The Wisdom of Insecurity in the Roadmap

The quarterly roadmap sits in a Notion doc, color-coded and confidently detailed. Q3 shows "AI Integration Phase 2." Q4 promises "Enterprise Scaling." The executive team nods. Investors are satisfied. The team knows exactly where they're going.

Except they don't. And they never did.

Alan Watts wrote about "the wisdom of insecurity"—the understanding that our craving for certainty is itself the source of anxiety. We build elaborate plans not because they work, but because they make us feel safe. The roadmap is not a map; it's a security blanket.

In product strategy, this manifests as the tyranny of the predetermined future. Teams commit to shipping features months in advance, then spend those months defending decisions made with incomplete information. The market shifts. User needs evolve. Technology changes. But the roadmap remains, a monument to outdated thinking.

What would it mean to embrace insecurity in product planning? Not chaos—insecurity is not the absence of structure. Rather, it's the recognition that structure must be responsive, not rigid. It must flow with reality rather than fight against it.

Consider the difference between a river and a canal. A canal is certain, predictable, controlled. Water flows exactly where engineers decided it should. A river is responsive—it finds the path of least resistance, adapts to the terrain, changes course when obstacles arise. Both move water, but only one is alive.

Product teams need river thinking. This doesn't mean abandoning planning—rivers have patterns, seasons, reliable behaviors. But it means holding plans lightly, as hypotheses rather than commitments. It means building feedback loops that allow the roadmap to evolve as quickly as understanding does.

The hardest part is cultural. Organizations reward certainty. Executives want commitments. Investors want timelines. The PM who says "we'll discover the right path as we go" sounds unprepared compared to the one with a detailed 12-month plan. Yet the detailed plan is often just elaborate fiction.

There's a middle path: clarity about principles without rigidity about tactics. Be certain about the problem you're solving and the users you serve. Be uncertain—deliberately, productively uncertain—about the specific features and timelines. This is not weakness; it's adaptation.

In practice, this looks like quarterly themes instead of feature lists. It's OKRs that measure outcomes, not outputs. It's a roadmap that evolves based on what we learn, not what we predicted. It's the confidence to say "we don't know yet" and the discipline to find out.

The wisdom of insecurity is recognizing that the future cannot be controlled, only engaged with. The best product teams don't predict the market—they respond to it faster than anyone else. They win not through certainty but through learning velocity.

Your roadmap is probably wrong. That's okay. The question is: how quickly can you update it when you discover a better path?