Planning

One or Seven Flights

Does our mindset change if our scheduled flight is delayed, depending on whether we are taking a short flight or embarking on an international itinerary that requires 7 flights to reach our destination? I have seen passengers deboard a delayed commuter flight because they were going to miss their meeting in the destination airport. I have also witnessed passengers who are going to miss a key connection continue their journey, knowing they will have to explore complicated alternative itineraries.

Our mindset is often influenced by both the proximity to our goal and the estimated timeline for reaching it. When we embark on an adventure with multiple phases, we might assume an infinite mindset. We will get there when we get there. When we plan a short-duration journey between two nearby locations, it is easier to adopt a fixed mindset in which the timeline is predictable and the destination feels visible from our starting point.

How might we remember that an infinite mindset might serve us well, even when our schedule and devices tell us we are running behind?

Legacy

What we leave behind after the project is over might say as much as what we accomplished while we were trying to achieve our goals.

Hiking in the Dolomite Mountains in Italy, World War I trenches, fortifications, and defensive strongholds are abundant. The amount of barbed wire strung across ridges and peaks is remarkable. Some of it is strategically embedded, while other strands seem to have slipped and tumbled to temporary resting spots.

How might we recognize that our success might get the headlines, but the legacy of our work may be judged by what we leave behind?

Pathways

When the pathway is smooth and well signed, it gives us reassurance that our route is viable. When it is hard to follow and there is a lack of signage, it can be discouraging. What type of experience are we trying to curate? If we want to create delight, it might be best to invest in a well-designed pathway. If we are seeking those who think and act differently, then a sketchy trail that causes moments of disappointment may ensure we attract the true adventurer.

Before You Fly

It is best practice to know what type of aircraft you are flying before taking off. How do you get out of a flying aircraft to determine its type once in flight?

The same is true with your organization. Best to be able to describe its Magnetic North (purpose, vision, mission, and values) before you decide to launch into strategic planning, expansion, capital campaign, or commitments for the future. If we do not know who we are, how are we going to wayfind in a way that accentuates our strengths?

First Glance

Upon first sighting an iconic peak, do we start climbing? Do we presumptively assume we have the right equipment, sufficient fuel, a safe weather window, and critical beta to launch our summit attempt?

Most expeditions prepare and conduct research before launching (see the Hudson’s Bay Company philosophy). How might we balance our enthusiasms with a culture of curiosity? Some opportunities need to be seized in the moment, such as catching a foul ball in the stands at a baseball game. Most epic opportunities allow for a moment of reflection and consideration.

How might we build tools to navigate between immediate actions unhindered by the thought process and preparing to act?

Choice

What is the right number of choices to feel a sense of autonomy but avoid overwhelm? If one visits an Apple Store, there are typically three or fewer models available in any given product line. The intention is that one of these models will fit the needs of the majority of customers, and there is always the opportunity to customize online.

When you ask your stakeholders for advice, do you offer two or three thoughtful choices? Or do you overpower them with a carnival-prize-tent level of options?

Decomposing Light and Decomposing Planning
Lesson in decomposing light
byu/Blues_Fish innextfuckinglevel

What might we learn from the decomposing light demonstration? Our perspectives change when we eliminate certain inputs from our environment. Nonprofit organizations that hold a planning retreat but decide not to include all staff members or to refrain from inviting the advisory council are effectively narrowing the range of ideas that will be illuminated. We do not have to invite everyone to every session, but when we are deliberately seeking a generative mindset, it might be valuable to pair people who do not meet in typical sessions.

How might our willingness to seek out weak ties actually strengthen the process?

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Vanishing Point

We can map out our route until we cannot. There is a moment at which our planned itinerary contains a gap or uncertainty. It may appear that we are traveling a continuous path, but serendipity and detours will appear, even in the most detailed schedule of events. How might we expect the unexpected and embrace the elements of our plan that fall into place?