For Every Writer Who Thinks They're “Doing Substack Wrong”

From paywalling too early to not sharing your work - here are the 5 common mistakes really holding you back.

I was on a call with a writer last week.

She had industry expertise. She could help companies generate millions. She wrote for a living and understood psychology better than most copywriters I know.

But she wasn't growing.

She was publishing regularly. Her content was good. Really good even.

And that's when I realized something.

I went to my community of thousands of Substack writers and asked them a simple question about how they promote their work.

Turns out 95% of them were making the exact same mistake.

The same mistake my friend was making.

I've been writing on Substack for two years now. I've built a thriving publication without a single paid subscriber. I've had hundreds of conversations through comments, DMs, lives, and podcasts about what actually works on this platform.

And I keep seeing the same five mistakes over and over.

These mistakes aren't just holding writers back from growth. They're keeping good people from making money with their words.

Here's what I've learned.

---

Mistake #1: Paywalling Content Too Early

The default culture on Substack seems to be turning on payments immediately.

Connect Stripe. Create a paid subscription. Post your content behind a paywall.

I get it. You want to get paid for your writing. You want to make a little money.

And paywalling feels like the simplest way to do that.

But here's what most people don't realize about the psychology and economics of this model.

Memberships and low-ticket offers are based on volume.

They require a large enough audience to make substantial money.

If you have 72 subscribers and you convert 5% of them to a $5/month subscription, you're barely paying your phone bill.

When you turn on paid subscriptions, you're not just creating a Substack anymore. You're running two separate businesses.

You need to create content for paying subscribers—exclusive stuff, courses, access, whatever you're providing them. But you still need to grow your free audience to keep the funnel flowing.

So now you're writing for two different audiences with two different needs.

I've seen this constrict writers' ability to grow. And ironically, it can actually limit their ability to monetize.

Now, there are exceptions. Justin Welsh had a multi-six-figure email list and a massive LinkedIn following when he started on Substack. He turned on paid subscriptions, sent a few emails, and immediately became a bestseller.

But that's the exception.

Most of us don't have that luxury.

I personally don't monetize through paywalls. I monetize through other means. And I might look at paid subscriptions in the future, but only when the economics make sense.

If you're happy making $50 or $100 a month, that's completely valid. Some of my best friends on the platform run paid subscriptions. Some are big. Some are small.

But it's important to understand how the dynamics change and what environment is required for paywalling to truly succeed if you want to make it a cornerstone of your business model.

---

Mistake #2: Not Sharing Your Work

Remember that writer I mentioned? The one with all the expertise who wasn't growing?

This was her problem.

95% of the writers I surveyed were sharing their long-form content maybe once or not at all. Only 5% shared it more than once.

I recommend sharing your work at least one to three times. If not more.

When I post a long-form piece on Substack, I'm probably sharing it five times.

Tuesday: I publish my posts, and share it.

Wednesday: I select a punchy quote or paragraph.

Thursday: I click "share as quote" with a different section.

Friday: I might hit the restack button.

Saturday: Another quote from the piece.

We have so many tools at our disposal. The restack button. Designed images from Substack. 1-click shareable quote Notes. Repurposing to other channels.

And here's something most people miss—you can leverage your back catalog.

I've written somewhere around 100-150 long-form articles on Substack.

The chances of somebody going back two years to read something I wrote? Pretty slim.

But when I scroll back through my archive and restack something I posted 18 months ago, I immediately get likes and comments on that post.

We have the ability to get more visibility by sharing our work.

Most writers just aren't doing it.

---

Mistake #3: Not Using Substack Notes

This comes down to one simple reason.

The algorithm.

There's an algorithm that drives the discoverability of Notes. It's the simplest way to get yourself in front of new people on the platform.

What newer writers sometimes miss is that we have two types of content on Substack.

Long-form content in the form of posts or newsletters.

Short-form content in the form of Notes.

Notes has an algorithmic feed that shows your content to people you don't know yet.

Your long-form content lands in people's inboxes—which is amazing. It's not getting lost in a feed. It's not dying after two days. It's there forever.

But if you have 72 subscribers, you're only landing in those 72 inboxes.

If you have zero subscribers, you're not landing in any inboxes.

