Hey from Chicago.

I was just thinking about how January is basically the Super Bowl for motivation. People head into the new year ready to reset, refocus, and finally take on the goals they’ve been putting off. And as a membership business owner, you can use that natural momentum to re-engage your community and win back canceled members while also upgrading free or lower tier members in a way that feels warm, supportive, and genuinely helpful.

One simple way to do that is by creating a 30 day New Year challenge for your members, then promoting it through a short series of year end win back emails.

A New Year challenge works because it gives people:

That combination is powerful in January. It’s exactly what people are craving.

Your challenge doesn’t need to be fancy. Pick one theme your audience already cares about, then create simple daily or weekly actions they can follow. Think:

The real value comes from the community showing up together.

Promote this challenge towards the end of December with a short, friendly win back email series. You might send this to:

Each email can be warm and straightforward, something like:

“I’m hosting a 30 day Start 2026 Strong challenge inside the community starting January 1. If you’ve been wanting more structure, accountability, and momentum, this is a great time to come back.”

The challenge gives returning members a reason to stick around. The email series gives them the nudge they need to rejoin. And your community heads into 2026 with fresh energy.

Your Challenge
Use this time as a way to re-engage yourself with your members. January is a great time to check in, learn their names, and notice the small details that make each person unique. Reach out, start small conversations, and remind people that there’s a real human behind the community they joined. That personal connection goes a long way!

A New Year challenge paired with a simple win back series gives you momentum, energy, and a fresh start with the people you serve. It’s a light lift with a big payoff, and a great way to start 2026!

Thanks for reading,