Though a project outline can be a helpful roadmap, for an outline to be radically useful, it can’t be traditional. It must be interrogative.
We often take it on faith that all outlines are useful: If you’ve got a destination in mind, you want (and often need) to know how to get there. After all, aimless exploration isn’t ideal or enjoyable when you have an end in mind and a timeline for your arrival.
Although for a big project like a book, the destination is typically “done,” the kind of outline we use can get us there or it can get us lost.
Traditional outlines get us lost. They’re passively structured and inert, articulating the themes and topics that need to be covered and connected to get a project to done.
But their structure makes it easy to lose your way. They’re simple and feel satisfyingly productive to create. We frequently confuse the effort we put into the outline with the effort required to turn the outline into a finished project.
However, our attention to it is reinforced by the traditional outline’s serial structure. An A, B, C pattern makes it incredibly obvious what comes next–D.
The obviousness poses a problem. By emphasizing structural connection, a traditional outline leaves unanswered the question of why A precedes B, and how we should make our move to B. The structure is maximally authoritative but fundamentally inert.
Question-based outlines, or interrogative outlines, on the other hand, are radically useful. Simply posing questions transfers the exploration of topics and subtopics and their connection to one another from the outline and onto the writer.
For instance, a theme like AI ethics in biomedical research, offers a nearly infinite number of topics and subtopics to be explored. A traditional outline encourages us to list out all the topics and subtopics that fit under this theme and connect them via seriation. It provides shape to infinitude, which makes it satisfying. But what is the shape of linearity? And when is it complete?
A question, on the other hand, solicits completion. If we turn the theme above into a question like, How will ethics shape the use of AI in biomedical research in the short-term?, we limit the topics under discussion while still allowing for maximal experimentation in our response.
Questions are dynamic. They imply not just one but many answers. They assume–by their very structure–an argument. Questions are also future-facing: A question mark solicits our future participation in meaning-making. And when we pose a question to ourselves, that question mark demands our participation.
So turn your traditional outline into an interrogative outline by reformulating your outline entries into questions. You may be surprised by how easy they are to answer.
Attending to the Work
A famous line from the Jewish text, Chapters of Our Fathers, speaks to the spiritual necessity of interminable effort: We do not need to finish the work, but neither are we free to abandon it.
“The work” is both the effort, and the object of the effort. It’s the energy we put into manifesting any complex, intangible good–justice, peace, love, art–and it’s the intangible good, too. Justice, peace, love, and art are ongoing processes requiring endless renewal.
“The work” is necessary, and it’s also impossible. Each individual is compelled, in some way, to return to it, again and again, somehow in pursuit not of perfection but of progress.
We can engage with this work in many ways, by attempting it, undertaking it, toiling at it, grinding away at it, trudging toward it, struggling through it, forcing it.
Or we can attend to it. We can stretch toward the work, direct our mind or observant faculties to it, listen to it work, apply ourselves to it, watch over it, minister to it, follow it, frequent it, wait for it, wait upon it, await it, expect it.
Attend is the operative word. As a transitive and an intransitive verb–as both an action complete unto itself and an action that must be directed toward something–it reminds us that we need not complete the work. We cannot complete the work. But we can attend to it.
Ask New Questions
When you’re feeling stuck in your work, stagnant in your thoughts, or bored in your writing, it’s easy to feel like the inner spring has run dry, or there’s no well of ideas to tap.
Boredom is frequently considered a prerequisite to creativity, maybe because, for some of us, boredom is so uncomfortable we’re willing to go to inventive extremes to sidestep it. The British Psychological Society points out that boredom provokes at least as much pain as does effort, and maybe more.
But to push past boredom’s dead-end, we don’t really have to get that inventive. We can instead approach it as a cue to formulate new questions about old ideas. When we feel its telltale signs–restlessness, disinterest, and a sense we’ve become flat and featureless, we can pause and ask:
Questions can be useful interventions because they direct us toward answers. They contain a provocation that pushes us toward places we aren’t. Just by asking the questions, we can generate the movement that makes effort seem less like a choice than an imperative. How else will we find our answers?
You’re Too Close
Like a middle-aged patron holding a menu at arm’s length to read its scribbles, writers must manipulate the distance to make their thoughts legible.
