Everything I Learned From Turning On My Paid Tier "Too Early"... And What You Need To Know Before Flipping The Switch

If you've been thinking of turning on paid but you're not sure... read this post

The most frequently asked question I get is, “How do I turn on paid?”

I get it. It’s not that it’s confusing “how” to turn it on… it’s just a setting and a Stripe connection and Substack does the rest, pretty much.

It’s more about what you do for people who join your paid tier that stumps people.

And it’s about how to get enough people paying that it makes sense to do something.

And it’s about how to get people to even see what you’re offering as valuable.

It’s much more complicated than just “flipping a switch” and earning money.

So, if this is your conundrum and you’ve been wondering this exact thing, you’re in the right place.

In this post, I’m going to break down 7 things I’ve learned since turning on paid “too early” and without an existing audience anywhere else.

So let’s dive in…

7 Things I’ve Learned Since Turning On My Paid Tier (And what I’m changing because of it)

I turned on my paid tier when I had around 340 subscribers.

That number definitely would make the Substack experts flinch.

The prevailing wisdom says you should wait — grow your list, build more content, prove yourself worthy of asking for money. I’d heard all of that and really had it in my mind that I should have at least 500 subscribers before turning on paid.

But — I turned it on anyway, and I’m going to tell you exactly why, what happened next, and what it’s taught me about building something that actually works.

Because here’s the thing: I’ve been building online since 2016 and I started with basically no business skills. I managed to make $50K in my first year with fewer than 300 email subscribers (but it took me far too long to have the confidence to even try).

I have lived on both sides of the “I need to be bigger before I charge” belief, and I can tell you with absolute certainty which side pays better.

So let me share the real numbers, the real lessons, and where all of it is taking me next.

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1. I turned it on before I felt ready — and that’s exactly why (I think) it worked.

So much opened up mindset-wise when I turned on paid. I don’t think anyone talks about that, but it’s probably the best benefit.

I was more excited when my first paid subscriber hit the upgrade button than anything I’d ever sold at far higher price points.

Why?

When someone opts in with their money on something that you’ve been working on, something you’ve been toiling over and showing up every day to create a vibe, a presence and something of value, and someone raises their hand and says, “This is valuable to me!”, it’s acknowledgement. You’re on the right path. If one can happen, more can happen!

But here’s what I need to share. When I launched my paid tier, I didn’t have a polished paid tier offer. I definitely didn’t have a content calendar mapped six months out.

What I did have was indication what the people already reading my work (this is KEY) and would likely want a way to go deeper on. And I had a hope that some would be willing to hang out with me while I grow and smooth everything out.

I said this upfront: I’m early. I’m new on this platform. By joining, you’re growing with me.

And I meant it. I didn’t see that transparency as a weakness, it was just part of what I was doing. It wasn’t meant to be apologetic or a pitty party (please pay me while I figure this out??) Not at all. More like, “this will probably change and grow over time, but I promise with every edit I make, it’s with you in mind to make it better and more valuable. And while I learn while doing, I’m going to be sharing all of what I learn on the way!”

What I didn’t expect was how much clarity would come from that single decision to turn on paid.

Turning on paid didn’t just generate income — it generates information.

I used the information I got from successful free posts to figure out what my subscribers would want, paired with what I was most energized to create. It was almost like that first “offer” (that’s what your paid tier IS) naturally leads to other offers and it opens up something in your mind to help you realize it. (especially if you’re not sure what your offers are yet)

2. My numbers are modest, and I’m sharing them on purpose.

Right now I have 1,234 free subscribers and 40 paid members. That’s roughly a 3% conversion rate.

I’m telling you this because the paid tier conversation online is dominated by people with 50,000 subscribers celebrating their numbers. Which is great for them — and completely useless for someone with 500 or 1,000 readers trying to figure out whether this is even worth doing yet.

I think it is. Forty people paying me changes my business. Maybe not in the way that replaces a salary tomorrow, but in the way that funds experiments, validates direction, and keeps me building without waiting for permission from an algorithm.

3. Paid posts taught me something I didn’t expect about reach vs. conversion.

Here’s where it gets interesting.

My paid posts do reach significantly fewer people than my free posts — that part is just how the algorithm works. People see a locked post, many don’t open it, engagement drops, and Substack throttles the reach further.

But the people who do open them? Many times some have converted to paid from them. The way I write my paid posts in a particular way make it too juicy not to upgrade to read the rest (this part is definitely going into my upcoming workshop on paid tiers!)

One paid post about content frameworks brought in 14 new subscribers and 4 new paid members. Another about Notes strategy converted paid readers too. Several of my paywalled posts have directly resulted in people upgrading — especially the ones about Notes and growth strategy.

So it’s not that paid posts don’t work. They actually convert at a surprisingly strong rate among the people they reach.

The real tension is this: my free posts are what grow my audience.

Notes and a handful of high-performing free posts have driven the vast majority of my subscriber growth. Every time I put my best thinking behind a paywall, fewer people discover me.

I found myself caught between two things that were both true at the same time.

Paid posts convert readers into members.

Free posts bring in new readers to hopefully join later.

I know how numbers work, and the more free subscribers you have, the more chance you have that more will join as paid subscribers.

I was splitting my creative energy between the two — and that tension is a big part of what led me to rethink what I’m doing.

(This is another piece of the puzzle that moved me toward the changes I’m making…)

4. More content is not more value.

I’ve been a consumer of online courses and programs for over a decade. I’ve bought the big flagship courses with 47 modules. I’ve enrolled in the membership sites with a new training every week. Ya know how much of that content I actually finished?

