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How I Made More than $1M from Writing Online in 8 Years

by | Aug 30, 2022 | Making Money Online, Money

Telling people you made $1M+ from writing is the #1 way to get hate mail.

So hate mail, here we come. I don’t care if you have daddy issues or get upset when someone talks about money. I don’t give a f*ck about the haters who are going to dislike this post.

This isn’t about bragging. Or saying “suckers.” Nope.

It’s about understanding that you can do anything when you put your mind to it, even if your skills, like mine, are mediocre.

If you’d told me I’d make more than $1M from writing 8 years ago, I would have slapped you in the face and called you a donkey.

I then would have kicked you in the genitalia.

But here we are. So let me deliver on the promise in the headline so the pretentious types don’t shout clickbait with their undies around their ankles while they take a crap.

Great writing gets you nowhere


Yep, being a good writer doesn’t count for much. There are loads of wordsmiths with fancy literature degrees that can’t rustle up $2 for a 7-Eleven coffee.

Nothing against them, they just don’t get it.

Let me give you solid evidence. Look below at what the Hemingway Editor and Grammarly say about my writing. They think it’s trash. Well screw you old man Hemingway. Wait, you’re dead. Oopsie.

Screenshots by author

Making great sentences is nice but I have no clue how to do that. What I do know is quality writing has little correlation to making money.

So what matters?

1. Self-awareness

People don’t buy writing. They buy you.

Read the opening of this story again. That’s self-awareness. I know my readers well enough to read their minds.

At the same time, I’ve developed a level of self-awareness that helps me see my flaws and ensures I don’t preach as if I’m Jesus and know everything.

Too many writers are full of their own sh*t. They swallow the brown stuff. Yuck.

2. Ability to read the room

Publishing into cyberspace is useless.

Most writers do this. They don’t read the room so they don’t know what readers want. They don’t notice trends on various platforms. They don’t pay attention to other writers. They’re so focused on themselves.

So they miss the entire point.

Money-making writing communicates what we’re all thinking and feeling at a singular moment in history. Money-making writing observes what’s going on. Money-making writing is full of depth, not shallow platitudes and cliches.

This type of consistency creates millionaires

Making money from writing largely comes down to your ability to do it.

I rarely feel like writing. I’m afraid. I’m full of fear. I don’t know what to write most days. But no matter what I show up two days a week and try to write a few stories.

The funny thing: when I look back on the writing that made me money it always makes me cringe. That’s how you know you’ve grown as a writer.

Always do this or you’ll have nothing to write about

I used to do stream of consciousness writing.

Whatever came to my head I’d throw onto the page and hit publish. Sure, a few times it worked. But a lot of the time it was word soup. No one could comprehend what the bloody hell I was saying. So they didn’t read.

Makes sense.

Writing that makes money starts with an outline.

I write 5-10 headlines a day. I add dot points under headlines as they come to me. I find the energy of a headline is highest when I come up with it. When I go back to headlines, often, the energy has died. Ahhh well.

On the day before a writing day, I pre-select the headlines for the next day and highlight them in orange in my Roam Research app.

Pre-written headlines are a superpower. The hardest decision is made. And the headline dictates the entire story.

Always start with the headline.

The #1 thing online writers understand

Most writers can write good enough for the internet.

But they don’t make over $1M because they don’t understand distribution. They think the work ends after they hit publish. They publish and pray to a fake god that people will read it.

It doesn’t work like that.

Writing needs distribution. You need people to share your writing. And you need to help share other people’s writing too. This isn’t like-for-like groups or engagement pods.

It’s about using DMs to connect with people similar to you and informally sharing each other’s work.

Without other writers, most people would never have seen my work.

Focus more on distribution and less on writing.

Learn how to sell (not tell) a story

Lots of people can write facts.

They can recite stories. They can make it look like their sentences are in fact sentences. But ‘telling’ gets you nowhere. It can even ruin your career.

Writing that makes money is persuasive. I think of it like high school debating. You have to go hard to beat the other side’s arguments. There are many skills needed to win an argument.

But you need more than persuasion. You have to understand the life of an average reader.

  • No time
  • Goldfish attention
  • Drowning in information
  • Sick of all the boring content they find

So you’ve got to write with this in mind.

The headline persuades a reader to click. The subtitle resells them. The first sentence tells them if you’re a liar. The first subheading keeps them interested. The first point gives them some evidence to trust you. The whole way through a piece of writing you’ve got to hold people’s attention.

That’s why walls of text get no reads.

They spit in the face of the reader and scream “I write essays and I’m the best.”

The trouble is we can’t read their huge-ass paragraphs on our tiny phone screens. It’s a sign of disrespect. Whereas writers who earn the real money use frequent subheadings.

Subheadings give readers dopamine hits.

Be super-kind to your competition

Some writers don’t get the internet.