But it’s hard to hold our own thoughts far away, much less figure out the relative success of our efforts. How do we know if we’ve explained ourselves sufficiently? How can we be sure we’ve rendered our internal monologue into something externally meaningful?
It’s not easy–making the internal external is challenging enough without bothering about the answer to the question of to whom readability refers.
But it’s also necessary if we want our thoughts to be understood. As with other intimacies, when we’re too close, our view is obscured.
To gain more distance, we can practice the arts of alienation. Alienate can help us, etymologically, at least (ali-us is other/another, and -ēn-us is to see), establish the distance required to see an/other.
In contemporary usage, the word is negative–alienating something or someone suggests a hard push into an otherness so radical that the other can no longer be seen. But this usage is mostly only expedient for political ideologies that seek to hide the friction of distance and difference beyond the horizon.
The rest of us know that distance and difference are also opporunities. When we identify them for what they are, we can decide how and where to build bridges of common understanding.
Somewhat similarly, when we make our writing distant and different, we gain a perspective we can’t otherwise take.
We can do this in a number of ways: We can take time and space from a project, separating ourselves from and forgetting for a while our prior closeness. We can also use tools that make our work strange. Interrogative outlines are useful for this purpose. So, too, are AIs, which can make our writing so different and distant that we must work hard to build that bridge of understanding.
Wherever we’re standing in terms of our writing, it’s probably too close. By holding it out further, much further away, we may see opportunities to create common understanding.
Loosening the Hold
The challenges writers face that feel so insurmountable are often habits of thought based on mistaken premises.
One of strongest and most hidden beliefs we hold is that writing is a linear process. It’s not. It’s iterative.
To loosen our hold on this strong opinion, we have to first see that we’re holding it.
Then, we can confront it.
Us…or Them
In These Dark Times, the question of whether you’re with us or them can be a crude tool of categorization. But that usage is for simple minds. By turning the divisive equation into a question and using the answer not as a conclusion but as a premise, we can all build more powerful extended arguments.
To persuade means to move, and the force required to move something depends on the weight of that which must be moved. We apply a different force when an argument is pitched to us than we apply when it’s pitched to them.
When we pitch to us, we pitch to the people who already agree with us. It’s not that we don’t need to move these readers, it’s that we don’t need to move these readers to understand that a problem is a problem. They already understand the problem exists. Instead, we need to persuade these readers of the merits of our proposed solution–we need to move these readers toward our answer.
When we write for them, however, we write for the readers who haven’t yet identified the problem as a problem, or haven’t yet identified its relevance to them. We can’t yet move these readers toward our solution–that’s too big a step. Instead, we need to persuade them that the problem is a problem that’s significant to them.
In this way, the answer to whether our argument is for us or for them determines its development. For us, we focus on identifying, describing, and explaining the solutions. For them, we focus on defining, describing, and supporting our identification of the problems.
A few examples make the difference clear. First, a manifesto, the ur book for us: The Lightmaker’s Manifesto: How to Work for Change without Losing Your Joy. From the title we know that Karen Walrond writes not for them, for readers who don’t know that a lightmaker is an activist and that activism is hard to sustain. The book is for us, for lightmaking readers who seek real solutions to the problem of burnout they already know they face.
Books for them look a lot more like Elizabeth Kolbert’s The Sixth Extinction or Michelle Alexander’s The New Jim Crow. As their titles indicate, the pages of these books are devoted to naming, describing, arguing, and supporting the identification of a new (or newly articulated, or newly relevant) problem. The books seek to persuade readers that these problems exist and are significant to them.
Answering the question of us or them can guide the earliest stages of argument development. But it can also act as a useful intervention. If you’re stuck, blocked, uninspired, or lost and confused about what you’re even arguing, ask yourself: Am I mostly identifying a problem and arguing for its relevance to people who don’t yet understand it? Or am I mostly suggesting a solution for people who understand the problem and are willing and ready to make change?
In other words, am I writing for them or for us?
Book, Pen, Notebook: The Use of Transitional Objects
Notes apps, voice memos, and–obviously–keyboards and screens are great ways to capture your thoughts. But sometimes a pen and a notebook can help turn those thoughts into a more resonant conversation.
