The Difficult Conversations You're Avoiding (And Why That's Costing You More Than You Think)
Let me guess: there's a conversation you've been putting off.
Maybe it's with your spouse about something that's been bothering you for months. Maybe it's with a friend who keeps crossing a boundary. Maybe it's with an aging parent about decisions that need to be made, or with your adult child about something that's affecting your relationship.
You know you need to have this conversation. You've rehearsed it in your head a thousand times. You've imagined every possible way it could go wrong. And so you've stayed silent. Waiting for the "right time." Telling yourself it's not that big a deal. Hoping it will somehow resolve itself.
Here's what I know: it won't.
And here's what else I know: that silence? It's costing you more than the conversation ever would.
In my latest podcast episode, "Difficult Conversations: A Survival Guide for Recovering People-Pleasers," I break down exactly why these conversations feel so impossible for midlife women, the myths keeping us stuck, and the practical framework that actually works. But I wanted to expand on a few key points here because this topic deserves more than one conversation.
Why We've Become Experts at Avoiding
If you're a woman over 40, you've had approximately 40+ years of training in the art of keeping your mouth shut.
I don't say that to be dramatic. I say it because it's true.
Think about what you learned growing up:
Nice girls don't make waves
Good daughters are accommodating
The peacekeeper is the valuable one
Your job is to make everyone comfortable
Speaking up makes you "difficult"
These weren't explicitly taught lessons—they were absorbed through thousands of micro-interactions. Every time your opinion was dismissed. Every time you were told you were "too sensitive." Every time someone praised you for "being so easygoing." Every time you saw what happened to the women who did speak up.
By midlife, this conditioning is so deep it doesn't even register as conditioning anymore. It just feels like who you are. "I'm just not good at confrontation," you might say. Or "I'm a peacekeeper by nature."
But here's the question: Are you a peacekeeper by nature, or are you someone who learned that speaking up was dangerous?
There's a difference.
The real problem: By the time you hit midlife, the stakes feel enormous. These aren't borrowed-sweater conversations. These are conversations about marriages, aging parents, grown children, decades-long friendships, careers you've invested half your life in. The potential for loss feels massive. And so the silence continues.
The Cost of Staying Silent
In the podcast, I talk about the biggest myth that keeps women quiet: the belief that difficult conversations damage relationships.
But let me tell you what actually damages relationships: resentment.
Every time you swallow words that need to be said, something happens in your body and in the relationship. A little bit of trust erodes, not their trust in you, but your trust in the relationship's ability to hold your truth. A little bit of resentment builds. A little more distance grows.
You start pulling back emotionally. You become less open, less vulnerable, less available. You're protecting yourself from a relationship that no longer feels safe, not because the other person did something terrible, but because you can't be honest in it.
This is what I call the slow death of authenticity.
The relationship looks fine from the outside. You're still showing up. You're still being "nice." But you're not actually there anymore. You've edited yourself down to the version that feels safe, and in doing so, you've removed the possibility of real intimacy.
Because intimacy requires truth. And you can't have real closeness with someone when you're constantly editing yourself around them.
Here's what that looks like in real life:
You stop calling your friend as much because you're tired of her always being late, but you've never said anything
You feel disconnected from your spouse because you've been pretending you're fine with things you're not fine with
You avoid your mother because every interaction leaves you feeling diminished, but you've never named what she does that hurts you
You feel resentful at work because you keep taking on extra responsibilities without ever saying you're overwhelmed
The silence isn't keeping the peace. It's creating a different kind of problem. One that's often harder to fix because it's invisible.
Beyond the Formula: What Makes Moxie Work
In the episode, I break down the "moxie approach"…that sweet spot between people-pleasing and aggression. But I want to go deeper into what actually makes this work, because it's more than just using the right words.
Moxie is built on three foundations:
1. Believing Your Experience is Valid
This is where most women get stuck. We've been taught to question our own perceptions so thoroughly that we don't trust ourselves.
"Maybe I'm being too sensitive." "Maybe I'm overreacting." "Maybe it wasn't that bad."
But here's the thing: your experience is your experience. You don't need anyone else's permission to feel how you feel.
If something bothers you, that's information. You don't have to prove your feelings are justified. You just have to be honest about having them.
Moxie means: I trust my experience enough to speak about it.
2. Separating Their Response from Your Truth
People-pleasers struggle with this one. We think our truth is only valid if the other person receives it well. So we bend ourselves into pretzels trying to say things in a way that won't upset them.
