I Made $5,000,000+ by Writing Online — Here Are 10 Lessons I Wish I Had Learned Sooner

The opposite of what you think

Image Credit-Midjourney

There’s no f*cking way I thought I could make a million dollars writing.

Everyone has told me writing as a full-time job is the stupidest idea ever. My previous music career wasn’t much better, they say.

I’m not the sort of guy that counts his money. But my accountant recently drew attention to my earnings. Yes, $5M+ is the current number. The weird thing is I’m not that smart and haven’t got any writing qualifications.

I break every rule because there are no rules.

In this article, I’m going to break it down. What you’ll learn will transcend writing and transform your mindset.

I’m not gonna flex Lambos or Rolex watches either. Nice. Let’s go.

The biggest secret I’ve learned

Be an absolute loser.

Be the opposite of a millionaire. Have nothing. Better yet, lose everything multiple times so you know what it’s like to be poor.

Being fed up with my situation is what led me to write online. Failure and rejection are some of the best motivation you can get.

If you come from a broken family that helps too. I’ve got half a family that doesn’t talk to me and I don’t even know why. Maybe it’s my dumbo ears, no clue. If you can throw in being fired into the mix as well, that’ll also help you start writing online.

There’s nothing better than picturing a dumb boss’s face and directing a well-written F U at them in the form of a Medium or Substack essay.

No one will know what you’re doing. But you will. And it’ll light a fire under your ass.

If you can also layer in some mental illness that’ll help too. When I started seeing a therapist in 2011, I used writing as a free form of therapy.

Writing was so therapeutic that I fired the therapist and just kept writing. Now I’m healed. Thank you writing gods.

Bottom line

Imperfection is the source of writing inspiration. Perfect people are unbelievable knobheads.

Do the opposite of what the gurus teach

Screw the writing gurus.

Most of them have a bee’s dick amount of experience. They teach like they’re Hemingway when they’re, in fact, Big Bird in a clown suit.

They say you should:

• Start a website

• Choose a micro-niche

• Write a book that takes 20 hours to read

• Build a #PersonalBrand and selfie yourself to death

• Comment on everyone’s stuff until you’ve passed out

• Just get a writing habit and all your fantasies will come true

Just ignore every f*cking thing these wankers say. None of it matters.

New rule: unless a writer has made at least $500,000 just ignore them.

The hardest part about writing is two things:

1. Getting attention ethically

2. Turning your writing into a one-person business

Where the freaking comma goes or how many followers you have is a silent disco that’ll murder your writing dreams and leave you in a bed of sardines with Garfield by your side wondering why he’s dressed in a tutu holding a Pokemon doll.

Ignore gurus.

Go faster

Most people decide to write online, then go too slow.

Just go twice as fast as seems smart. Write like you’ve just had a line of cocaine and watched Indiana Jones on 3X speed. A built-in sense of urgency helps you get traction faster. Why does that matter?

Because if you don’t get a tiny bit of traction early on, you’ll have no dopamine or momentum and give up.

I’ve always written faster and published more content than most because it was my get-out-of-banking-jail-free card. I hated it. I just wanted to write and stop going to endless back-to-back meetings in an oversized suit.

Write your writing goals down. Set timeframes. Then take your 5-year goal and make it a year. It’s bloody amazing what you can do in 12 months.

Stop waiting for the right time because life will always get in the way.

Pick a topic and get on with the show

People waste years thinking about topics.

Not me. I just wrote about as many topics as possible until the crowd told me the handful of topics they wanted me to write about.

Turns out the audience liked the topics I was obsessed with. Anything I was lukewarm on got no views – like relationships and politics – and whenever I wrote about life lessons or money people threw their g-strings at me and cheered.

You can learn a lot by keeping it simple.

Think about the dark impacts of AI

AI going mainstream means you now have millions of robots competing against you.

These terrify some people. But it makes me smile. I love it. Why? We can defeat the robots in the writing world by being so human they can’t copy.

That’s why I swear like a drunken sailor, say “mate”, and write unfiltered words that are messy and sloppy at the best of times.

AI can’t copy me because it’s not me. It doesn’t have my stories and it didn’t lose $1.2M. It also hasn’t had mental illness, fainted on stage in front of the entire school, or passed out in a pile of vomit and poo.

A strong writing voice is what leads to millions of dollars. It’s how you differentiate without a $200K marketing plan and becoming some useless personal/corporate brand. Who knew being yourself could be so profitable.

Turns out humans follow humans – not topics, formats, trends, etc.

Have s*x with your co-worker, then have a kid

Seems random. Hear me out.

Earlier in my banking career I slept around the office like Bruce Bigalow Male Gigolo. I’m not proud of it. Never sh*t where you eat comes to mind. This led me to date a co-worker and get trapped in a religious cult (no joke).

We later broke it off, then I went on Tinder and proceeded to go on something like 100+ dates in a few months. I’ve been on dates with half the population of Melbourne (in Australia).

This led me to find my wife. Then we had a snot-faced kid that’s kicking my office door right now as I write this, screaming “Daddy watch me jump!”

The point is you must live life to have stuff to write about. Otherwise, you’re all out of stories and end up writing Wikipedia articles for Medium dot com hoping to be blessed by the boost gods and collect $200 for passing go.

Live. Then write.

Go where there are millions of people

Too many writers get sucked into writing where no one is. Or writing on a platform that’s dying.

Stick with X, Substack, & LinkedIn and you’ll do fine. These platforms have enormous momentum and aren’t startups that’ll go bankrupt.

Never write alone unless you’re into BDSM p*rn

I heard singer Billie Eilish give an interview once.

She said from the age of 11 she was addicted to BDSM p*rn. She said it was a dark experience. She spent a lot of time in her room alone watching other people “do it” instead of making music.

