My Substack was Dead. Then, I Built My Newsletter Around a Community and Grew it 5,400%
How I transformed my failed newsletter into a thriving community by changing one core approach
Back in 2023, I stared at my Substack dashboard one last time before putting it on the shelf.
My newsletter wasn't dead - but it sure felt like it. Every post felt like shouting into the void. The few subscribers I had weren't engaging. My carefully curated remote work content and "helpful" tips just sat there collecting digital dust.
I got the occasional “great post” comment here and there, but it just wasn’t worth the time and effort.
You might be able to relate. You're doing everything "right":
Publishing consistently
Creating valuable content
Following all the expert advice
Sharing insights and tips
Building in public
But something isn't clicking. Your subscriber count barely moves. Each new post gets less engagement than the last. While other newsletters seem to grow effortlessly, you're stuck wondering what you're missing.
I know exactly how this feels because I hit that same wall. Hard.
Then, in early 2024, things got even more frustrating. I was burning out from my career coaching and resume writing business. The endless Zoom calls, constant client revisions, and relentless trade of time for money - something had to change.
Here's what made it really painful: While I was struggling to get even 10 new subscribers a month, other newsletters seemed to grow effortlessly. Every time I opened Substack, I saw writers celebrating milestones while I couldn't even get past the starting line.
That's when I had my breakthrough moment.
The problem wasn't my writing. It wasn't my expertise. It wasn't even my topics.
The problem was my entire approach to what a newsletter could be.
Instead of just writing about remote work trends or sharing basic tips, what if I helped people escape the 9-5 altogether? What if I showed them how to build their own thing online, just like I was learning to do?
I decided to restart my Substack with a completely different strategy. I put in real research to discover specific problems people had with "escaping the cubicle" and building their newsletter and personal brand online.
But here's what really changed everything: I stopped thinking about my newsletter as just content delivery. Instead, I focused on building a genuine community where people could collaborate, connect, and grow together.
The results surprised even me: I went from a dead newsletter to growing over 5,300% in just six months. That’s around 100 subscribers to 5400 in about 6 months. Because of community.
But before I show you the exact steps that made this transformation possible, let me share something important about why this matters right now...
Why Community Changes Everything
Here's something most people get wrong about newsletters: They think it's about the content.
After studying hundreds of successful Substacks and growing my own to 5,000+ subscribers, I've discovered something different: The most successful newsletters aren't built on content - they're built on connection.
When I first started my remote work newsletter, I was just aggregating news and tips. Sure, it was "valuable" content, but it was missing something crucial: genuine human connection.
Think about it:
We have more information than ever at our fingertips. Google can tell you how to write better. ChatGPT can give you templates. YouTube has endless tutorials about building online.
But here's what's missing: Real people on the same journey, supporting each other, sharing wins and losses, and building something meaningful together.
That's exactly what changed when I relaunched with a community focus:
Instead of just readers, I had people engaging in conversations in the comments
Instead of passive consumers, I had creators supporting each other's growth
Instead of surface-level tips, we had deep discussions about real challenges
Instead of just another newsletter, I built a space where people actually felt encouraged to keep going.
The result? My average post now gets 10x more engagement than my old "tips and tricks" content ever did. Why? Because people don't just want more information - they want to feel understood, supported, and connected.
This is why I completely restructured my approach to focus on building genuine community. These aren't just tactics - it's a complete shift in how you think about your newsletter's purpose.
Why Most Newsletters Fail to Build Real Community
After watching hundreds of newsletters come and go on Substack, I've noticed something interesting:
Most writers confuse broadcasting with building community.
They think dropping a "let me know what you think in the comments…" at the end of posts counts as community building. Or that getting a few dozen likes means they've created connection.
I know because I made the same mistake.
Here's what most writers & creators do:
Push out weekly content
Share tips and advice
Post motivational quotes
Add generic "join the conversation" CTAs
Network superficially with other writers
(Yes, LinkedIn I’m looking at you…)
But real community is different. Much different.
Think about your favorite online communities. The ones you actually engage with daily. The ones that make you feel like you belong.
They're not just content feeds. They're not networking groups. They're spaces where you feel genuinely seen, heard, and supported.
This is exactly why 90% of newsletters struggle with retention. They're great at attracting subscribers but terrible at keeping them engaged. People subscribe for the content but leave because they never feel connected.
I learned this the hard way with my first newsletter. Even when I wrote good content, something was missing. My subscribers would read, maybe even appreciate the information, but they weren't sticking around. They weren't engaging. They weren't becoming part of something bigger.
