When we highlight an opportunity that contains tension, we are captivated by the narrative that follow. A single blade of grass is less remarkable when found on a lawn. Place the grass pushing through a broken section of asphalt and the struggle creates tension. We are uncertain of the outcome and more likely to be captivated by the journey.

We might incorporate the same mindset in our planning. The outcome of a shopping run to the grocery store is low risk. A strategic plan that considers an initiative that might transform a community increases the tension. Our fans are engaged when we share goals that are resonate but not common and repetitive. We are working on addressing problems that are challenging to solve. What is our role in the solution?


Do we need flexibility or are we committed to a specific approach? If versatility is necessary, then best to carry a Swiss Army knife. If we are certain, then a flat head screw driver will work. But if drop the screw into a tight space the tweezers on the knife would be helpful. Or, if we need to read small print the mini-magnifying glass could be handy. At a certain point, even the Swiss Army knife cannot possess all the options. So, how certain are we that we have the right tool for the job? A specially designed instrument can be a powerful resource. A pair of alpine downhill skis will get us to the bottom of a ski hill fast. However, if we need to ascend the mountain afterwards, the skis are a major liability. Unless we have an alpine touring setup with climbing skins and a binding that transitions to climbing mode.

Specialized equipment or multi-tools? A good question to ask before we launch on our next adventure.


If we have confidence in the future, we can rely on data and numbers to guide our decision-making. If the future is ambiguous, we are better served by employing creativity and wayfinding. Numbers become irrelevant if we do not posses a map and the destination is uncertain. Fantasy sports leagues work because we can agree on what to measure and how to determine the winner. Predicting what to track in a box score for 2021 is less certain. Based on the number of trips I had pre-booked in 2020, prior to the pandemic, I was was planning the wrong course of action. The reality of the world I encountered required a pivot to a new perspective.

How are you planning for 2021? Are you using a fixed mindset and goals linked to data? Are you approaching it with an open-mindset with flexible goals? Are your objectives tangible or experience based? Are you employing a scorecard or a human-centered approach?

We can be presented with new scenarios in seconds. Our focus shifts to a new reality, with different rules, and altered outcomes. In the words of Don Cheadle’s character Cash in the movie Family Man, “Well, you’re working on a new deal now baby.”

Planning Might Change Our Destination

When take time to plan, we are better prepared to navigate the terrain we encounter. We can ford every stream we approach or discover that a bridge exists along the route. If we are on foot, the outcome of using the bridge is we move a little faster and keep our feet dry. If we are running a railroad, the impact is the difference between reaching the end of the line and continuing our journey.

Scott Young has an engaging article about the power of planning, published in the SmartBrief on Leadership Newsletter. I encourage you to check out both resources.

Fire Lookout

Fire lookouts do not universally occupy the tallest peak, the most alpine perch, or the easiest to access. When well placed, they offer a panoramic view, a platform where multiple mountain ranges might be visible, providing a higher value to those assigned to fire lookout duty.

When we commence strategic or scenario planning, perhaps the best location (or mindset) is the proverbial fire lookout. A place that affords us an informed view of the terrain around us. Maybe a bit set back from the iconic landscape that defines our work. Many organizations refer to their off-site gatherings as ‘retreats’ an opportunity to disengage from our sense of place and view the environment from a new perspective. It is a chance to recon routes we wish to travel on our next adventure. We posses a more informed sense of the landscape by being removed from it instead of stopping mid-trail and speculating during our journey.

Critical Moment

A 200-mile cycling competition might start as a large pack until the peloton encounters an obstacle. The selection might be forced by a significant climb, strong crosswind, change in riding surfaces, a team employing tactics, or a crash. The race splits into smaller groups, or even individuals riding solo. Ultimately, the race may finish in multiple groups, or it may come back together for a sprint. Competitors must assess if an event represents the critical momentDo they need to accelerate to remain at the front, or do they believe the group will come back together further down the road?

How we assemble ourselves and prepare for the competition will ultimately be impacted by our assessment of the critical moment. If we believe the race will end in a sprint, then it will change our preparation compared to a competition that will be decided by several long climbs.

