How I Repositioned My Newsletter [Many Times]- What You Can Learn From It

Who are you writing for?

Newsletter Circle is your go-to source for building a successful newsletter business through a paid subscription.

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If you're building a newsletter and especially if you're aiming to grow paid subscribers, there’s one question you probably ask yourself on repeat:

“How can I deliver the highest value possible to my readers?”

It’s the right question.

But I’ve learned it’s not the first one you should ask.

Before value comes clarity.

Clarity about:

• Who you're writing for

• What problem you help them solve / What need you address

• That thing you want your newsletter to be uniquely known for

When you’re not clear on exactly who you’re talking to, everything starts to blur.

As Emily Kramer puts it, whatever you do turns into “Random Acts of Marketing.”

You might be working hard, but you don’t see results because you spend the majority of your time on low-impact efforts.

But, once you know those three things, everything else starts to click:

• What content to publish

• Where to promote it

• Which growth strategies actually make sense

That’s what positioning is all about.

If you’re serious about generating revenue through your newsletter, never forget the fact that:

Your newsletter content is your product.

And similar to all types of other products, you should be clear about your positioning.

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The Real Reason I Felt Stuck (Multiple Times)

Since launching Newsletter Circle nearly 2.5 years ago, I’ve had many moments where things felt... off. Growth slowed. Excitement faded. I wasn’t sure what to create next.

And every single time, I eventually realized the same thing:

It was one of these 3 problems related to my positioning:

• I wasn’t clear on exactly who I was targeting

• I didn’t fully understand how my readers were using the information I shared

• There was inconsistency across the messages I put out on different channels

So I paused and asked myself those three big questions again.

I made time to find the answers. I reviewed subscriber profiles, ran surveys and calls, studied similar newsletters in my niche, scanned social media comments etc.

Then I made adjustments and kept going.

Last week, I crossed 5,000 subscribers. A milestone that felt big.

But more importantly, it felt like a moment to stop and reflect again.

• Where am I really heading?

• What should I stop doing?

• What should I double down?

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Why My First Positioning Didn’t Work

When I first started, I had a simple pitch:

“A newsletter for newsletter creators.”

At the time, it felt niche.

But in hindsight, it was way too broad.

I interviewed anyone, from creators with 500 subscribers to media companies with 500,000.
That range was too wide. Their challenges and focus areas were completely different. And my content lost focus.

So I narrowed it:

“A newsletter for creators building newsletter businesses.”

Closer. But still vague.

There are so many ways to monetize a newsletter:

• Sponsorships

• Digital products

• Affiliates

• Events & webinars

• Paid subscriptions

Still too scattered.

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The Positioning That Finally Made Everything Click

At the end of last year, I took a step back to better understand the newsletter ecosystem I’m part of. I gathered data from 75,000 Substack newsletters and turned it into a free comprehensive report.

That analysis worked well as a lead magnet. It brought in 700 new subscribers. But more importantly, it helped me clarify my positioning.

Here’s what I discovered:

• There are around 20,000 paid newsletters actively publishing new issues. But only a small portion has reached their first 100 paid subscribers. Many are struggling.

• There are also 21,000 free newsletters actively publishing, and a portion of these creators want to launch paid subscriptions but don’t know how.

• Substack is growing. More creators are switching to it and turning on paid subscriptions every day.

This showed me something simple but powerful: there are tens of thousands of creators who need help growing a paid newsletter.

So, at the begining of this year, I switched back to Substack and niched down again:

“A newsletter for newsletter creators building a business through paid subscription.”

With that lens, everything got clearer.

I started interviewing only Substack Bestsellers, creators who reached at least 100 paid subscribers.
I started publishing mini-reports that break down how paid newsletters grow.

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But Then Came the Bigger Question: Am I Delivering on That Promise?

Once I had clarity on who I serve, a new challenge appeared:

How can I deliver the best possible value for my paid members and build a sustainable paid newsletter?

