Ideas for Cultivating Conversations & Calm This Season

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Dec 12

Listen to Episode 189 Here / Apple / Spotify

The holidays bring all kinds of gatherings—some joyful, some a bit tricky! I’m sharing simple ways to steer conversations toward connection and positivity. Plus, one of my favorite traditions: writing a letter to your future self. You’ll leave with tips to bring more ease to your holiday season!

Let’s Be Honest About the Holidays

This time of year brings festive gatherings, celebratory dinners, and plenty of opportunities for meaningful connections. But it can also come with small talk that feels uninspired or exhausting!

If you’re craving deeper, more intentional conversations (and less gossip or complaints), I’m here for you. Keep reading for practical ideas to cultivate more connection, calm, and joy this season!

Your Energy Makes All the Difference

Let’s start with the conversations. How often do you find yourself falling into predictable patterns talking about the weather, being buy, or venting about things that aren’t going well?

While there’s nothing inherently wrong with these topics, I’ve been reflecting on how conversations can feel more nourishing and connected with a bit of intention.

Before heading to a social event, take a moment to pause and ask yourself:

• What kind of energy do I want to bring?

• How do I hope to feel at the end of this event?

• What am I curious about in the lives of the people I’ll see?

Intentional Conversation Starters for Holiday Gatherings

Whether you’re at a casual gathering, dinner with friends, or your partner’s company holiday party, here are some conversation starters to keep things fun and meaningful:

Holiday Traditions:

• What’s your favorite holiday tradition, past or present?

• Are there any new traditions you’re hoping to start this year?

Food & Festivities:

• What’s your go-to holiday dish or treat?

• Do you have a favorite Christmas morning breakfast?

Memories & Stories:

• What’s the most memorable gift you’ve ever received?

• What’s a holiday activity that’s on your “never again” list?

Music, Movies & Books:

• Do you have a favorite holiday album or movie?

• What’s the best book, show, or movie you’ve enjoyed this year?

Looking Ahead:

• Do you have any goals or intentions for the new year?

• If you could fast-forward to next December, what’s one thing you hope to have experienced?

Remember this: conversations are a two-way street. When you ask someone a question, they’ll often ask it back to you, so it can be helpful to reflect on your own answers first.

For more conversation starters check out the Cultivating Conversations Card Deck from Wilde House Paper. I’ve used this with friends and at a group event I led. Both times it resulted in juicy, meaningful convos!

A Year of Calm for *You*

When you’re overwhelmed and uninspired, a few deep breaths won’t cut it. What you need is a whole new way to connect with yourself.
Get ready to finally feel grounded in who you are and where you’re headed.

learn more

Grounding Practices to Protect Your Energy

The holiday season is full of opportunities to connect, but it can also be draining. Protecting your energy is key to making the most of this time of year. Here are a few tips to stay grounded:

Set Intentions: decide how you want to feel and let that guide your choices.
Take Breaks: a five-minute pause to breathe or rest can do wonders for your energy.
Say No: You can’t do it all! Prioritize what matters most and release the rest.
Focus on the Present: Instead of planning every detail, trust that things will unfold as they’re meant to.

A Calming Tradition: Writing a Letter to Your Future Self

One of my favorite traditions for cultivating calm during this busy season is writing a holiday letter to my future self.

Here’s how it works:

At the end of the holidays, I write a letter reflecting on what went well, what I’d like to remember, and what I want to do differently in the future.
Then I pack it up with my holiday decorations so I can read it at the start of the next holiday season.

This practice helps me process my experiences and offers “future me” a kind, encouraging reminder when the holidays roll around again.

In last year’s letter, I shared reflections on overcoming unexpected challenges and celebrated small but meaningful moments, like my dad helping us fix a coffee spill disaster on Christmas Day. I also reminded myself to prioritize downtime and not say yes to every holiday commitment.

The beauty of this tradition is that it creates a time capsule of wisdom and insight. Reading my past letters feels like receiving a warm hug from my former self, and it’s a practice I highly recommend.