2025 Holiday Blog: What if the Hardest Holiday Conversation is with Yourself?

By Kimberly Best, RN, MA Conflict Management, Founder Best Conflict Solutions

Every year I write a holiday conflict blog. I do it because I know that many people – myself included - are silently struggling with the approaching holidays - the family dynamics, the old wounds, the exhausting expectations. And every year, I hear from readers who tell me something in these posts helped them show up differently, helped them breathe a little easier, helped them remember they had choices. This year's approach is about the most powerful tool I know - deciding who you're going to be before the holiday begins.  I’m reminded of what I heard William Ury say once, “For me, the most difficult person in any conflict is….the one in the mirror.”  That’s a thought worth exploring. Because what if in 2025 the hardest holiday conversation is with yourself?

I had a conversation with a client last week who said, "I'm already dreading Thanksgiving dinner, and it's still weeks away." She laughed, but I knew she wasn’t joking. Between her uncle's political commentary and her sister's passive-aggressive remarks about her career choices, she was mentally preparing for battle before even accepting the invitation.

Sound familiar?

Here's what I've learned through years of conflict resolution work and my own imperfect holiday experiences: Most of us spend more time anticipating what will go wrong than deciding who we want to be when things get hard. We write stories about how others will show up, but we forget we're co-authors of the experience we're about to create.

This Thanksgiving, I'm suggesting something different. Not a survival strategy, but a preparation strategy.

Before You Go (or Before They Come): Decide Who You're Going to Be

Think about this: You wouldn't walk into an important meeting without preparation. You wouldn't start a difficult project without a plan. Yet we often walk into family gatherings reactive instead of proactive, hoping for the best but braced for the worst.

What if you took some time before Thanksgiving to ask yourself: 

Who do I want to be at this table? What experience do I want to contribute to the memory of this holiday? When any of us look back on this, how do I want my contribution to be remembered?

Not who will everyone else be. Not what will probably happen. Not how to defend yourself or prove your point. Just: Who do I want to be?

I remember coaching someone who was hosting Thanksgiving for her family. She was very intimidated by her sister-in-law and tended to feel small around her. The anxiety was building as the day approached.  Her experience was that her sister-in-law was very critical of her and my coaching client told herself that she could never get it right.  We talked about her role, who she was and who she wanted to be.  We talked about how her home was her safe place, her castle. I asked her: "What kind of queen do you want to be in your own castle?"

That question changed everything. She got quiet for a moment, then she got excited.  She leaned into the idea of being a queen in her own space.  She said, "I want to be a gracious queen. A confident queen. The kind who makes everyone feel welcome but doesn't apologize for existing in her own space."

She rocked that holiday. And it changed the relationship between her and her sister-in-law forever. More importantly, it changed how she saw herself AND how she saw her sister-in-law. When she stopped showing up small and apologetic, her sister-in-law stopped dominating the space – or maybe my client stopped perceiving her as dominating the space.  The dynamic shifted because one person decided who she was going to be and had a plan for how she was going to show up.

That's what I mean by deciding who you want to be. It's transformative.

Do you want to be the person who listens with curiosity? The one who finds reasons to laugh? The family member who sees what's good in people, even when it's hard? The one who chooses connection over being right? The queen or king of your own castle, dedicated to being proactive in designing who you want to be this Thanksgiving?  If you aren’t the person hosting, you can still be the visiting royalty, the magnanimous guest, the grumpy party pooper.  You get to choose.  But in the absence of choosing ahead of time, there’s a pretty good chance you’ll show up reactive instead.

Think about this. Write it down. Make it concrete. "This Thanksgiving, I'm going to be someone who asks questions instead of making statements." Or "I'm going to be the person who changes the subject when conversations get heated." Or even "I'm going to be present and kind, even if I need to leave early."

When you decide ahead of time who you want to be, you give yourself something to return to when the moment gets difficult. And it will get difficult, because that's what happens when humans gather. We step on each other's toes. We say the wrong thing. We trigger old hurts without meaning to.

But having that anchor - that clear picture of who you've decided to be - that's your game changer. 

A caveat: while writing who you’re going to be, be careful not to write how others should be or how they should respond to how you show up.  Instead, just observe what happens.

The (Dangerous) Story We Tell Ourselves

Here's where we get into trouble: We write the script for how everyone else will behave before we even arrive.

"Uncle Bob will definitely bring up politics.""Mom will criticize my parenting.""My brother will make that same joke that stopped being funny years ago."

Maybe these things will happen. Maybe they won't. But when we decide ahead of time that they will, we start looking for evidence to confirm our story. And when we're defensive and looking for what's wrong, we will absolutely find it.

I'm not suggesting toxic positivity or pretending problems don't exist. Instead, I'm talking about honest positivity - the kind that speaks truth clearly and kindly.

What does that actually sound like?

"You know, I'm just not willing to have that conversation this year. I want us to leave this gathering still liking one another."

No blame. No defensiveness. No pointing fingers with "you always" or "you never."