If this newsletter is for creators growing paid subscriptions, then everything I publish, especially for paying members, needs to directly reflect that promise.

It’s not just about publishing more.

It’s about making sure every piece of content helps you get closer to building a sustainable paid newsletter business.

So I started asking myself:

• Are my interviews with Substack Bestsellers alone enough?

• Am I offering the level of actionable value I aspire to?

• Is there a clear reason for free readers to upgrade?

That’s what I’ve been sitting with.

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The Paid Subscriber Email That Brought Instant Clarity

Just as I was in the middle of these questions, I got an email from a brand-new paid subscriber.

He wrote:

That message hit home.

It was the exact validation I was waiting for.

The way he described things perfectly captured my target audience and their challenges. It reminded me that both my free and paid content should speak directly to those points.

Now, I’m ready to take everything I’ve been learning and package it into something even more useful, more focused, more actionable.

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What’s Next: A Sharper Focus + Actionable Playbooks

So here’s the plan:

I have five more interviews already in the pipeline, which are gold. But after that, I’ll reduce the number of written interviews and start sharing more hands-on content like:

• Step-by-step strategies

• Actionable tips & tricks for growing paid members while growing your free base

• Experiments I run

• Behind-the-scenes from my own journey to become a Substack Bestseller

• Unique patterns I’m spotting across creators who’ve done it before

And here’s what will set Newsletter Circle apart:

I’ll continue acting like a content journalist, constantly studying other Substack Bestsellers’ strategies and digging into best practices.

So you’ll get a blend of:

• Unique insights you won’t find anywhere else

• Actionable, strategic content you can apply to your own newsletter

Next week, I’m sharing how to apply a marketing funnel mindset to your newsletter and the most underrated way to grow paid subscribers.

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Your Turn: Reevaluate Your Positioning and Value You Deliver

If you’re feeling stuck, unclear, or unsure what’s working in your newsletter right now, take this as your sign to pause and revisit your positioning.

Here are the questions I asked myself and also will guide you:

• Who exactly am I writing for?
  Be as specific as possible. Think about their current stage, goals, and challenges.

• What core problem or need does my newsletter solve for them?
  If you solve multiple problems, which one is most important to your audience?

• What is that thing I want my newsletter to be uniquely known?

  How do you differentiate yourself from similar newsletters and what UNIQUE value do you offer?

• Who is my addressable market?
  Get clear on the size and nature of your niche. Make sure there is enough demand for you to reach your goals.

• Am I visible on the right channels to promote my content?
  Are you showing up where your ideal readers already hang out, or are you stuck in the wrong places?

• Does every piece of content I create support my positioning?
  Look at your recent articles, social media posts, lead magnets, all types of audio, video and written content you created. Are they aligned with what you promise?

• Do my paid benefits clearly reflect what I offer?
  Would a free reader instantly understand the why upgrade story?

• Am I balancing value for free readers while creating urgency to go paid?
  Free builds trust. Paid should feel like the natural next step.

• What’s one thing I should stop doing—and one thing I should do more of—to serve my readers better?
  Focus on high-impact efforts instead of “random acts of marketing”. Define what to pivot, stop or start.

But, don’t be too hard on yourself trying to figure everything out from the start.

You’ll discover a lot along the way.

Just keep the big questions in mind, be intentional and let them guide whatever you choose to experiment with.

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Final Thoughts: Turning Reflection Into Momentum

I started Newsletter Circle as a way to learn.

Now, it’s becoming a way to teach, strategically, transparently, and with a sharper focus than ever.

I’m not seeing myself as solely a content creator anymore. I’m building a business.

And if you’re growing a paid newsletter business, I hope you’ll keep building it with me.

Let’s do this together.

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Thanks for reading, and feel free to reply if you’d like to connect!

See you on Sunday.

Ciler

Find me on Substack Notes & LinkedIn