29. How Knowing Yourself Better Can Bring More Joy to Your Holiday Planning

In this episode of Holiday Headstart, we dive into how understanding yourself through Gretchen Rubin’s Four Tendencies framework can completely change the way you plan for Christmas—and reduce your stress while you're at it. We break down each of the four tendencies—Upholder, Questioner, Obliger, and Rebel—and explore how your response to expectations shapes your ability to plan, prep, and actually enjoy the holidays. Whether you love a checklist or resist all structure, this episode will help you create a holiday planning system that works with your natural tendencies, not against them.

We’ll share personalized tips for each tendency, including how to build in flexibility, avoid analysis paralysis, use accountability to your advantage, or embrace your inner maverick. If you’ve ever felt like your holiday prep always falls short or leaves you burnt out, this episode might just be the mindset shift you need. Plus, check the show notes for a link to Gretchen Rubin’s quick Four Tendencies quiz so you can discover your own type and start planning smarter today!

Episode Highlights:

[00:01:03] - Tradition Spotlight on a Today’s Your Special Day plate

[00:02:51] - Introduction to the 4 Tendencies

[00:08:26] - Using your tendency to thrive

[00:10:16] - Tips for Upholders

[00:12:38] - Tips for Questioners

[00:15:49] - Tips for Obligers

[00:19:07] - Tips for Rebels

[00:21:37] - This week’s Get A Headstart Tip for getting holiday tasks done in advance

[00:24:37] - What’s on our to-do lists this week

[00:27:47] - Our Nice Lists

Resources Mentioned:

• Gretchen Rubin’s 4 Tendencies Quiz
• Kitchen Shears
• You Are Special Today plate
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed this episode, you'll love this too:

• Episode 25 - Why You Should Write Yourself a Permission Slip for the Upcoming Holidays