Let’s be honest: we don’t always get the luxury of planning when everything is calm, clear and certain. More often than not, planning happens in the messy middle — when the future feels murky – when the external environment is shifting fast, community needs are evolving, and decisions still need to be made. And still, we have to lead. We have to make decisions, and keep moving. You don’t need certainty to do that, you need the right orientation — and the right tools. We know this can feel overwhelming. But it can also be a powerful moment for courage, and creativity.
At PENN Creative Strategy, we sit alongside organizations navigating these very moments. Whether it’s a leadership transition, a funding cliff, or a world that just doesn’t look like it did five years ago (or even one year ago), we believe planning doesn’t require certainty — it requires intention.
Let Go of the Myth of the Perfect Plan
When the world feels unpredictable, the idea of making a multi-year strategic plan might feel absurd. Let’s start here: Planning does not require knowing exactly where you’re going or how you’ll get there. It requires:
- Clarity about what matters most
- Curiosity about what’s emerging
- Commitment to learning and adapting as you go
Instead of chasing the illusion of a “perfect” five-year plan, we help organizations build strategies that are responsive, and rooted in purpose.
We’re not here to predict the future — we’re here to prepare for it. That means naming what we do know, acknowledging what we don’t, and building strategies that are grounded in purpose, not perfection. Planning is a way to align your team. It is an opportunity to sharpen your focus, and make thoughtful choices — even when the path ahead isn’t fully mapped.
Tools to Help You Plan in Uncertain Times
Here are some practical approaches we often use with clients facing uncertainty. You don’t have to use them all — think of this as a menu, not a checklist.
Scenario Exploration
This one gets a lot of airtime for a reason. Mapping out 2–4 different, plausible futures — based on key uncertainties — can help you:
- Stretch your thinking
- See early signs of change
- Prepare for a range of outcomes
Scenarios don’t need to be highly technical. Even naming “what if demand doubles?” or “what if key funding ends?” helps you create strategy that’s ready to flex.
Near-Term Strategic Priorities
Instead of a 3- or 5-year plan, try defining strategic priorities for the next 12–18 months. Ask:
- What do we most need to learn?
- What’s essential to stabilize?
- Where do we want to take bold action?
This keeps your planning cycle shorter — but still purposeful.
Adaptive Learning Loops
Build in space to reflect and adjust. For example:
- Set quarterly or biannual check-ins to review your strategy
- Create feedback loops with staff, board, or community
- Track what you’re trying, what you’re learning, and what you’re shifting
When change is constant, learning becomes your superpower.
Anchor in Values and Purpose
When everything feels like it’s changing, your values are your compass. Use them to:
- Filter decisions (“Does this align with who we are?”)
- Communicate with clarity and authenticity
- Reconnect your team with the “why” behind the work
Purpose can be your north star and your grounding wire.
Strategic Questions Over Fixed Answers
We love helping teams frame thoughtful questions to guide their work. Questions like:
- What does “impact” look like in this moment?
- How do we stay responsive without losing focus?
- What risks feel necessary to take right now?
You don’t need to rush to answers. Naming the right questions can build shared understanding — and open new possibilities.
Contingency Thinking
Contingency planning doesn’t have to feel scary. It’s just about asking:
- What are the “triggers” or signals that might require us to pivot?
- What early warning signs should we watch for?
- What’s our plan B (or C) for critical areas like funding, staffing, or policy shifts?
This builds confidence — not paranoia.
Right-Sized Planning
Not every moment requires a full strategic plan. Sometimes, a smaller tool is just right:
- A decision-making framework
- A program-specific theory of change
- A one-page roadmap for the year ahead
The key is to match the tool to the moment.
We’ve found that organizations often thrive when they give themselves permission to move forward without every answer.
Leadership in Uncertainty
There’s a special kind of leadership that shows up in uncertain times, and it’s not about having all the answers. Instread, focus on fostering trust and reflection, and helping your team move with purpose.
In these moments, we encourage leaders and boards to ask:
- What is emerging right now that deserves our attention?
- What do we want to hold steady, and where might we need to shift?
- What can we try — knowing we can learn and adjust?
This is planning as learning — a mindset that honors both your expertise and your willingness to stay open.
Anchored in Mission, Open to Change
Uncertainty can feel destabilizing — but it can also be clarifying. Planning in this context isn’t about control — it’s about connection. Connection to your mission and to your team. To your community and the future you’re trying to build, even if you can’t see it all yet. You don’t need a crystal ball to plan well. You need space to reflect, tools to make meaning of complexity, and the confidence to take the next step — even if it’s a small one.
At PENN Creative Strategy, we believe that the act of planning — asking big questions, naming what matters, designing thoughtful steps forward — is in itself a hopeful one.
We’re here when you’re ready to take that step. Whether it’s for a strategic tune-up, a full planning process, or just a conversation to see what’s possible — let’s talk.
Because planning in uncertainty isn’t a problem to solve — it’s an invitation to lead with clarity, creativity, and care.
