Outlining used to be the bane of my existence.
For some reason my brain has never been good at it.
I used to skip it, and would get lost in editing hell for days (sometimes a full week) at a time.
Creativity will always strive if you give yourself some rules to play within.
That is what an outline is, a creative constraint.
I want to teach you how to outline a long form post with your own brain.
No AI.
Specifically, so you can write long form posts that actually perform well, consistently, without spending days feeling stuck staring at a blank page, or editing like mad.
Here’s how this guide will help you achieve this:
First, I’ll tell you why we outline (as per the learning science, of all things).
Then I’ll show you:
How I come up with key points to write about
How I think of structuring those key points in the form of a highly impactful and persuasive argument
How I think about writing each key point section
Lastly, I have an outlining drill/exercise you can follow for executing on the knowledge this post teaches.
I - The Importance Of An Outline
If you already use outlines to help you write, great.
If you don’t, or you think outlines are stupid, pointless, and act like a fiery pit of decay for your quote-unquote “honest writing,” guess what?
You are always writing with an outline.
It just isn’t conscious to you, and it will vary in terms of depth or fidelity.
In order to build knowledge, information must get encoded into memory.
This happens in 3 ways:
Organizational Encoding - Grouping, categorizing, and organizing related information into chunks or parts. Outlining itself is literally about deciding what parts make up the problem your title poses, and solving them in a logical order (section by section).
Semantic Encoding - Understanding “why” something works, is true, or happens to be the case, in terms of mechanics. Each key point you make not only states a claim, but explains why it is true, and how it benefits the reader if they understand why it is true.
Elaborative Encoding - Connecting new information to prior knowledge. The most novel and thus engaging key points to read stem from connecting an idea from one domain to a problem in another.
Reading and writing are analogous.
Research is no different than learning, which means if you don’t have ideas it means you lack knowledge.
You can’t recall or write about a topic you don’t understand or know of.
When you create an outline, with your own brain, it means that your own brain is creating a structure for grouping, categorizing, and STRUCTURING information it already has encoded.
Outlining is how you organize your ideas into an argument you are trying to communicate to your reader.
In this case, you are arguing for a perspective (your ideas) on a problem (topic, title, headline) that you think would benefit them if they those chose to act on it (solution to the problem).
I wish more people knew this.
The people clicking on your content are almost always beginners in your topic. They are scrolling without search intent. They are looking for something to entertain them while waiting in line for a coffee, or while chilling on their 30 minute lunch break.
People don’t naturally care about any idea unless they see a clear benefit in caring.
Your outline has to showcase those benefits clearly, taking them from being unaware of the problem to being convinced of your solution.
That is the sole purpose of the argument you are structuring.
II - Pick A Title/Topic
All my best long form posts get written by first choosing a title.
The title is 70% of the content game.
If nobody clicks, nobody reads, which means you don’t grow or have the chance of growing.
I like to choose a title (or create one of my own that I think has a good chance of doing well) based on two principles:
Validation - Titles or title structures that people are already proven to click on. The posts have higher views and engagement than normal, compared to other videos the creator has posted.
Interest - I will write about my own genuine interests and profound ideas but angled and positioned UNDER that title as the solution to it (there’s no difference between a title and a problem people care to learn about or have solved)
I wrote this post titled “How to become dangerously articulate.”
Because the title structure worked so well, I decided to emulate it for other topics:
Is a title guaranteed to do well?
No.
It’s about doing what you can for increasing the chances of you hitting a bullseye. You’d rather not try and hit a bullseye in the dark, with your eyes closed, while drunk, and have the dart board moving on the wall… while you yourself are spinning in circles.
Validated titles and topics prove there is a demand to hear more about those titles and topics. The problems and thus solutions to those problems. So why not talk about those titles and topics with your own novel perspectives, ideas, and interests?
Do what works, because it works. Don’t try and reinvent the wheel.
I’m talking about titles and title structures here.
Not stealing what other people have to say about those titles (the content/writing/ideas themselves).
What YOU might have to say about a validated topic is what makes it your own.
For now, choose a title to write about, or even a broad topic.
If you want to find validated titles to write about, Eden has excellent research features that I absolutely swear by.
Let’s talk about choosing key points to say about that title.
III - How To Think Of Key Points To Write About (And Structure Them Persuasively)
I can’t tell you exactly what key points to make about any title you’ve picked.
I am not you, and you are not me.
Key points are the chunks (parts) that make up the problem your title is promising to solve.
The issue now, is that most people either have no key points outlined (so they stare at a blank screen and think “writer’s block” is a real thing), or they have too many key points, which causes them to ramble.
Either way, the outline isn’t doing it’s job.
Let me break this into 3 parts.
(a) The What-Why-How Thinking Framework
This is how I think about and process anything clearly.