You already know the answer. 😬

My audience — coaches, consultants, people building their Second Act — they’re doing this while parenting, while working full-time jobs, while managing everything that comes with being in your late 40s and beyond. The last thing they need is a pile of content and the guilt that comes with not getting through it. And even at the level I’m providing paid perks now has resulted in some unsubscribes with the reason being “time”. That could be that it’s too much, or it could be that in general, they’ve got a lot to read on Substack. I get it. (which is one of the things that inspired one of my changes… more on that in a second)

What I’ve come to believe is this: value isn’t volume.

People need something they can actually use — something bite-sized enough to absorb, specific enough to apply, and delivered in a way that respects the fact that they have an actual life happening around this.

5. I’ve edited my paid tier three times already — and that’s actually ok.

When I launched, I offered paid posts as the feature. Then I added a monthly live Q&A call. Then I added a limited time Notes cohort that comes with all of the other paid tier content.

Each change has taught me something.

Not to mention… the more time I spend on Substack, the more I see other people doing really cool things that make sense for my model.

The goal for me is to create something that stands OUT, not blends in. It’s taken me a few months to figure out what that looks like for me (this is what “building in public” looks like! 😅 ) and I don’t think I would have figured it out this fast witout doing it publicly.

I reallly think that’s what stops most people from starting — they think they need to have it all figured out before the start. For me, I learn from doing, so it worked to figure it out while I was doing it.

The paid posts taught me about the reach-versus-conversion tension.

The Q&A calls taught me what people were actually wrestling with.

The cohort taught me that live, contained experiences are valuable and a great connector.

All of these things that I’ve offered to my paid tier have shown me super valuable things about what I want to do and what my paid tier members want.

If I had waited until I had the “perfect” offer before turning on paid, I would still be waiting.

Instead, I’ve been iterating in public, with real people giving me real feedback. Every edit brought me closer to what I’m building now — which I genuinely believe is the best version yet.

6. The paid tier is a front door, not the whole house.

Math wasn’t my best subject in school, but I do know simple math. (especially when it has to do with money! 😂 )

To reach my income goals through subscriptions alone, I’d need roughly 1,000 paying members. To get 1,000 paying members, I’d probably need 35,000-50,000+ free subscribers. That kind of growth doesn’t happen overnight — and I refuse to work for free while I wait for it.

So — what I’ve realized is — I think all of the mainstream advice about paid tiers is wrong. Even Substack’s own messaging around it messes people up.

They give you a way to lock the post. They give you some options about where to put a paywall. You need to figure out the rest. But there’s more nuance than just figuring out what to lock and where to put the paywall.

I think of the paid tier as a front-end offer — an affordable entry point where people can experience what it’s like to learn from me, to be inside my world. Some of those people will hopefully want to go deeper: a 1:1 customized experience, a mini course, a VIP day. The paid tier is where that relationship begins, but it’s not where my business model ends.

It’s easy to dream big numbers and “getting paid for your writing”. Lots of people have achieved that goal and I really admire them.

But when I really looked, I realized that to get there will take a while.

I see a lot of writers on here poo-pooing the paid tier. They say the obvious: don’t turn on paid as your income goal, you’re never going to get there with 200 subscribers.

Duh, and thanks. (I wrote about the fact that most people saying it are literally selling you something else) 🙄 but whatever.

What I know is: Substack created a paid tier for a reason, and it’s not actually only to help you make money. It’s also to make THEM money. For every paid subscription they receive 10% of that. So why wouldn’t they want you to turn on paid? Going forward in the Substack story, it’s hard to imagine that people “using Substack only for discovery” will be the algorithm’s favorite accounts. 😏

So — for what it’s worth — I stopped pressuring my subscription revenue to be my dream income, and I started seeing it as the foundation that supports and informs every other offer I build.

7. I am never going back to “I need to be bigger first.”

You have no idea how long I waited. I spent years creating free content, never asking for anything (not even an email address!) and believing I needed a larger audience before I could charge for my work. I stayed stuck because of really bad advice.

So when people say, “likes and comments don’t pay the bills”, that hurts a little bit right in my mid-gut region. I can even feel it a little bit in my heart, like a real dagger going in. 😂

That belief cost me years and probably tens of thousands of dollars.

What actually happened when I stopped believing it?

I hired a coach and watched her do it. I launched a few months later and enrolled 4 people into a high-ticket cohort. I launched free challenges into group cohorts that eventually turned into more than 40 people joining and over $80K in collective revenue when they also believed that they could get paid with their expertise and a small audience.

I did this with social media following of less than 2K and an email list of around 300 people.

If only I had started sooner!

So this time around, when I saw that limiting belief of “wait until you have 500, wait until you have 1,000” — even from Substack experts swearing up and down that they knew what I should do? I turned it on anyway and I’m way further along in my journey than I would have been if I waited.

The audience you have right now is paying attention to you for a reason. The question isn’t whether you’re big enough. The question is whether you know you have something they want and you want to give them a way to get closer to you… and then once you know that, it’s about building the path that helps them get there.

All this to say… I'm now in the process of renovating my paid tier around a system I wish I'd had from day one.

So if you’re reading this and you’re feeling the itch to get started with your paid tier, I’m going to be doing a deep-dive on the topic in a workshop I am creating just for paid subscribers… and that workshop will be part of something much bigger inside my paid tier.

I really can’t wait to reveal it to you, and all of the people who opted in early will be getting a major upgrade, as well. I’m doing some things based on all the data I’ve been collecting to make it even more valuable — not in terms of quality, but in terms of experience.

Because I really do believe you can create a paid tier that is a pleasure to run and creates a world your members want to stick around in.

So stay tuned… and if you want to be the first to know when that workshop drops… make sure you’re subscribed!