Most strategic plans follow a familiar formula: assess where you are, define where you want to go, and plot a path to get there. But what happens when the future is too uncertain or full of possibilities for a single path to make sense?
That’s the question behind the Odyssey Plan, a framework developed at Stanford University to help individuals imagine multiple versions of their life over the next five years. Each version is viable, each built on different assumptions, and none positioned as the “correct” one. Created as a personal reflection tool, the Odyssey Plan has gained traction among professionals looking to expand their thinking beyond traditional goal setting.
Yet its most powerful application may lie outside the realm of personal development.
For cultural organizations and creative enterprises navigating a rapidly shifting landscape where audience behaviors, funding models, and social roles are all in flux, this approach offers something many strategies lack: room to think expansively.
By adapting the Odyssey Plan to the context of cultural leadership, organizations can move beyond incrementalism and explore what they could become, not just how to improve what already exists.
A Different Kind of Strategic Planning
The Odyssey Plan was first introduced through Stanford’s Life Design Lab and the popular course Designing Your Life. The premise is simple: individuals map out three distinct five-year futures. One continues along their current trajectory. Another assumes their current path is no longer available. A third imagines a future where practical constraints—financial, reputational, and logistical—don’t apply.
When this model is adapted to organizations, particularly in the cultural sector, it shifts from a tool of personal reflection to one of institutional foresight. The exercise encourages leadership teams to challenge assumptions, explore unexpected directions, and identify latent aspirations.
Unlike traditional strategic planning, which tends to focus on optimization and risk management, this model opens space for redefinition. It emphasizes curiosity over certainty, exploration over prediction.
Applying the Framework
Consider how a cultural organization might use this approach to articulate three strategic paths:
Path One: Evolve the current model. A museum scales its digital programming, invests in audience data, and expands regional partnerships to strengthen existing value propositions.
Path Two: Reimagine the model. The same museum shifts from exhibition-making to community-driven storytelling, using its space and staff to support participatory cultural practice.
Path Three: Explore radical potential. The museum becomes a global platform for experiential learning, collaborating with scientists, artists, and technologists to redefine cultural experience.
Each path is developed in concrete terms: programs, partnerships, revenue models, capabilities, and risks. The aim isn’t to pick one immediately. It’s to explore the spectrum of what’s possible—and in doing so, clarify what the organization truly values.
Strategic Usefulness
The Odyssey Plan can be embedded into strategic retreats, governance sessions, or scenario planning exercises. It is especially useful when organizations face inflection points—such as leadership transitions, changes in funding ecosystems, or shifts in public engagement.
Rather than asking “What’s our next step?” this approach prompts deeper questions:
- What assumptions are driving our current direction?
- What would we pursue if we weren’t protecting legacy models?
- Which version of ourselves are we most afraid — or most excited — to explore?
It also encourages organizations to build narrative capacity: the ability to tell compelling, coherent stories about different futures to boards, funders, collaborators, and the public. In a sector where relevance is often linked to imagination, this becomes a strategic asset.
Beyond the Comfort Zone
One of the biggest obstacles in strategic planning for cultural organizations is the pressure to be reasonable. The Odyssey Plan introduces a discipline of structured unreasonableness — it invites leadership teams to test bold ideas within a grounded framework. The Plan provides a shared language to navigate uncertainty and it reminds institutions that, in culture as in design, innovation often starts by asking better questions.