This is what it’s like to write alone. It’s weird. It’s creepy.

For the first 5 years of my 10 years of writing online, I wrote alone in a dark room. I got no feedback. I didn’t hang out with other writers. I didn’t swap tips and tricks for different platforms. I just sat there and thought I was a god.

In the second 5 years, I’ve joined writing groups and masterminds. I’ve also paid for editing, coaching, and courses.

If you’re not willing to invest a little money in yourself, you’re just fooling yourself.

You’ll never figure out writing online through trial and error. Instead, what will happen is you’ll write online, face an obstacle, then give up and vow to come back to it later in your life after you’re retired or have free time (which is never).

Most wannabe writers live a fantasy. “I’ll write when I have time.”

I’ve never bought into that lie. I’ve just forced myself to write daily and dropped all the excuses. Honestly, you can make up all sorts of stories about how you’re gonna write, or you can just do it like Nike says.

If you really want to write you’ll write.

The competition are lazy mofos

I always thought writing about business was a bad idea.

It’s a saturated topic. But when a market is saturated it secretly means “there’s money over here peeps!” The worst decision is to write about a topic no one cares about where there’s no money. Poetry is one example.

I never worry about the writing world being saturated because the competition are lazier than Homer Simpson. They can write daily for a month or even 6 months, but they’ll never do it for a year or more.

And the writers who make it past a year normally start writing boring stuff. Then they fall in love with themselves and become desperate to make money.

Let me be real:

On each social media platform I can barely find 10 decent writers to read. My bookmarks folder for great writers is tiny. There just aren’t any.

The market is busy but it’s full of amateurs who don’t care about the craft and have no intention to help anyone other than themselves.

So you dear reader are sitting on one of the greatest opportunities on the internet.

How to get paid writing

This is the part you came for. I teased you all this time before giving it to you. Spank me big boy/girl!

Most people won’t make $5M writing.

Wait, what?!

Yep. The law of numbers says these types of success stories will be rare because elite performance in any field requires:

• A limitless mindset

• The skill of non-needy networking

• A dedication to mastery and going beyond the surface

• Thick skin to deal with jealous haters when you succeed

• A supportive partner who’ll let you write for long stretches

• An obsession with a topic that almost makes you a psychopath

• An ROI mindset that sees you invest stupid amounts of money in new, complimentary micro-skills

• Basic entrepreneurship skills that make you feel salesy, like a sellout, and cause critics to say “they’re just trying to make money from you”

Maybe if you read this Substack for long enough you’ll get the tools. But I’ll assume you don’t and unsubscribe after a few f-bombs while screaming “DENNING!!!”

This isn’t a sad story though.

A more achievable goal for most up-and-coming writers is to shoot for 6-figures. Once you make it to that level there’s a better chance of hitting 7-figures if you really want to.

Writing income streams

Let’s get practical.

1. Paid newsletter

That’s what this is. Simplest and dumbest business model there is. Works best if you sell your newsletter in a place like Substack where that’s the norm.

2. Writing royalties

Writing on a platform like Medium that pays royalties. This is a good place to start, but if you stay stuck there, it becomes a 9-5 job without a guaranteed paycheck.

3. Writing for others

Influential and wealthy people also want to be writers but they don’t have time.

So they pay chumps like us a heap of cashola to write for them and sign off with their name. Once you realize the bulk of the internet is made up of words, and someone has to write them, you see opportunities everywhere.

4. Coaching and group coaching

One of the best ways to take the topic you write about and turn it into money.

There’s no minimum audience size to do it and you can start at $20 and scale to as high as you want. As you climb the income ladder, you replace lower paying clients with higher paying ones.

When you get good at 1-1 coaching you then go into group coaching (10 people at a time) to leverage your time better and make more money.

5. Information products

People love to buy books, courses, templates, backgrounds, swipe files, libraries of content, hacks, cheat codes, etc.

A writer can easily create these things with 95% profit margin. Why not you?

6. Consulting

Businesses need help and they pay well.

Some topics you can write about show credibility in a certain field and become a magnet for businesses that need help with that exact problem.

When they reach out you just say “Sure, I can consult to you on that.” It’s code for “I solve this problem for money.”

7. Product-based business

eCommerce is huge.

You can build a following then sell real products that need to be shipped to a customer’s house. Or sell merchandise if you become the Mark Manson of your corner of the internet.

8. Board seats

Smart people can even get offered board seats.

I’m not smart at all and this happened to me. It sounds like “Join our board for $50,000 a year and help advise us on these matters.”

9. A better 9-5 job with free cappuccinos

Not every person who writes online wants F U money, a Lambo, and to tell their boss to stick their job where the sun don’t shine.

The first way I got paid writing was by getting promotions at my bank job. Writing helped me stand out. It made me appear smarter. It got leaders to notice me and go, “Ahhh that Tim guy says some interesting stuff on LinkedIn, doesn’t he?”

The last promotion I got, thanks to my writing, even earned me limitless free cappuccinos that I paid for on my corporate card. Don’t tell my old employer (whoopsies).

That’s how to make $5M+ from writing

The final thing to decide is whether you will write online.

And if you already do write, will you dedicate yourself to it? Will you write more and go faster than before? Will you take writing seriously and stop screwing around?

If a skinny guy from Australia with dumbo ears, no grammar or spelling skills, and one hell of a mental illness can make $5M+, then you can at least make $100K.

The best part isn’t the money. It’s who you become through the process.

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P.S. Last day to watch the replay of last week's free masterclass:

Secrets to Six Figure Newsletters

A newsletter email list has been a massive chunk of my $5M+ writing income. 

You can get my secrets by clicking here before tomorrow (June 13)