#125 How To Architect A High Value Member Journey

You know those weeks when every conversation seems to echo the same theme? That was me this week.

First, I spoke with a learning designer who builds behavior-change programs inside enterprises. Then I hopped on a sales call with a prospect launching a membership that will help people over 50 build sustainable habits for long-term health and success.

This was the theme – If you want your membership to work, and if you want the authority to charge real money for it, you need a structured learning journey.

Let’s get into it –


You can hand someone all the ingredients for a five-star meal — but without a recipe, they won’t know where to start, what order to follow, or when to call the dish “done.”

Memberships work the same way.

The prospect I spoke with had plenty of good ingredients: a challenge, assessments, live calls, even some bonuses. But without a clear member journey that connects point A to point B, the experience risks feeling scattered.

Members don’t just want resources. They want to know:

  • Where am I right now?

  • What’s the next step?

  • How will I know I’m making progress?

When you give them that recipe (a structured learning journey) you move from offering access to delivering outcomes.

Structure creates value

A structured learning journey doesn’t have to be a three-year curriculum. It can be simple, but it has to be clear.

That means:

  • Defining your transformation (“We take people from A to B”)

  • Naming the milestones in between

  • Mapping programming like challenges, live calls, events, directly to those milestones

  • Creating touchpoints for connection and accountability along the way

This is all about designing serendipity.

When you pair the right members together at the right moment – maybe they’re working toward the same milestone or tackling the same challenge – it creates the kind of “lucky” connection that keeps people engaged far longer than content alone.

Why this gives you pricing power

On that sales call, the prospect told me he wanted to charge over $1,000 a year for his membership.

At that price point for what he was offering, members need more than access to the monthly call and content he had planned. You need to design a member journey that proves you can deliver transformation – because that’s what creates pricing power.

Here’s why it works:

  • Lower risk for buyers: Prospects see a path with milestones, not just a list of features.

  • Faster time to value: Onboarding delivers an early win, which builds trust.

  • Value over volume: Pricing is anchored to transformation, not content quantity.

  • Retention advantage: Milestones and designed connections keep members engaged, which increases lifetime value.

Premium pricing doesn’t come from stacking more content. It comes from making the path to results undeniable.

Your next step

Write your transformation statement.

We take [your ideal community member] from [A] to [B].

Then jot down the 2–3 milestones in between.

That’s the start of your structured learning journey – and the difference between a membership that feels like a “nice-to-have” and one people will confidently pay more for.

Quick note: If you're thinking that what you offer is more peer-driven and focused on connection, I bet if you go deeper there's a member journey you can enhance that experience with. Give it a shot!


Thanks for reading!

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#124 4 Retention Strategies That Don’t Require More Content