December is chaos. Holidays, travel, weather, kids, hosting, work, pressure to “make it special” – and then we act shocked when the credit card statement smacks us in January. In this 12 Days of Giving episode, I bring back money expert Rachel Duncan to walk through the one simple system she built to stop December from blindsiding her every single year: a recurring “Holiday Lessons Learned” calendar event that future Rachel is very, very grateful for.

Rachel breaks down exactly how she built her holiday playbook: what went wrong, what worked, who actually enjoys which tasks, how much candy they really need for Halloween, why New Year’s hosting hits different, and how all of that quietly adds up to real money. She shows you how she turned a chaotic season into a repeatable checklist that lives in her calendar and gets better every year instead of starting from zero every time.

From there, we go straight into the money. We talk holiday “specialness” spending, why the real budget busters are the so-called “one-off” expenses, and how seasonal stuff like camps, hobbies, gifts, travel and parties are exactly what push people into debt. Rachel walks through her “holiday specialness” category, sinking funds, and even a controversial but smart use of a dedicated credit card you pre-load like a savings bucket. This isn’t theory – this is how real families actually spend.

Then we zoom out into the psychology. We hit future-self research, the idea of seeing your future self as a real person, and why we’re willing to plan better for others than we are for ourselves. Rachel shares how aging a photo of herself, naming future-Rachel, and literally thanking “past me” changed how she spends in the moment. It’s not about guilt. It’s about taking responsibility for the version of you who has to live with December’s decisions.

If you’re tired of swearing “next year will be different” and then repeating the same pattern, this episode is your line in the sand. We’re giving you a concrete way to capture your own holiday lessons, track the real costs, and start funding them like adults instead of pretending we’ll remember. This is part of our 12 Days of Giving series – one raw, practical episode every day from December 12–23 to get your money and mindset right heading into 2026.

👉 Watch the full episode on YouTube: https://youtu.be/AUn_SwFDK5M

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