Permission to Act: The Psychology of Effective Planning | LSW#59

Accuracy is not the point

Dec 12, 2024

We’re told that “proper planning prevents poor performance” and that “clear goals” are essential for success. But conventional wisdom often misses the real value in planning. What if a plan's real value isn't in its accuracy?

In a data-obsessed era, this is heresy. After all, isn't the whole point of planning to predict and control the future? Yet, when we examine how plans unfold in reality, we find something surprising: some of the most successful ventures succeeded despite starting with grossly inaccurate ones. Or even because of.

Consider Airbnb's original plan: renting air mattresses to conference attendees. Or Amazon's initial vision as an online bookstore. These "maps" were hilariously wrong about where these companies would end up. But they gave their founders just enough structure to start exploring.

An exclusive focus on forward-looking prediction accuracy often misses the point. And when executing a plan, paying too much attention to what’s not working can be counterproductive.

In today’s edition, I share two illustrative stories to challenge how you think about planning and its implications. As you contemplate the coming year, check your default stance through these lenses.

Hey! It’s Sheril Mathews from Leading Sapiens. Welcome to my newsletter, where I share strategies for getting savvier at leadership and work. Previous editions of this newsletter and articles from my blog are at the bottom of this post.

The power of imperfect maps

Nick Obolensky shares a Native American story of “magic buffalo maps”:

The North American Indians depended on buffalo for their survival. They used the meat to eat, the skins to build their tepees and the fur to keep themselves warm. The system of survival was fairly simple. They would set up camp and then hunt for buffalo.
The buffalo were not stupid – when the Cheyenne moved in, they tended to move out. So the Cheyenne had to hunt from their camp and then it was a simple trade-off – how far did they need to go in order to find buffalos with how much energy expended vs how much energy they would expend to move the camp closer to the buffalo herds. A ‘key success factor” was to find and kill buffalo, and to move camp in the right direction (when the buffalos were too far away).
The initiation of young men into the tribe included the test for them to go and find buffalo, kill it and bring it back. Such a day was full of great excitement, when the young men would have their faces and horses painted and, with loud whoops, they would canter off across the plain.
But the further they got from camp, the more uncomfortable they became and the lower their spirits and bravery sank. For many…this was the first time they had left the safety of the camp, and as the tepees got lower and lower on the horizon behind them, so too often did their courage.
When the tepees were low on the horizon, more often than not the young men would pull their horses into a turn and ride a wide and long circle around the camp, looking far onto the horizon and yet keeping the tepees just within sight. They would come back late that day to tell the chief that the buffalo were no longer in range so he had to move the camp.
But the chief would send them to the Medicine Man saying there was a ‘magic’ buffalo map that would help them. So they went to the Medicine Man and he pulled out of his tepee a crinkled piece of buffalo skin with strange markings. He smoothed the “map” out on the ground and said:
Pay attention. This map will help you find the buffalo. You see this mark here - this is where we are now. You see this ridge here – this is that line of hills low on the horizon over here. This mark here is the mountain you can see way over there. You will need water for your hunt, and you will find it at this point here. And you will find the buffalo in this region here…
With that he gave the map to the young men, who with renewed courage and much whooping would gallop off and disappear over the horizon. One or two days later they would reappear with a buffalo. And there would be great celebration and recounting of deeds and adventures they had along the way.
The old Medicine Man would come and say ‘Can I have my buffalo map back please…?’ and more often than not the reply would be ‘I do not have it, Running Bear had it last I think … But anyway, did you hear how we …’; and he would then ask Running Bear ‘Do you have my buffalo map please …?’ And the reply would be, ‘No, I gave it to Stalking Wolf, but did you hear about the adventure and the person giving it back would say ‘Many thanks! Oh, by the way, the water was not here, it was there, and the buffalo were not where you said they would be, but we found them over here ….’
The moral? Much of what is written in this book… can be simply seen as a buffalo map. It is not so much the truth it proposes that is important as the encouragement it can give to venture beyond a horizon, and to go further than one would normally feel comfortable … and when you cross that horizon you will be in a new place and see things differently and further than you have ever before.

