You cannot write productively if you do not have a plan.

That’s why most people struggle with writing: they have an idea to communicate but no specific plan of action to express their thought. As a result, they either procrastinate and never begin writing in the first place, or they hit writer’s block and spend hours staring at a blinking cursor on the top of a blank page.

The reason why people don’t plan writing is counterintuitive. They think they know how to write because they know the alphabet. But just like learning how to drive Toyota Prius in the suburbs doesn’t make you Michael Schumacher on track, knowing how to write symbols doesn’t make you a professional writer. You need to learn the skill.

The secret to good writing, as to any kind of knowledge work, is deliberate planning. If you do not have a plan, writing becomes a mysterious process you do only when you’re inspired. But if you document what you’re going to do, writing turns into a professional act with less opportunity for sloth. And the best way to plan writing is to ask questions.

Questions

If you think about something proactively, you run two mental processes at once. First, you keep the subject of your thought in your working memory. And second, you actively search through your mind for the object of interest. That’s a problem, given how much effort it takes to stay focused on a task.

But if you present yourself with a question, you change that. When you write the question down and look at it, you stay focused for longer. You benefit from your sensory channels to stay engaged, and you also run one mental process instead of two.

That’s why I’ve built a simple routine of asking myself a set of questions about what I’m planning to write. I apply it whenever I experience an itch like, “Oh, I could write an article about this!” After running the process for two months, I’ve empirically discovered how important it is to capture the idea right at the moment when it’s being formed. If I don’t turn my thought into an objective artifact that I can revisit later, I lose it.

Here are five reasons why questions work so well for writing:

1. Good questions are like an advanced Google Search query to your mind. They have high suggestive value because the parameters that you pass to a question light up relevant areas of memory for you. If you do not have a question in mind and just roam through ideas, you’re like a first-time Google user who blindly presses “I’m Feeling Lucky” all the time.
2. Questions exist in the physical world. When you write a question down, you can get back to it later and think about it again. If you do not write your thought down, it will fly away from your unstable working memory, and you may never get into the same situation that triggered that thought in the first place. As it’s tough to trace back the system one thinking [1], you’re way better off writing things down.
3. Questions are discovery satellites for new knowledge. The best thing about questions is that you can ask yourself something you do not yet know. When you write down a problem with no answer, you may revisit it later and add new information as you develop more understanding. More interesting and less obvious is that asking yourself questions for which you have no answers triggers curiosity and programs your subconscious to think about it in the background.
4. Questions convince yourself that your work is important. This may sound trivial at first, but I’ve discovered that if I don’t have a decent argument why what I’m writing is important, I produce bad writing or get stuck in writer’s block. And it’s way easier to stay convinced that what you’re doing matters if you documented the reasons on paper – you can get back to your questions and get inspired when things get tough.
5. Questions help you avoid obvious mistakes. In many professions, checklists are a must. If you’re a pilot or a surgeon, you spend years mastering simple procedures because you don’t have time to do system two thinking when you have a problem in the field. You need to have already thought. I believe writers benefit from checklists even more because writing is considered to be a creative act, and most creative tasks usually benefit from systemic approaches and vice versa.

Below are the questions I routinely ask myself when I’m profiling an idea.

1. Why do I want to write this article?

When you answer that question, you will discover the actual problem that you want to solve with the piece. Often, the problem will be different from the original idea of the article. If you have experience with the topic, you’ll likely see a better solution, a different angle of attack you can use to solve a reader’s problem.

For example, when I started my work on learning, the original idea was to produce a theoretical piece describing the research that I’ve done. But when I answered the first question, I realized that my work aims to help a reader improve their learning process, and the best way to do that would be to write a description of my own process and embed principles into it of preaching theories.

The answer will often contradict the initial idea that you’ve come up with. That’s fine – just update the idea. What you must avoid doing is continuing with the initial plan if you’ve clearly discovered a better one after answering the question. Even if you already have the draft done, you must rewrite the whole thing because your job as a writer is to not waste reader’s time.

Here’s how I defined the “why” for this work:

Q: Why do I want to write this article?
A: I want to help people improve their writing process by adding a simple routine of asking questions.

The “why” question is also a test for abstractions. If you do not have a concise answer, you will find yourself attempting to write an all-covering piece. Avoid that mistake and define the purpose of the work first.

If you cannot answer the question, do not write this article.

2. What do I want to write about?

The answer to the question determines the subject of your article. The subject is what the article is about, the broader topic of the work [2]. For example:

• “I wanna write about productivity.”
• “I want to write about learning.”
• “I want to write a post about habits.”

