Mental cartography

Ryan James Spencer

Organizations that learn are organizations that, luck granted, succeed. While success requires sharp teams, healthy cultures, sound strategies, and adequate resources, what separates thriving organizations from stagnant ones is their ability to adapt and learn from experience.

But excellence requires action. Competitors are constantly innovating and improving. This is physics: systems naturally grow in entropy towards equilibrium. In other words, a system without intentional changes stabilizes, which is ultimately decline in a competitive environment.

The framework

The framework works through two complementary approaches:

  • Mental agility and cartography allows us to thrive in an uncertain world.

    • Failure is inevitable, but that shouldn't stop us from observing, deciding, and acting
    • We can be conscious of our feedback loops, and tighten them to rapidly learn
    • As we learn, we are building up, throwing out, and changing all kinds of maps to help guide us
    • Every round of a feedback loop is an experiment, and it is possible to design experiments to maximize learning
    • Every action we make has costs and risks we should be mindful of, but the most important cost is opportunity cost, and the most important risk is stagnation
    • Quitting and pivoting early is important to keep moving in the best direction
  • Keeping focus on outcomes and impact allows us to build products users love

    • Asking excellent questions is an art that leads to rigorous thinking, and the most important question is always "why?"
    • We focus on the work that matters, identifying opportunities that will give us an order of magnitude or more returns
    • High performing teams support one another, building each other up with true curiosity and kindness
    • We need to design to make quitting and pivoting trivial through concepts and systems thinking
    • To avoid getting lost in design, we need to make things tangible as quickly as possible
    • High performing teams know how to radiate intent, spread information, and realign continuously

Together, these approaches give you the tools to experiment with confidence rather than guess and hope.

Mental agility and cartography

The only man who never makes a mistake is the man who never does anything. -Theodore Roosevelt

You are going to fail. The sooner you can embrace this fact, the sooner we can get to the real work. No one has perfect predictive power, but we can sharpen our predictive abilities by being clear about our mental models and feedback loops, and ruthlessly updating each. The only true failure is failing to learn from the failure or mistake.

None of us can tell the future, thus every decision we make is a bet. And whenever you are heading into the unknown, it helps to have a map. Whether we can find existing maps or have to make them ourselves matters little, as maps are tangible artifacts that we can share, increasing our collective knowledge rather than pooling that knowledge in a single person's head. A mental map is anything that helps you understand the system you're playing with or in.

Maps can be information dense and come in various types and sizes. There is no one true map, and "the map is not the territory," as Alfred Korzybski put it, which is to say that maps can never exactly capture reality. Nonetheless, maps help tell us if we are on track and what alternative paths we can explore.

All models are wrong, but some are useful. -George Box

The good news is that all of us are fundamentally learning systems. We are always picking up new information that we can use to drive more accurate outcomes. We do this through identifying and optimizing feedback loops around us, which gives us richer, higher quality, and fundamentally more data we can choose to integrate with our maps. Consult your maps, make predictions and decisions, act, update your maps.

Sound familiar? That's because it's effectively the scientific process. We take available data, make a hypothesis, run an experiment, and adjust our available knowledge based on the result. Each feedback loop provides different input or varying levels of fidelity. The tighter these loops, the more we are acting and, by extension, learning.

Designing effective experiments

In this sense, everything is an experiment. Experiments, and by extension bets, should be safe, small, cheap, and quick:

  • Safe means avoiding ruin, allowing us to see another day of experimentation
  • Small means being minimal as can be to provide valuable insights, where size is a judgment call where time and resources are used wisely
  • Quick means tightening the feedback loops such that we get information before the surrounding context changes altogether
  • Cheap means using minimal resources (time, money, people) to gain valuable insights

To maximize our learning, we should design experiments that:

  • Take place in new territory with credible opportunity to advance toward desired goals
  • Are informed by available knowledge and hypothesis-driven
  • Exist in contexts that present opportunities to learn something meaningful
  • Are small, cheap, safe, and fast to execute

And for any bet we make, it is imperative we ask "why?" If we aren't sure why we are doing something, we are most likely reacting, and if we are reacting we won't be learning as much.

When to quit and pivot

The only mindsets worth keeping are the useful kind. Making steady progress means being quick to quit or pivot from our efforts when they are no longer serving the intended purpose or achieving the predicted outcomes we set out to achieve. One way to know when to quit, pivot, or discard is to decide on "kill criteria"—chosen signals that, if identified, would allow us to move onto other more critical tasks. Good kill criteria are straightforward to measure, have high signal-to-noise, and are fundamentally tied to explicit decisions that help change course.

In due time, with more bets hitting the mark, we make steady progress like a ratchet, snapping into place as it is wound, never unwinding unless the tension is released on purpose. This requires being vigilant with our subconscious and being willing to make change.

