The Myths About Going Paid on Substack That Keep Writers Stuck
Join other midlife Substackers for a workshop on Substack monetization
Last week, I asked our Midstack community about monetization on Substack in our chat. The question was simple: Are you offering paid subscriptions? Do you want to? What’s stopping you?
I’ve also asked the same question in my Midstack survey onboarding and in Midstack meetups.
What has struck me wasn’t the diversity of answers I get — though there was plenty of that. It was the pattern underneath them for many Midstackers (though not all!).
Fear. Confusion. Guilt. A sense that going paid meant becoming someone different. Someone more commercial. Less generous.
And woven through many responses: I want to, but I don’t know if I’m ready.
Here’s what I want to say about that.
If you are a midlife woman showing up consistently on Substack — writing, connecting, building trust with your readers — you’re already doing the work of a paid publication.
You’re crafting essays that maybe took hours to write. You’re responding to comments. You’re thinking about what your readers need. You’re refining your voice. You’re building something real.
The only difference between what you’re doing now and what a paid publication does is that one of you is getting compensated for it.
Going Paid Doesn’t (Necessarily) Mean Paywalling
This is the biggest misconception, and it’s keeping a lot of us stuck.
Going paid doesn’t mean locking your best work — or really any of it — behind a paywall. It doesn’t mean your free subscribers suddenly get little scraps while only paid subscribers get your best work.
Some writers do it that way. Many don’t.
You can go paid and keep every single post free. You can go paid and offer community access, bonus resources, Zoom calls, or many other offerings as your paid benefit. You can go paid and simply ask people to support your work — no extra perks required.
Your paid model is entirely yours to design.
You Don’t Have to Figure It All Out First
One Midstack member told me, “I would like to [go paid], but I don’t post consistently enough at the moment, and don’t know what I could write every month that would bring value to people paying to read it.”
You don’t have to have it all figured out before you start.
You can turn on paid subscriptions and offer nothing extra except gratitude. You can experiment with perks and adjust as you go. You can start with a simple model and evolve it as you learn what your readers actually want.
The only way to figure out what works is to start.
The 5 Myths Keeping You Stuck
Over the past months, I’ve heard many of the same concerns over and over. The same worries. The same myths that keep us midlife writers from taking the leap.
So I’m hosting a free live workshop for us to talk about what it means to go paid.
We’ll explore:
The “right time” to go paid
What to offer paid subscribers when you don’t want to paywall your posts
How to ask for money without feeling gross
What actually converts free subscribers to paid
The myths about list size, consistency, and “being ready”
How to use Substack’s brand new Perks feature to deliver real value beyond your posts
This workshop is for you if you’ve been thinking about monetization but haven’t gotten around to it, if you’re stuck between wanting to get paid for your work and not knowing how to make it happen or if it’s right for you. It’s also for you if you’ve set up paid tiers, but you’re not sure that they’re working or just want to rethink them.
Join me on July 14th at 1 p.m. Eastern. Register for the Zoom link HERE.
Before the workshop, I’d love for you to tell me about your experiences with going paid on Substack. Share them HERE in a short survey.
So glad you're doing this, Jessica. I agree with all of your points. When I work with clients, and they say don't want to turn on paid, I encourage them to do it anyway. The point that I make is "why would you deprive your audience of the opportunity to say thank you for what you do?"
There's no reason to paywall in my opinion. I have three stacks, and none of them are paywalled. I think it's important to keep the door open to all. When I go to someone's site and there's paywalls, most of the time, I leave.
I understand people paywalling who are very controversial as a way of limiting trolls and bots, but I feel that in those cases, it's important to offer comps to people who have economic challenges who want to be part of the community. Elitism doesn't work, and it's always what comes up for me when I encounter paywalls. That's just my reaction. And I let it guide my decisions.
I'm into giving, and trusting the universe and people to do what's right for them. And, I also ask for support, because I need to generate income.
When I started my first stack, I became a bestseller in 11 months. I came in with only 25 subscribers and I grew. It's doable. I'm sure I'll never get rich here, but I don't need that. I need to attend to the needs of a simple life.
xo
That's great, Jessica. Going paid, especially when first starting out, is really a head-scratcher. I must say though I wish I'd turned on the Getting Paid switch sooner. Since I'd blogged for many years prior to Substack-ing it, I had a nice cushion of steady readers. I didn't realize that they would support me as a paid subscriber bc they'd been with me so long and liked my writing. In this current climate (whatever that is) I don't think readers are turned off if someone adds a Paid suggestion. I personally don't paywall, so really, it's kind of the same either way. Either someone wants to pay you for your services, or they continue to read for free. Imho.