How to Navigate Holiday Conversations with Family

The holidays often bring a range of emotions—from joy and celebration to stress and loneliness. For those grieving, the season can feel bittersweet, making the absence of a departed loved one all the more poignant.


The past few months since October 7th continue to be excruciatingly painful for many. I've been going through my own process of healing ancestral pain, grappling with the complexity and contradictions of Jewish history, and (re)educating myself about the history of the Holy Land by listening to interviews and reading voraciously.


I wonder how it's been for you, and how you are managing?


With so much afoot (I haven't even mentioned the latest climate news, or the upcoming election cycle here in the US), many feel anxious about conversations with family. So, for those who are getting together with others or visiting family, I want to share some tips for navigating holiday gatherings with their messy, often tense conversations. While we can’t control other people’s behavior, we can choose consciously how we show up.


With some forethought and care, we can approach these interactions with more clarity, love, and skill—to steer clear of an argument, enjoy your time, or simply stay sane with family over the holidays.


1. Choose a wise intention

One of the most powerful ways to stay grounded in any conversation is to set a clear intention ahead of time. Intention is about how you wish to be in the interaction, rather than aiming for a specific outcome. What values do you want to embody this holiday season? What's your purpose for getting together?


Some classic, helpful intentions include to be curious, patient, or kind; to relax and have fun, to focus on the good in others, or to stay connected to oneself. 


Choose a word or phrase for your intention, then think of an image or memory that represents this quality. For example, if your intention is to be flexible, you might think of bamboo bending in the wind and rebounding upright. For patience, I imagine a redwood tree standing strong for millennia. Before and during the conversation, recall your intention and image as often as you need.  


2. Ask better questions; practice deep listening

Conversations can have a way of meandering into useless chit-chat or contentious territory. Come prepared to holiday gatherings with some engaging topics or meaningful questions that uplift.


Here are a few of my favorite questions to connect and draw out the good in others: What brings you joy these days? What’s something you did for fun in the last month or so? How are you managing to stay balanced with all that’s happening in our world? What’s an important lesson you learned this year?


When you ask a question (or introduce a topic), really listen. Quiet your mind and give the other person your undivided attention. Listen not only to their words, but to what’s in their heart. Try to get curious about what matters to them. Can you connect with something they care about? 

 

3. structure the conversation

A common question I receive in my communication classes is, “How do I deal with others who leave no space in the conversation?” In my family’s culture, speaking over one another is common, even an expression of enthusiasm! Yet as someone who enjoys having space in dialogue, this can feel hard. 

One strategy to shift this pattern—especially if you plan to engage in more substantive political or emotional topics—is to introduce some structure for a period of time. At the group level, try suggesting an activity or playing a game. For example, invite each person take a turn sharing something they’re grateful for, or one thing that touched them this year, while others listen. Or, invite people to share something about themselves that others don’t know. You can also add structure by playing a game, which shifts the group’s focus of attention and can interrupt habitual tendencies.


For heated topics, propose making agreements ahead of time about how you’d like to have the conversation. Do you want to set a timer and take turns speaking? Is there someone present who can moderate? Could you each agree to try to listen with empathy and an open mind, seeking to understand the other person’s point before rebutting? Can you agree to start from a place of feeling well-regulated? How do you propose to handle either party growing over-activated?

 

4. Know your limits

Another way to stay oriented during conversations is to reflect beforehand on your limits. If we’re clear about what we are willing to discuss and what we’re not willing to discuss, what kinds of behaviors we’ll let slide and which ones we plan to call out, it’s easier to relax because we’re not continually recalibrating our boundaries.

Perhaps arguing about the war, history, politics, or the ecological crisis isn’t how you want to spend the holidays. You may do enough of that already, or have reason to believe that it’s a waste of energy with certain relatives. On the other hand, you may be equally clear about confronting certain kinds of comments that land as racist, hateful, antisemitic, Islamophoboic, transphobic, xenophobic, and more. If you expect to encounter situations where you need to set a limit, memorize a few phrases you can use in the moment to express your values.


5. speak your truth, share personal stories

We all probably know that awful experience of being frozen, swallowing our emotions, and later feeling small, ashamed, or angry. It can takes courage and tremendous fortitude to confront long-standing dynamics in our families and do something different. Having some compassion for yourself here before, during, and after a gathering can go a long way to ease some of the heaviness.

One way forward is to prepare some short statements that express your views, feelings, or needs, and think of a personal story you can share to illustrate where you’re coming from. Telling a personal story creates more connection than stating facts, and can pave the way for more meaningful conversations down the road.


6.  Be present and recall impermanence

Conversations are complicated. Relationships are messy, especially with family. Staying aware of change can bring balance amidst the tangle of old hurts and dysfuncational family patterns. Use the tools you have to stay present and grounded: feel your breathing or your feet on the ground, bring something soothing to hold in your pocket, or quietly clasp one hand in the other feeling the warm contact.


Everything passes, the beautiful moments and the excruciating ones alike. Recall how briefly we are each here on the planet, which brings perspective. Knowing that everything is changing, that this too will soon be a memory, helps us to cherish the sweet moments and to bear the painful ones gracefully.


I hope this has been helpful, and wish you, your friends, and family a safe, happy, and healthy holiday season.

Like what you've read?

Subscribe and receive six free guided meditations.
Photo by Erol Ahmed on Unsplash