially individual giving teams, tend to have fewer resources and less flexibility than other parts of the organization. I have worked with hospital systems bringing in hundreds of millions of dollars where the events team struggled to scrape together money for volunteer swag. Revenue responsibility does not equal budget authority.

That is the lived reality most tools are not built for.

When people talk about innovation, digital transformation, or artificial intelligence in this sector, they often skip over that constraint. But it is the constraint that shapes behavior, decision-making, and risk tolerance more than any strategy document ever will.

Why Scenario Planning Keeps Pulling Me In

I read one of the most influential planning pieces in my professional life just before the pandemic: How to Do Strategic Planning Like a Futurist by Amy Webb, published in Harvard Business Review (2019). I worked through it carefully at the time and later helped advise my former company as it began pivoting earlier than many organizations that were still treating disruption as theoretical.

What stuck with me was its infinite ability to ensure I was ready for anything.

The key idea in that piece is that traditional strategic planning leans too heavily on linear timelines and fixed horizons. Futurists like Amy Webb argue that uncertainty is not a nuisance to be minimized but a condition to be managed. In her framework, planning is not about setting a target year and then marching toward it. Instead it begins with understanding that the present moment is the only place we have abundant data, and that the further we look into the future the more uncertainty widens around us. This yields a conceptual tool called a time cone — the present at the point narrowing into multiple possible futures as you move outward in time. Strategy is built not on a predetermined date but on a set of plausible futures that emerge from what we know now.

In practical terms this means organizations benefit from thinking through scenarios that vary not just by likelihood, but by how they would feel, how they would force choices, and where they would stress current assumptions. Webb and others recommend framing these possibilities in narrative form. One simple exercise she describes is writing future headlines that assume a particular event has already happened. The headline is not a prediction. It is a sense-making device that forces you to take a hypothetical situation seriously and then work backward to what it would mean for strategy and operations.

For a small nonprofit this does not need to be complex. It can start with a list of plausible yet impactful events: turnover in fundraising leadership, a major economic downturn, a shift in donor demographic behavior, a successful or failed campaign, a sudden influx of unrestricted support. Then, for each one, take a moment to write, as if it were already true, what that headline might look like.

That single act forces a shift in perspective. Instead of reacting only when a scenario emerges — typically under stress and pressure from boards or executive teams — this method lets leaders psychologically rehearse responses in advance. It makes visible the tacit assumptions that often govern decision-making, and it surfaces questions that might otherwise only arise when timing and stakes are against you.

Once you have a small set of alternative futures articulated as headlines and brief narratives, you can start to see which aspects of your current strategy are vulnerable and which are resilient. That helps with two things that nonprofit leaders routinely grapple with.

First, where to focus attention. Not all plausible futures deserve equal weight. Some may hinge on external forces beyond your control. Others will reflect internal choices you can shape today.

Second, how to calm a nervous board or executive team when a disruptive scenario appears to be unfolding. Having pre-articulated what you anticipated and why you prepared for it gives you a shared language and reference point. It grounds anxiety in something tangible rather than leaving it to speculation or fear.

This approach does not eliminate uncertainty. Nothing does. But it nudges a team away from overly linear thinking and toward a practice where strategic judgment is exercised in a way that is grounded in both data and imagination. It bridges short-term operational choices and longer-term decision frameworks without pretending that one will unfold neatly into the other.

The mistake many nonprofit leaders make is treating uncertainty as something that must be solved before decisions can be made. The futurist approach outlined here flips that assumption. You do not wait for certainty. You practice judgment in advance.

What matters is not whether the exact headline ever comes true. What matters is what the exercise reveals about how your organization behaves when urgency arrives early and information arrives late. Who is empowered to act. Where trust already exists. Which decisions quietly require consensus and which ones only feel like they do.

Used well, this exercise becomes a way to focus attention. It helps leadership teams distinguish between noise and signal. It creates a shared reference point so that when something disruptive does happen, the conversation is grounded in prior thinking rather than fear-driven reaction.

For boards and executive teams, this is often where the real value shows up. The exercise offers reassurance without false confidence. It makes visible that uncertainty has been considered thoughtfully, not avoided. That alone can lower anxiety and improve the quality of discussion when stakes are high.

This is not about forecasting the future. It is about building the muscle memory to navigate it.