This is powerful because you're stating your boundary AND your intention. You're being honest about what you won't engage with, while being positive about what you're choosing instead - connection.

Other ways to practice honest positivity:

• "I care about our relationship too much to let this topic come between us right now."

• "I'd rather hear about what's going well in your life than debate this."

• "I'm choosing to focus on what brings us together today."

  
  

Notice what's missing? The word "you" as an accusation. When we start sentences with "You always..." or "You make me..." we're handing over our power and putting the other person on defense.

Honest positivity means owning what we're choosing, stating it clearly, and inviting others into the experience we're committing to create. It's not fake. It's not avoidance. It's intentional.

And here's the thing about humans: Moods are contagious. It's so easy to pick up bad moods and bad vibes. We've all felt that tension the moment we walk into a room. But here's what's equally true and often forgotten - it's also pretty cool to be around someone who's upbeat and genuinely present. For some families, this might be unfamiliar territory at first. Your siblings might give you a sideways glance. Your aunt might wonder what's gotten into you. But positive energy shifts dynamics just as powerfully as negative energy does. Someone has to start. Why not you?

For just this one gathering, commit to looking for what's good while also being clear about what you need. That's the balance.

Gifting the Yes

My personal counselor shared something with me that shifted my entire perspective on obligation. She said, "I realized I could keep feeling resentful about going to Thanksgiving, or I could choose to go as a gift."

This isn't about martyrdom or self-sacrifice. It's about reclaiming your power.

When we feel obligated, we're victims. We "have to" go. We're trapped. But what if you reframed it? "I don't really want to spend five hours with extended family, but I'm choosing to go as a gift to my mother who loves having everyone together." Or "I'm giving this afternoon as a gift to my kids who deserve to know their cousins."

The situation hasn't changed, but your relationship to it has. You're making a choice where it might not have felt like there was one. That's empowering.

And here's the interesting part: When you gift the yes, you often show up differently. You're not bitter or resentful. You're conscious and intentional. You might even find moments of unexpected joy.

Your Thanksgiving Preparation Plan: Seven Essential Steps

These steps are also skill cards in my Best Conflict Conversation Cards in more detail.

Step 1: Set Your Intention for Who You'll Be

Before the day arrives, write down three qualities you want to embody. Kind. Curious. Present. Humorous. Compassionate. Pick what feels true to you, not what you think you "should" be. Keep this somewhere you can glance at it - in your phone, on a small card in your pocket. When things get tense, this is your anchor.

Step 2: Decide Your Boundaries Before You Arrive

How long will you stay? What topics are you willing to engage with? What's your coping strategy if things become too much?  (You really need to have a strategy for when you’re triggered!) These aren't selfish questions. They're self-care questions that help you show up as your best self for the time you are present. There’s always the deep breathing and counting to ten yet humming a silly tune in your head can be a reset.  So can having a meme on your phone that reminds you why you’re choosing this new strategy.  Get creative! And if you need to leave early, practice saying it simply: "I need to head out now. Thank you for having me. I'm glad we had this time together."

Step 3: Prepare Your Curious Questions

Instead of countering or correcting, have genuine questions ready: "Tell me more about that" or "What made you think about it that way?" or "What's been the best part of your fall?" Curiosity diffuses tension in ways that debate never will.  This means going in seriously wanting to learn these people as if you’ve never known them.  You will be surprised to learn what you didn’t know about them.  You may be equally surprised how powerful this is in connecting with people.  We all want to be seen.  Not assumed, but seen.  Think about what things do you not know about these people that you’re curious about and then ask them.

Step 4: Practice Separating the Person from the Problem

Someone will probably say something that lands wrong. That comment is a problem. That moment is a problem. The entire person is not the problem. We all have moments we're proud of and moments we're not. When we label people as the problem, we make the problem bigger and fail to see their humanity. Try this from my Best Conflict Conversation Cards: "What do I appreciate about this person?" Find one thing. Hold onto it.

Step 5: Remember What Matters More

Think about the long-term relationship. Will you care about this disagreement in five years? Ten? Sometimes being right costs us more than being connected. Also remember that being right means we have to make someone else wrong and I’m pretty sure none of us like to be made wrong.  Relationships are built brick by brick. Sometimes a brick falls out, but the whole structure doesn't have to collapse. Value the relationship over the issue.  And seriously, in the history of forever, has a political or religious argument at Thanksgiving ever changed someone's mind?

Step 6: Release Your Script for Others

Be aware of when you’re writing the story of how everyone else should behave. "Should" is based on our own rules and values, and it's not our place to impose those on other people.  There’s a lot of judgement from us when we’re deciding what people should and shouldn’t do.  When we release expectations that likely set others up to fail, something surprising happens. We create space for what actually is, rather than mourning what isn't.

Step 7: Own Your Story, Not Theirs

Just because someone doesn't agree with you doesn't mean they're against you. It means they're different from you. They're themselves. And you get to be yourself, too. Multiple truths can exist at the same table. You're writing the story of who you want to be. Let go of writing who someone else should be.

