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.
This article makes a lot of sense for writers starting online. I love how it emphasizes giving free value first to build trust—like offering the first few chapters or helpful tips—before asking readers to pay. The idea of introducing paid offers naturally, like bonus chapters or guides, feels fair and respectful to the audience. I also agree that balance is key: giving too much away or charging too soon can both hurt your growth. It’s inspiring to see the author experimenting, learning from readers, and even using tools like affiliate marketing to support their writing journey. This approach shows patience, respect, and a smart way to build a steady income.
Paul.
Thank you for the validation, Paul. ????
Wow, I am at a loss for words.
JD
Balancing free and paid content is such a tricky part of building a writing business, and I’ve often struggled with finding that middle ground myself. Offering too much for free sometimes makes it harder to convince readers to invest in paid work, while holding back too much can limit growth and trust. How do you personally decide which pieces of content should be free and which should be paid? Do you think it’s better to prioritize giving more away at the start to build credibility, or is it wiser to set clear boundaries right from the beginning?
Hi, Slavisa. Thanks for returning, reading, and for your comments and questions. As I have said, I myself am just starting out on this journey. I decided to post the first five chapters for free because of my story, The Trade. The original story that was inspired by a picture from Bobby-Jean Pentecost became the fifth chapter of the tale.
From there, I just decided that I am good with giving five chapters away if they decide to subscribe to my JayDeeGresham.Substack or not. The reason is that it’s like my buddy “Michael: TheMagicBrad” said in his blog, “Perfect Copywriting and Captivating Graphics and Videos – That Nobody Ever Sees– Visibility beats perfection every time,” on Wealthy Affiliate.
Also, I am not relying solely on my books and stories. I am working on Affiliate Marketing.
I hope this helps.
JD
I write Christian devotionals and study guides, and until now, I’ve only shared them for free.
I appreciate how you offer the first five chapters of your stories for free; it seems like a great way to build trust with your audience. Do you think a similar approach could work for devotionals? For instance, offering the first few entries or a short sample study for free, then creating a paid option for the full series. I want to find a way that allows people to freely access God’s Word while also recognizing the value in supporting more in-depth resources.
Hi, Alice. Thank you for reading and commenting. Truthfully, I am not sure. You see, I have issues with God, since my mother was afflicted with Dementia before passing away on the 23rd of last month. Please don’t get me wrong. I have no problem with people who have faith in him. My problem is with a God that would allow the children who love him most to suffer illnesses and diseases beyond normal old age.
I apologize for my Rant.
But as to your question, I think your best bet would be to ask your readers. Ask them if they value the work you put into your devotionals and study guides. And if they do find value in the work you do, would they be willing to pay for it? If you were on Substack, I would suggest that you try my method and see how. If you have your own website, you might be able to do the same thing. I don’t know about this part, though. If you don’t have a website, but are thinking along those lines, then Wealthy Affiliate could help you out. They are running a great promotion for joining, which you can try out for free, but if you upgrade to Premium+, it is $200 cheaper than normal. Wealthy Affiliate is a Fantastic Affiliate Marketing platform and community.
I hope this helps in some way.
JD
This really hit home, especially the “giving everything away” part. Why do we do this to ourselves?
I’ve watched writer friends give away entire courses and manuscripts, then wonder why they can’t make ends meet. Is it fear that nobody will value our work? Your five-chapter approach makes sense – it’s a sample, not your whole product. What do you think drives that “give it all away” mentality?
Hello, Linda. Thanks for reading, commenting, and for your question.
In answer to your question, I can only speak for myself. When I would give things or money away, quite often it was to try to buy friendship. Which worked out about as well as swimming in a piranha-infested part of the Amazon River. It has taken me many years to get to the point I am at, which is pretty much similar to what I saw on a T-shirt on Pinterest. It had a little white baby dragon that had bits of their colors on its ears, wings, etc. And the caption read, “I don’t care what your opinion of me is. All my imaginary friends think I’m special.” Which puts it another way, it doesn’t matter what others think about you. Only what you think about you is what matters.
I hope this helps in some small way.
Blessed be
JD
I really appreciate how you frame balance as both strategy and respect—for yourself and your readers. The idea of free content as the “foundation” resonates so much, especially since trust is what makes people willing to support in the long run.
When you first introduced your paid tier, did you notice more hesitation or curiosity from readers—and how did you keep that transition feeling natural rather than pushy?
Hi, Jenny, Thanks for reading and commenting.
In answer to your question, I am still waiting for people to see the value in my work. I am just starting out, and these blogs are meant to be a journal of my journey, as well as a guide to what I think, what works, and what doesn’t.
