Introduction

Suppose you are lost in a forest. It is dark; you have no path to follow and no map or compass to guide you. You don’t know where you are. What do you do?

Many of us first encounter the dark, dangerous forest in the folktales and stories we hear as children. In those stories, losing the path often means struggling to find the way home. But this image has also captured the imagination of poets and philosophers. For René Descartes, for example, the lost traveler’s predicament offers a lesson about living with uncertainty. In 1637, he wrote:

…travelers [lost] in a forest, ought not to wander from side to side, far less remain in one place, but proceed constantly towards the same side in as straight a line as possible, without changing their direction for slight reasons […]; for in this way […] they will come at least in the end to some place that will probably be preferable to the middle of a forest.¹

Descartes argued that when a decision cannot wait for certainty, we should make the best judgment we can and act on it with resolve. If we remain where we are, or change direction whenever we feel unsure, we never learn what sustained effort could have accomplished.¹

This is persuasive advice. Taken literally, however, the metaphor leaves an important question open: how does a traveler lost in a forest know they are walking straight?

This may seem like an odd question. Yet experiments have repeatedly shown that without reliable external bearings, people trying to walk straight can drift off course and even end up circling without realizing it. In blindfolded trials, some participants walked in circles less than twenty meters in diameter.²

Two aspects of this matter here. First, intending to hold a course and actually holding it can be two very different things. Resolve alone does not tell us whether we are on course. We need a reference against which to check our direction and notice when it has begun to drift. Second, and more unsettling, we can be lost without experiencing ourselves as lost.

The forest offers an image of how we can lose our way in life—not physically, but psychologically. We often intend to do things but get derailed, drift off course, or forget our direction altogether. We end up circling, repeating the same approaches without understanding why they fail. Often this is merely frustrating. But just like in a real forest, we can also lose our bearings while seemingly being on the right path. Each step along the way can make sense at the time, until one day we realize that our achievements have led us toward a life we would never consciously have chosen.

This book is about finding and keeping your bearings—and learning to regularly check them even when you feel no need to. Whether you are facing a crisis of meaning, stuck in a complicated undertaking, or making steady progress along a familiar path, this book will help you examine where your efforts are taking you and exercise judgment under uncertainty: Should I persist? Try something else? Reconsider what I’m trying to achieve?

For much of our lives, these are slow, ambient questions. Sometimes we can leave them open while experience gives us more to go on. An upheaval, however, can make them suddenly urgent and seemingly existential. This is exactly what happened to Brunetto Latini, a thirteenth-century writer and diplomat, on his way home to Florence.

In 1260, Florence was, in Brunetto Latini’s words, flowering and bearing fruit. That year, the city sent him to Spain as its envoy to seek the support of King Alfonso X of Castile. He delivered his message and set off for home without delay. While he was away, however, Florence’s army was destroyed in battle, and the government that had sent him fell.² Latini learned on the road home that he had been banished, and he later put that moment into verse in his poem Il Tesoretto (The Little Treasure):

And I, in such grief,

thinking with my head bowed,

lost the great road

and turned off across

a strange wood.³

For Latini, finding the road again would have solved only part of his problem. Even if he had known every turn back to Florence, he would still have arrived at a place where he could no longer safely stay. Knowing how to hold a course does not tell us whether it is still worth following.

Latini’s most famous pupil was Dante Alighieri. Four decades after Latini’s exile, Dante lost Florence in the same way: in 1301, he was away on the city’s business when his enemies took power. The poem he wrote in exile, the Divine Comedy, opens with a strikingly similar predicament:

Midway upon the journey of our life

I found myself within a forest dark,

For the straightforward pathway had been lost.⁴

In both poems, an inward experience of lostness takes the shape of a landscape. In Latini’s poem, grief carries him off the road; in Dante’s, the dark wood expresses moral and spiritual disorientation. Something has happened to the traveler’s understanding of his life, and the place around him has become unfamiliar.

Where Descartes emphasized how to act when certainty is unavailable, Latini and Dante portray what it can feel like when the direction of a whole life becomes uncertain.

Their use of the forest suggests that we can lose our way among ideas and concepts just as we can among real trees. Our intentions, commitments, and possibilities form another kind of territory, extending from the details that occupy an ordinary working day to the larger questions of what we want our lives to become. We have to find our way within it while seeing only parts of it at a time.

Throughout this book, I will refer to this territory as The Forest. It can take different forms in our lives. Few forests we encounter are as daunting as those of Dante and Latini. We enter most of these forests willingly, though we are tossed into others. Some forests are huge, and we walk through them our whole lives. Others are small enough to cross in an afternoon. Depending on our perspective, we may be navigating several forests at once or focusing on just one. Some are dangerous. Others are places we enter to write, learn, build, and care for others. We may want to find our way through a particular difficulty while continuing to inhabit the larger undertaking. Finding our bearings can also help us slow down and notice its beauty.

