The First Curated Story at ILLUMINATION Writing & Reading Academy

"In August 2024, I Made a Decision that Changed Everything" by Yana G.Y.: A boosted story on Substack.com

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Link for readers on Medium

Why I curated this story

Dear friends, today marks a special beginning. This is our very first curated story, and I wanted it to be something that speaks to every writer’s heart — something powerful, helpful, memorable, nuanced, and deeply relatable. A story that not only offers practical hope but also reminds every reader that even in uncertain times, new paths can be built with courage, consistency, and belief in your own voice.

As the Chief Editor of the ILLUMINATION Writing Academy, I chose this excellent story to open our inaugural publication because it captures everything we stand for — courage, authenticity, resilience, and building something real from the ground up.

In a time when many freelance writers are seeking new beginnings beyond Medium, this story offers not just hope but a practical path. It shows that success on Substack is not a matter of luck, but the result of daily commitment, hard work, smart adaptation, and community spirit.

I believe this exceptional story will inspire every writer who dreams of creating a lasting impact through their own voice and effort. I believe you will enjoy this story as much as my curation team and I did.

Here is what

Yana G.Y.

wrote from the heart to mark this special beginning ❤️:

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In August 2024, I Made a Decision that Changed Everything.

From Frustration to Freedom: How Going All In on Substack Led to My First $10,000 from Scratch

Image courtesy of Yana

In a way, I had to. It was following the many changes on Medium that brought more frustration than joy from my work. So I had to find a better way to build my online business.

It was not just a business move. It was a moment of reckoning, filled with doubt, urgency, and hope for something better.

I knew you had to have a strong newsletter to build a solid online business. Out of the many ways I could have chosen to start building my list, I opted for Substack.

Building an email list is challenging, and Substack is the only platform that offers a unique feature: massive discoverability. That is Substack Notes.

It also has a business model that helps you grow. Unlike most other platforms, Substack earns money only if you earn money too.

So I went all in on September 1st.

And about three months later, on November 15th, I woke up to the email every Substack writer dreams about: a Bestseller badge.

I stared at the screen in disbelief, my heart racing. After months of invisible work, doubts, and long hours, this tiny badge felt like a thunderous yes to all the whispers of “keep going” I had clung to.

Three months later, I earned another badge: first $10,000 in annual recurring revenue.

It is official! I have built a 5-figure newsletter in 6 months.

But the headlines are not important, especially if you cannot keep them coming.
The real story is in the dozens of decisions, pivots, failures, and lessons that made it possible.

Today, I am going to walk you through exactly how it happened.

The moves that worked, the mistakes that almost tanked my momentum, and the strategies that got me there without a team, a budget, or an external audience.

Yes, I started from scratch.

And here is how it all happened.

1 - August to September: The Boring Stuff That Matters

The first 30 days were not fun.

No viral growth. No big wins. No magic tricks.

It was pure setup from scratch:

• Defining my niche: helping writers and creators grow on Substack with real, actionable strategies. I initially wanted to write about AI (as Medium made it sound evil), but I also shared my journey on Substack and since many new writers were joining, I got a lot of questions about that. So I positioned my newsletter to help people grow their paid newsletter. With AI. I had to keep my passion alive.

• Defining my paid content: the biggest pain. For the whole month in August I tried to figure what should I paywall on Substack so that it’s not duplicated with Medium. It had to be unique. I made an extensive research and chose to go with a dedicated column about selling thorough writing and a Notes challenge. I also created some custom GPTs to help writers generate ideas for Notes and Headlines faster.

• Building systems: posting consistently, writing daily Notes, optimizing my free and paid content. From my research I also found out that bestsellers usually post more frequently than once a week. Few times per week seemed the optimum. So I decided to go with this pace and also post one Note per day.

I grew slowly but steadily: a few new subscribers a day, nothing flashy.

Consistency beats everything.

When you are new, you have a temptation to grow fast. You chase the hack, the shortcut, the viral moment. But the real hack is becoming someone people can rely on, to build meaningful connections, and that only happens when you show up. Over and over again.

2 - October: Gaining Traction

By October, my subscriber base started growing faster. I had roughly 300 new subscribers per month and about 30 paid.

I realized two things early:

• Writing alone is not enough.

• You have to sell an outcome, not just articles.

You have to listen to your audience and adapt your offers.

I launched my paid tier at $36 annually to make it a no-brainer, but it was not enough. I added a discount of $60/year so that it looked more attractive. Same money, presented differently. Marketing classics. Old, but gold.

I also launched a Writing Challenge, as my audience requested.

I also changed the way I presented my paid offer. I focused on the outcomes I deliver and my unique angle. I spent more than 15 years in product management, leading teams that built and sold subscription-based services. Helping people on Substack felt like home, so I made sure this was visible in my content and offers.

3 - November: Becoming a Bestseller

November was the month. I gained my Bestseller badge. Finally!

I got so excited that I decided to share how I got there for free, and I wrote this story. It became my most engaging story with more than 100 likes.

Here is what happened:

I ran a Black Friday promotion: lifetime access to my newsletter via Gumroad at a special price.

I celebrated my Bestseller milestone with my audience, giving them a special discount.

My revenue exploded: almost $3,000 that month, mostly from writing alone. This was my all-time high.

I managed to achieve above the Substack average free-to-paid conversion rate of around 8%.

Core lesson: The more you paywall, the more you grow your paid subscribers.