The truth is that people don't need more content. We're drowning in content. What they really need is:
Genuine connection with others on the same journey
A safe space to share their struggles and wins
Real support from people who get it
Encouragement to keep going when things get tough
A sense of belonging to something meaningful
This is why community-focused newsletters are thriving while content-focused newsletters are dying. In a world of infinite information, connection is the new currency.
Let me show you exactly how to make this shift in your own newsletter...
Key Insight #1. Solve Problems (Actually Solve Them)
Here's something that completely changed my approach to newsletter growth:
The size of your community is directly proportional to the size of the problems you solve.
When I was writing about remote work, I thought I was solving problems. I'd share tips about Zoom meetings, home office setups, and maintaining work-life balance. But here's what I missed: I was solving surface-level problems that a thousand other creators were already addressing.
Then I noticed something interesting in my 1:1 coaching calls.
Clients weren't just asking about resumes or interview prep. They kept circling back to deeper questions:
"How do I stop trading time for money?"
"How can I build something that's actually mine?"
"What's the path to legit side hustle?”
That's when it hit me: The biggest problems aren't always the most obvious ones.
Instead of just writing about tactics, I started addressing the real pain points keeping people up at night:
The fear of being stuck in the corporate grind forever
The overwhelm of trying to build something on the side
The confusion about where to even start with digital products
The loneliness of the creator journey
But here's what really matters: I didn't just identify these problems - I created specific solutions for them.
Do your market research. Find out what are people's actual problems in your niche. Not the surface stuff everyone talks about - dig deeper. What keeps them up at night? What do they wish they could change?
If you can identify and clearly communicate how to solve these problems, you'll have subscribers for life. You want to build a community of loyal fans, and that comes when they feel understood and supported.
The best part? When you genuinely help people solve problems, they share your content naturally. Your growth becomes organic because your community does the work for you.
Remember: People don't join communities - they join solutions to their problems. Make sure you're solving the right ones.
Key Insight #2. Build Real Conversations (Not Just Comments)
When I relaunched my newsletter, I made a simple but powerful change:
I stopped treating comments as metrics and started seeing them as conversations.
Here's what most writers do wrong: They add a generic "What do you think?" at the end of their posts and hope for engagement. When nobody responds, they assume their audience isn't interested in engaging.
But here's the truth: People want to engage. They want to share their experiences. They want to be part of the conversation. They're just waiting for the right invitation.
Think about the last time you were at a party where you didn't know anyone. It's awkward, right? But then someone comes up and asks you a specific question about yourself. Suddenly, you're comfortable. You're talking. You're connecting.
Your comments section works the same way.
Instead of "Let me know your thoughts…" try:
"What's the biggest challenge you're facing with your newsletter right now?"
"Share a win from your creator journey this week"
"What's one thing you wish someone had told you before starting your online business?"
But here's what really matters: When people do comment, show up for them.
Don't just drop a "Thanks!" or a 👍. Engage in real conversation. Ask follow-up questions. Share your own similar experiences. Make them feel heard.
I spend at least 30-60 minutes each day really talking with my subscribers in the comments or DMs / Chat. Not because some growth hack told me to - but because these are real people sharing real parts of their journey.
The result? My comments section has become a place where:
People actually help each other solve problems
Real friendships form
Subscribers become active community members
Growth happens naturally through genuine connection
Remember: Comments aren't just engagement metrics. They're opportunities to build real relationships with the people who trust you with their time.
Key Insight #3. Use the Chat Feature (Most Writers Don't Even Try)
Here's something most Substack writers completely miss:
The Chat feature isn't just another social feed - it's your community's living room.
When I discovered Substack's Chat feature, I honestly wasn't sure what to expect. Would anyone actually use it? Would it be worth the time investment?
Fast forward six months: My Chat has become the heartbeat of my community.
But here's what makes it really powerful: While other writers are waiting days between posts to engage with their audience, I'm building real connections every single day in Chat.
Think about it:
Your newsletter is like a weekly workshop
Your comments are like after-class discussions
But Chat? Chat is where the real community magic happens
Here's exactly how I use Chat to build engagement:
Notes Boosts in Chat
Every week, I open up a thread where writers can share their latest Notes. But it's not just about dropping links - we give each other feedback, share what's working, and genuinely support each other's growth.
These sessions consistently drive new subscribers and create lasting connections within our community.
Ask Me Anything (AMA) Sessions
I host regular AMAs where subscribers can get real-time feedback on their newsletter growth, marketing strategies, or any challenges they're facing. Instead of waiting for my next post, they get immediate help when they need it most.
The secret? I don't treat these like formal Q&As. They're more like coffee chats with friends who are building something meaningful.