Here’s my subject for this post:

Q: What do I want to write about?
A: I want to write about the writing process.

When you answer the second question, you will grasp the category of knowledge you’re dealing with and enrich your writing.

Categories are a form of abstraction that we use to deal with complexity. Imagine a fridge. What I just did is I put some mental image in your head. But the refrigerator that you see is not some specific fridge, like the one you have in the kitchen, although it might be close. The fridge’s image in your head is an abstract fridge that combines details of fridges you have seen in the past. That’s what a category is.

The most value of categories comes from enrichment. When you see a new, tall, metallic rectangular object with two sections and a handle, you can’t help but guess it’s a fridge, because its properties match with the properties of fridges you have seen before. But you not only deduce the category of the unknown object based on how its features compare with the category representation that you know. You also enrich the concrete object with the features you expect an item of this category to have. In the fridge that you imagined, you’d expect to have some shelves inside, maybe a pack of eggs, or a cold bottle of Guiness. Without knowing it for sure, you pre-suppose to find this stuff in a new fridge that you see because of enrichment.

Once you understand the category of your work, you will be able to pull different ideas from the category level to enrich your article and better serve the reader. For example, suppose you’re writing a piece on fitness habits. In that case, you may jump to the category level and understand that fitness is about fitness habits and nutrition, and sleep. You could also level up to the habits category and see if there’s anything to pull from there – any similarities between building a habit of jogging and learning to play the piano? And if you have something to say on those things and it fits the context of your work, you can enrich your work.

The process of jumping between categories may sound complicated. I’d recommend taking a piece of paper and a pen to draw things when you’re getting started. The paper will make it easier to see the category literally “above” the object because of spatial cognition [3], and you will discover other objects from that category (i.e., nutrition, sleep) because of the white space effect when your mind fills in the missing details for you.

With experience, the process of jumping across categories of knowledge, and looking at a thing from different angles becomes automatic. It integrates into your perception so well that you don’t even notice it happening. Like a chess grandmaster, you just know a good move.

3. What do I want to say about the subject?

The third question determines your theme. The theme is what you have to say about the subject you’re writing about. For example, here’s a subject-theme pair for this work:

Subject:

Q: What do I want to write about?
A: I want to write about the writing process.

Theme:

Q: What do I want to say about the subject?
A: I want to convince my reader that asking yourself simple questions about an article helps a) flesh out the idea better and b) notice more ideas for writing. To make the process easier, one could use shortcuts and think of an article as a set of blocks rather than one big monolithic piece.

The purpose of selecting your theme is to limit what you’re writing about and outline a course of work. As you may have noticed, there are many things one can say about the writing process. If I attempted to write a piece on the “writing process” as a subject, it’d take years to produce. Even if you’re writing a book, you must limit yourself to your theme to be clear.

When you ask yourself the theme question, you naturally begin producing an outline. It’s still surprising to me how well this works: when you structure your question in this specific way, “what do I want to say about X?” it pulls information from your head that you have long forgotten. Moreover, formulating your answer as an explanation to yourself helps to avoid writer’s block, which usually happens because you’re translating the stuff in your head (in the first person) to the stuff in the world (in the third person). To avoid that error, write for yourself first.

If you change the theme question slightly, it may serve as a good trick to find ideas for writing. Most people have opinions on most things, so if you ask yourself, “What do I think of X?” and begin documenting your thoughts, you will get a decent article idea in just a few minutes. For example, “What do I think of movies?” yields a genuine article that expresses my view on the topic.

Finally, note that there are as many takes on one subject as people with different points of view. For example, I can write an article about movies with my theme being that movies are one of the rare things that put you in the flow state because I know a bit of cognitive science. Another person could write about film as an art, and yet another one would cover movies as a waste of time because they believe in extreme productivity.

4. What does the reader need to know in order to agree with the conclusion?

Once you define your theme, you can work backward the structure by asking, “What does the reader need to know in order to agree with the conclusion?” When you ask yourself that question, you step out of your mind and begin thinking as a reader. It’s the most challenging part of a writer’s job, but also the most lucrative one. If you do it right, you will end up with a logical progression of ideas that a reader needs to learn to convince themselves of the point you’re making.

Here’s how I answered the structure question for this work:

Q: What does the reader need to know in order to agree with the conclusion?
A: I must explain why questions are a valuable tool for writing, how shortcuts help answer questions better, and how thinking of an article as a set of blocks rather than one big thing changes perception.