Slate movie critic Dana Stevens suggested this when she noted that she always watches movies with a pen and notebook in hand. She described them as her “transitional objects”–evoking Donald Winnicott and his use of the term. For Winnicott, a baby’s beloved and ever-present transitional object–a lovey, instance–helps them negotiate their subjective experiences and the objective world.
Transitional objects aren’t just for babies. Many of us rely at least a little bit on talismans to mediate between our inner life and the world’s objective insistences.
Like Stevens, I prefer a pen and notebook. I want to write down nearly everything I hear, and many things I see. I do this to stay focused in the present, to keep from daydreaming, to keep my roving mind in line, literally on the line.
It’s a medium-useful habit for life–that issue of focus, which the habit both fosters and divides–definitely requires further analysis.
It’s a maximally useful habit for work, however. When it comes to making books, a pen and notebook can make for an incredibly useful intermediary intervention.
You don’t need to use pen and notebook to write (unless you want to). Instead, you need to use them when you run into trouble. For example, when your sense of your argument diminishes in proportion to your growing pile of pages, take out a pen and notebook. Then:
The most powerful argument is (usually) the one that resonates most strongly. When it asserts itself, use it as a throughline to join your loose sentences into something tighter. This means:
A pen and paper can help to mediate between our instinctive (internal) knowledge and our readers’ (external) needs. Though the merits of assimilation and the ideal balance between subjective and objective experiences must still be determined, transitional objects can help us expand beyond ourselves.
Future Failure, or Esprit de L’Escalier
“[O]ne has only learnt to get the better of words for the thing one no longer has to say, or the way in which one is no longer disposed to say it” —T.S. Eliot
The doing and thinking required to write and revise means that writers are constantly calculating the output of their subtractions and additions.
We’re counting on precision, but there is no exact answer. We can’t use perfect words; we can only use words that serve the moment. But, blink, and, as Eliot points out, that particular moment has passed. Those words, “shabby equipment always deteriorating,” which were so apt, are already wrong.
The attempt to fix moments in time, with words, frequently feels impossible and pointless. This discomfort can coalesce into an unmovable obstacle, encountered by some as writer’s block.
Writer’s block does not mean that you’ve failed. It means that you’ve stumbled onto the failure of words.
Such failure is constitutive of language because language is not commensurate with meaning. Our words always say less (and sometimes more) than what we mean. We can never really say just what we want to say–first because we don’t always know exactly what it is we mean, and second, because if we do, we don’t usually have the just-right words to convey it.
In other words, our thoughts and words can’t coordinate precisely. Writing lets us pretend otherwise by offering itself as a tool for facilitating closer connection. But its mechanism merely extends the variable of time, which magnifies imprecision.
There’s a solution to this problem, but it’s not without remainder. We must free ourselves from the tyranny of exactness by acknowledging our future failure. It’s not a personal shortcoming: It’s a consequence of communication, which is only approximate.
Similarly, esprit de l’espalier. is linguistic melancholy. The perfect words–like the perfect comeback–often only arrive (if they arrive at all) when the moment has passed.
We can still write, we just have to tolerate that it’s almost always wrong.
Revision: The Sum of Subtraction
While some writers approach revision as a set of fun problems to solve, most approach it as a set of high-stakes, anxiety-producing riddles.
Revision, like all writing, requires both thinking and doing, or, in John Warner’s more evocative words, “expression and exploration.” Because we tend to subtract when we think, but add when we act, the work of writing is particularly difficult. To write–and revise–well, we must strategically wield apparently opposed forces.
Our subtractive thinking is represented by heuristics, those mental shortcuts that slice through the abundant inputs we take in every second of every hour of every day that we’re alive and awake. Heuristics subtract; they help us move from the potential paralysis of contemplation to the decisive movement of action (while also abetting our many and diverse biases).
Meanwhile, our actions, particularly when directed toward object transformation, are frequently biased toward addition. In the linked study, participants were asked to change a Lego structure to make it more stable. Most participants, unless explicitly cued with directions to “streamline” their structure, added to it. They only rarely used subtractive strategies, though those typically yielded greater stability, and were more efficient.
If (to adopt a gritty heuristic), we subtract when we think and add when we act, how should we handle the work of writing and revision?