Quick Tips Between Posts
Found a new Substack feature? Discovered a growth hack? Had a breakthrough? Share it in Chat. These quick wins keep your community engaged between your main posts and show you're actively involved in their success.
But here's what really matters: Consistency.
You don't need to be active 24/7, but having regular touchpoints builds the kind of engagement that turns casual readers into community members.
While everyone else is focused on just publishing, you can build deeper connections every single day through Chat. That's how you turn subscribers into superfans.
Key Insight #4. Be a True Encourager (Negativity Never Wins)
People always remember how you make them feel, not what you say.
When I started my first newsletter, I focused on being "helpful." I shared tips, strategies, frameworks - all the usual stuff. But something was missing.
Then I noticed something interesting in my most engaged posts:
It wasn't the tactical advice that got people talking. It was the moments where I shared struggles, celebrated wins (even small ones), and genuinely encouraged others to keep going.
Think about the current state of the creator economy:
Everyone's battling imposter syndrome
Most people feel behind or "too late"
Building in public feels scary
Success seems to come easier to others
The journey can feel incredibly lonely
Your community needs more than just another how-to guide.
They need someone who:
Celebrates their small wins
Understands their struggles
Believes in their potential
Reminds them they're not alone
Shows up consistently with encouragement
Here's how I build this into everything I do:
I actively invite subscribers to share their dreams and goals. Not just in comments, but in dedicated threads where people can be vulnerable about what they're really trying to build.
Every day I ask myself: "How can I help or encourage someone to keep going today?"
When someone shares a win - no matter how small - I make sure they know it matters. Because in the creator journey, those small wins are what keep us going.
This isn't about being artificially positive. It's about creating a space where people feel safe to share their journey - both the ups and downs.
Remember: Negative people might get attention, but they never build lasting communities. Your power lies in being the encourager your audience needs.
Key Insight #5. Create a Story (Don't Just Create Content)
Here's something most people get wrong about newsletters:
They think it's about the content. After growing my Substack to 5,000+ subscribers, I've discovered something different: The most successful newsletters aren't built on content - they're built on story.
When I first started my newsletter, I was just aggregating remote work tips and news. Sure, it was "valuable" information, but it was missing something crucial: a compelling narrative that readers could connect with.
But everything changed when I relaunched with "Escape the Cubicle."
Instead of just sharing information, I started telling a story:
The journey of breaking free from traditional employment
The transformation from employee to digital entrepreneur
The ups and downs of building a newsletter on Substack
This shift changed everything. Why? Because stories do something that pure content never can - they create emotional investment.
Think about the newsletters you never miss reading. I bet they're not just information dumps. They're journeys you're following, transformations you're witnessing, stories you're part of.
Your story matters because:
It makes your content relatable
It helps others see what's possible
It creates connection through shared experiences
It gives context to your advice
It makes your community feel like they're part of something bigger
This is why I regularly share my origin story - how I went from a burnt-out career coach to building a thriving newsletter community. Not because I love talking about myself, but because it helps others see their own potential transformation.
But here's what really matters: Your story isn't just about you.
It's about inviting others to share their stories too. When community members share their journeys, struggles, and wins, they become part of a larger narrative. They're not just consuming content - they're contributing to a collective story of growth and transformation.
People don't follow newsletters. They follow stories. Make yours worth following.
Key Insight #6: Host an Ask Me Anything (AMA)
Here's something I discovered completely by accident:
The most engaged subscribers in my community aren't the ones who read every post - they're the ones who've interacted with me in real-time.
When I first tried hosting an AMA (in the Chat), I was nervous. What if nobody replied? Or worse…what if nobody really cared?
But something interesting happened:
That first casual AMA…people did show up. And they did ask questions. They started replying to other people’s questions. There was a real conversation going. It was fun.
Think about it from your subscriber's perspective:
They read your posts
They follow your journey
They implement your advice
But getting real-time feedback? That's next level.
It's the difference between watching a cooking show and actually cooking with someone in your kitchen.
Now, with Substack opening up the “live” feature to everyone, you can take your AMA’s even further. You can show up and interact with your audience in real-time.
This is community.
The magic of AMAs is that they create genuine, real-time connection. Subscribers get to ask you or the community questions about anything related to your niche. They receive immediate help when they need it most.
But here's what really makes AMAs powerful…
They're not just Q&A sessions. They're community events where:
Subscribers help each other
Real connections form
People realize they're not alone in their struggles
Your community comes alive
I've found that the best questions often lead to my next newsletter topics. It's like having a direct line to what your community actually needs help with - no guesswork required.
People don't just need more information. With the age of Google and AI, we have all the information we need at our fingertips.
