What destination have you selected? What direction are you currently headed? Sometimes, we must head opposite our destination, but we are still on course. During the New Year’s resolution phase of the calendar, it can feel that we have planned poorly; however, do not confuse destination and direction. If the journey is a priority, we deploy our wayfinding skills to keep moving, even when the best route suggests we revisit paths already traveled.
Planning
Celebrating Yesterday or Tomorrow?
Seeing and Not Seeing the Way
Wrong Route
Somebody planned to climb Mount Massive in Colorado’s Collegiate Mountain Range. They discovered the Highland Trail was not the correct way to the summit and left a note (graffiti) for their hiking companion to save them the experience of repeating their mistake.
What wrong turns have you made? How do you share your trail knowledge with others? What mistakes are worth leaving for others to encounter on their own, and which require notification in your judgment?
How might we point out what is worth noting and not be a constant flashing amber light of ‘caution everywhere?’
Horizon Lines
What horizon line has our focus? The houses sitting on the closest ridge? The mountains in the mid-ground? Is it the sunset taking place in the background? Depending on our mindset and the intended impact of our journey, one of these horizon lines might be more appropriate than the others. Is our expedition team aligned around the same horizon line? It might impact the supplies we procure in advance, the team we assemble, and the speed with which we proceed.
Future Me
Future me benefits when current me acts thoughtfully. Before a trip, I might make the bed with fresh sheets, clean, and leave a reasonable supply of food for my return. Current me might unpack my bag completely and leave items in easy-to-find locations so future me can pack without stress for the next adventure. Current me can wax skis, clean bikes, dry out muddy running shoes, place new batteries in the headlamp, and repair a small leak in the tent, so future me launches with a higher degree of success and enjoyment.
What actions and decisions can your current team make that would set up the future team for a higher degree of impact? How often has a topic or barrier been raised that never gets resolved, knowing it will ultimately be decided once it is an emergency (burning platform)? Have you served an organization that inherited disruptions that could have been avoided by the team that proceeded your tenure? What if your gift to the board/staff/members that follow is to wrestle with the obstacles they will encounter? Even if we cannot make definitive progress, we can leave a record of how we tried to iterate and what succeeded and failed.
My hope is that current you assumes a force for good mindset so future you can focus on the work that matters.
Blazing the Way
Somebody had to figure out how to put in the first path. Then it the trail was updated and perhaps improved. Maybe another individual found a better route. Eventually, a group decided to construct a road. It was not easy, but now buses, cars, and cyclists pass without considering the obstacles.
What paths have you blazed or improved? What is their impact? Does anyone notice anymore? If they are well-designed, perhaps the purpose is not to point out what was near impossible during construction.
Defined By The Unseen
We cannot always see the route to the summit. It might be visible on our map but not from our current location. Does that mean we abort the peak ascent? If we are committed to the journey, we move forward, wayfinding as we encounter each obstacle while focused on keeping ourselves oriented to the summit. Even when we lose sight of the pinnacle, we ascend, knowing the journey will forever change the context of the work that inspires us.
Time vs. Energy Management
What if we thought of planning as a calculation of energy management? What if we deprioritized the role of time in our planning efforts? What if we were more honest about where to focus our energy instead of what schedule we might reverse-engineer on a calendar?
We might assume the forest fire can be extinguished in 24 hours, but external factors may change the reality; a significant weather event, the inability to secure needed resources, or a more pressing fire closer to a town changes the energy we invest in fighting the current fire. There is a scenario where the first winter snowstorm ultimately extinguishes the fire. The ‘let nature take care of it’ option usually does not appear on the first draft of our timeline.
Definitism vs Indefinitism

Gapinvoid’s compelling insights on planning. Well stated and relevant to all. Most important, not planning in any form is the strategy certain to fail.









