6 Questions to Ask When Your Newsletter Feels Stuck
Consider the "giving-to-asking" ratio and five other questions to get your newsletter flowing again
It happens to the best of us—sometimes, despite your best efforts, your newsletter hits a wall. Reader engagement drops, growth stalls or the flow starts to feel forced. As someone who's spent years experimenting with email and communication strategies, advising other writers and studying audience behaviors, I know firsthand how disheartening this can be. But I’ve also learned that hitting a block is often a sign that something needs a small adjustment—not a complete overhaul.
When someone tells me their newsletter is stuck, I turn to these six questions, which have helped other entrepreneurs and writers get unstuck and back on track. Here’s how you can use them to regain momentum.
1. Have I Rolled Out Too Much Too Soon?
One of the quickest ways to overwhelm yourself and your readers is by adding too many new features or engagement opportunities at once. When I feel like my newsletter is losing focus, I stop and ask: Have I tried to do too much?
Building a sustainable newsletter happens in layers. If you’ve been leaning into a season of “tending” with your readers—adding chats, polls, special features or additional posts—it’s easy to lose sight of what your readers loved about your newsletter in the first place. Choose just one feature or tool to add at a time, and make sure it’s built on the core ingredients your readers already enjoy. Simplicity can be the key to regaining momentum. (Use my free mini editorial audit to help you focus in on what readers really love about your newsletter, and then think creatively about how to introduce, say, a monthly Chat thread that your readers can’t resist.)
2. Am I Balancing Free and Paid Offerings Effectively?
If you’ve transitioned your free newsletter to include paid subscriptions, it’s easy to get stuck in a place where your readers start feeling like they’re being asked for too much. If engagement drops after rolling out a paid option, I ask myself: Am I giving enough before I make the ask?
I try to follow a giving-to-asking ratio of at least 3 to 1. This means for every time I ask my readers to subscribe or upgrade, I’ve already delivered three pieces of high-value posts for free. If your newsletter feels stuck, try reassessing how often you’re making “asks” versus how often you’re simply delivering value. Reader relationships thrive on trust and reciprocity, so it’s important to maintain that balance.
3. Am I Honoring My Bandwidth (and My Readers’)?
Sometimes, newsletters get stuck because you’re asking too much of yourself—or too much of your readers. When my workload feels overwhelming, I use my red, yellow and green coding system to reassess: Am I biting off more than I can chew?
Green: For quick, easy posts (under 1,000 words or 5 minutes).
Yellow: For moderate effort posts (under 1,500 words or 10 minutes).
Red: For more demanding posts (over 2,000 words or 11 minutes).
If I’ve been putting out too many red or yellow posts, I take a step back and mix in some green moments. It’s not only easier on me, but it also gives my readers time to digest what I’m sharing without feeling overwhelmed. Consider how your own bandwidth—or theirs—might be affecting the flow of your newsletter. And if you need help applying the red, yellow, green labeling system, check out this free resource (with video instruction) here.
4. Am I Filtering My Essay Ideas with Intention?
Essays that don’t feel quite right can make your newsletter feel stuck, too. When that happens, I ask myself: Am I being intentional about my essay ideas, or am I just throwing them out there?
To make sure my newsletter stays in a good rhythm, I put my ideas through a simple filter:
Is this substantive enough to become a longform essay, or would it work better as a reflective, casual email in my nudge cycle?
This approach helps me navigate how I’m connecting with my readers and ensure that I’m sending the right message at the right time. If you’re stuck, try reassessing how often you make contact with your readers and with what invitations — this can help create perspective and make sure each piece fits naturally into the flow of your newsletter.
5. Have I Lost Touch with My Reader Persona?
Sometimes, when you feel like your newsletter is in a rut, it’s because your understanding of your readers has evolved, but your newsletter hasn’t caught up. When this happens, I ask: Have I revisited my reader persona lately?
Reader relationships aren’t static—they change over time, and so does your audience’s engagement. I make it a point to regularly revisit my reader persona, reflecting on both data (like surveys and engagement stats) and my own intuition. If you’re feeling stuck, take some time to reassess who your readers are, what they’re responding to, and whether your newsletter is aligned with their needs. To get started on your own reader persona, check out my Reader Connection Blueprint.
6. Am I Looking at the Data?
Sometimes, the loudest feedback comes not from direct reader comments but from the data. Whether it’s open rates, click-through rates, or subscriber trends, paying attention to what the numbers are saying is essential to understanding where your newsletter may be getting stuck.
One of my clients recently used a pricing gut check with me to dig into her data and discover her newsletter’s sweet spot for pricing. This insight helped her align her offering with both her values and what her audience was able to invest, leading to renewed growth in her newsletter. If you're feeling stuck, take a closer look at your data—it may hold the key to identifying what needs to shift to keep your newsletter moving forward. (Not sure where to look in the data? Hop on the waitlist here for my next workshop: Audit Your Substack Data Like a Strategist.)
Realign and Move Forward
When your newsletter feels stuck, it’s often a sign that something needs to shift in your approach. By asking these six questions, you can start to pinpoint where the issue lies and find a way forward with more clarity and intention. Here’s a quick reminder:
Have I rolled out too much too soon?
Am I balancing free and paid offerings effectively?
Am I honoring my bandwidth (and my readers’)?
Am I filtering my ideas with intention?
Have I lost touch with my reader persona?
A stuck newsletter isn’t the end—it’s just a chance to realign, adjust and move forward with renewed purpose. Every month, I guide my readers through the complexities of publishing a newsletter that truly resonates, helping them build something sustainable, distinctive and full of heart.
If you're ready to take the next step in aligning your newsletter with your voice and reader needs, my Editorial Launch Pad is designed just for that purpose. This resource is here to ensure your Substack is not only ready for readers but that it’s also a space where your creativity can thrive. With it, you'll be equipped to make magic with your writing voice and keep your newsletter moving forward with intention and clarity.
New to Amanda and The Editing Spectrum?
Explore My Work: Join the waitlist for my next workshop, Audit Your Substack Data Like a Strategist, or explore my 🌙 paid member Editorial Launch Pad.
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So helpful! Thank you, Amanda. I'm in the midst of trying to plan for 2025, but am reliant on data + the 1% of my readership who have answered my first survey 🥲 Will check out your in-depth guides. :)