Planning in 2025 has felt like packing for a trip where the destination keeps changing and you have absolutely no idea what the currency is, much less whether the current exchange rate is any good —and let’s be real, 2026 isn’t looking much clearer.

The Question: How do we do strategic planning in a time of elevated uncertainty? 

Because we all have dreams to build, things to do, and businesses and people depending on us, so standing completely still isn’t really an option. 

The Humans

First things first. Attend to the humans. The people matter. The world is not operating in a “status quo” state right now. Do not make the mistake of assuming that the people ARE operating in a “status quo” state.  

• The humans are stressed and more fragile than usual. There is just a lot going on right now, and it is hard to find stability anywhere. Even if you are creating a utopian professional environment for them at work, most of them are experiencing above-average cumulative stress. AND we are coming into the holiday season, which is a predictable juxtaposition of joy and stress wrapped up with a big red ribbon and covered with gravy. 

• What does this look like in real life? Shorter fuses. Moments of distraction. Dissociation and apathy (signs of burnout). Less lightness and laughter. Higher probability of misunderstanding, hurt feelings, and resentment.  

• What can you do about it? When uncertainty is high and budgets are tight, the connective culture-building stuff is one of the first things to go. Do not make this mistake. This doesn’t mean you all need to be doing karaoke every Friday night, but don’t skip opportunities to celebrate the end of the year, recognize people, and connect. Specifically, when it comes to strategic planning, do not skip the connection, level-setting, and learning portion of the strategic planning retreat in an effort to get to the problem-solving part faster. Knowing who and what we are invested in is more important now than ever.  

Futuring: A Strategy Mindset Shift

Strategic planning has always been a lot of energy and good intentions, mixed with some data, a splash of projection, and a sprinkle of wishful thinking. If we are honest, most strategic plans are just wishlists with deadlines. Did we ever really know what was going to happen in 10 years? No. Were we able to pretend that we knew with more confidence? Probably, yes. 

In this moment of unprecedented uncertainty, let’s borrow a page from futures study and Strategic Foresight to shift our view of strategic planning to something that feels a little more do-able in the chaos of the now. To be clear, this is a suggested mindset shift that can help individuals and teams unstick themselves from the “freeze” response that can happen with increased uncertainty. We are not promising to solve all your problems. We are hoping to offer a gentle nudge toward an alternative perspective/mindset that we hope you will find helpful. 

Note: For those of you who are unfamiliar with creative futuring, futures study, and foresight, there is a deep, deep rabbit hole waiting for you, and it is fascinating. But, to level set expectations, and to keep the Foresight purists from coming after me, here is the disclaimer. This is the baby-baby-baby conceptual introduction to a robust area of study and practice.    

In the broadest strokes, traditional strategic planning looks like this:

It is an extremely linear timeline, anchored by projected goals and objectives. There isn’t much space in a linear model to conceptually accommodate flexibility, agility, and the unknown. 

Enter, the futures thinking cone model. We like exploring a futures model for a couple of reasons.

1. Relevance: It feels very relevant to what the world is experiencing right now. In our conversations with leaders from all sectors, there is an abundance of “What the heck are we supposed to do when so many things are up in the air?!?!?”
2. Driven by HUMAN Ingenuity: Strategic futuring is about harnessing human creativity, imagination, and storytelling to unlock possibility, inspiration, and motivation.

The foundational concepts are simple and intuitive.

1. The farther we project into the future, the greater the uncertainty, hence the broader the range of possibilities.
2. The closer we are to the present, the more tactical and task-oriented we can be in our planning. See the image provided by Amy Webb, quantitative futurist and CEO of Future Today Institute, in the Harvard Business Review (article linked).
3. The goal is not to predict the future with precision, but rather to take a proactive position that works with uncertainty to make better decisions in the present by considering a range of future possibilities.  

If this makes sense to your strategy brain, expand this 2D model to its 3D version and layer on considerations of projected, probable, plausible, possible, and preferred. 

Image courtesy of IDEO Blog Post: How to Think Like a Futurist: A Leader’s Guide to Strategic Foresight and Better Decision Making – Read this article as your starting point down your Strategic Foresight rabbit hole!

Think of these as progressively deeper dives into the uncertainty and creative-imagining thought-experiment pool.

1. Projected: Futuring challenges us to be realistic with our projections. In a futurist frame, projections refer only to estimates closest to the now, tied to realistic probabilities. How close to the now? It depends on your industry, business, and risk tolerance. What is reasonable certainty? It depends. But be real. What can you predict with a high level of certainty?
2. Probable: Inject a dash more uncertainty. If circumstances were to progress much as they are now, what would the future look like? This is in the same vein as “traditional strategic planning.” What do 5 and 10 years look like if we assume minimal disruption?
3. Plausible: Okay….going a little deeper into the uncertainty pool. Expand the realm of possibility a little bit wider….assume less certainty…..what else could happen? What things have come out of left field historically? What are the considerations that are unlikely, but not craaaazzzy.
4. Possible: This is where we dip our toe into crazy-town. How crazy? It is up to you. Worldwide pandemic? A new technology that is not even on our radar at the moment? Zombie apocalypse? World peace, and now no one cares about status or designer clothing anymore.  

All of this thought-experimenting to finally get us to PREFERRED. Preferred is a dialed-in range of possibilities that we like. One that feels flexible, agile, realistic, and motivating. 

In Conclusion

As we all careen into the end of 2025 and start seriously thinking about 2026 and beyond, consider giving your strategic planning plan a little shake-up. 

You know us —we are always going to be telling you to invest in and focus on the humans! 

1. Invest in Connection: Don’t obliterate the culture-building and connection-driving efforts and budgets. Every industry and business is driven by its humans. 
2. The Power of Human Creativity: Combat uncertainty with an invitation to creative strategizing.
3. Experiment with Baby Steps: You don’t have to do it all. You don’t have to be a strategic futuring expert to incorporate some of the principles into your planning. You don’t have to fully adopt a totally new system. Don’t let perfection be the enemy of progress. You can try a little piece and see if you like it. You can try it and decide that it’s total crap and not for you. All of these options are okay. 

Happy Strategic Planning!

Let us know how it goes, and as always, reach out if we can be helpful.

XO,
AB

P.S. If you want to dive deep into strategic futuring, check out the articles linked, and here are a few more direct links and references for your research pleasure.

Future Today Strategy Group, Founder & CEO, Amy Webb
Copenhagen Institute for Futures Studies
What is Futuring? How Leaders Can Prepare for Uncertainty – IDEO U

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