But I also made a mistake. A decision that was supposed to help more people in my community, but it did not: I opened up my Notes and writing challenges to free subscribers only for participation. I kept the supporting materials paywalled. I wanted more people involved, more energy in the community. I believed that helping people create momentum for free would bring more engagement and future upgrades.

I was wrong.

4 - December to January: Mistakes, Virality, and Implementing Systems

December brought my first viral Note with more than 10,000 likes and more than 160 new subscribers.

When the Note exploded beyond anything I imagined, it felt surreal. The likes kept climbing, the new faces kept arriving — and for the first time, I caught a glimpse of what real momentum feels like.

I was so happy I finally figured out how the Substack Notes algorithm works. Virality was not my goal, but I wanted to find a way to start growing faster. I was still at 300 new subscribers monthly, and I saw people growing with thousands.

I knew it was probably because of my focus on conversion rate, so I had to figure out a way to grow without sacrificing conversion rates.

Virality helped. But my conversion rate suffered. Partially because of virality: I expected it, because usually people need more interaction with your content before they decide to pay. New subscribers did not know about my already published valuable content. I had to educate them.

But my growth slowed also partially because I opened my challenges to free subscribers.

That is when I realized I needed to change.

So I started building a lead magnet: a 10-day free Substack kick-started course helping you grow your first 1000 subscribers in about 3 months. I aimed to gain more free subscribers.

I already know how to grow more paid subscribers:

• An automated sequence designed to educate new subscribers on my paid content

• A sales sequence right after the educational sequence to promote my offers on autopilot.

I have already started importing and tagging Substack subscribers automatically to Kit as a workaround (since Substack does not offer automations and sequences), so I only needed the free 10-day course to use it as an educational sequence.

The next thing I did was to paywall my challenges again. When I analyzed who was actually participating in the writing challenges, it became obvious:

The most active members were already paid subscribers.

Free subscribers mostly consume without contributing.

Lesson: Free attracts attention. Paid creates action. Implement systems to grow on autopilot.

Result:

• My paid subscriber growth doubled.

• Paid upgrades became consistent, not random.

• I no longer had to worry about selling and promotions, and I could focus on content and community.

But one problem remained: I still grew by 300 subscribers per month after the viral effect faded away.

5 - February and March: Scaling the Machine

Since Notes and recommendations were contributing to 95% of my growth, I had to boost both.

I updated my Notes Writer GPT with 400+ viral Notes from small creators to improve its outputs.

I ramped up posting from 1 Note per day to 3–10 Notes daily.

I treated Notes like a growth channel, the top of my funnel. The content there had to be the hook for subscribers.

And it worked.

The second viral Note hit. And the third. And many more with more than 100+ likes. Subscriber growth surged from around 300 a month to 900 a month.

People from my paid community also reported multiple viral Notes using my GPT.

I finally figured out the system. With my custom GPT, it takes me just 15 minutes per day to post around 10 Notes. It was so good that I built a 3-hour course about it and gave it to my paid subscribers, because people need to know how to use it.

I also launched Substack Quest — my flagship course. A collection of paid courses, tools, templates, and coaching offers to help writers and creators accelerate their own journeys on Substack and beyond. I downloaded my 15+ years of knowledge and how I applied it to my online business to grow consistently. I am still in the process of delivering it.

But now I feel it is all implemented. I only need to deliver and improve.

And that is when I crossed $10,000 in annual recurring revenue, getting my new badge from Substack.

6 - Where I Am Today

Today, I’m standing at 4,365 subscribers and 258 paid. And they keep coming. But it’s not on autopilot. You need to be present. You need to stay active and build relationships with the community.

Because communities are the greatest power we have online, my community helped me grow, but it was because I gave so much in the first place. And I still do. I also collaborate with other creators to help them grow. That brings me some additional revenue when I do affiliates, so it’s a win-win.

Today I’m also back to daily writing on Substack and on Medium.

I treat Medium like social media: a place to drive discovery, build my brand, and attract new readers. Not as an income source. That mental shift killed all the frustration. Medium is still a great place to start writing.

But if I could sum up everything I’ve learned so far into one message, it would be this:

Consistency + Quality + Selling = Growth.

And remember to stay alert. Watch the numbers and improve. Growth needs constant learning and constant improvement.

Not sometimes.
Not when it feels good.
Every single day.

A few final tactical lessons:

• Talk about your paid offer often. If you don’t, no one will magically guess it exists. I automated it in Kit, but I also added a lot of links and mentions in my free content.

• Deliver insane value at the free level. But make sure your best, deepest tools stay paid. And deliver it consistently.

• Invest in systems early. Automation and AI don’t replace human connection, but they multiply your effort and save you tons of time.

• Don’t chase virality. Play the long game. Trust the boring stuff. Virality will come as a byproduct.

Success on Substack isn’t an accident. It’s an output of small actions, done daily, compounded over time.

Beyond badges, beyond numbers, this journey gave me something more precious: the proof that small, daily acts of courage can build a life you are proud to call your own.

If you’re willing to show up when it’s slow, scary, and uncertain, the Bestseller badge won’t even be the biggest thing you earn.

You’ll build a business, a brand, and a life most people only talk about.

Stay Unplugged!

Yana

Image courtesy of Yana G.Y.

👉 Grab my FREE 10-Day crash course on how to build your newsletter and gain your first 1000 subscribers organically, working just 15 minutes/day!

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You can learn more about

Yana G.Y.

from a recent interview story I created for her on Medium and Substack. I also blogged it on my website.