The paywall test: does your writing make the cut?

Readers need high quality, value and unique insights to upgrade through a paywall: does your writing stand up to that test?

If you’re a regular reader on Substack, let alone a writer, you’ll be familiar with the paywall experience.

Dive into an interesting post, get hooked… And then greeted with a big fat paywall. Want to read the rest of this post? That’ll be $8, please!

It’s annoying enough as a reader, so trying to establish a paywall strategy that works as a writer can be a difficult endeavour. We’re all seeing them a lot these days, after all. And how many posts should I paywall anyway? Where do I place it?

Creating a strategy that works is as much about the quality of your work as anything else. Research shows people will pay for content when it’s of high value, insight or uniqueness - so does your writing fit under that umbrella?

What makes content worth paying for?

That anyone can create a Substack newsletter and earn from their work is amazing. And while anyone can, not everyone will. Readers aren’t gullible, and getting them to part ways with their money isn’t easy.

Even with the Freelance Writing Network as established as it is - with 14,000 free subscribers and hundreds of paid - it often takes 2-3 months before someone is convinced enough by the content to upgrade.

And if your writing is something a reader could easily get for free elsewhere, your paywall is going to have a limited impact. What are you offering, or what’s so good about your work/writing that makes it worth paying for?

If most readers only pay when they can’t find your insight anywhere else, then it needs to be consistently sharper, more honest, useful or insightful than what’s free. Given how quickly Substack is growing, the bar is higher than ever before. And it’s only going to rise as more and more people join the platform.

Does your writing have value?

Yes, probably. That’s the honest truth. I read lots of writing on Substack, and many writers are competent enough to be worth paying money for. But we all read too many newsletters and can’t support them all, so we know people have to choose.

Before you set your next post to ‘paid’, consider whether it gives something your reader can’t get elsewhere:

• Is the writing, reporting or analysis original?

• Are you sharing hard-won expertise or a truly new angle?

• Will a reader feel like they got their money’s worth, even if they only read that one piece?

This doesn’t mean that you need to reinvent the wheel each week. Plenty of successful writers cover familiar topics, but they do it with a distinct taste, voice or perspective. Your take on the same subject might land because it’s unique in some way.

It also doesn’t mean you have to be offering a service or product of some kind. There are plenty of successful writers making money from essays of some kind, even if it’s just a small side income.

The key factor that all those writers have in common is that the writing is really, really good. Is it well written? Is it engaging? Have you invested time in editing? You can always get better at writing of course, but you might want to practice for a while if you’re less experienced before expecting someone to pay for your work.

Editors exist professionally for a reason. And the brutal reality is that it shows sometimes when you read work here. Taking the time to polish and refine your posts is absolutely vital if you’re serious about your newsletter.

How do you judge your writing?

Being objective about your own work is difficult. If you’re considering paywalling a post, I would absolutely suggest giving it a day between writing, rereading and posting. That’s just good editing advice anyway because you’ll have a much clearer sense of how much value is in your work when you look at it with fresh eyes.

Imagine you’re a random reader of your newsletter, or stumbled across it for the first time. Would you like it? Share? Subscribe after reading it? If you’re confident the answer is a no (for whatever reason), it doesn’t mean the post doesn’t have value - just that it might not be one to monetise.

I also recommend using surveys to assess how your work is doing (once per year maximum). This can help you explore what is landing well, and what you might be able to offer more of. Even asking for comments is helpful, as many Substack writers get post ideas from their audience suggestions.

Outside perspective is the quickest way to determine if your writing has value. If you get great feedback, and you know your readers appreciate the work, it could be time to think about placing a paywall somewhere if you’re keen to monetise.

And if you’re unsure, check engagements. Comments, replies, and reshares are often good indicators of readiness.

Do you even need a paywall?

Not everyone needs (or wants) a Substack paywall to monetise.

I’ve written in the past about ways you can monetise without a paywall, so it’s not the only method. Some people don’t ask for anything, with optional paid subscriptions that function somewhat like tips.

CAFÉ ANNE, a weekly newsletter with a focus on New York City, is a best selling newsletter that runs without a paywall. Ran by Anne Kadet, a big aspect of the appeal is it’s welcoming and accessible to everyone. With a strong community feel, the perspective is that this leads to kind and generous supporters, who pay simply to support the work.

Other creators on Substack make their money through courses, coaching, live sessions or sponsorships. If your work naturally drives opportunities elsewhere, a paywall might not be your best route anyway.

A paywall works when it matches the shape of your writing and audience. If your posts are long, analytical or packed with useful detail, people are more likely to see the value in paying for more. But if you’re often writing short reflections or updates, you might find a free model with optional support feels more natural.

I’d always suggest playing around with your strategy, and finding a formula that works for you over time. It’s unrealistic to copy someone else’s approach and expect their strategy to work for you, unless your type of content is extremely similar.

There’s also no shame in keeping everything free - plenty of successful writers do that. Their goal isn’t to convert readers to paying subscribers, it’s to build reach, reputation or future income in other ways. That could still lead to monetisation, it just happens later down the line.

Tom Orbach, who monetised his Substack ‘Marketing Ideas’ more recently, built a large audience before starting to paywall. It meant tons of people got to see the value for free while he built out, and then when he chose to paywall, many of his readers already knew the value in paying for his work and upgraded immediately.

Finding the balance is important, and it might take some trial and error before you can determine what’s right for you.

Keep writing, keep editing and keep trying things out. Monetising on Substack is possible, but there’s a lot of trial and error happening that you never really notice when reading on here.

So just keep at it!

---

Need personal help growing your newsletter?

“George, this has been an amazing help for me so far. I’ve got a dozen new practical growth tactics to try in the next few weeks and I’m already seeing the impact on my free and paid subscribers. I wish this had been available when I was getting started!” - A message from a creator enrolled in The Growth Sprint: 3-Session Newsletter Accelerator.

If you’re launching, stuck, or ready to grow faster, I offer private, 1-2-1 coaching for Substack writers at all stages. Whatever support you need to help grow your newsletter, and whatever stage you’re at, I’m here to help.

• Ready to go all-in? I also offer a comprehensive deep-dive package with three tailored sessions and full, extensive support as you build.

• Already publishing? I’ll audit your setup, content, and strategy and give you a hyper-focused plan to boost growth or conversions.

• Just getting started? We can pressure-test your idea, review your positioning, and tighten your launch plan.