I Quit My Job Because Of Substack. (Paid Subscriptions Had Nothing To Do With It).
The writing built the audience. This built the business.
Today, I’d like to share the story of Derek Hughes - a Substack bestseller and someone I've admired for years, ever since I started writing on Medium. Today, he has a big announcement - he quit his job because of Substack.
Big move. Bold move. And yet Derek took that step, all because of Substack.
Here’s what happened and what made him take the leap.
Hope you enjoy it.
I clicked it on a Tuesday afternoon like it was nothing.
Turn on paid subscriptions.
Clean little button. I’d just arrived from Medium. 21,000 followers. A couple of Top Writer badges I referenced in conversation more than I should have. Substack looked like the obvious next step. The button looked like the obvious first move.
I posted my best work. I waited.
Six months later I had three paid subscribers. One was my mum. The other two I’ve never been able to account for.
I stopped blaming the platform around month four and started looking at what I’d actually built. The answer, honestly, was not much. A list of free readers who liked my writing and had no particular reason to pay for it.
The list wasn’t the problem. What I was asking it to do was.
The maths nobody warns you about
These days I’m a Substack Bestseller.
165 paid subscribers. 7,000 free. Earns me $600 a month.
Here’s what that actually means: at my current conversion rate, I’d need 60,000 subscribers to hit $5k a month from subscriptions alone. I’ve done the maths a few times. It doesn’t improve.
Paid subscriptions give me predictable income from two hours work a month. I’m not complaining about that. But I knew, fairly early, that it would never be the business. Most writers keep publishing and hoping the numbers shift. They don’t.
The model is the problem, not the output.
The paywall will not save you
You’ve been at this six months.
Three posts a week. Genuinely good work. The subscriber count is moving in the right direction, slowly but visibly. So you flip the paywall on, put your best stuff behind it, and wait for the economics to arrive.
They don’t.
The paywall slows your reach at exactly the point you need it most. And now you’re running three jobs at once: free content, premium content, growth. Most of us are doing this between kids, clients, or a job we haven’t quite left yet.
Burnout at that stage isn’t a discipline problem. It’s a model problem.
After the early flop I kept asking the same question: how do I get more people to pay for this?
It was the wrong question. The right one was: what if the writing earns trust, and something else earns the money?
The week the numbers changed
A reader replied to one of my posts asking if they could get hold of the templates I’d mentioned. Just a short message. No pressure in it. But I’d had a few of those replies by then and started to wonder if the thing I’d built to help myself write faster was actually the product.
I had a folder full of templates, frameworks, and prompt structures I’d developed over eighteen months of figuring out what worked. My own Resource Bank I used it every time I sat down to write.
I packaged it up. Priced it at $69. Emailed my list. People bought it. Over the next few months it made over $8,000. I sat with that number for a while.
Then I built another one.
I didn’t need 10,000 readers to make that work. I needed a few hundred who trusted me enough to buy something that solved a specific problem. That’s a different target. Smaller. More achievable.
By the time I’d built a small suite of products, something had shifted. It wasn’t one big number. It was the accumulation. Each product adding another layer of evidence that this was real and repeatable. That’s what gave me the confidence to go back to my employer and start the conversation about reducing my hours. Not a plan. Not a leap.
Just enough proof that the floor would hold.
Stop trying to monetise the writing
The algorithm rewards generosity.
The more useful free work you put out, the faster your audience grows. Lock it down early and you trade long-term reach for short-term income. And most writers make that trade before the audience is big enough for it to matter.
Keep it open. Use it to draw in readers who care about the problem you’re solving. Then give them somewhere to go. Something specific. Something that takes the next step they can’t quite take on their own.
Substack fills the room. The product is what happens when someone walks through the door.
You build it once
My first product sold to a list that most people would call too small to bother with.
A well-priced digital product sells more cleanly than a subscription because the buyer knows exactly what they’re getting. A result. Something they can point to. A $69 guide beats an $8 monthly charge because the value is visible upfront, not something they have to wait and see about.
The other thing: you build it once. It earns while you’re writing the next free post, sleeping, or doing something else entirely. The writing brings people in. The product does the work you can’t do at scale.
You don’t need thousands of readers to make this viable. You need the right readers and one thing that solves a problem they’re already trying to solve.
What I wish I’d understood at the start
That button looked like the business model.
It was just the front door.
The income that doesn’t require me to write something new every week and hope enough people click. That came when I stopped trying to sell the writing and started building things that solved problems people already had.
If you want to see how I built my first digital product. The process, the pricing, the mistakes I made along the way. I put together a free masterclass covering the whole thing.
The writing earns trust. Everything else earns the money.
Derek Hughes went from no online presence to a $60,000 writing business in 18 months. He writes about audience growth, writing craft, and digital products on Substack. 12,000 subscribers read him every week. Find him at:The Irresistible Writer.
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