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7 Writing Strategies That Will (Likely) Never Make You Rich

by | Apr 17, 2023 | Writing

The tragic thing about writers is most don’t earn enough money to live.

I predict this will change with the digital renaissance AI has brought upon us. In the meantime, the best thing you can do to make money as a writer is to stay away from fake opportunities like these.

1. Publishing behind walled gardens

  • INC
  • Forbes
  • Entrepreneur.com

These websites sell dreams, not reality. They want you to be paid in “exposure.” LOL. Social media gives you exposure for free.

The challenge with old school publications with editors is they create a permission slip environment. Actually, having written for many of them, it’s much worse.

They don’t even ask your permission to do whatever they want.

They’ll take your Picasso writing that you spent hours crafting and piss all over it. They’ll give it some lame headline like “5 Better Ways To Life.” What the hell does that even mean?

They’ll edit out the stories and just leave the actionable takeaways. Man, this has happened to me more times than I can count. They’ll even take your carefully selected cover image and just insert some random photo that’s been used millions of times on Unsplash.

Run. Like run real fast. This world is dying.

The ads that pay the bills for these publications are drying up. They’re starving and you’ll be hungry too if you stick with them. Run.

This dinosaur publication model is dying — and everyone knows it.

2. Running to the latest and greatest platform

“There’s a gold rush Timmy, I tell ya.”

No there’s not. Stick with saturated writing platforms. Saturation equals “there’s already money over here.”

Don’t worry, I’m a knobhead too. I’m guilty.

Bitclout. News-break-my-balls. Vocal.

I’ve tried more places to write than I’ve had tumbled dried underwear since 5 years old. The mindset that enables poverty is trying to make lots of money overnight from writing.

There isn’t a single great writer I can think of that made money overnight.

Writing online is a slow burn with a huge payoff for those who can stick at it — like 5+ years.

Takeaway: make $20 online. Then we’ll talk.

3. Getting coffee tips

Tried this on Vocal. Absolute joke.

Stop wasting your precious call-to-action space with crappy ‘asks’ that pay you peanuts. Build the email list. Email the email list. That’s how you make more money than you could ever dream of.

4. Waiting for a book publisher to choose you because your writing is so damn awesome

Oxford university professors have conversations about you. Your sentence structure and prose blow them away.

(Side note: I have no freaking idea what ‘prose’ is even after I’ve googled it 100 times and screamed at ChatGPT to tell me. It sounds like wankery.)

Believing people are thinking about your writing behind closed doors is the first sign of insanity. Hint: they’re not.

Book publishers aren’t either. The mind of a book publisher employee looks like this.

“How many email subscribers does this writer have?”
“Okay, email them for a Zoom.”

Nothing else is happening other than that. Once you have an owned audience they’ll step in and help you elevate an idea.

Before then, you’re a bum with a dream and they don’t have enough time or money for dreamers. Harsh but true.

Writers need to get real if they want to earn a living.

5. Using sympathy as a way to ask for money

This is one of the worst writer business models I’ve ever seen. Seriously.

Post a few hard luck stories and then link to a Patreon or some other charity platform begging for money.

In my banking career my employer had a lot of issues with donation marketplaces. There were so many scams. People will pretend to have been hit by a car and stage all the photos. Or they’d simply make up stories.

So my employer just banned them all from using our services to accept payments. Problem solved.

Readers buy stories and helpful advice. Learn to do that and you won’t need to beg on the main highway of the internet for pennies.

6. Sending cold DMs to get writing gigs

Another day, another cold DM offering to write for me.

Sending messages to strangers doesn’t work for 99% of writers. Let me explain why. You send me (or anybody) a DM telling me I can pay you to write stuff. Good on ya.

Here’s what happens:

  • I open the DM
  • See if you can spell (often not)
  • See how many followers you have (normally less than 50)
  • Check out your writing on google (nothing with engagement)
  • Look at your last post (there isn’t one or no one read it)

Then I say to myself, “Well, if they can’t write successfully for themselves, they probably can’t do it for me.”

So I delete the message and move on with life.

Sending cold DMs only works if you have a little (not a lot) of social proof. Otherwise you’re wasting your time.

It’s just another form of begging. And beggars are likely to starve in this fast-paced online writing world — especially now that AI can write “content.”

7. Writing ChatGPT threads

You know the ones. They’re written by tweet thread boys.

They jump on whatever hot trend there is and copy a hook from someone else that’s supposed to make them go viral.

Here’s one: “ChatGPT is like a free university.” LOLLLLLL.

What these thread boys forget is facts and logical information is boring as hell. It has no personality or stories behind it. Yes, a ChatGPT post might get a few extra likes, but likes ain’t cash bro.

Jumping on topic trends doesn’t work unless you actually give a crap about the subject and have some unique take or story to add. Otherwise, you just blend in with the other boring writers and drown in a race for likes.

The biggest money-making topics are timeless.

Just look at what Ryan Holiday did with Stoicism.

The writing strategy that made me 7-figures

A lot of articles on this exact topic give bad advice.


They’re written by people who haven’t actually made money from writing. Or not enough money to be called “a practitioner.”

Without bragging, I’ve eaten this writing game for breakfast every day for 9 years straight and made 7 figures from it. Here are the boring ways to get rich writing that’ll never die.

  • Tweet daily — everyone needs a short-form strategy to test ideas.
  • Publish a weekly newsletter — communicating with an owned audience via email is a license to print money.
  • Be on multiple platforms — times are-a-changing and no one knows what tech bro company is the next to go bust.
  • Be nice to everyone you meet on the internet (even the goddamn trolls who want what you have) — money is the result of who you know, not what you know. Financial opportunities always go to good people. Your writing is the business card that brings ’em in.
  • Sell information products as an upgrade to your writing — books, cohorts, group coaching, courses … whatevs.
  • Publish content that leads to a related online business — oldest trick in the book, I tell ya. Just don’t oversell it. In fact, don’t mention the business.

One strategy I haven’t tried

I’m ashamed to say I’ve never done much with this one: affiliate links.

But I’m a dumbass. Writer Lauren Como made $318K in affiliate sales by stuffing a few links in her articles. Writer Victoria Kurichenko made $3000 from one article with affiliate links.

I hear this story repeatedly. This is one writing strategy I’ll swear by in front of all of you to try this year.

Write on the internet and help people. That’s how you get rich slowly.

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