One of the biggest questions writers face when they step into online publishing is this:
When should I start charging for my work?
It’s tempting to rush, thinking, “If I don’t monetize right away, I’ll never make this sustainable.” But the truth I’ve learned so far is this: it’s less about timing and more about balance.
Free Value Comes First
Before anyone is willing to pay, they need to trust you. Free value is how that trust is built.
For me, this has meant giving away the first five chapters of each of my stories on Substack. Readers can sample, get hooked, and decide if they want to keep going. My newsletter, Words from the Hollow, is also free, giving everyone a place to join the journey without a paywall in the way.
Free isn’t wasted effort. It’s the foundation. Every free story preview, every helpful tip, every shared thought is a seed you’re planting for later growth.
Introducing Paid Offers Organically
So when do you ask for payment? My answer: when it feels natural, not forced.
For my fiction, the paid tier starts at Chapter 6. Readers who’ve made it through the free section already know if they’re invested. At that point, a paywall doesn’t feel like a wall — it feels like a door.
There are other ways to do this, too:
- Writers who offer bonus chapters or alternate endings.
- Nonfiction creators who include behind-the-scenes research notes.
- Educators who build companion guides or resources.
The point is, the paid offer should flow directly from the free experience.
Avoiding the Two Extremes
There are two traps new writers often fall into:
- Giving everything away. If you never ask readers to support you, many won’t — even if they would have been happy to.
- Holding everything back. If your entire presence is just “buy my stuff,” people won’t stick around long enough to care.
Balance is what makes readers respect your work and value your time.
My Experience So Far
I’ll be honest: I’m still new at this. I don’t have all the answers. Right now, I’m testing what works and listening to readers along the way.
Fiction is a tough genre to monetize, so I’m pairing it with affiliate marketing as a second path. My website is hosted through Wealthy Affiliate, where I’m building out not just my author brand, but also an income stream that supports the writing.
It’s not about chasing quick wins. It’s about building something steady, one step at a time.
What About You?
Now I want to hear from you:
- Have you tried offering something paid yet, or are you still focused on free?
- Do you prefer gradual paywalls (like mine), or bonus extras as the first step?
- What balance feels right for your audience?
Drop your thoughts in the comments. Your answers might help another writer who’s wrestling with the same questions.
Because at the end of the day, balance isn’t just strategy. It’s respect for yourself, your readers, and the stories you’re bringing into the world.
👉For more context, here’s the original article that sparked this post: Build Sustainable Online Income As A Writer — No Publishers, No Ads
This is such a thoughtful take on the tension between free and paid content. I like how you framed free value as planting seeds — that really resonates. I’m curious, though: do you think there’s a “sweet spot” in terms of how much free content is enough before introducing paid tiers?
For example, is five chapters about right, or could fewer still build enough trust? I’d love to hear how other writers are approaching that balance.
Hi, Jason. Thanks for reading and your kind words. I think five chapters are good, at least for me. You might find that three chapters fit you better. One reason I chose five chapters is because of my story, The Trade, on Substack. https://jaydeegresham.substack… The original story was inspired by a picture by Bobby-Jean Pentecost. I asked her permission many years ago to write a 1,000-word short story about it. That became the fifth chapter in the storyline of that book. I am really proud of The Trade. I have been told, after reading it and then looking at the picture, that the picture is what they saw. But my stories won’t be my only source of revenue. I am also pursuing Affiliate Marketing through Wealthy Affiliate. I believe that some diversification of income is the best way to go.
I hope this answers your question.
JD.