Two Reasons Why Most Substack Content Fails (And You Are Probably Doing Both)
Trust me, I've been there
There are two reasons why most content doesn’t convert on Substack. We are going to go through both, and fix both.
The First Reason Why Most Substack Content Fails
Who is your audience, and why are you writing for them?
If you can’t answer that question immediately, you have a problem. Identifying your audience, as well as the change that your content will create for that audience, is the most important question you need to answer in regards to your substack.
Everything you will build here hinges on that answer.
And the more specific of an answer you can give, the better.
“Well I am writing for anyone that wants to read me!”
No you aren’t, you’re being lazy. I love you guys too much to let you get away with that.
There are three key questions you need to ask and answer before you begin creating content:
1 - Who is my audience?
2 - How will my content be relevant to them?
3 - What change do I want to create for them with my content?
If you can answer these three questions, everything else you do with your substack will become MUCH easier!
Defining your audience also defines your content calendar. Once you know who your audience is, how your content will be relevant to them, and what change you are trying to create for them, your content calendar literally fills in itself.
Here’s an example. When I defined my audience to be creators who wanted to turn their substack into a sustainable business, that let me to 4 problems my content would solve for these creators:
1 - How to do a better job of converting free subscribers into Paid.
2 - How to do a better job of retaining Paid subscribers.
3 - How to create content that building authority and credibility.
4 - How to better engage with an audience and build a community.
That gave me 4 topic areas, one for each problem my content solves. I can then plug and play those 4 topics into my content calendar. It made filling my content calendar infinitely easier.
How do you do this? Start with your audience. Who do you want to write for? Be as specific as possible. Don’t think men, think single fathers. Think parents over the age of 50. Think about their lives and how that helps define them. Where are they in their careers? School? Marriage? Hobbies? Politics? Sports?
Find characteristics that help define the audience.
Once you have defined your audience, then think about how your content would be relevant to them. Are they looking for help? Information? A support group? Are they happy and looking to share their happiness? Worried and looking for comfort? Curious and looking for information? Think about who your audience is, and how your content will connect with them.
Finally, think about the change that your content will create for your audience. They will read your substack and…what will happen next? Are you going to educate them? Humor them? Support them?
At the end, when someone says “Who is your audience, and why are you writing for them?”, you should be able to say “My audience is (people) who (are either engaging in or want to learn more about a certain action or behavior), and I show them how to get started or improve their efforts.”
The key is clarity. By clearly defining your audience and how you will connect with them, you make it easier on yourself, but you also make it easier for these people to find you. If your audience is “Anyone who wants to read me!” then how would I possibly know that I want to read you if you can’t tell me who you are writing for?
Start today: Write down who your audience is. Think about the person you want to help, and how you will do so.
Then start creating content that does.
The Second Reason Most Substack Content Fails
It’s one thing to be frustrated because you aren’t sure what to do to move forward. But there’s a different kind of frustration that shows up when you are sure what to do.
It shows up when you’re doing what you’re supposed to be doing, publishing consistently, engaging in Notes, responding to comments, maybe even picking up a few new subscribers here and there, and yet nothing seems to stick. Nothing compounds. You don’t feel momentum building. You don’t feel closer to clarity. And you definitely don’t feel closer to income.
From the outside, it looks like progress. From the inside, it feels strangely flat.
I’ve been there, and I bet many of you have as well. You don’t feel stuck because you’re not putting in the work. In fact, it’s usually the opposite. You’re showing up. You’re trying. You’re doing what other people say works. That’s what makes the disconnect so disorienting. When effort doesn’t translate into results, the natural assumption is that you must need to do more. More posts. More frequency. More experiments. More energy.
That assumption is where most Substack content quietly goes off the rails.
The core issue isn’t volume. It’s direction.
Your Content Needs a Direction
Most Substack content fails because it’s created without a destination in mind. People write posts, but they don’t build systems. Each piece of content exists on its own, disconnected from the next, instead of intentionally stacking toward something larger. It’s not that the writing is bad. Often, it’s quite good. But good writing without direction doesn’t accumulate value over time.
Think of it like building a road that doesn’t lead anywhere. You can pave it beautifully. You can keep extending it. But if there’s no destination at the end, all you’ve really built is motion. Not progress. Or imagine piling bricks in your yard instead of assembling them into a house. The materials are there. The effort is real. But without a plan, nothing livable emerges.
This is where so many Substack writers get discouraged, even if they can’t quite articulate why. They sense that their work should be adding up to something, but it isn’t. Posts go out into the world, get read, maybe even get appreciated, and then vanish. The next post starts from zero again. No memory. No carryover. No leverage.
What’s missing is directional content.
Directional content isn’t about selling. It isn’t about manipulating readers. And it definitely isn’t about turning every post into a pitch. It’s about clarity. Directional content answers three simple questions every single time you publish: Who is this for? What does this help them understand or do? And what should happen after they read it?
When those questions are answered, even quietly, even implicitly, your content starts to behave differently. It stops floating in isolation and starts pointing somewhere. Readers feel that, even if they can’t name it. They feel guided instead of entertained. Supported instead of impressed.
This is where many writers get tripped up, because they confuse “authentic” with “unstructured.” They treat Substack like a journal, where the goal is expression rather than construction. There’s nothing wrong with personal writing. But if you want growth, conversion, or community to emerge later, your content needs to be infrastructure, not just reflection.
Without direction, the cost sneaks up on you. Writers burn out not because they write too much, but because nothing they write seems to matter long-term. They second-guess themselves constantly. They change topics impulsively. They chase engagement metrics that spike one day and disappear the next. Activity becomes a substitute for progress, and that’s an exhausting trade to make.
If this has felt hard for you, it’s not because you’re doing something wrong. It’s because you’ve been trying to build momentum without a compass. That realization alone can be deeply relieving. It reframes the problem from “I’m not good at this” to “I haven’t been aiming yet.”
The fix doesn’t require more output. It requires a shift in how you think about each post before you hit publish.
Before you write your next piece, pause and ask one question: What behavior am I trying to reinforce in the reader? Not what you want them to think. Not what you want them to feel. What you want them to do differently because this post exists. That behavior might be as small as thinking about their Substack differently, replying to a Note, or paying attention to a specific pattern they’ve been ignoring. Small is fine. Direction is the point.
Once you start writing with that lens, everything changes. Topics become easier to choose because you’re no longer writing for “everyone.” Posts begin to connect to each other naturally because they’re reinforcing the same ideas from different angles. Readers start to recognize themselves in your work, not just enjoy it. And when the time comes to introduce Paid content, it feels like a continuation of a conversation, not a surprise turn.
In August, I went through this exact process. I felt lost and frustrated because I couldn’t clearly define my audience. The reader I wanted to reach, and as a result, I couldn’t decide what I needed to write about. Remember when I used to write those Marketing & Movies and Marketing & Music posts? I enjoyed writing them, and I know many of you enjoyed reading them. But that wasn’t content that was aimed at my core audience.
Once I defined my core audience, everything became easier. Suddenly, I knew who I was writing for, and how my content could help them.
That’s why this month is focused on content, and not tactics or growth hacks. Direction is the foundation everything else sits on. Growth becomes easier when readers understand where you’re leading them. Conversion becomes logical when your content has already done the work of framing the problem. Community becomes possible when people feel like they’re walking the same path together.
None of that starts with writing more.
It starts with knowing where you’re going, and letting every post quietly point in that direction. We’ll build on this in Thursday’s post.
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Activity vs. direction — that’s the unlock.
This reframes stagnation without shaming the work.