I’ve been harping on Why Pay sequences because THEY WORK.
In fact, you’re probably here because of one of my Why Pay emails.
It works because you remove mental blockers or confusion your readers have that get in the way of them paying you. How often do you see someone say “I’m gonna subscribe soon” and wonder what’s stopping them? This is your chance to grease the wheels.
Some of you participated in last month’s Why Pay sprint and we’re putting a bow on it tomorrow with a little Show and Tell.
Here’s how it’s gonna go:
- I’ll ask for volunteers who want to show us their Why Pay sequence (with or without results)—we’d love to hear more about how this process went for you too!
- We’ll talk through the recipes and discuss which ones make sense for you
- We’ll review some more great examples of Why Pay messages to inspire you
- And we’ll close with a clear commitment to actually try this method
Great for those who attended the sprint AND for anyone curious about what a Why Pay sequence could do for you.
I really want to encourage you to incorporate this kind of messaging, if you haven’t already, because like I said a couple weeks ago, the old “upgrade to paid” is getting pretty damn tired.
Tomorrow’s session is a good chance to share how you’re thinking about this and to give me feedback on what would be most useful to you right now.

P.S. Have you joined us in Slack yet? You’re getting this email because you’re part of the Creator Journalism Bundle. A big part of that is an invite to our Slack community and we’re having some really useful discussions in there about cross-promotion, about what to charge sponsors, about hiring freelancers and more. Come join us! ➡️
📗 New in the Paid Sub Playbook
- Upgrade page: If your pricing page is not cutting it, try an upgrade page
- Swipe files: Over 100 examples of subscription upsells from journalists
- Recipes: "Why Pay" sequence to get more longtime free readers going paid
- Automation: Cancel Reasons and Subscriber Winbacks
🎯 Good starting places with the Paid Sub Playbook
- The Foundation Map: EVERYTHING you need to run a paid newsletter or blog
- The 3×3×3 Growth System: A framework for testing, validating and systematizing your growth and revenue channels
- Convince me to pay you: 10 motivation messages and why they work
💬 Upcoming events
- Tuesday 5/13 | Your next milestone: Come talk about your next goal and how you’re going to get there REGISTER
- Thursday 5/22 | Promo party: Find partners for cross promotion REGISTER
- Thursday 5/29 | Pitch Slam: Workshop your project pitch REGISTER
- Wednesday 6/4 | Why Substack is the worst choice for your subscription newsletter and what to use instead REGISTER