This Was Supposed to be Easy Podcast

S2 Episode 37: We Want the Holidays to Be Easy

Listen Later

When the calendar starts bossing you around, joy taps out, so Amy and Cheryl share how they took it back: trading obligation math for memory-making, flexing dates, and building traditions that actually fit real life.

Key topics & takeaways

  • Why “the day on the calendar” doesn’t have to rule your plans
  • Swapping obligation for flexibility (and sanity)
  • Thanksgiving reimagined: restaurants, leftovers, and low-lift joy
  • Christmas Day at home: open-door, pajamas, and appetizers all day
  • New traditions: Christmas Eve movies, turkey trots, Black Friday sister dates
  • Making room for teens/partners/in-laws, and for people who’d otherwise be alone
  • The magic question: “What’s the one thing that makes it feel like the holidays for you?”

    • Moments we loved

    • “Control is expensive, presence is richer.”
    • “It’s not the number on the calendar; it’s the people in the room.”
    • “Our garage becomes the auxiliary fridge. #Michigan”

      • Challenge for the week

      • The One-Thing List: Ask each person, “What one activity/food makes it feel like the holidays?” Prioritize those, skip the rest.
      • Pajama Open House: Appetizers all day, drop-in welcome, no formal meal.
      • Date Drift: Celebrate with extended family on the nearest low-stress weekend.
      • Outsource Thanksgiving: Book a restaurant/hotel buffet; play games afterward.
      • Anchor & Float: Choose one anchored tradition (e.g., Christmas Eve movie) and let everything else float year to year.

        • Shout-outs mentioned

        • Turkey trot (walkers welcome)
        • Christmas Eve movie + Chinese takeout tradition
        • Matching family pajamas (dog bandana optional… or not)

          • Note: While we talk about our own family holidays and traditions, we know that it does not fully represent all that people celebrate. Please help us learn more about the holidays that you celebrate and the traditions that you share!

          Connect with us

          • Website: https://supposedtobeeasy.com/ 
            • Our Podcast Home: https://supposedtobeeasy.podbean.com/
              • Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
                • Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy

                  • We want to hear from you! Follow and share your key takeaways, ideas, and inspiration!

                  ...more
                  View all episodesView all episodes
                  Download on the App Store
                  This Was Supposed to be Easy PodcastBy supposedtobeeasy