Primarily, we should separate the work into separate processes. Writing and revision both mean doing transformative thinking, but addition and subtraction serve each activity differently. Writing is all about adding–if we prioritize subtractive thinking and heuristics, we risk subtracting meaning.
Revision, however, should be understood as an implicit directive to “streamline” the object of our thinking. We practice efficient revision when we apply our subtractive powers to the writing we wish to transform.
Ultimately, when facing the challenge of revision, we may need to subvert our instinct to add more to stabilize our work. We should first consider the sum of subtraction. Subtractive revision makes the additive force in/of further action possible. Once we’ve taken out the extras, we can see what else should be included.
Interrogative Outlines: An Easier Way to Write
Though a project outline can be a helpful roadmap, for an outline to be radically useful, it can’t be traditional. It must be interrogative.
We often take it on faith that all outlines are useful: If you’ve got a destination in mind, you want (and often need) to know how to get there. After all, aimless exploration isn’t ideal or enjoyable when you have an end in mind and a timeline for your arrival.
Although for a big project like a book, the destination is typically “done,” the kind of outline we use can get us there or it can get us lost.
Traditional outlines get us lost. They’re passively structured and inert, articulating the themes and topics that need to be covered and connected to get a project to done.
But their structure makes it easy to lose your way. They’re simple and feel satisfyingly productive to create. We frequently confuse the effort we put into the outline with the effort required to turn the outline into a finished project.
However, our attention to it is reinforced by the traditional outline’s serial structure. An A, B, C pattern makes it incredibly obvious what comes next–D.
The obviousness poses a problem. By emphasizing structural connection, a traditional outline leaves unanswered the question of why A precedes B, and how we should make our move to B. The structure is maximally authoritative but fundamentally inert.
Question-based outlines, or interrogative outlines, on the other hand, are radically useful. Simply posing questions transfers the exploration of topics and subtopics and their connection to one another from the outline and onto the writer.
For instance, a theme like AI ethics in biomedical research, offers a nearly infinite number of topics and subtopics to be explored. A traditional outline encourages us to list out all the topics and subtopics that fit under this theme and connect them via seriation. It provides shape to infinitude, which makes it satisfying. But what is the shape of linearity? And when is it complete?
A question, on the other hand, solicits completion. If we turn the theme above into a question like, How will ethics shape the use of AI in biomedical research in the short-term?, we limit the topics under discussion while still allowing for maximal experimentation in our response.
Questions are dynamic. They imply not just one but many answers. They assume–by their very structure–an argument. Questions are also future-facing: A question mark solicits our future participation in meaning-making. And when we pose a question to ourselves, that question mark demands our participation.
So turn your traditional outline into an interrogative outline by reformulating your outline entries into questions. You may be surprised by how easy they are to answer.
A Call Sheet Can Direct Your Outline.
An outline is a roadmap to a complicated project. It marks out the destination, as well as the big and small side trips you want to take along the way. An outline offers orientation and direction. With it in hand, you can see where you’re going and how to get there–you don’t need to wander around lost.
However, an outline can leave open the question of how, exactly, you’re supposed to get to where you need to be.
To answer this question–a question implicitly posed by the blank page or blinking cursor–consider the call sheet. It’s a tool that can help your execution.
A call sheet is typically used to organize the production of a film. It’s the daily memo from the assistant director to the cast and crew that describes the day’s shooting and production schedule, as well as related logistics like on-set participants and call times.
Like an outline, a call sheet breaks down a big project into its component parts. Unlike an outline, which provides more of a map toward a destination, a call sheet breaks down each leg of a trip into its component parts.
Consider it an itinerary— a companion document to support your on-time arrival. Its daily schedule includes the day’s most pertinent details, making actualization straightforward.
If you’ve created an outline and are wondering why the project isn’t really easier to complete, first turn your outline entries into questions, and then create a call sheet to guide tomorrow’s work. Include on the call sheet the date, the project’s title, the number of words completed, and the number of words to complete that day. Include, too, the title of the part of the outline on which you’ll focus, the segments you’ll write, and the research required to support/complete those segments. Then, specify the times you’ll allot to the work and your daily schedule, including anticipated interruptions and other necessary breaks.
When tomorrow comes, review your outline, consult your call sheet, and start writing as fast you can.