One Substack Mistake I Wish I Could Take Back
What 12 creators would change if they could start their Substack over
I’ve been running my own business for seven years and ever since I started, I’ve believed in learning from other people’s experiences. Not just to analyze their wins and successes, but also to learn from the ugly mistakes and failures.
And I've always been open about my own mistakes on this journey as well.
When you look at the content creator space, 99% of the stories that are being shared are successes.
And don't get me wrong: success stories can be incredibly motivating, but the truth is that for every success, you typically have to fail a few times as well.
That's why I recently asked 12 Substackers one simple question.
What’s one Substack mistake you wish you could take back?
Their responses were honest, personal, and sometimes even a little painful.
But all of them hold a lesson that can help you grow faster and smarter.
from How to Write for a Living
I wish I'd built my brand specifically around myself from the beginning - it would've given everything more focus (particularly my podcast). But I had almost zero subscribers in the beginning, and imposter syndrome took over.
If anyone wants to build a one-person business, put yourself at the core of it right from the start!
from Unstack Substack
I wish I had known several years ago that I could have started additional publications under the same email address.
I have several abandoned pubs scattered across Substack that could have been under one main account.
from The IndiePreneur
The biggest mistake I made was not sending DMs as soon as I started.
Substack has a hard limit on how many chats you can start with new users that are not following you, and having a large pool of DMs of people with whom you have even the tiniest connection is invaluable.
from Sacred Business Flow
Waiting too long to truly engage. I wish we had started on Substack earlier, but even after we joined, I made a critical error: I treated it like other social media platforms. I'd scroll through Notes and long-form posts, have genuine thoughts about what I was reading, but rarely share them.
I was consuming instead of contributing.
The breakthrough came when I realized Substack isn't about passive scrolling—it's about authentic connection. Once I started actually sharing my thoughts, responding to others, and engaging in real conversations, everything changed.
The platform transformed from a feed I browsed into a community I belonged to. The richness of exchanges here is unlike anywhere else, but you only access it when you participate.
My mistake was being a spectator when I should have been a participant from day one.
Now I know: on Substack, your voice matters, but only if you use it.
from Course Builder’s Corner
Started writing on Substack Notes for a month or so, and then stopped for over a year. That's the mistake I wish I could take back. My solution is to have a minimum viable Note that you will post every day and have a few of these.
Restacking a quote from my own newsletter or someone else's, restacking another Note, rewriting a past Note in a different way, etc.
Don't always feel the pressure to create something new. Just be there at least once a day.
I wish I had started identifying and engaging with my superfans, those who consistently open and engage with my newsletter issues, from day one.
That’s how you truly:
Understand your audience
Craft the most relevant, high-quality content
Build real relationships that convert
Especially in the early days, when there’s less pressure, it’s the perfect time to experiment.
This is exactly what I’m working on now to grow my paid subscribers.
I broke down the full strategy called Superfan Engagement Method (SEM) in my latest article, so other Substack creators can apply it too.
from Unplugged by Yana G. Y.
I created my Substack account in March 2023, but I only started doing something in June 2024, because I believed I needed to bring my own audience, which was true back then, but for a very short time.
I knew nothing about Notes - it was launched in April 2023 - a huge oversight.
If there’s one thing I could take back - that’s it. I’d start much earlier - in April 2023.
from Wander Wealth
One thing I wish I had done sooner on Substack: opening my chat room.
I assumed my posts were enough to build connection, and I worried the chat might be too quiet or too much to manage. But once I launched it, everything changed.
It became the heart of my publication. A space where writers show up daily, share wins, ask questions, and support each other.
Some even found their first paid subscribers there.
Now, it’s one of the most valuable parts of my community.
from Landon’s Letters
I wish I started posting on Notes the moment I started reading them.
from The Lemon Tree Mindset
I wish I had focused less on size and numbers and more on connection and depth. Instead of only focusing on output and sending emails to a list, now I prioritize engagement, relationships and collaboration with people. It's less one-way and more interactive. It's evolved from an audience to a community that I proudly call my lemon grove.
from Sacred Business Flow
The mistake I wish I could take back was trying to be too clever at the start and going against the grain with the paid subscriptions.
We tried to leverage the paid membership in a non-traditional way using compensations, and while we still got members, it set us back a bit from hitting our goal for being a Bestseller.
Technically, by the numbers in our membership, we should already be there, but we are 10-12 members short through the Substack billing system to get credit.
from The Irresistible Writer
I stupidly thought people wanted more information. So I offered that to my paid subscribers: deep dives and detailed advice. But no one upgraded because they didn’t need more to read. They needed something to do.
Everything changed when I looked at what was actually working in my growth — the tools, prompts, and strategies that got real results.
Then each week, I shared one with my paid subscribers. Not guesses. Not recycled advice. Just one proven thing they could plug into their own writing right away.
That’s when the paids came flooding in. Not for more content. For results they could feel.
from Write • Build • Scale
Our biggest mistake at Write • Build • Scale was underestimating the power of visual consistency.
For too long, our Substack looked like a patchwork of ideas—no clear brand identity, no design language, no visual rhythm.
And we’re not alone. Most publications we come across feel scattered: different colors, clashing fonts, inconsistent headers, random thumbnails.
But as a reader, when I land on a publication, I want to feel like I’ve stepped into a carefully designed space—like the creator has thought through not just what they say, but how it’s presented.
That’s why we’ve now refined everything from our thumbnail design to the publishing rhythm.
If you subscribe to Write • Build • Scale, you know what to expect: what day each email lands, what kind of value it delivers, and how it’s going to look. Branding isn’t just aesthetics—it’s about trust, clarity, and showing readers that you care about their experience.
These creators didn’t hold back, and I hope their honesty helps you avoid a few of the most common obstacles on this journey.
Mistakes are inevitable, but you don’t have to make them all yourself. Learn from others. Move faster. Create better. And if you’re stuck on something specific, feel free to send me a private message.
Our DMs are always open for Substackers who are looking to learn, grow, and scale.
These are all so good. Especially yours, Sinem. I'm passionate about the branding packages I offer because I too, want to feel like I've stepped into a cohesive community space.
Thanks for sharing all these! It was great to read what some of the other "greats" wish they'd done differently!
This is so valuable in terms of advice and also a delight to read! @derek Hughes’ advice especially resonates with me as I’m an overdeliverer!