But, right now, the main reason main reson I am not getting traction on Substack is because I haven’t been posting consistently. Most of my time is spent on getting my stories ready to be published, along with my newsletter. Another big slice of my time is spent on Wealthy Affiliate, which is hosting this website and the other side of my income Strategy. While the third and last slice of my time is taking care of my father and the house we live in.
But I am still getting my stories out. One day, I will find a rhythm that works, and I will gain traction. What I am saying is:
DON’T GIVE UP! You can do this, whatever you are trying to do. You’ve Got This!
I hope this helps
Blessed be
JD
This was really insightful — thanks for sharing! I love how you frame “free value” not as something you just give away, but as planting seeds of trust with your readers. The idea of letting people sample the first chapters, then offering the paid content naturally after they’re hooked feels respectful and smart. Also, calling out the two extremes — giving everything away vs. making everything paid too soon — helps writers see why balance is so key. It’s inspiring to see you experimenting, listening to your audience, and building something sustainable rather than rushing.
Thank you, Kiersti, for reading, commenting, and validating the path I am on.
It really means a lot to me.
JD
Thanks for addressing the tricky balance between giving away value and charging for your work. I’ve struggled with this as a blogger—I want to build trust by sharing tips and tutorials for free, but also need to justify the time I spend creating resources. How did you determine what types of content (blog posts, email freebies, mini courses) to keep free versus what to package into a paid offer? Do you think it’s better to start with a premium product early on, or wait until you’ve built a loyal audience through a lot of free content? I’m also curious how you avoid overwhelming readers with constant offers—are there signals you look for before pitching something paid? Great topic; it’s reassuring to know other writers grapple with the same questions.
Welcome back, A. Thanks again for reading, commenting, and asking your question. The direction that your comment suggests, guides, and tutorials is not my main focus, but it might need to be something I consider. Truthfully, there are a bunch of people on Substack that you could possibly get these answers from. If you decide to check out Substack, give me a shout out, and I will try to introduce you to a couple of people I talk to. I might be going off base here, A. But every article, blog, reply, or story I write, I try to make it a premium piece of work. I am not saying that you don’t do the same. But our goal should always be to do the best we can. If that is not the way you meant, I apologize.
Let me try again. Offer you reader something of value for free. If they want more then ask for a fair and reasonable amount of money. If they come for some other information, repeat. If they do this several times, only getting the free stuff, then offer a bundle set of all they have asked about. But again, for a fair and reasonable price for the whole bundle.
You have to decide what you are worth and how you are going to present yourself and your product.
I hope this helps.
JD
This was such an interesting read for me, I’m also an aspiring writer/author trying to monetize my fiction! I love crafting novels, and I adore short stories as well. I’ve recently self-published a collection of short stories, but, of course, the money is in the marketing, especially when the market is so saturated. So I’m working on that. To date, my “free content’ is basically just my blog, where I offer insights, writing tips, reviews, etc. I may consider offering a free preview on Substack. I like this idea.
For a short story anthology, how much of it would you suggest offering for free? One story? Five stories?
Hi, Steph. Thanks for reading, commenting, and asking your question.
In answer to your question. I suppose it would depend on how many stories are in your anthology, and if they have a connected theme, or if they are distinct from each other. But here are a couple of thoughts. 1) Offer only a portion of each story over time. In other words, tease them a bit. Maybe take the number of stories there are and tease readers with a portion for that many days, or weeks even. Maybe after the snippet from a story, you could ask them what they think will happen, or something like that. 2) Run a contest for a number of days equal to the number of stories. Give them a snippet each day and ask them which story the snippet goes with.
Really, it is up to what you are comfortable with. I hope this helps.
JD
Paid offers may feel scary. The best way is to land on them organically. I have been hesitant to start charging people. But I fee that right now, I’m ready. Thanks for your post because it made me realize I am not rushing this. I have waited enough and learned a bunch and now is time to charge! Should I charge by packages or for individual works?
Hi, Henry. Thank you for reading, commenting, and asking your question.
I would say that depends on you and your product. As an example, my story, The Trade that is published on
Substack will be a thirteen-chapter story that can stand alone or be published as part of the series, like I plan to do. To take this further, the original The Trade story is a one-thousand-word short story inspired by a picture from the artist, Bobby-Jean Pentecost. It can be a standalone product. So to answer your question with this example, the original short story would be the individual work, and the thirteen-chapter book would be a packaged deal, or individual work, that could be bundled with other books to be a bundle.
I hope this helps.
JD