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Depersonalize the Process

In life as in art, our point of view is our primary lens. We may seek objectivity, but we can’t always (can’t hardly ever) escape the limits of our vision.

The myopia can impede progress in very personal ways. In this post, I discuss the problem of personalization and offer suggestions for finding the space to expand your vision.

Writing a book requires an externalization of interiority. It’s hard work, and it provokes some epic, though predictable, struggles. There’s the grating irritation we might feel when our ambition scrapes uncomfortably against our ability. There’s the painful friction the results when an imagined product rubs up up against practical progress.

For writers who can’t not write, surrender is not an option. We must cope instead. Sometimes (or often), we do so by personalizing our challenges: I’m not smart enough or good enough to say what I want to say; I don’t know enough to have an opinion; I’m not qualified to have an opinion; or, Readers don’t get what I’m going for; People aren’t ready for my insights.

In other words, we personalize the difficulties that are typical of the process. As a result, we remain locked inside our interiority and blocked.

If you can’t see beyond your struggle, you need some space. Get it through depersonalization. First, ground yourself: Notice the struggle that you feel. Let yourself feel it. Then, remind yourself that this is just the uncanny byproduct of the work. There’s no solution–not for you, and not for anyone else.

Next, identify a handful of very simple, project-adjacent tasks that you want to and can easily complete. You might reformat a section. Or you might create and complete a personality questionnaire for a character. Or you might tell a friend which three sources you’re going to summarize over the next few days.

These and other simple interventions can offer a very gentle way to insert some space between you and your work. This space creates the distance you may need to depersonalize your struggle and engage in the process a bit more comfortably.

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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:

  • What am I interested in?
  • What do I not yet know about the things I’m interested in?
  • What else do I want to find out about?
  • What do I think I already know about the things I don’t know?
  • What other intuitions do I have about my interests?
  • How can I test my intuitions?

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?

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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.

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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:

  1. Identify the draft’s rough sections.
  2. Distill each rough section into a sentence.
  3. Collect the sentences into a rough paragraph.
  4. Test out a few different arguments such a paragraph could support.

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:

  1. Using the throughline to write a connection between each sentence.
  2. Circling these new connections.
  3. Breaking the connections out as the start of new rough sections: This is the material left to create.

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.

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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.

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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.

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The Gap Between Ambition & Work

When beginning a new project, especially one that requires skills not yet acquired and experience not yet gained, we often encounter a gap between what we envisioned for our project and what it seems poised to achieve.

This chasm is an unavoidable feature of the creative landscape. It’s there, and we know it’s there, and if we’ve ever before created something, we know that sooner or later, and typically when we’re just about ready to release our new project into the world, we’ll arrive at its edge. 

The crevice is the beginner’s gap, and Ira Glass of This American Life candidly defines it as the space separating our work from our ambitions for it. Encountering this gap is demoralizing–and arriving at its brink over and over again makes it seem unnavigable.

Plus, there’s the irritating truth that the gap remains open for a surprisingly long time. “Beginner” is somewhat of misnomer here because the gap is always present, it just goes by other names.

Luckily, the gap gets easier to navigate. In fact just the work of creating a lot of material over an indeterminate but necessarily long period of time builds the bridge required to reach the other side of our efforts and feel real satisfaction.

Unfortunately, most of us don’t get there. We might encounter the gap once or twice or more and decide we never want to encounter it again. We experience the disappointment of the gap’s darkness as a message to turn back. 

We should instead experience it as a message to keep going. The beginner’s gap is just one element in a larger scene: It’s true that there’s no way to really close it (in part because disappointed ambitions are a frequent companion to creation). However, we can prepare for it and build a bridge across it by expecting our projects to fall short of our ambitions, and by keeping going anyway.

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Creative Friction

When it comes to writing, AI can generate poems, songs, stories, and fiction and nonfiction books. It can produce interviews and summaries and evaluations and copy of all kinds. As it gains more, better, and potentially multisensorial training, it will be able to do much, much more.

For some, the sudden surge in applications uncovers previously unexploited conveniences. If, for example, you spend too much time writing articles to refresh SEO relevance, AI offers a convenient solution.

For others, however, the purpose of writing is not always—or not only—to get the work done. It’s also to do the work. This is the case even though, as a proxy for thinking and reflection, and/or as a means for information exchange, writing is an inefficient, inconvenient medium.