Whatever The Forest represents for you right now, what would it mean to find your bearings there?

Latini’s poem also describes what happens when his attention returns. In the lines after he loses the road, he comes back to himself and looks around. He is still in the strange wood, but now he sees the living world around him and, at its center, the figure of Nature. She instructs him at length, and when they part, she does not send him back to the great road. She points him along another way. “Now I must guide myself,” he writes, “toward where she told me.”⁵

Finding our bearings begins with this return of attention: noticing what we are doing, what is happening around us, and whether our understanding still fits our circumstances. An undertaking may have changed since we began it. A commitment may keep slipping, or work we once found worthwhile may have become an obligation we no longer examine. Awareness means allowing these things to register. It requires occasions to look around, including when we feel certain of our direction.

But attention alone is not enough. Latini also encounters someone who can help him interpret what he sees and find a way forward. Dante connects the forest with a similar need for guidance. In his unfinished philosophical work Convivio, he considers how an adolescent might find a path through life:

Just as someone who had never been in a city would not know how to follow its streets without instruction from someone who knows it, so an adolescent entering the bewildering wood of this life would not know how to keep to the good path unless shown it by their elders.⁶

Much of our initial direction in life comes from other people: parents, teachers, employers. The need for guidance continues into adulthood. A mentor may recognize a difficulty we are encountering for the first time. A coach may help us articulate what we are trying to achieve and question assumptions we have stopped examining. People who have faced similar difficulties can enlarge our understanding of what is possible. Sometimes another person’s question is what first makes us aware that we have lost our bearings.

Support for our attention can also come from books, tools, and methods. Even a landscape full of landmarks can be difficult to navigate if we cannot recognize them or place them on a map.⁷ Guidance in our own lives likewise needs to be understood in relation to our circumstances. Someone may understand an undertaking well while knowing little about its place among our other commitments. A project may be worth pursuing and still ask more of us than we can give without neglecting something else that matters.

To make that judgment, we need to see more of the forest than the path right in front of us. When nearby trees fill our view, it can be difficult to tell where that path is taking us or how it connects with other paths. In many situations, stepping back can help, but distance has its limits too. From far enough away, we can see the forest but no longer make out the paths through it. We may know where we want to go and still be unable to see where to put our feet. The wider view has answered one question while leaving another unresolved.

The management thinker Peter Drucker expressed this need when he wrote:

To make knowledge productive we will have to learn to see both forest and trees. We will have to learn to connect.⁸

In our own lives, connecting these views means looking at the same effort at different scales: the action we are taking, the project it contributes to, and that project’s place in our lives. Each view helps us notice something the others leave out.

This matters because the level at which a difficulty appears is not always the level at which it can be solved. When work stalls, we may need help with the task itself. We may also need to change a plan that leaves too little time for it, or reconsider whether the undertaking still deserves our effort. Those possibilities call for different responses.

I call the ability to choose and move between these views scale-smartness. Becoming scale-smart means learning when to stay with the details, when to examine the larger undertaking, and how to use what we discover at one scale to guide our efforts at another.

The task is to unite the grand with the granular: to connect our larger aspirations with the small, often messy actions of an ordinary day. Our commitments should help us decide what deserves our time on Tuesday afternoon. But that Tuesday must also be allowed to change our plans. We act on what we currently understand, and what happens when we act can deepen or revise that understanding.

This book explores how to develop that ability in practice: deciding what deserves our effort, organizing our work, acting on our intentions, and recognizing when experience calls for a different approach or direction.

My ambition with this book is to bring us closer to a unified theory of productive life: an account of how our purposes, commitments, goals, projects, habits, and everyday actions relate to one another. Such an account should help us judge where a given method or approach fits and what to reconsider when it stops helping.

We already have systems for keeping track of commitments, organizing projects, protecting time for demanding work, and building habits. Some also help us examine our values and connect our daily actions with larger purposes. There is much here worth learning. But knowing how to use each method does not yet tell us how to use them together. Combining methods requires us to examine how much control they presume we have over our time, which responsibilities they account for, and what they treat as progress. Their terminology may differ too. We can understand each author’s system and still struggle to develop an approach of our own.

I have worked through these questions for two decades, mostly through my career in software engineering and my side business of writing. Both of these disciplines make traveling the ladder of abstraction a practical necessity. A programmer as much as a writer needs to reason about a whole system or chapter without attending to every line of code or sentence, yet remain able to follow a problem down into those details. Abstraction helps by leaving things out. Its usefulness depends on whether we have left out the right things. This is a concern I bring to methods for organizing our own lives: the simplifications that make a method useful also help determine where it will fail.

