Issue #36 - November 11th, 2025
Written by Michael Gillespie
In this issue:
Perspective: The holidays unlock a different kind of motivation in your audience: emotional, reflective, and value-driven.
Insight: How to connect authentically during this season, build trust and deepen relationships that last well beyond it.
Outlook: Notes on leading with heart
QUOTE OF THE WEEK
“During the holidays, people don’t just buy - they reconnect with what matters. Your membership can be part of that story.”
The holiday season brings a kind of energy that no other time of year can match.
People are reflective. They’re generous. They’re searching, often unconsciously, for connection, for meaning - and for something that feels like they can belong to.
And that’s exactly where a strong membership fits in.
While most brands flood inboxes with discounts and countdowns, smart membership operators use this season to do something different: to connect.
Because what drives decision-making this time of year isn’t logic - it’s emotion.
It’s the desire to give, to belong, to start anew, or to be part of something that feels intentional.
I don’t know about you, but to me, that sounds a lot like the big idea of membership that I’m always talking about in this newsletter.
And right now, you’re sitting on the best time of year to be an operator.
Let’s dive in.
PERSPECTIVE
The Emotional Window
The weeks leading into the holidays create an emotional window unlike any other - and it’s one that membership operators rarely capitalize on.
It’s a season when people pause long enough to reflect on their work, their relationships, their habits and their goals.
This reflection opens a unique kind of receptiveness. People aren’t just spending; they’re seeking.
They’re more open to stories, more moved by purpose, and more ready to invest in things that align with who they want to become.
That’s what makes this moment so valuable for membership operators. But too often, it’s overlooked by the rush to attract discount buyers that will never stick around for the long term.
I say it all the time: Your membership isn’t another “thing to buy.”
It’s a way to belong - to connect with an idea, a mission, or a group that reinforces something people already feel stirring within them.
When you approach this season through that lens, you stop marketing and start inviting.
INSIGHT
Designing Connection, Not Campaigns
The opportunity this season isn’t to sell harder - it’s to connect deeper. And the difference between those two approaches is everything.
Here are a few ways to meet your audience where they are - emotionally and authentically during the season.
Tell the Story of Belonging
Frame your membership as something to be part of, not something to buy.
Use language that celebrates shared values, purpose, and togetherness.
Example: “This time of year reminds us why community matters - and why we built this one.”
Appeal to Reflection, Not Urgency
Instead of countdowns, create moments of meaning.
Share a reflection on what your members accomplished this year or what’s ahead for them in the new one.
Invite Participation, Not Just Purchase
Give prospects or members a simple way to engage: a year-end question, a gratitude post, a small challenge, or a reflection prompt.
Engagement, not incentives, is what deepens connection during this season.
Design Memorable Moments
Think of small, sensory touchpoints that create warmth and memory: a message, a story, a surprise thank-you.
Emotional memory lasts longer than transactional memory.
Anchor It All in Authenticity
The tone matters most. Speak from the heart, not from your funnel.
This is the season to sound like a person instead of a marketer.
The holidays aren’t about conversion - they’re about connection.
And if you build real connection now, when the environment is just right, I can assure you that conversion will follow naturally from those who will want to be around for years to come instead of a few weeks after a promotion.
OUTLOOK
The Long Tail of Emotion in Membership
When done well, the emotional tone you strike this season doesn’t fade when the lights come down - it carries into the new year.
Members who join or engage during this time often stick longer and participate more deeply because their decision wasn’t driven by impulse - it was driven by meaning.
That’s the real opportunity of the season: not a sales window, but a trust window.
So as you plan your next few weeks, remember, this is the time to lead with heart, not hype.
Today, I’m leaving you with this question to consider:
Are you chasing someone’s attention, or earning a place in someone’s story?
Think about it.
