The Art of Finding the Right Question While You Write

Questions are powerful.

When you ask yourself questions, you can work this mysterious magic to transform a “train” of thought into a more flexible fluid thing where anything can happen.

When we’re writing something, it can happen that we get caught up in the momentum. We think that because we started out a certain way, we are supposed to follow a line of thinking to its predetermined destination.

Except– when writing is predetermined, it lacks vitality. The author’s presence isn’t as palpable for the reader.

The truth is, when we start writing a sentence, we don’t actually even know that sentence will end. We don’t know until we reach the end. Of course we have a general idea, but the exact words only happen when they happen.

Decoding the Art of Subtle Questioning

Lots of stuff is going on behind the scenes while writing.

Imagine a scenario where you are standing in front of a person explaining something to them.

When you speak, you draw from your well of experience and knowledge. You understand the general concept and you understand all sorts of specifics that grow outward from that central topic like branches of a tree.

So, having all this knowledge and experience, what determines the things that you will say?

As you speak, you are reading the person you are talking to. Maybe they’re giving you body language cues and maybe you’re simply reading the general vibe. Little navigations happen as you talk based on the input you receive from your listener.

Maybe they ask you questions. Those can totally change the topic entirely and you can choose to weave what you are saying back to relevance or simply answer the question and abruptly return to the topic at hand.

Before you know it, you have said hundreds if not thousands of words. In twenty minutes you might have spoken 2000 to 3000 words.

When we talk to someone we often organically explore multiple subtopics while returning to a main topic.

You can use these tools solo as you freewrite by bringing more awareness to your internal questioning.

To some this might sound artificial, like something extra you have to bring in — “Oh now I’m supposed to ask myself questions on top of everything else I have to do?”

The fact of the matter is that we’re already doing this all the time as we write something. Anytime there is a subtle repositioning of consciousness, it might be fair to say there is an implied question happening behind it. The more intentional we are with our questioning, the more we can benefit from this aspect of consciousness while in the flow.

So yeah. It’s already something we do as we write, often without being conscious of it. We ask questions and then we answer them in our writing.

A few examples:
“OK, so where am I going with this?”
“Yeah, but can she prove it?”
“What would that look like long-term?”

Maybe you have had the experience of giving a speech or talking to a group of people about something, and whenever anyone in the audience asks a question about what you’re showing them, they interrupt you with their question. You then address their question and continue with your presentation.

If someone asks a question in the middle of a presentation, it’s an interruption, but when you ask yourself questions in the middle of a writing session, it can actually keep you on track.

Questions can be remarkably helpful to sharpen your language into specifics and illustrations. Even a simple one such as “What else do I mean by this?” or “What is a plainer way of showing that?”

Asking questions is a way of imbuing more of your own sense of spontaneity and presence into your writing. Your reader will be able to feel your engagement. Just as when someone else asks you a question, your own questions invite more specifics from you, which gives you the opportunity to write more about it.

Say you’re writing a description of a new setting and it isn’t feeling very interesting to you. “What would it look like through my main character’s eyes?” or “What secret about this place lies just beneath the surface?”

You can benefit by drawing from an unending pool of questions without having an audience read your work. All of us actually already have an audience ready made inside us. By this I don’t mean different personalities… I mean the ability to see from different perspectives.

It’s about being able to let loose and be spontaneous so you don’t have to have anything memorized or rehearsed. Who you are is all you need. You don’t need some fancy list of premade totally perfect questions.

And anyway, it’s not so much the question as how you relate with the asking of it.
Suppose you’re having a hard time writing that description of a new setting. You might just as well find great results by asking “How can I make a bigger impact here?”

The thing to watch out for is any sort of questioning that puts you on the spot, such as a question that invites only a specific answer. Maybe you don’t know the answer to that question right away. A part of you is like — “Dude, if I knew that, I wouldn’t have to be doing this right now. I don’t know.” So ask a different one (one that is more open-ended) or move on.

Honoring the process, it is beneficial that you do ask the central question even if you don’t immediately know the answer to it because the heart of the matter is that you are real with where you really are. It may turn out that a different question unlocks everything, and you only could have gotten there by asking the wrong one first.

It’s important that you follow through with asking the question, simply leaving it when you don’t know. If that question doesn’t unlock the door, let it sit there, don’t let it stop you. Let the fact that you are presencing these statements help bring you closer. Honor the momentum even if it doesn’t seem like forward momentum. You don’t know which way you need to go, and there are unlimited options for how questions can unlock things for you.

No wrong questions. Don’t let a question block you, just ask another one.

Suppose you ask “How can I make a bigger impact?”

And you draw a blank. So you continue the flow of writing. That question might evolve into

“What do I love about what I’m doing?”
or “What are some things people have hinted at being missing?”

Let yourself answer the questions as yet another way of unloading anything that happens to be on your mind. Use freewriting as a tool for unburdening yourself of whatever doesn’t make sense or serve you.

The very act of doing this will stir things up. The more forbidden or annoying or frustrating, the better the results can be if you follow the process and let it out. By failing to unload, you’re not doing anyone a favor. You’re telling yourself I want to hold on to that and let it cointinue to get in the way. The truth is, whatever is in your mind that is pestering you and taking up space can potentially be uncovered to reveal something else. Sometimes it’s not about the question, but about what’s beneath it.

It’s not about following the momentum behind these thoughts – it’s about making them visible. You aren’t giving this gift to the thoughts, but to yourself.

You become bigger and more empty of them because they get seen. The innate spaciousness that is more truly you is claiming more of the space.

That open space, that spaciousness, is you resting in your authority.

From there, the things that are truly you can be known and seen.

Use questions to get beneath your blocks

One of the best ways to make use of questions is when you feel blocked or are doubting yourself. It’s not necessary or probably fruitful to psychoanalyze yourself, but rather to ask questions that help you get beneath your blocks and doubts and find a pathway into more of the innate joy and inspiration there.

When you use your writing like this, to press back against your doubts, you’re instilling more vitality into your writer’s voice.

When your doubts come up and press against you, they want to stop you or divert you. When you engage the flow of language to ask questions that press back against your doubts you instill more of your own force and flexibility and ability and confidence into your language.

Plus it feels better, and it helps you get where you want to go.

I encourage you to experiment with the power of questioning and see what it unlocks for you.

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