You post on Notes to gain subscribers either from people directly subscribing or clicking through to your content. Then you send long-form posts to those subscribers' emails so you can build trust, rapport, and develop relationships.

If you're just posting regular newsletters without using Notes, it's like having a product but no traffic driving people to it.

It's like having a blog that nobody knows about.

---

Mistake #4: Not Making Offers (Or Being Afraid to Sell)

It is possible to make money with Substack.

Through paid subscriptions, sure. But also through products, services, consulting, coaching—whatever it might be.

But we don't need the perfect offer.

We don't need a flagship program or a 12-module course or fancy landing pages.

Very simple solutions can sell.

As simple as writing a post about an insight or someone you worked with and mentioning, "This is what I helped so-and-so with. This is one of the five components inside my program."

Or having a link in your navigation bar that takes people to your resources.

Simply mentioning the things you do is a very easy and casual way to make offers.

Without ever coming off like a pushy snake-oil salesman.

I've had instances during a live stream where someone asks me a question and I casually reference, "Yeah, this is something I teach inside my workshop."

People watching will go to my profile, buy the product, and post in the comments that they just purchased—while we're still live.

That wasn't a hard pitch. There was no fake urgency or scarcity.

It was just relevant. And I let them know it was something I had available.

You can make money with Substack. It doesn't have to be complicated.

And you don't need 10,000 subscribers before you can start.

But you need to give people an opportunity to buy.

---

Mistake #5: Writing for Yourself Instead of Your People

This one's nuanced.

It depends on your goals. Your situation. Your comfort level with compromise.

I generally see people on Substack falling into three buckets.

Bucket one: People who just want to write. Share. Create. They're here for the love of it.

Bucket two: People who want to make money from writing. Professional writers, authors, fiction writers, poets, journalists, etc. They're (often) here to sell access to their writing.

Bucket three: People who are using writing to make money. That's where I fall. I'm not selling access to my writing. I'm using my writing to build a personal brand, build authority, build an email list, develop connections and rapport—and then leveraging that to solve problems for people.

When you're writing for yourself versus your people, the dynamic changes.

If I'm here to make money for my business through writing, I need to think about what people want to learn. What questions are they asking? What problems are they experiencing? What value can I deliver?

That's what forms the content I create.

Now, I understand there's compromise here.

If I was just here to write, I might be writing about Pokemon cards or my new gym routine or this new productivity app I discovered.

But if that's not serving the business I'm trying to create, writing about those things might not generate income.

Even as a business owner, there are still things I write about that I know won't make me as much money.

I know that specific how-to content and tutorials perform better. Talking about money and growth and making 6-figures gets shared more.

But I also have a deeper mission. Helping people who have struggled to see success. Talking about things bigger than business. Things aligned with my values.

Sometimes those posts don't have a call to action. They might get fewer likes.

But they're part of the mission I have with this platform. The movement I'm trying to create.

So there's compromise.

When I post about that, I'm writing for people, but it's also very aligned with me. And I understand it might not have the same profitability as different content.

On the flip side, if you only want to write for yourself and never want to make an offer, you have to accept that compromise too.

If nobody's engaging with your content and you don't want to listen to the signals and adjust, you have to accept that compromise.

I don't think it's black and white. Right or wrong.

It's more nuanced than that.

There's always going to be compromise at play when we're trying to make money.

There are certain things that allow us to do that more effectively.

We don't have to play that game if we don't want to.

But if we choose not to play that game, we have to understand the compromise we're making.

---

If Substack Isn’t Working, It Could Be One Of These Mistakes

I've had dozens, if not hundreds, of conversations about these topics over the past two years on Substack.

And I think if we can systematically work through these mistakes, we can start to build publications that allow us to grow.

Publications that are aligned with who we are.

I don't think we have to compromise our values to grow on Substack.

I think we can understand that there's always going to be a compromise somewhere.

But we can find our unique path.

It just might take a little time to get there.

Hope this helps.

Landon

---

P.S. Speaking of simple ways to grow—I've compiled the exact frameworks and templates I used to grow from 0 to 9,063 subscribers. No paid subscription, no endless content to consume. Just the strategies that actually moved the needle. You can get instant access here.

P.P.S. If this shifted how you think about monetizing your writing, share it with another creator who might be feeling overwhelmed by launching and growing a paid subscription. Sometimes the best gift is permission to do things differently.