It’s also often annoying, irritating, unpleasant, and very, very hard. Even writers consider writing torturous—a point made in Hemingway’s oft-quoted description of writing as “easy”—you just have to “sit down at a typewriter and bleed.”

But inefficiency and inconvenience—and annoyance and irritation (probably not the blood)—are important parts of the process. They’re cause and effect of the friction created when we attempt to match what we want to express with expression. 

AI can make the match easy by smoothing away this friction, but the convenience comes at a cost. In fact, Tim Wu writes in the still-relevant “Tyranny of Convenience” that although convenience helpfully and necessarily sands down some of life’s rough corners, if we sand away too much, we lose the edge.

Making easy our primary goal radically limits our choices, and thus the individuality we express in the act of choosing. Yes, AI can make the work of writing easy, but it smoothes away the friction that invites (perhaps requires) individuated expression.

We can and will turn to AI for a wide variety of tasks. But when it comes to writing, the hard work of enduring the annoying, irritating, unpleasant, and terribly inconvenient friction of writing is (part of) what makes us meaningful.

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When It’s Not Working

When we’re faced with disappointments on a project to which we’ve committed time, effort, money, and emotion, it can be hard to know when to persist and when to quit.

On the one hand, grit can get us over the finish line, argues Angela Duckworth, even when our lungs are labored, our legs are heavy, and the race is too long. 

On the other, quitting the race can save us from overvaluing persistence for its own sake, claims Annie Duke. Why should we keep running, Duke asks, when we know we can’t win, and when a loss means more than just a hit to our pride?

To dig deep and show grit, or to pull up short and quit? It’s a timeless question many of us must ask about the commitments we care about, whether it’s a project, a job, a race, or a relationship.

It’s a hard question to answer because we often assess the costs and benefits of persistence versus abandonment only when things go wrong. Yet, when things go wrong, we’re not especially good at neutral assessment. The sunk-cost fallacy and other cognitive biases typically limit our thinking and confine our actions. We end up overvaluing our investments when they aren’t paying off, or blowing long-term equity in a short-term fit of pique.

Because life is uncertain and so many variables shape our experiences, there’s no easy way to decide when to show grit or when to quit. But we can get closer to the least-wrong answer by identifying the root of resistance. Ask yourself:

  1. Am I saying no (or, I don’t want to; I can’t: I don’t feel like it; I prefer not to; uggghhhhhh), more than I’m saying yes?
  2. What are my reasons for saying no?
  3. Are those reasons bounded by time and space, or are they existential and timeless?

The preceding exercise won’t tell you what to do, but it may give you enough clarity to make a plan. For example, if your resistance is rooted in overwhelm, take a break, or take steps to reduce contextual chaos.

If, on the other hand, your resistance is related to the possibility that we are mere drops in the swelling ocean of humanity, that there’s nothing new in its depths, and that nothing you say or do can really change the rhythm of the waves, well, quitting isn’t going to change that, so you might just need to make a plan to comfort yourself before keeping on keeping on.

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The Cutting Room Floor

Producing quality writing depends on successfully wielding two opposing forces: creation and destruction (addition and subtraction; expansion and reduction). On the one hand, you have to make it. On the other, in the process of making it, you have to let go of some of what you’ve made.

Unsurprisingly, the letting-go part of the process seldom gets its due. Writers refer to it as “killing your darlings” or “the cutting room floor.” Though the pain of the effort is communicated through verbs like “kill” and “cut,” it is a fundamental part of producing quality writing.

In fact, journalist Kevin Sullivan, in conversation with journalist Chip Scanlon, cites it as the best writing advice he’s ever received: “Don Murray, my college journalism professor and friend, said you can always measure the quality of a piece of writing by the quality of what you cut.”

It’s hard to let go of our brilliant turns of phrase, or our tightly crafted paragraphs. It’s harder to let go of whole narrative arcs. But Sullivan confirms that quality writing requires us to recognize that what we’ve created will almost always benefit from what we can cut.

To make it easier, save your cuttings as clips. The benefit is practical—you can consult your clips to develop new darlings. It’s also emotional—you can keep what’s not currently required, saving it for another creation.  

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