Clear thinking must happen before deep thinking.
What - What is the proposition, claim, or insight? (Define the thing, and its parts too if there are some)
Why - Why is it true? What is the mechanism, evidence, or the premises? (think semantic encoding)
How - How is it relevant or beneficial, and how would I solve this problem in my own unique way?
Let me write out a quick example:
Let’s say my title is “You need to start writing.”
The first key points that come to my mind, are:
Writing is formalized thinking (What)
Thinking is how you solve problems and suffer less (Why)
How to think about any problem and solve it faster and more efficiently through writing (How)
I like to keep my key points to 2-3 at most. Sometimes more if I have a lot to say about a title.
Notice how my key point order follows a natural problem → transformation (solution) progression? See how logical it is since we’ve went from what to why to how?
We’ll discuss this shortly in more depth.
(b) Where Ideas For Key Points Come From
If you don’t have ideas… once again… you lack knowledge.
You can’t recall and thus use an idea that hasn’t been stored in your long term memory. A key point is a claim about your title. You have to pull it from memory. If you don’t have ideas encoded about the topic, or ideas adjacent to it, nothing will come out.
It’s like trying to run a tap without a water supply.
The fix will always be to go fill up the water supply.
Read a book. Listen to a Substack article. Watch a video. Talk with AI. Talk with human beings.
You’re looking to find that missing chunk. Which means when it’s time to sit down and write or outline, it’s there inside your brain.
This part gets interesting, actually.
If your title is about topic X or topic Y, the obvious key points are the ones everyone automatically associates with those topics.
Those are fine… but they won’t make your writing stand out.
Because every other post about topic X or Y makes those same key points.
The key points that make a good piece of writing great come from knowledge that is somewhat connected to the topic, but not in a way that seems obvious.
You could connect a philosophy book to articulation, or learning science to building a personal brand, or even a principle from neuroscience and connect it to writing.
See how I’ve connected learning science to outlining with this very post?
You’ve likely never seen that connection get made before, between how the brain learns… and outlining, of all things.
See how elaborative encoding makes this piece feel novel and thus interesting and thus engaging to read?
Create a key point outline early in the week.
Even if it’s just the title and 1-2 key points.
Everything you consume and do away from your desk will be feeding on it subconsciously.
You’ll read a random tweet, or a paragraph from an old book, and notice it maps perfectly onto your outline.
Or you’ll be at jiu-jitsu, talking to people, and a single idea that you overhear will spark an array of ideas that connect to your title.
This only works if the outline exists before you sit down to write.
Outlining and writing in the same sitting means you only get to write about what’s already in your head.
(which might be enough, but this is worth mentioning nonetheless)
Be ready to write down any ideas that hit you away from your desk!
(c) How To Structure Your Key Points Persuasively
Once you have a list of potential key points, order becomes crucial.
This is what distinguishes teaching information and offering a transformation.
You’re not just stating any old information you can find using ChatGPT. There’s no value in that anymore. What you’re doing is structuring a novel argument that comes from your unique perspective on that any old information, that moves the reader from where they are now to where they want to be.
I’d like to give you 3 basic copywriting frameworks that do this (research/study these in your own time with AI):
PAS (Problem → Insight → Solution) - State the problem, twist the knife on why that problem hurts, then present your key points as the solution. This works well for “How to fix/solve/achieve X” titles.
AIDA (Attention → Interest → Desire → Action) - Hook the reader’s attention, build interest with a novel concept or profound idea/insight, create desire by showing them the beneficial outcome, then give actionable steps. I love using this framework, it’s dead simple and highly impactful.
PIS (Problem → Insight → Solution) - Every copywriting framework is a variant of this. Even the two above. This is how I think of writing all my long form posts. Lay out what most people do wrong, offer a new/novel perspective on the problem, then share the action steps that solve the problem.
Here’s an example of how my last newsletter outline for How To Live A Deeply Intellectual Life looked like using AIDA.
Attention (Hook): People are losing the ability to think
Interest (Key Point 1): Surface-level thinking became the new normal because overstimulation raised the threshold for what your brain finds worth thinking about.
Desire (Key Point 2): The three levers of profound thinking (curation, curiosity, creativity) as a model for taking control of your intellectual life.
Action (Key Point 3 - Framework Section): 11 action steps organized under those three levers which are small enough to start today.
Your key points must follow some logical progression from problem to solution. The framework you choose simply determines the basic structure of that progression.
IV - The Profound Outlines Drill
I’ve given you all the knowledge needed to become a master at writing outlines.
Becoming better and faster at outlining comes from volume.
Not theory.
Reading about how to outline will only take you so far. You need to act on what you’ve read. If not, this has all been a waste of your time.
Follow this drill to write lots of bad outlines first, before you can start writing great ones quick.