What they truly crave is connection. AMAs give them closer access to you and each other - creating the kind of engagement that turns casual readers into community members.
Key Insight #7: Use Your Paid Subscriber Tier to Deepen Community
If you’ve been following me for very long, you know that I’ve been a bit anti-paywall. But, my mind has been changed a bit and I’ll tell you why…
Recently, I saw a Note from Substack founder Hamish McKenzie talk about how Substack isn’t chasing TikTok or trying to be a video creator platform.
He said their mission to fix a broken monetization model that creators have fallen pray to for years.
Most creators spend years building their platform on rented land and they’re rarely paid for it directly by the platform. For example, I’ve spent so much time growing to 125K+ followers on LinkedIn and no, LinkedIn most definitely doesn’t pay me a dime.
I thought, “What if I was able to convert just 1% of those 125K followers to a paid subscriber?” That would be life-changing.
That’s the power of Substack I’m just now realizing. We get to build a sustainable platform and some of those subscribers will pay for your paid tier.
Your paid tier isn't just about exclusive content - it's about deeper community.
As I’m working on building out my own paid subscription, I want to think of it more like a community. People don’t need more information, they need support and connection.
It’s my firm belief that if you decide to turn on the “paid subscription button” we need to offer more than just content. We need to provide some type of additional support, assistance, and community. Help subscribers connect with each other.
I’ve heard from other successful membership creators that they think of their community like a gym. They create a space with all the tools to workout and get it. It’s up to the member to show up and use those tools, trainers, whatever else is provided…to workout.
People don't pay for more content. They pay for closer connection.
Think about it:
We're all drowning in content already
Nobody needs another 10,000-word guide
What we're actually craving is belonging
I think this realization can transform our paid tiers from just another content channel into a thriving community hub.
Instead of focusing on "premium content," we can create:
Weekly office hours where subscribers get direct access
Private discussion threads for deeper conversations
Behind-the-scenes looks at our own growth journeys
Dedicated support for their specific challenges
We can think of our paid tier as a "secret club" rather than a content library.
This subtle mindset shift changed everything on how I view Substack. People aren’t just buying information - they’re joining a community of like-minded creators supporting each other's growth.
In a world overwhelmed with information, genuine connection is the true premium experience. When you make your paid tier about community rather than just content, you create something people actually want to pay for.
Or Next Steps to Building Community
Let me bring this all together with a confession:
Six months ago, I was ready to give up on the entire creator economy. My first newsletter had failed. My coaching business had left me burned out. And watching others succeed while I struggled was killing my confidence.
But that's exactly why I'm sharing this with you today. Because if I can relaunch and grow, you can too. I'm nobody special - I've just focused on building community first and content second.
Those seven key insights we just covered?
Solve real problems (not just share information)
Build genuine conversations in comments
Use the Chat feature to create daily connection
Be a positive encourager for your people
Create story throughout your newsletter
Host AMAs to provide real-time value
Use your paid tier to deepen community
They're not just theory. They're the exact framework that took me from total newsletter burnout to building a thriving community that generates growth while actually helping people transform their lives.
This isn't about copying what I did. It's about understanding the principles that drive sustainable newsletter growth and adapting them to your unique voice and audience.
The truth is there's never been a better time to build on Substack. While other platforms become increasingly pay-to-play, Substack is creating tools that actually help writers succeed.
But tools alone aren't enough. You need a proven system for building community.
That's exactly why I created the Six-Figure Substack Growth Masterclass.
📌 Join 100’s of Writers in the Substack Growth Class
If you're feeling overwhelmed by all these options, I get it. I've been there. That's exactly why I created my masterclass where I walk you through:
Exactly how I grew from ~100 to 5,400% growth in 6 months
How to identify audience problems and create community solutions
My proven templates for building engagement and consistent growth
Step-by-step implementation plans for monetizing your newsletter
Join hundreds of other newsletter writers who are already using these strategies to build thriving communities. If you're ready to finally start growing (and monetizing) your audience this year, click the button below and join us inside the masterclass:
Your newsletter isn't just about writing - it's about building something meaningful. Something that doesn't just share information but creates transformation. Something that doesn't just generate income, but changes lives.
A lot of things to think about. Some that came to mind immediately:
* The only problem I solve is offering a terrific alternative to the scary world.
- I haven't thought of chat yet.
- An AMA will never happen. I can't be understood.
This is really inspiring and making me think (as a new travel coach). I've had my substack for about a year and can admit the growth and engagement is so haphazard. You gave me lots to think about how I can make this a community instead of sometimes it feels like a one woman show. Thank you!