— from Complex Adaptive Leadership

Cartographic myths

In organizational strategy, Karl Weick shows how simplified models, however imperfect, drive effective action using what he calls "cartographic myths":

What is fascinating about organized life is that small structures…, general presumptions, and incomplete expectations can all lead to large outcomes and effective action.
The way in which this happens I have chosen to call "cartographic myths", in honor of the wonderful story in which a Hungarian army unit, lost in the Alps, finds a map, and follows it to safety only to discover that it is a map of the Pyrennes and not a map of the Alps.
The heart of a cartographic myth is the belief that whatever map one has in hand or in mind, is a sufficiently credible version of the territory, that one can act intentionally. The important feature of any map is that it leads people to anticipate some order "out there". It matters less what particular order is portrayed than that an order of some kind is portrayed.
— from Sources of Order In Underorganized Systems

These stories reveal key aspects of our psychology: we don't need perfect information to take action. We just need enough structure to feel safe stepping into the unknown.

This has powerful implications for how to think about planning:

1. Plans are permission slips

The most important function of a plan isn't prediction - it's permission. Like the Cheyenne hunters with their "magic map," we need psychological scaffolding to venture beyond our comfort zones. A plan, even an imperfect one, provides that structure.

It explains why many successful entrepreneurs started with business plans that looked nothing like their eventual companies. The plans weren't valuable as predictions - they were valuable as permission slips to start exploring.

2. Movement creates clarity

We think we need clarity before we can act. But the opposite is equally true: clarity comes from movement. The Hungarian soldiers found their way not because their map was accurate, but because the act of following it forced them to engage with their environment and learn from it.

This is why "analysis paralysis" is dangerous. The perfect map isn't waiting to be discovered through more research - it can only be created through action and adjustment.

3. Delusion as productive

Sometimes, acting on a flawed map is more useful than having an accurate one. Why? Because perfect accuracy can be paralyzing. If the Cheyenne hunters had known exactly how far they needed to travel and how dangerous it would be, they might never have left camp.

This isn't about self-deception. It's about creating useful simplifications that enable action.

Think of it like the simplified maps in subway stations. They're technically wrong (they distort distances and geography), but they're more useful than geographically accurate ones. It's the distortions that actually make them useful.

4. Confidence, not certainty

Certainty is fragile. When reality deviates from expectations, it collapses. Confidence, on the other hand, thrives in ambiguity. It’s the belief that you’ll figure it out, even if the map is wrong.

Build self-confidence (or the more accurate concept of self-efficacy) by focusing on your ability to adapt rather than predict.

5. The trap of accurate maps

The need for a perfect map often reflects our desire to avoid responsibility. "The map was incorrect" is easier to accept than "I made a mistake."

Recognize when you’re using the quest for the perfect plan to delay action. Accept that the map will never fully match the territory.

6. Flaws as intelligent feedback

A flawed map isn’t a failure — it’s a feedback mechanism. When it doesn’t work, it reveals something about the terrain and teaches how to navigate it better. Each mistake refines your understanding of what works and what doesn’t.

The key is viewing your plans as hypotheses to be tested rather than prophecies to be fulfilled.

7. Choice in map-making

While it's tempting to borrow others' maps — especially "proven" formulaic ones — there's real value in grappling to create your own. The struggle of map-making forces you to clarify what matters to you and builds a stronger sense of agency.

Even when following others' paths, explicitly acknowledging this as an active choice builds power.

Putting it into practice

When planning a career move, a project, or a business venture, consider:

The plan doesn't need to be right. It just needs to be useful enough to get moving.
The best time to make a new map is while exploring the territory, not before.
When reality disagrees with your plan, that's not failure - it's intelligent feedback.

The most dangerous map isn't the wrong one. It's the one that keeps us in camp, waiting for certainty that never comes. What "map" can you draw - however imperfect - that will give you permission to begin?