5. What is the element of novelty in my theme?

The fifth question is a novelty check. Too often, people come up with themes that have already been covered. No surprise, given how many people can write and how few people study what others have done before them.

To avoid wasting time and electricity, ask yourself why your work is novel. If it’s not, then figure out what makes it different from everything that has been written before. If you have no idea, then do not write that article. It may sound discouraging, but you must never, ever, fool your readers by rephrasing the same thing that has been said before you.

The novelty question is the most tempting to skip. Avoid that temptation. The answer defines what’s unique about your article, what’s it’s core. Once you understand your work’s nature, writing will be at least 2x easier because whenever you struggle with an argument, you can get back to your roots and reason from there. This is the approach we used at Y Combinator when preparing a demo day deck, and it works just as well in writing.

For example, here’s my answer to the novelty question for this work:

Q: What is the element of novelty in my theme?
A: There are many works on the writing process, but none cover questions as a tool for thought and shortcuts as a method or improving the performance of questions.

Answering the novelty question has a nice side effect: it produces a perfect short summary of your work. You may discover why your approach is unique and use that for excerpt, promotion, or anything else.

6. Why would someone else be interested in my article?

You also want to check your theme for objectivity. I’ve spoken about finding a good theme in the 3rd question, but the purpose of question #6 is to step out of your own game and try to answer objectively why your work is worth reading.

A good answer to the objectivity question yields a perfect introduction. When you ask yourself why someone would be interested in reading your work, you can’t help but trigger your defensive mode, your instincts, and begin barking why the stuff you’re working on matters (even if it doesn’t). As the introduction is an excellent place to capture the reader’s attention, I almost always use a variation of the answer in my works.

Here’s my answer to the relevance question for this article:

Q: Why would someone else be interested in my article?
A: Because for most people writing is a chore. They struggle with getting more ideas for writing and turning their existing ideas into published works.

7. Who is my reader?

The missing part of the subject-theme triad is your reader.

If you do not understand the person you’re writing for, you will not produce great work. There are many reasons for that, but here are the three most important ones:

1. First, you will have trouble editing. As you cannot fit everything in an article, you must understand why to leave some arguments and cut others. If you only have a vague idea of the person who will read the piece and what they already know, you will not edit well.
2. Second, your explanations will be inconsistent. If you don’t understand your reader and their current reality, you will not have a baseline of what they already know. This will make your arguments challenging to agree with.
3. Third, you will fail to find the right words. Two articles with the same subject and theme but written for different readers will be totally different. If you do not understand your reader, you will fail to identify the best language to communicate meaning.

One helpful trick here is to select one person you know well and write for them. The single reader hack works because it’s way easier to picture a concrete, specific person and their qualities than an abstract, vague reader. So if you have trouble deciding who you’re writing for, just pick a friend you know well and write for him.

Here’s how I defined the reader for this article:

Q: Who is my reader?
A: A person who wants to write but has a problem getting ideas for writing or turning them into published works. Friend: [redacted].

8. What do I intend to communicate to them?

In nonfiction writing, there are two intents: to inform or to convince. If you do not select your goal, you will produce a Frankenstein piece that will either be too long or hard to understand.

I made this mistake with my work on shortcuts. The idea was that shortcuts restructure your thought by connecting small symbols that communicate a lot of meaning with your fingers’ movements. It was meant to be a practical article that explains how to build these tools for thought. But I spent too much time explaining the history of keyboards, and my readers got bored. Most people have never read the core idea at the very end. What a shame!

Both intents require a specific approach. For example, if you’re writing a manifesto to promote action like I did with my work on learning, you do not need a lot of theory explaining your point of view. When selecting a reader for a manifesto, you assume that they’re somewhat familiar with the subject and do not require an explanation from scratch. You focus on practice rather than theory.

But if you’re writing a general information article, you should sequence arguments differently. If your intent is to inform, you may even add some plot elements if that doesn’t hurt clarity. For example, in my writing as a tool for thought article, I sequenced arguments from more abstract information processing stuff to specific experiments on the speed of symbol manipulation.

Here’s how I defined my intent for this work:

Q: What do I intend to communicate to them?
A: This is a practical article. I want to convince my reader to try out shortcuts for questions to improve their writing process.

Shortcuts

To make the process of asking myself writing questions simpler, I built a set of iOS/Mac shortcuts. For example, when I type “ww” and hit a space bar, it expands into “Why do I want to write this article?” And if I type “wa”, it turns into “What do I want to write about?” The same shortcuts work on my iPhone, and I draft many outlines on the go.

