The Paywall Decision: When is the right time?
What to consider before you lock your work, and how to know you’re truly ready.
Paywalls are stressful. And we rarely talk about why.
Sure, we all know the benefits: a potential income, commitment and so on. But the reality of using one is often much messier.
I mean, not in practicality. You write a post, you add a paywall, share said post and wait for the money to start rolling in.
Except it rarely works quite like that.
The problem with paywalls is that they can quickly become disheartening or lead to slow growth that adds pressure on you to keep producing content.
Let’s use a newer Substack writer as an example. We’ll call them John.
John starts a Substack. After 6 weeks of consistent work and gradual growth, he decides to paywall some of his writing. He sets up Stripe, flicks the switch, and sends out a paid-only post to his 100 subscribers.
Then… silence. Or one or two upgrades.
And that’s when it gets hard.
That’s because even with a large audience, let alone a newer or smaller one, it’s entirely plausible he’ll get zero upgrades, or just one or two.
But wait! How can even a small number of paid subscribers be a bad thing?!
We don’t talk much about the pressure of writing a Substack, at least internally if not externally. Sure, not everyone experiences it, but many of us do.
The initial excitement is incredible. I’ve been getting paid subscribers since May 2024, and I still get the same buzz when I see a new one arrive on my Stripe dashboard. But I also know it’s easier for me now because I do this full time. New subscribers help me justify the time I spend here producing content.
The thing is, as soon as you have one paid subscriber who has upgraded because of a paywall, you’ve made a promise of sorts. A commitment to keep providing exclusive content. After all, the assumption will be that they’re paying for more paid content than just this one post.
There are get-outs, of course. You can offer to refund or close paid subscriptions. You never have to keep going. But who wants to refund or quit on people paying for your writing? That’s something many Substack creators dream of!
The writing is easy for a while. But if the growth doesn’t continue? It can be incredibly disheartening. I know, because I’ve had previous newsletters suffer from this. Either the crushing feeling of no upgrades or limited growth but with a commitment to produce more than I had the enthusiasm for.
It can make you feel like you’re letting your readers down. That you’re not up to scratch or simply not cut out for writing on Substack.
That’s where I’d offer one key piece of advice: If you want to add paywalls, be absolutely certain that this is a topic you want to write about for a long time.
I’ve made newsletters about subjects I enjoy but not love, and that made it hard to keep producing when it wasn’t going the way I envisioned.
For the Freelance Writing Network, that never happened. Even in the early days. I loved supporting freelance writers, writing about the craft and finding the opportunities. It was always obsessive, even before my first paid subscriber.
Looking back, I can understand how I was able to keep going when it made either very little or nothing at all. At the time, it wasn’t about that. And to be honest, if you’re in the early days of your newsletter, that’s probably the right approach.
This post isn’t a warning not to use paywalls. It’s to ensure you evaluate the right factors first.
You don’t have to rush. Just because the tools are there, it doesn’t mean you’re behind for not using them. What matters more is that you feel ready—creatively, practically, and emotionally—to make that commitment.
If you do? Great. But if you’re not there yet, that’s perfectly okay too.
So, if I were starting from scratch and considering a paywall, here’s what I’d be focusing on:
Build trust first. Share free, high-quality content consistently so readers can understand your voice, values and what you offer.
Grow your free list deliberately. If I was a completely new creator, I’d focus on growing an email list or follower base first before gating (too much, maybe any) content. Build trust, grow your audience, plan to monetise that reach later.
Identify what only you can offer. A paywall works best when what’s inside can’t be easily found elsewhere. If they can Google the title and find the exact same information, is it worth paying for?
Use engagement as your key metric. Are people reading, replying, sharing, and engaging with your work? These metrics are more important for showing you’re ready than thousands of subs who never open your emails.
Be ready to experiment. Try soft paywalls, timed access, or premium extras. You don’t have to treat it as an all-or-nothing from the start.
Check you have the time. Can you really commit to running a paywall consistently? Are you able to get the work out if you’ve promised it to paid subscribers? Paywalls can make a blog feel serious, and you need to know that you’re ready.
Have any thoughts on paywalls?
Let me know in the comments. I’d love to hear some of your thoughts and reflections on this one.