An excerpt from the first chapter of my new book, Planning for Everything.

One child, one teacher, one book, one pen can change the world.
– Malala Yousafzai

We are several hundred feet into the cave when Claudia whispers in the dark “I’m so mad at you for bringing us here.” I’m not surprised. It’s my fault. I planned this vacation. I chose to bring my wife and our teenage daughters on this expedition to Actun Tunichil Muknal, a subterranean cave in Belize that contains the sparkling, calcified skeletons of children. Over a thousand years ago, the Maya believed the Cave of the Crystal Sepulchre with its demons, scorpions, and rivers of blood to be an entrance to hell and a fit place for ritual, human sacrifice.

The Maya had a point. After hiking through rainforest in the rain for an hour, swimming an icy stream into the cave mouth, and scrambling over slippery rocks with only headlamps for light, we are cold, tired, fearful. A man sits in the shadows, his face darkened by blood. He must have fallen. That’s why our daughter is angry. It’s treacherous, and our three hour tour of the underworld has just begun. I’m excited by the wonders of this cave, but I’m also aware of the danger. Since I’m the one who instigated this adventure, I imagine my family may leave me here, a human sacrifice given readily to appease the Gods.

I knew the risks when I planned this holiday. In fact, risk was one of the goals. I asked Susan and the girls what they wanted. We explored options and reflected on past trips. Our teenagers did not want to sit on a beach. They were eager for adventure. So we devised an itinerary to include swimming with sharks, ziplining the jungle, and hiking in caves. I researched hotels, restaurants, transport, things to do. I booked flights, made checklists, and checked passports. I built flexibility into the schedule to allow for weather and mood. I did all of this happily, knowing full well that something would go wrong.

Planning is a skill I love to practice. Whether advising clients how to structure a website, helping teenagers apply to college, or organizing a trip, I love imagining and shaping the future. Not that I have a choice. My brain models possible scenarios obsessively. This is not all good. Yesterday, lost in thought, I walked into a wall. To be in the moment, I must practice mindfulness, which is also essential for planning. Surprise is inevitable. Both the plan and the change need to happen. To manage disruption with grace and a sense of humor is part of the challenge. That’s why planning is about more than a plan.

Definitions of Planning

Planning is the design of paths and goals. That’s a simple way of describing a complex process that shapes our lives, careers, and dreams more than we realize. It’s worthy of study, so let’s unravel this humble definition the way we plan: backwards.

Our plans begin with goals. We aim to build a better product, buy a home, survive cancer, throw a party, learn to dance, or teach a class. Of course, it’s never that simple. Often we must juggle competing goals with sub-goals and co-goals. In Belize, we want serenity and adventure, freedom and togetherness, beaches and jungles; and our time is limited by commitments at home. Objectives don’t exist in isolation. That’s what makes planning hard. We must prioritize and make tradeoffs, and to achieve multiple ends, we must carefully choose our means.

All paths are not equal. And, even with a clear goal, it may be true that given one wrong move, you can’t get there from here. That’s why we imagine steps into strategy in advance. We search for options, model scenarios, estimate risks, and visualize results. There’s no one right way, and the shortest path may not be the best. How do we travel from rainforest to beach? We could rent a car, but it’s costly, and what if we get lost? How about a bus? It’s eco-friendly, and along the way, we may learn about the people and culture of Belize. Our choice of paths is clearly about shaping the future, but it’s driven by our beliefs, feelings, and values right here and now.

Have you ever realized a goal only to realize it didn’t deliver what you hoped? Perhaps you bought your first house and regretted it two years later, or got that promotion only to hate your new job. The successful execution of a plan often results in failure, due to faulty mental models in the here and now.

To plan backwards by starting with a goal isn’t all wrong, but a satisfying outcome is more likely if we take time to explore the sources of our needs and wants in the past and present. A goal can be a way to channel angst. As Winston Churchill said “Let our advance worrying become our advance thinking and planning.” But before we commit to a plan, let’s question our feelings and beliefs. Is your fear sensible? Is the path true to your values? Will the plan create the change you want to see? And will that change in the world make you feel what you hope? Plans are built on predictions which are built on beliefs. That’s why metacognition – awareness and understanding of one’s own thought processes – is essential to good planning.

