Most people track retention the wrong way—and in this episode, I get real about why that’s a huge mistake if you run a membership. Let me take you behind the scenes of a series of conversations and lightbulb moments I’ve had lately, all sparked by one shocking stat: most of our members decide to stay or go within the first 30 days. Not month six, not when the novelty wears off, but right at the very beginning.
It’s something I see again and again with my clients and fellow membership builders. You’re pouring all your effort into “saving” members in month four or six, but the reality is, you’re aiming at the wrong window. If your onboarding isn’t spot-on, you’re missing your biggest chance at keeping people.
The inspiration for this episode came as we prepped for our upcoming summit. Scott Paley (from Numbers Are Sexy) is leading a session called “Your retention rate is lying to you.” The core idea just floored me: the retention numbers most of us obsess over don’t actually help us prevent cancellations. They only tell us what’s already happened, never who’s about to hit the cancel button. We’ve all been tracking what’s easy to see, but not what tells the real story.
Then I heard what Erin Kelly of MemberVault is sharing in her talk, “The First 30 Days Fix: How to Set Up Your Membership So People Don’t Cancel.” The whole mindset shift here is wild—if you want people to stay, it’s about what they experience their very first week, not gizmos and bonuses months down the road. Your onboarding has to deliver those quick wins and make people feel at home, fast.
And then there’s the idea that some people simply never wanted your main membership offer at all. Jessica A, one of my clients, runs Double the Stitches (a knitting membership) and realized a smaller, lighter offer wasn’t just a “downsell”—it attracted a totally different type of buyer who wanted something more focused. Those folks never would have bought the “full” version no matter the price. If you only offer one way in, you’re leaving an entire category of people out in the cold.
The big takeaway I want you to have from this episode is this: it’s not about frantically tracking more data, launching more bonuses, or adding extra tiers just to add them. It’s about deeply understanding the systems at play—what actually predicts a member will cancel, when that decision gets made, and who you’re missing entirely.
I’m so fired up for the upcoming What’s Working Now Summit because we’re not just handing you more tactics. We’re getting under the hood and teaching you to spot those critical signals before a member is gone for good. It’s free, runs October 5th to the 9th, and includes 38 sessions you can access all week—plus live presentations, Q&As, and, honestly, one of the most energetic, supportive community experiences we’ve ever pulled together.
If you want to see retention differently, attract the right members, and keep them without burning out, you need to carve out space for this summit. Grab your ticket at whatsworkingnowsummit.com and come be part of the movement—I’d love to see your membership thrive alongside ours.
(c) 2026 Sandra De Freitas | SandraDeFreitas.com | All Rights Reserved
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