But here's what moxie understands: you cannot control how someone responds to your honesty. You can be kind, clear, and thoughtful and they might still get defensive, hurt, or angry.
Their response is about them. Their capacity in that moment, their own triggers, their history. It's not a referendum on whether you should have spoken up.
Moxie means: I can say what's true for me and let them have their reaction.
3. Being Willing to Disappoint
This is the hardest one. Because for many of us, the fear of disappointing someone feels worse than betraying ourselves.
But every time you choose their comfort over your truth, you're teaching them (and yourself) that your needs don't matter as much as theirs do.
Moxie means: I'm willing to disappoint them in service of honoring myself.
Not because you want to disappoint them. Not because you're trying to hurt them. But because sometimes being honest means someone won't be happy with you, and you do it anyway.
The Questions That Spin The Truth On Its Head
If you're sitting with a difficult conversation you've been avoiding, here are the questions that will help you move forward:
1. "What am I making this conversation mean?"
Often we're not actually afraid of the conversation itself, we're afraid of what we've decided it will mean.
If I say this, it means I'm difficult. If I set this boundary, it means I'm selfish. If I speak up, it means I don't care about their feelings.
But those are stories, not facts. Get clear on what story you're telling yourself about what this conversation means, and you can start to question whether that story is actually true.
2. "What's the cost of my continued silence?"
Not just to you, to the relationship. Because often we stay silent thinking we're protecting the relationship, but we're actually eroding it.
What's happening in this relationship because you're not saying what needs to be said? How are you pulling back? How is the dynamic changing anyway?
3. "What would I tell my daughter/younger self/best friend to do?"
Sometimes we can access our wisdom more clearly when we imagine advising someone we love.
If your daughter came to you with this situation, what would you tell her to do? Whatever that answer is, that's probably what you need to do too.
4. "Am I trying to control their response or just communicate my truth?"
If you need them to respond a certain way for this conversation to be "worth it," you're probably setting yourself up for disappointment.
But if you just need to say what's true for you, regardless of how they respond, that's something you can do.
When Walking Away IS the Conversation
Here's something I learned the hard way, and I share the full story in the podcast: sometimes the difficult conversation is choosing to stop having conversations.
I spent months trying to have necessary conversations with family members about planning for the future. Important conversations. Conversations that needed to happen.
But they weren't ready. And no amount of my pushing, preparing, or perfectly phrased questions could make them ready.
I kept trying because I thought that's what you do. You keep showing up, you keep trying. But my body started screaming at me to stop. I wasn't sleeping. I was constantly stressed. I got physically ill.
Finally, I walked away. Not forever. Not dramatically. But I stopped trying to force conversations with people who weren't ready to have them.
And here's what I learned: Walking away from a conversation doesn't mean you don't care. It means you recognize that you can't want change more than the other people involved want it.
Sometimes discernment looks like accepting that some people will never be able to meet you in honest conversation, and that's sad, and it's also okay.
You can't force readiness. You can't carry the weight of transformation that others aren't willing to carry themselves.
And you can't set yourself on fire to keep other people warm.
Your Next Step
If you've been avoiding a difficult conversation, here's what I want you to do:
Step 1: Get quiet and put your hand on your heart. Ask yourself: "Is this avoidance or discernment?" Trust what your body tells you.
Step 2: If it's avoidance (if your body says "not yet finished"), write down your bottom line. What's the one thing you absolutely need to communicate? Not the whole conversation, just the core truth.
Step 3: Decide when you're going to have this conversation. Not "someday." An actual date and time. Put it on your calendar.
Step 4: Listen to the full podcast episode for the complete 5-part structure and strategies for handling every reaction you're afraid of.
You don't have to be perfect. You don't have to have all the answers. You just have to be willing to be imperfectly honest.
Because your voice matters. Your needs matter. And you are absolutely worth the difficult conversation.
Listen to the Full Episode
Ready to dive deeper? Listen to Episode 26 of Midlife Moxie with Nicole Hate podcast where I share even more stories, strategies, and the messy truth about transforming relationships through authenticity.
Let's Continue the Conversation
What difficult conversation have you been avoiding? What's one small step you could take this week toward having it?
Ready to bury the good girl and reclaim your dangerous, unapologetic self?
I guide women through deep pattern recognition and identity reclamation using various practices.
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This content is for educational purposes and is not a substitute for professional mental health treatment. If you're experiencing concerning symptoms, please consult with a qualified mental health professional.