They treat it us like an ex-girlfriend. They shout at us. Their thoughts are unfiltered. They have zero manners.

So what happens…

They think they’re the internet police. Or worse, they start to attack other writers. This is a deadbeat loser’s strategy. If you’ve named and shamed another writer then shame on you.

Most people are awesome though. If it wasn’t for the support of other writers, I’d still be stuck in a cubicle playing with myself and hoping to escape.

Writers who make real money support other writers.

Diversify like a venture capitalist

One thing I did from day one was diversify.

I learned this from stock investing. You don’t chuck all your money on Papa Elon’s car company and hope to get rich. No.

So with writing I’ve always published my work in plenty of places. When one platform goes bad or has a quiet period, another platform rises up. Recently, for some strange reason, my personal WordPress blog has fulfilled that role.

Other times it’s a naughty censorship-resistant orange newsletter platform that’s stepped up to the plate.

This isn’t a dig at social media apps. Their job is hard. But in the end you’ve got to make sure you aren’t a one-platform pony.

Oh, and the best thing I ever did was follow my mate Gavin’s advice.

“Build the email list. Email the email list.”

Image supplied by author (pictured: me)

The making money part of writing online

Let’s get to the good stuff you’ve been waiting for. No more theory. Let’s talk how I made $1M+ from writing on the internet.

I’m not going to break down earnings. I’m not sharing screenshots. Why? One: privacy. Two: my journey will be different to yours. Three: I have no effing clue what money came from where. I don’t track any of it.

Money is a giant distraction if you focus on it. So I don’t. Soz.


Your best articles are chapters of an unwritten book. So multiple times I wrote eBooks and sold them. I still haven’t published a formal book yet. Penguin Random House should call me maybe?

Online education

The beauty of writing non-fiction is you solve problems through words for a living. Writing is nice, though many people want more.

A few years ago I built an online academy. It’s become my full-time gig. But let me be real for a second cause that’s what I promised you.

My current online academy was my 4th attempt at it. I tried 3 times before. So there are a few lessons you must learn if you want to do the same. It’s 100% possible to do though if you adopt the lean startup method.

If you think you know everything, you’re screwed — and courses will never make you a dollar.


Your library of content online becomes like a sales page.

People learn a lot about you. 1% of them will say to themselves, “I want what he/she has” and they’ll reach out.

They won’t ask to pay you for coaching. You have to spot good questions, answer them, see if they keep replying, and if they do, simply say “I have a coaching business if you want to go further.”

Coaching is time-based so it’s not infinitely scalable. But it’s fun as hell. Except if you get a client that becomes more counseling than coaching. Those people suck. Avoid.

Writing royalties

Some platforms pay writers. (Use your imagination.)

Uncommon ways I made money writing online

So far the ways I made money might seem obvious.

But my writing journey is like an iceberg. What you can see on the surface is only a small part of what actually happened behind the scenes. As I wrote more online these two newer strategies emerged:

Writing about this naughty topic

Web 3 and crypto are taboo.

I’ve written a lot about them because, frankly, I love it. And you should write about things you love, as the passion bleeds through the page.

As a result I researched Web3 more than I normally would. This led me to invest the money I made from writing into all sorts of projects. Some of those have done 50–100x the money I put in.

Money you make from writing is only one type of income source. The best use for money is to use it to make more money.

I got hidden promotions at work

Writing has been a great career accelerator.

When I worked in banking I wrote on the side. Many of my colleagues, customers, and suppliers read my work. Most of them loved it and it brought them closer to me and deeper into their world.

Multiple times I doubled my salary thanks to writing.

  • No job ad.
  • No resume.
  • No application process.

Just an “I like Timbo” referral to the right person, and voila, new job + fat bonus.

Writing makes you a people magnet for the right humans.

The dumbest thing I didn’t do that cost me millions

This one isn’t one I see get mentioned.

Let me take off the Iron Man costume and get real with you. I’ve lost millions by being a dumbass. I’ll explain…

Email lists are one-way communication channels. A community is multi-directional. Most of my community-building efforts have been one-directional. Other writers have done a much better job at me than this, so they’ve made substantially more. Examples: Nicolas Cole and Justin Welsh.

If you want to make real money writing, you need to build a community around your work. This is done by getting readers to join a Discord, Slack, or Circle group chat that you control.

One powerful thought to leave you with

You might think I’ve got the midas touch with making money online.

Like I said, not quite. I lost a bunch of money on a few bad decisions.

I put money into investments I shouldn’t have. I trusted people who betrayed me. I got lied to. And I got too cocky last year when the markets were out of control.

That’s the thing about money…. If you don’t let it humble you, it’ll wreck your life. So never get ahead of yourself. And remember:

Stop giving a damn about what other people think. That’s where the money is.

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