My Plan to Write a Daily Article on Substack

7 radical rules to become a writing machine

Yesterday, I announced going on a Substack sprint:

1 long-form article a day for the next 30 days.

Today, let me share with you how I plan to do it in ~30 minutes/day:

1. Spend more time on your outline and ideas

Most people waste time polishing garbage.

I used to do it too. I’d write a rough draft, panic that it wasn’t “good enough,” and then spiral into five rounds of editing. You know what I ended up with? A slightly shinier mess. No amount of Grammarly green lights could fix a boring idea or a sloppy outline.

Now I flip it.

I spend most of my time upfront:

• thinking

• outlining

• and building the skeleton.

If the bones are strong, the body holds itself.

If you get the ideas and outline right, writing becomes assembly. If your outline is messy, writing (and editing) is a mess.

Before writing, spend 5–10 minutes outlining your big idea and breaking it into 3–4 bullet points.

2. Give perfect content the middle finger

Perfect is where ideas go to die.

For years, I obsessed over every sentence. I’d re-read drafts a dozen times. Fix commas. Rephrase intros. Then still not publish because it “wasn’t ready.”

You know what that got me? A folder full of unpublished drafts (and zero readers.)

But then I decided to slaughter the perfectionist trapped in my head.

I started writing on Medium. And some of my most viral articles on Medium had typos. Some had grammatically incorrect sentences.

People still loved it. Why? Because the ideas hit hard. And that’s what matters.

Nobody’s reading your stuff with a red pen in hand.

They’re reading it:

• On the toilet.

• On their phone.

• Half-distracted.

They’re not looking for grammar. They want something that makes them feel seen. Something useful. Something real.

The best writing feels like someone just slapped you awake with an idea. That doesn’t require flawless grammar.

This is not a permit to publish content full of typos. But a few typos here and there won’t kill your reader.

Perfection is a security blanket. Burn it.

So publish something today with a typo you didn’t fix. See what happens.

3. Use AI (sorry not sorry)

AI isn’t the villain. Laziness is.

I don’t treat AI like some magic button that spits out genius. I treat it like a ghostwriter who works fast but needs constant supervision.

I’ve been writing close to a million words with AI. And all I say is this: It doesn’t replace my thinking. It just accelerates the parts that don’t need my brain – like writing first drafts.

Here’s how I use it:

I come up with the idea. I outline the structure. I jot down all ideas, stories, and other elements I’d like to write about.

Then I feed it samples of my past work–stuff that sounds like me on a good day. I already have over 300 articles and 1,000+ emails under my belt. That’s a massive pile of raw material. I can feed any of it into AI and get something that sounds exactly like me.

Because I’ve trained it. Not with gimmicks. Just by using my own damn work.

I spend time figuring out the point (Remember #1?). Then I map the angle, write one line per idea, and feed that to AI. If the idea’s clear and the structure’s tight, the first draft needs minor editing.

Then I edit. Hard. I fact-check. I rework lines. I gut anything that feels off or doesn’t' sound like me.

Instead of spending 45 minutes working on a first draft, I do it in 5 minutes flat.

This tool only works if you know what you’re trying to say. Otherwise, you’re just generating content salad–words with no spine.

Some people get pissed when they know the article has been written with AI. A guy on Substack even mocked me and told me I’m a clown for admitting it.

But hey, as I said in this note:

There are 3 levels of writers in the AI era:

• Uses AI but pretends they don’t

• Uses AI openly but adds no personal value

• Uses AI strategically with personal stories nobody else has

Only the third one survives.

Using AI doesn’t mean you’re cheating. No.

Cheating is publishing fluff you didn’t even read. It’s using generic ChatGPT ideas.

4. I don’t write with a keyboard

My best ideas show up when I’m not in front of a screen.

Like when I’m out walking. Moving clears my head. My body’s busy. My brain starts solving problems in the background.

That’s why I use voice dictation.

I pull out my phone, open an app like Letterly, and just talk.

It’s not pretty. There are filler words. Half-finished thoughts.

But who cares?

I’m not writing a novel out loud. I’m capturing momentum. The rough clay. I use AI to polish that first draft later.

Here’s what I don’t do anymore: sit frozen at a desk, waiting for genius to strike.

That method?

Garbage. Doesn’t work.

Your brain’s not built to think creatively while slouched in a chair you hate.

Talking while walking turns your body into a writing partner. It’s like brainstorming with your legs.

Sure, you’ll feel weird the first few times. Talking to yourself in public looks unhinged. But you get over it. And once you do, it’s like having a second brain–one that doesn’t mind bad grammar or stupid metaphors.

Dictation = superfast writing.

5. Ugly thumbnails

Back in my Medium days, I treated Unsplash like an art gallery.

I’d scroll for hours, hunting for the perfect image. Something poetic. Maybe a foggy forest. Or a lonely man on a bench. Something that screamed, “This is a serious article.” I thought if I nailed the image, the clicks would follow.

Yeah… no.

Turns out nobody cared. The piece either hit because the title landed–or it flopped because it didn’t.

The image didn’t save it.

So now? I’ve simplified it. I don’t scroll Unsplash anymore like I’m curating an exhibit. I’ve got clear brand colors: black background, orange icon.

I can find an icon in 30 seconds and smash it into my Photoshop template. Export. Done.

6. Wordcounts is for schmucks

Nobody cares how long your article is.

Seriously. Nobody’s sitting there with a ruler checking your word count. They either get value–or they bounce.

That’s it.

I used to obsess over length. I’d check the word count after every paragraph like it was some magic number. As if 800 words = insight. Spoiler: it doesn’t.

I’ve read 2,000-word articles that say nothing. I’ve read 500-word ones that punch you in the face.

Guess which one sticks?

What matters is getting your point across. As fast and clearly as possible. I want you to read my stuff, nod, and move on with something useful. Not sit through five analogies just so I hit my quota.

Some days I have more to say. Some days less. That’s okay.

Stop writing to hit a number. Write to hit a nerve.

7. One outline to rule 'em all

I was wrong about creativity.

When I first started writing, every article was a new experiment. New structure. New rhythm. New rabbit hole.

I’d open a doc and just start typing, hoping something smart would happen along the way.

Waste. Of. Time.

Now? I stick to a structure that works. One angle for the whole article.

5–7 subsections. Each subsection is about ONE idea that supports the angle. (The Zettelkasten helps here.)

Think of it like a restaurant menu. If every time you walked in, the dishes moved around and the prices changed, you’d leave confused. But if it’s the same setup every time, you know where to look, what to expect, and how to get what you need fast.

That’s how I want my readers to feel. Like they’re in familiar territory. So their brain doesn’t burn calories trying to decode the layout. They can focus on the message.

And bonus: it makes writing 10x easier. I don’t have to build a new skeleton each time. I just swap in the organs.

Simplify your outlines.

Let’s finish here

Daily writing isn’t a motivation problem.

It’s a decision problem. Every day you waste energy picking fonts, rewriting headlines, and second-guessing ideas–until you’re out of gas before you even write a word.

I’m done with that.

Put all your creative energy into what you’re saying–and how you say it.

That’s the only part that moves people.