Bring Your Big Questions to The Pivot Hour — and Share One You Plan to Ask

From AI and ads to MailChimp and creative clarity, let’s tackle the newsletter questions you’ve been wrestling with

Whether you’re scaling your newsletter, exploring monetization or figuring out what’s next, you probably have questions about how to keep growing, connecting, and sustaining momentum. Questions that might include:

• How to plan for renewals so your subscribers stick around.

• Whether creating a digital guide is worth it as a sign-up bonus.

• How to use AI efficiently without compromising your writing integrity.

• When it’s time to think about ads or how to balance free vs. paid subscribers.

• How to build your newsletter toward becoming part of your business.

That’s why I’m hosting The Pivot Hour — a live, open strategy Q&A session where we tackle the questions that often go unanswered.

Here’s how you can join — and help spread the word:

1. Think about a question you want to ask during The Pivot Hour.

2. Reshare this post with that question included (and tag me so I can see it!).

3. Join me tomorrow to get clarity, ideas and momentum for your newsletter.

Whether you’re thinking about growth, strategy or creative systems, this is your chance to ask and recalibrate for what’s next.

Here are just a few kinds of questions you might bring:

Scaling and Monetizing

• How do I know when my newsletter will start making money?

• What’s the best way to get readers to upgrade to paid subscriptions?

• How do I decide if a digital guide is worth creating as a sign-up bonus for free or paid readers?

• I have a lot of renewals coming up soon—how do I make sure readers are ready to renew and I won’t see a mass drop-off?

• What is considered a premium newsletter price for monthly or yearly subscriptions?

• What’s the best way to create upgrade offers and promotions that don’t feel pushy?

Making Strategic Choices

• How do I know if I need more free or paid readers to grow my newsletter?

• When should I consider outside advertisements to help grow my audience?

• Is MailChimp or another email platform a worthwhile investment alongside Substack?

• What’s the best place to start building an income stream adjacent to my newsletter?

• I launched with a great idea on Substack, but now I can’t sustain it—what should I do?

• What is the best way to use data to make decisions inside my newsletter?

• My newsletter is part of my business—how do I keep it from sounding like spam emails?

• I’m building toward having my newsletter support my business. What steps can I take to get there?

Looking to Balance Growth and Creativity

• How can I use AI to improve my efficiency without compromising my writing integrity?

• Can I just write and not worry about growing my newsletter?

• How do I know if my Instagram or social media is a good fit for promoting my newsletter?

• What’s the best software, tool or system you’ve found this year that improved your newsletter workflow?

• How can I stick to a writing plan and build a steady rhythm?

• How can I get more readers to subscribe without feeling like I’m shouting into the void?

Seeking Creative Clarity

• How can I turn my half-formed ideas into a clear, actionable writing plan?

• How do I know which of my ideas deserves my energy right now?

• What practices can help me balance creative exploration with consistency?

• How can I reconnect with my writing when it starts to feel flat or disconnected?

• What’s the best way to harness inspiration without getting overwhelmed by it?

• How can I bring more of my authentic self into my writing without losing focus?

If any of these resonate — or if you’ve got something else on your mind — this is your space to ask.

What You’ll Walk Away With:

• Clarity on your next steps.

• Momentum for your newsletter goals.

• Tools and insights to help you move forward.

This is also the last open Pivot Hour before it becomes a benefit exclusively for paid members of The Editing Spectrum, so if you’ve been curious, now’s the time to join us.

I’d love to hear the questions you’re bringing to Pivot Hour — reshare this post with one you plan to ask. Let’s make it a space for the big, overlooked and practical questions about newsletters that need answering.