What If Data Helps Us Ask the Right Questions?
Discover how reader insights can fuel your intuition and shape your Substack journey
Asking the right questions has always guided me toward clarity, in both work and life. I wrote this piece before the U.S. election, and I’m sharing it as originally intended because the insights remain valuable — relevant beyond any single outcome. Now more than ever, your voice matters. I hope we continue to hear it.
When I send my writing into the world — whether it’s an essay, a book or digital guide — I think of it like releasing a message in a bottle. I never know quite where it will end up or how it’ll be received, but data offers me a window into that journey.
For me, data isn’t just numbers on a dashboard; it’s a flashlight that illuminates where my work resonates, where it quietly lands and, most importantly, how I can keep experimenting. Each metric and each reader interaction represents a tiny voice speaking back, letting me know I’ve connected.
This curiosity is especially important to me as an autistic person and is part of what I love about being an editorial strategist. Data provides a language I can use to interpret the often subtle or opaque reactions people have to what we are all creating. It helps me track patterns that reveal how a voice is received. For the last 12 years, in every interaction — every click, comment, share — I know there’s a way for me to find deeper context. It’s the foundation of my 5x5 editorial audit and my pricing gut check, where I dig into the data to uncover not only what works in our newsletters or businesses, but why.
In my 5x5, I start with five core questions that act as a compass:
What made people like this?
I ask myself, what is it about this piece that drew people in? Whether it’s a headline that struck a nerve or a personal anecdote that resonated, understanding this gives me insight into what first catches attention.What made people comment?
Here, I’m diving deeper. Comments indicate a willingness to engage, to share an opinion or experience in response to mine. What topics are sparking conversation, and are these comments revealing a shared mindset with my readers?What made people restack or share?
When someone shares my work, they’re vouching for it in front of their own audience. I want to understand what’s in these pieces that compels readers to advocate for my message. Is it an idea that feels urgent, something they want others to see?What made people pay money to read this?
There’s something uniquely valuable in posts that inspire a paid subscription. What need or motivation led to this choice? I want to understand what makes my work worth supporting financially and what themes or experiences I can deliver to make that commitment worthwhile.What role am I standing in within these pieces?
I’ve come to see that different roles — be it storyteller, guide, curator or voice of honesty — resonate with readers in distinct ways. Reflecting on this lets me understand what creative channels resonate most deeply and how I can lean into these roles to bring value.
With each question, I’m dissecting what makes my work meaningful to my audience. But this isn’t just about popularity or performance metrics; it’s about uncovering the themes and perspectives that compel people to engage, return and invest in what I create.
Using Data to Nurture Reader Relationships
Data is also a way to observe the journey my readers take with me. How long does it take for someone to go from free subscriber to a paying one? What was their path to that choice? Every time I run a promotion or experiment with new offers, I can see what truly works — and what I can refine.
Each time I hold this data in my hands, I have a moment to check in with myself: Am I surprised by what I see? Do these numbers give me confidence, or do they challenge my assumptions?
→ Data has the distinct ability to reflect my readers’ behaviors back to me in a way that feels deeply revealing and usually reassuring.
Yet even as I hold this feedback, I’m careful to keep my voice distinct from the data that informs my strategy. I can let data show me where I am without letting it blindly dictate where I’m going.
Building a Bridge Between Intuition and Resonance
As I approach a new year, I’m looking for the bridge between what has resonated and where I sense my voice wants to go next. Each data point and trend acts as a guidepost, showing me the impact of past work, while my own intuition keeps steering me toward new terrain. Together, they create a dynamic between what I know resonates and what I hope to bring forward in my work.
Data motivates me to keep experimenting because it speaks in patterns, in glimpses of consistency. Each time I publish, it’s another chance to connect, to gather more insight and to refine that understanding in ways that let me grow alongside my readers. This constant dialogue — between data, intuition and the audience I’ve come to know — feels like a bridge I can trust as I move forward.
Ready to Dive Deeper? Join the “Audit Your Substack Data Like a Strategist” Workshop
If you’re interested in understanding how data can help you plan for 2025 and uncover clues about your relationship with your readers, I invite you to join my workshop, Audit Your Substack Data Like a Strategist. We’ll be covering the questions and frameworks I use in my 1:1 work (and which costs several hundreds dollars per engagement) to connect data to meaningful insights — so you can gain a clear view of what resonates with your audience and where your voice is taking you next.
In this session, you'll learn how to conduct a 5x5 editorial audit and a pricing gut check to get the most from your Substack data. Whether you’re looking to refine your writing plan, grow your audience or strategically shape your essays, this workshop will give you the tools to audit with intentionality and confidence.