Of course, it’s near as hard to know our own minds as to know the minds of others. Whether we decide to start running, stop smoking, eat less, or study more, we tend to overestimate our ability to stick to the plan. Similarly, when we reach a goal, happiness often fails to endure as expected. We can enhance self-awareness by introspection, but biases and false beliefs are hidden to the mind’s eye. That’s why planning needs design.

The design of paths and goals invites us to make the invisible visible. A sketch, map, or model helps us think and collaborate by getting the ideas in our heads into the world. While a plan may be defined as a series of steps, planning itself is nonlinear. Diagrams help us see the system. Prototypes let us play with behavior. Together we can find errors and experiment with drivers, levers, metrics, and feedback. By taking the time to make our ideas tangible, we’re better able to render our intent.

But we must not be seduced by the artifacts of this process. As Dwight D. Eisenhower warned “plans are useless, planning is indispensable.” The truth in this hyperbole is that no plan is perfect, the map is not the territory, surprise is inevitable, we must be prepared to pivot. Planning up front isn’t only about making a plan. It’s about learning, awareness, and practice; so we can identify options, understand feedback, and deal with disruption. Improvisation favors the prepared mind and body.

The right balance of up front and in process planning depends on context. A software startup in a new market must lean into agility, while a construction firm that builds skyscrapers must commit to blueprints. For both, plans and planning are vital. It’s a matter of degree. For our Belize trip, I had a choice. I could have done nothing in advance but book flights, with all places to stay and things to do chosen day to day upon arrival. Some folks love this embrace of serendipity. It can be a lot of fun. In our family, it would create anxiety, so we plan up front while leaving room to respond to weather, mood, and advice.

Ike’s famous line on useless plans affords a second insight. No artifact alone can create shared vision. When we plan together, we’re able to inspire each other to see and feel what’s possible. Leaders can build team loyalty that’s tribal. And it’s emotional commitment that gives folks the courage and spirit to endure.

Plans are not useless, but they do have their limits, and so do definitions. No statement can fully convey the nature, scope, and meaning of the word it describes. The dictionary defines planning as “the process of making plans.” This makes it too easy to see the artifact – the plan – while missing the point.

In this book, to navigate the design of paths and goals, we’ll use a map. The plan is to make planning visible by illumining its elements. But our voyage isn’t bound by a fixed course nor divorced from execution. We’ll tell stories and take detours in search of divergent views. We shall explore multiple paths on purpose. To understand planning, there’s no one right way.

For example, cognitive psychologists have studied the ability to guide action by intention for decades. Together with attention regulation, working memory, impulse control, and empathy, they view planning as an executive function, a core mental process for managing behavior. While researchers struggle with its definition, they mostly agree on its elements.

The planning process includes at least the following six functions: forming a representation of the problem, choosing a goal, deciding to plan, formulating a plan, executing and monitoring the plan, and learning from the plan.

They recognize that organizing future actions in a complex, uncertain world is difficult and important, noting that planning is the crowning achievement of human cognition. And while they may argue over experimental methods, these scientists all see planning as an ability that can be measured.

One of the most widely used tools to study planning ability is the Tower of Hanoi. This ancient puzzle consists of three pegs and a set of rings of varied sizes that can slide onto any peg. The game starts with all rings on one peg stacked neatly from biggest at the bottom to smallest on top. The goal is to move the stack to a new peg while following the rules: you may only move one ring at a time, a move consists of placing the upper ring from one peg on top of another, no ring can be put atop a smaller ring. A game with three rings requires a minimum of seven moves, but play with five rings and it takes thirty one.

The puzzle tests our ability to organize a sequence of actions. Players may be evaluated by completion time and number of moves. Since it’s costly to backtrack, it helps to plan ahead by simulating moves in the mind. Of course, some folks are better at this task than others, and that’s the point of the experiment.

Unsurprisingly, age plays a role. Most three and four year olds are unable to solve the puzzle with three rings. Success rates rise dramatically in the 7-9 and 11-14 age ranges, then fall gradually as we transition from adulthood to old age. Health is also a factor. People with Alzheimer’s, Parkinson’s, or attention deficit hyperactivity disorder often struggle with these tests. Beyond the obvious, it’s hard to identify what influences our ability to plan. Children in low income families tend to be poor at planning, and this correlates with academic success, but there are too many variables to declare causality. Studies show the relation of planning skills to IQ is moderate at best. So why do we differ so widely in our ability to plan?