With shortcuts, creating a new draft is a matter of seconds:

Here’s a list of keyboard bindings that I use:

• “ww”: “Why do I want to write this article?”
• “wa”: “What do I want to write about?”
• “ws”: “What do I want to say about the subject?”
• “wdn”: “What does the reader need to know in order to agree with the conclusion?”
• “wn”: “What is the element of novelty in my theme?”
• “wq”: “Why would someone else be interested in my article?”
• “wh”: “Who is my reader?”
• “wi”: “What do I intend to communicate to them?”

To turn shortcuts on, head to Settings > General > Keyboard > Text Replacement. Hit the plus button, and write your shortcut-phrase pair. It’s that simple.

The purpose of shortcuts is to bring down the complexity of asking myself a question. If I have a shortcut, I don’t have to remember the exact formulation; I just remember a small symbol. This is super helpful because when I get an idea for writing, I don’t have time to recall the questions. And as keep using the symbol, my mind maps my fingers’ specific movement that produces the symbol on a keyboard onto its meaning. As a result, I literally think with my hands [4].

Here’s how my current workflow looks like:

• I get an idea for an article.
• No matter where I am, I immediately create a new note in Drafts and start asking myself writing questions with shortcuts. Sometimes, I may document an idea as a sentence to not lose it before I flesh out the thought with questions.
• I go through all the questions using shortcuts such as “ww”, “wa”, “ws” and others.
• I tag the note with a “draft” label, and it gets filed as a draft to a separate workspace.

Here’s how the drafts workspace looks like:

When I started writing that way, I noticed something: the article stopped being one giant monolithic piece. Instead, I started perceiving the post as a set of LEGO blocks like subject, theme, reader, arguments flow, etc. And this perception change is the first step to mastery because I began noticing way more writing ideas. I started looking for blocks separately rather than waiting when they all come together into a puzzle.

Before integrating shortcuts and writing questions, I’ve been jotting ideas for writing in all sorts of places. This led to forgetting was I meant to say even a few days after I produced the initial draft. But once I started documenting my drafts in a structured manner, I stopped forgetting meaning because it was safely captured with questions. I come back to my outlines anytime and can even expand them by adding a few things to the bottom or adding a new question that I’ve just come up with.

The business of getting ideas for writing is a separate inquiry. Almost everybody has something worth saying, but they lack a proper method of thinking to express their thought. That’s why in this work, I’m concerned with what you do with the ideas that you already have and how you can turn them into published works. If you’re interested in ideas, email me, and I’ll write a post on how to get them.

FAQ

Do you ever begin actual writing before answering all questions?

Of course. If I feel the words flowing, I may write a few pages and then begin writing an outline. But since I’ve discovered this process, I never attempt to write the whole thing without asking myself writing questions. I’ve found that asking myself questions is the only way to avoid the inside view bias when we tend to outweigh personal experience to objectivity [5].

Do you have examples of questions I could use?

Besides eight questions above, here’s a list of good list to start with:

• If I wasn’t writing this article, would I be interested in reading it?
• Why what I have to say is valuable to the reader?
• Have I seen this view expressed before?

Can I replicate shortcuts with templates?

You can’t because templates do not have sequential expansion. They throw at you a bunch of questions at once, and it’s the best thing to do to block yourself from thinking clearly.

References

1. System one is a category Kahneman uses to describe more intuitive, “fast” thinking. You can read more about two systems in his book or watch his lecture at Google.
2. The definitions of subject and theme are taken from Ayn Rand’s work, The Art of Nonfiction. It’s the best book on writing I’ve ever seen and the book I most frequently gifted to friends. If you write, give it a read.
3. Spatial cognition refers to our ability to process information presented spatially better than information that comes sequentially, like a list. For an excellent intro to spatial thinking, watch Barb’s talk at Stanford.
4. That is audacious speculation, I know. But I’ve been experimenting with blind typing for months already, and I can put myself into a focused mode of thinking by just typing on a table with no keyboard being present. If you’re curious to hear more, I’ll be happy to chat. Also, consider watching Barb’s lecture on how hands help us think.
5. You can read more about the inside and outside views in Kahneman’s book, Thinking, Fast and Slow.

P.s. If you have read this work and found it interesting, you will enjoy reading Ayn Rand’s book, The Art of Nonfiction. It’s the best book on writing I know.