How to Write for a Living

How to Write for a Living

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How to Write for a Living
How to Write for a Living
How to Make $500 a Month on Substack
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How to Make $500 a Month on Substack

From someone who never believed it was possible.

David McIlroy's avatar
David McIlroy
Jan 14, 2025
∙ Paid
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How to Write for a Living
How to Write for a Living
How to Make $500 a Month on Substack
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➡️ Hate the thought of self-promotion? Same. That’s why I made Sharing Without The Cringe — a free guide to help you share your writing with confidence. Get it here.


What you’ll learn in this paid post:

  • Why the “overnight success” narrative is complete nonsense, and what to aim for instead

  • A realistic path to earning your first $500/month as a Substack writer

  • How to turn free readers into loyal paying subscribers using trust, value, and smart offers

  • Why social proof, testimonials, and limited-time discounts make a real difference

  • How to land your first sponsor (even with a small list) by pitching strategically

  • Three monetisation streams that can work together to build long-term income

  • A few bonus income ideas you probably haven’t considered, but should


Have you ever read the subject line of an email and thought what a load of… well, you know.

I get those kinds of emails every week.

  • “Here’s how this creator went from 0 to 100,000 followers in 3 days”

  • “You should be making six-figures a year already - why aren’t you?”

  • “My 5-step plan will guarantee you’ll be a millionaire by this time next year”

And so on. And so forth.

We read these subject lines and scoff because, quite frankly, they’re often garbage.

And why are they garbage? Because no-one jumps from zero to Scrooge-McDuck-sliding-down-a-big-pile-of-gold-coins overnight. Or in 12 months. Or in less than 3 years, if we’re being honest here.

There are almost always a plethora of steps in between. And each of those steps takes time, effort and patience to reach.

So today, let’s dial back from our Big Audacious Financial Goals as writers who want to make a living and focus on a smaller, more manageable step. For now, let’s forget the distant six-figure dream. Let’s even put aside the five-figures-annually target. Or even the four-figures-a-month goal.

Today, let’s talk about how to add a handy and very doable $500 a month to your bank balance through Substack.

We’ll start with the most obvious one: converting free subscribers to paid.

Let me give you 5 ways you can go about doing this.

The rest of this post is for paid subscribers. If you want to dive in (and support me in the process), consider upgrading to my paid tier. You know it’d make my day. ☺️

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