The assumptions behind an approach can also be difficult to recognize when its central terms carry several meanings. Consider the idea of productivity. We might call an afternoon productive because we answered a large number of emails, because we answered them faster than before, or because one exchange resolved a disagreement that had been holding up a project. The amount of work, the efficiency of the work, and the importance of what it accomplished give us different reasons for that judgment.

If we move between these meanings without noticing, advice about working faster can appear to answer a question about what deserves our time. I call this the Lost Crispness Problem: familiar words cease to preserve the distinctions we need to think and act. Words can legitimately mean different things in different settings; the difficulty is losing track of which meaning an argument depends on. I have done this in my own writing. Part of the work here is to make those distinctions clear enough that we can examine the reasoning they support.

Clearer terms would also allow us to bring separate frameworks into conversation. We could recognize when two authors address the same difficulty in different language, or use the same language to address different difficulties. I hope this book contributes to a shared pattern language: connected descriptions of recurring problems and ways to respond to them.⁹

This is how I approach self-help as practical philosophy. Questions about how to organize our work lead us to questions about what deserves our effort, and our answers have consequences for how we live. The examples and accounts of my own system let you examine how I have worked through those questions. I want the reasons for my choices to be visible, including the tradeoffs, so that you can judge whether those reasons apply to your circumstances.

The distinctions in this book have to earn their place. They should help you notice something consequential, reconsider a decision, or change an action.³

Even a useful system cannot remove the need to choose. Our time and energy are finite. Some commitments make competing demands on us even when we understand them clearly. We will have to leave some worthwhile things undone. A practical philosophy of productive life should help us face those choices without pretending that better organization will make them disappear.

The seven parts of this book follow our efforts from how we understand a situation and decide what matters to how we organize our work, act, and learn from what happens.

Part I: Mindwork begins with the premise: Your mind shapes your experience of reality. What we notice, what we believe, and how we interpret a situation influence the choices we can see and the actions we take. Mindwork is our deliberate effort to examine and guide this inner experience. We explore how to clarify intentions, question beliefs, understand our values, and work with the attention and mental energy available to us.

Part II: Scale-Smartness develops the contextual judgment we need to choose and move between views at different scales. Its premise is: Context determines appropriateness. A method can be useful under one set of circumstances and become an obstacle under another. We examine the assumptions behind familiar advice and develop principles for deciding when to follow it, when to adapt it, and when to reconsider it.

Part III: Effort Scoping brings those choices into our current workload. Its premise is: Getting the size right makes work flow. We consider what we are actually taking on: what belongs in our work now, what can wait, and what we can release. A simple list on paper may provide all the equipment a day requires. The judgment lies in deciding what deserves to be there.

Part IV: The Work Fractal examines how that work connects to our projects and larger aspirations. Its premise is: Every scale affords different moves. A project may contain smaller projects, each with its own actions and decisions, while belonging to a larger undertaking itself. We learn to move inward until we can see a manageable next step and outward until we understand what that step contributes to.

Part V: The Art of Action takes up what happens when we try to carry out our intentions. Its premise is: Planning is clean; execution is dirty. Even a well-chosen action can be hard to begin. We get tired, become distracted, encounter difficulties, and lose our place after interruptions. We explore how to begin, continue, and return to the work, paying attention to friction, habits, engagement, and recovery as our motivation and circumstances change.

Part VI: Scale-Smart Setups considers the tools and arrangements that support these efforts. Its premise is: Every tool needs a job. We examine what we need our tools to do, how they work together, and whether their usefulness justifies their upkeep. A useful setup keeps commitments visible and relevant knowledge available, so that returning to work does not require reconstructing the whole picture each time.

Part VII: Fostering Effectance explores how our approach develops through use. Its premise is: Keep checking your location and bearings. We try an approach, observe what it makes possible and where it falls short, and adjust it as our understanding and circumstances change.

Brunetto Latini eventually returned to Florence. Years after his exile, another change in the city’s political fortunes allowed him to come home and resume his public life. The destination he had been forced to leave behind had become possible again.

In our own lives, a commitment may endure even when the way we pursue it has to change. We may also discover that a plan has outlasted the reasons for making it. Finding our way through The Forest requires us to distinguish between these possibilities. We need to understand what deserves our continued commitment and what continuing that commitment now asks of us. That means looking beyond the next step while remaining attentive to what taking it reveals.

I recommend reading the book in sequence the first time, because the later parts draw on distinctions developed earlier. Keep one of your own undertakings in mind as we begin: something you want to accomplish, a responsibility you want to honor, or a direction you have begun to question. We will start by examining how you see it—what you notice, what you assume, and what your present understanding may leave out.