The answer lies partly in our personal biases towards initial or concurrent planning. In a Tower of Hanoi study, pre-planners performed best in the three and four ring games, but those who declined to plan up front were best at the five ring game. Apparently, initial planners gain an advantage by simulating moves, but their minds can handle only so much complexity. But that doesn’t explain why low initial planners outperform high initial planners in games requiring 15 or more moves. In analyzing the data, which included verbal statements by participants, the researchers made an intriguing observation.

Those who tend to plan extensively before attempting the solution to a problem also tend to plan much less as they solve the problem. In contrast, those who do not plan in an initial preparation phase tend to plan concurrently as they solve the problem.

In short, it’s not a matter of whether but when we plan, and our habits may help or hinder based on the context. There’s another piece to this puzzle worth grasping. It’s hard to imagine and solve the Tower of Hanoi in your mind. And while a picture helps, it’s no substitute for the puzzle itself. To see, touch, and move wooden rings makes a huge difference.

Interestingly, the pieces need not be physical. If you’ve ever played Tetris, you know that to succeed at this tile matching video game, it’s vital to think-spin concurrently. Novices tend to rotate falling zoids in their minds before rotating them in the game, but in time players learn digital spins are faster. Studies show manual rotation to be as quick as 150 microseconds, whereas mental rotation takes five to ten times longer. So novices plan and then act, whereas experts act-plan together.

It’s an illustration of embodied cognition and extended mind. To think and plan, we use bodies, tools, and environments; not just our brains. Consider the goal of making a hot breakfast of eggs, bacon, toast, and coffee. What are the steps? What are the risks and tradeoffs? How might you organize your tools, ingredients, and physical space? How is your plan shaped by your body? Will you be relying on your eyes, ears, and nose?

Using puzzles and games to study planning in the lab enables scientists to control the variables, but it does so at the expense of ecological validity. In the real world, even daily tasks such as cooking and shopping are complex. A study can measure path efficiency, but it’s not feasible to account for all the risks and tradeoffs inherent in planning a trip to the grocery store. When should you go? Which route will you take? Does the car need gas? Do you make a list? Do you need milk? Do you call your spouse to find out? What if you run into that person?

It’s not feasible to list all the questions, as the mix of desires and anxieties we bring to the task is idiosyncratic. And, once in the store, our plans may change. What we see, hear, smell, and taste may make us buy on impulse. How we feel affects our planning and behavior. The variables are out of control. Planning is an art that can’t be contained by science.

However, an insight we can draw with confidence from the body of scientific research is that we can get better at planning. Countless studies have charted the development of planful behavior from infancy into adolescence. In one 1980s survey, children were asked “what kinds of things are planned?” For 5-year olds, top responses included recurrent daily actions and searching for lost items, while the 7-year olds planned to avoid commitments and manipulate grownups. The top response of 11-year olds was relations with peers. In the same study, when asked “what’s difficult about planning?” the 11-year olds cited memory and information gathering, whereas most 5-year olds answered “nothing.” Clearly the Dunning-Kruger effect – the cognitive bias that renders people unable to realize their own incompetence – applies to planning. The good news is that for most of us self-awareness and planning skills improve as we mature. The better news is that we can speed up this process.

A substantial body of evidence suggests that planning abilities can be enhanced by education and experience. In particular, exercises in planning together help people get better at problem solving, decision making, and metacognition. When we share responsibility for planning, we share strategies, insights, tools, and tactics that improve our ability to design paths and goals.

These findings aren’t just academic. For instance, research by the U.S. Marine Corps revealed “the most successful Marines were those with a strong internal locus of control – a belief they could influence their destiny through the choices they made.” An internal locus of control is linked to self-motivation, social maturity, professional success, happiness, and a longer life.

It’s also vital to a Marine since no plan survives contact with the enemy. In the field, a Marine must adapt plans to reconcile changing conditions with commander’s intent. It may not be possible to follow orders. For this reason, the Marine Corps encourages a growth mindset and builds planning skills. And it works. Studies show “the average recruit’s internal locus of control increases significantly during basic training.” Or in the words of J. D. Vance who credits the Marines with saving his life “I left the Marine Corps not just with a sense that I could do what I wanted but also with the capacity to plan.”

by Peter Morville

To continue Planning for Everything, please read the Preface or buy the book. Thanks!