The same approach holds for our organizations. Are we preparing ourselves for the critical moment? Even if we do not know what it might be, how it will unfold, and when it will happen? Are we building an organization that can adapt, pivot, or stays the course? Are we discussing other iterations and disruptions? Assuming that we will continue forward at the same pace, cadence, power, and tactics will leave us behind.



Sometimes the journey is difficult and we seek safety and certainty about the outcome of the adventure.  Sometimes the conditions turn, our assumptions prove wrong, and the final result tips towards failure.  When these moments finally pass, we are able to reflect back with sharper details and sensations than most moments.  I recall how cold my hands felt at the end of a winter training session when I under dressed and the headwind generated polar windchill factors.  I hunker down when I feel intense heat, memories of crawling into structure fires as a volunteer firefighter.   I skip a breathe thinking of my front road bike tire unable to maintain traction as I slid across the pavement, five hours into a twelve hour cycling competition.  I see traces of the cycling wound, my fingers are haunted by a phantom numbness, and the heat from a bonfire sets off a reflex to go low.

These memories from our wildest adventures add depth to our being.  They do not define us because we will find new journeys with equally perilous outcomes.  To believe we are defined is to suggest that we have finished exploring.  Seek out the difficult and challenging.  The reason we continue to plan and set goals is due to the human element and that is what adds depth to the journey.


Profound Planning in History


I have seen versions of the above image in history textbooks.  A quick glance and brief text were enough to know that this was a harbor constructed to support D-Day Invasion on Normandy.  An impressive number of ships, lots of activity, and roadways stretching into the harbor seem to tell the story.  What I did not know was the detailed plan behind the harbor.  Nicknamed Mulberry B is was located in Arromanches, France on Gold Beach with the intention of serving the British and Canadian forces.  The harbor was completely devised using old ships scuttled in place, and pre-fabricated pieces flooded on-site as no historical harbor existed in the location.  It was planned over a year in advance, constructed in England, barged over behind the invasion forces on June 6, 1944, and almost finished on June 19th when a ferocious storm hit it.  Mulberry B survived while the United State’s harbor, Mulberry A, on Omaha Beach was abandoned due to storm damage.  All Allied supplies and equipment disembarked upon this floating structure, thoughtfully designed to adapt to 30 feet of tidal flow.  Today, a few remnants sit above sea level, enough to give perspective to the magnitude of Operation Overlord.  The Allied forces understood that getting personnel on the beach was the first obstacle.  The second challenge was hastily placing enough equipment and supplies on-shore to avoid the Axis time to pin the Allied troop against the Channel.


It is worth remembering the power of thinking about the steps beyond the next step.  The actions that are required to allow us to thrive once we have reached a critical benchmark.  The planning and execution of a temporary harbor made a profound difference to the outcome of World Wat Two.

Long Term Progress

Seth Godin’s asked: What are you willing to give up today in exchange for something better tomorrow? Next week? In ten years?

The immediate place this resonates on most social sector agendas is during the financial report.  How often has the balance sheet driven the mission of an organization?  When did doing what is right become the brave thing to do?  Are we perpetuating a problem so our coffers stay full or are we willing to tackle obstacles while acknowledging that our efforts may or may not work?

In my experience, while brainstorming during long-term visioning exercises the most frequent organizational wish list item: an endowment/reserve fund (bigger endowment if one already exists).  It is not always the first thing mentioned but once the words ‘endowment’ are put forth there is a chorus of support.  As if the idea of financial security is more important than solving the very problem/furthering the opportunity the enterprise was founded to address.  Protecting the organizational shield outranks the desire for great quest.  Yet, I am short on stories about the knights of the roundtable who stayed home and collected membership fees.

Some people will risk a lot in pursuit of long-term progress.  Embarking on the journeys that are uncertain.  This is the edge where we should be planning.  Being self-sustaing but unremarkable is not original.  Far too many groups have traveled the path and their legacy (at best) is a mountain full of treasure guarded by a dragon and off limits to almost everyone.

What are you willing to give up today?  Why does it matter?