Being exceptional at running experiments and making changes means being exceptional at considering the costs and returns of our efforts. We must consider hidden costs such as opportunity cost—what we give up by spending time on the wrong things. By taking calculated risks and making intentional decisions, we avoid the biggest risk of all: stagnation and irrelevance in a changing world.

Outcomes and impact

It is possible to commit no mistakes and still lose. That is not a weakness; that is life. -Jean-Luc Picard

As we make steady progress, we need to be mindful of the outcomes and impact of our work. Success requires mental flexibility—the ability to discard and rebuild our mental models, test our claims, and adapt no matter how much uncertainty or ambiguity we face.

The art of asking why

It all starts with the why. To do our best work we must understand the motivating drivers deeply, which will allow us to work intentionally. Deliberate action means we aren't spinning in circles, doing work that doesn't push us further toward being an elite team with exceptional outcomes.

To discover these motivations, we must practice the art of asking incredible questions. Part of this art is possessing genuine curiosity and wonder for the world around us. To be exceptional, we must deeply want to support one another, and that means helping each other by being kind as opposed to nice, candidly expressing our thoughts to help build up and refine the thinking and work of our teammates.

This rigor can also be applied to what outcomes we want to pursue, pruning the outcomes that don't lead to an order of magnitude or more improvement. We focus on the work that matters, identifying opportunities that will give us outsized returns and starting with the critical tasks first.

Systems thinking and design

We need design to make quitting and pivoting trivial. But how do we actually do this without creating chaos or wasted effort?

This is where systems thinking becomes powerful. A system is a collection of elements with relations between them. This simple but powerful idea lets us view the world as interacting systems, cutting through complexity to see the essential patterns underneath.

Given this understanding, we can approach designing differently. By designing, we mean strategic architecting of your approach to encourage rapid creation and iteration. The emphasis is on designing for flexibility and learning—you're designing the way you'll figure things out as much as the final outcome. This means building modular, adaptable solutions where you can create, delete, and change things freely as you learn. This applies whether you're designing your approach, your solutions, or both.

Once we have motivations and rigorous thinking, we can start designing. The crux of good design is understanding the underlying concepts, and from there we can begin sketching out several paths to achieving the outcome we want. Having many options available gives us optionality—the characteristic of considering and paying for many options upfront, again allowing us to quit or pivot on a moment's notice.

By viewing our work as systems—collections of elements with relations between them—we can create modular, adaptable solutions by treating the parts as building blocks we can reconfigure and reuse. Once we have modular pieces, we can lean heavily into composing elements together. A small number of powerful patterns, technologies, and ideas used more heavily, rather than a large number of specialized tools, establishes a means for us to build on our prior work rather than building from scratch every time.

Making things tangible

To avoid getting lost in design, we need to make things tangible as early as we can, linking up initial functionality for ourselves to continually iterate. This isn't to say focus on the easy work upfront; sometimes we need to roll up our sleeves and focus on the hardest work first to get the largest gains. Do the hard things up front; time will come for the easier things, but they will distract you early on.

Communication and alignment

High performing teams know how to radiate intent, spread around information, and repeat their messages enough to continually realign over and over again. Be clear about what you're doing, collaborate a lot with people, and don't be reserved in what you communicate. More information means more alignment, and more alignment means more autonomy.

Practical implementation

To make this actionable, consider these steps:

Map creation and maintenance:

  • Document your current understanding of the problem space
  • Identify what you know, what you don't know, and what you think you know
  • Share maps with your team to build collective intelligence
  • Schedule regular map reviews and updates

Designing effective experiments:

  • Define clear hypotheses before testing
  • Establish measurable success criteria upfront
  • Set kill criteria—specific conditions that would indicate it's time to pivot
  • Choose the smallest viable test that provides meaningful data

Building feedback loops:

  • Identify key metrics that indicate progress toward your goals
  • Create regular check-ins to review results and update predictions
  • Build systems that surface problems early
  • Cultivate environments where honest feedback is encouraged

Learning from outcomes:

  • Conduct post-mortems on both successes and failures
  • Document what worked, what didn't, and why
  • Update your mental models based on new evidence
  • Share learnings across the organization

Focusing on impact:

  • Start every initiative by clearly articulating the "why"
  • Prioritize work that has potential for order-of-magnitude improvements
  • Design systems for easy pivoting and iteration
  • Make abstract concepts tangible as quickly as possible

In summary, to be exceptional we must take calculated risks in the form of decisions. To make exceptional decisions we need to thrive in ambiguity. To thrive in ambiguity we need to construct mental maps, identify and optimize feedback loops, and make and reflect on our predictions. Feedback loops are set in motion by deciding and acting: consult your maps, make predictions and decisions, act, update your maps.

By holding these mindsets and principles, we can move mountains—achieving the kind of transformational progress that separates good organizations from truly exceptional ones.