When It's Not About the Turkey

Sometimes Thanksgiving is hard because of who's not there anymore. Empty chairs. Changed traditions. Grief that shows up uninvited alongside the stuffing and sweet potatoes.

This deserves acknowledgment. Holidays amplify everything, including loss.  I think we honor someone’s memory when we speak their name.  They are still with us when we talk about them. We shine light on a dark place and it becomes less dark.  

If this is your reality, give yourself permission to feel it. Create small rituals that honor what was. Light a candle. Tell a story. Skip the gathering entirely if that's what you need. There's no wrong way to navigate grief, and showing up authentically matters more than showing up perfectly.

The Wisdom of Letting Go

I think about my friend's wisdom from years ago. She said when she argued with her husband, she always won. Then one day she realized: For me to win, I have to make him lose. She decided she wanted to love him enough that she didn't need to make him lose.

That gift works with right and wrong, too. For me to be right, I have to make someone else wrong. I want to care enough about people that I don't have to make them wrong.

This doesn't mean you accept poor treatment or stay silent when something truly matters. It means you choose your battles with wisdom. It means you recognize that proving your point might cost you the relationship. And sometimes, the relationship is worth more than being right.

If there are things you’re holding onto, the deep hurts that are part of being human, maybe just choose to let them go for now, for this day.  All the hurts and worries of the past will still be there the next day.  Maybe you can let them go for just this day and see what happens.

Your Day-Of Checklist

I’m not historically a checklist person, but I’ve recently started doing it and it’s actually kind of fun.  Kudos to Murphy Funkhouser for suggesting a book by Atul Gawande: “The Checklist Manifesto.”  She was very subtle in suggesting I might consider checklists and she wasn’t wrong.

Print this. Adjust it if you need to.  Keep it in your phone. Whatever works for you:

• [ ] I've decided who I want to be today (and I've written it down)

• [ ] I'm choosing to look for what's good in others

• [ ] I know whether I'm gifting my yes and what that means

• [ ] I have curious questions ready instead of rebuttals

• [ ] I've set my boundaries and my exit strategy

• [ ] I've released the script I wrote for how others will behave

• [ ] I remember I'm writing my story, not theirs

• [ ] I'm bringing positive energy, even if it's unfamiliar for my family

• [ ] I know the difference between toxic positivity and honest positivity

• [ ] I'm valuing relationships over issues today

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The Legacy You're Creating Right Now

Holidays are legacy in the making. Years from now, your kids, your nieces and nephews, your grandchildren won't remember the perfect meal or the expensive gifts. They'll remember how people treated each other. They'll remember whether love showed up when things got hard. They'll remember the story you helped write about what family means.

You have the power to influence the memory you help create.

Every moment doesn't have to be great. You don't have to agree with everyone. You just have to remain open to the possibility that you can be different and still find ways to care for each other. Because here's what I've learned: Most people genuinely want harmonious relationships. They just lack the tools to navigate disagreements effectively.

This Thanksgiving, you get to be different. You get to show up prepared instead of reactive. You get to write your own story instead of living out the one you've always told yourself or reliving old family patterns. You get to be the person who shifts the energy in the room simply by being intentional about who you choose to be.

Make this one the best year yet.

Lastly, Please Remember

Sometimes life gets hard and that’s true for every single one of us.  Holidays can be the hardest time. Right now, that there are a lot of people who are alone.  There are a lot of people who are without.  You have a lot of gifts.  Consider what you can share.  We make huge impacts in people’s lives, often without even realizing it.  It becomes part of our story and our story lives on. 

Wishing you a wonderful Thanksgiving and many blessing to count!

I Really Want to Hear from You

After your Thanksgiving gathering, I'd love to know: What from this guide was helpful? What resonated with you? How did your Thanksgiving go? What worked? What was harder than you expected? What surprised you?

Your experiences help me understand what truly helps people navigate these complex family dynamics. Share your story with me - the good, the challenging, and everything in between. You can reach me through my website or connect with me on LinkedIn. I read every message, and your insights matter.

MORE NEWS:

I am excited to be cohosting an EVENTBRITE pre- Thanksgiving preparation conversation with my very good friend Rachael Moebes on November 20 at 11AM CST.  Rachael is a nutrition and wellness coach.   We’d love to see you there! Link Below:

Dreading Thanksgiving? A Survival Guide for Food, Family & Making Memories

The Best Conflict Conversation Cards offer 30 Conflict Management Skills Cards and 20 Conversation Cards. Perfect for personal reflection or group discussion.  It's conflict coaching in a box! Learn more here.

Ready to deepen your conflict resolution skills? My Emotional Intelligence course provides the framework and tools to transform how you navigate challenges, not just during the holidays, but in every relationship and situation. Discover how developing emotional intelligence can change your approach to conflict from reactive to intentional. Explore the course on Thinkific.

“How to Live Forever: A Guide to Writing the Final Chapter of Your Life Story” Available on Amazon and Major Booksellers