Love Your Voice

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Do I Need to Have This Difficult Conversation?
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Do I Need to Have This Difficult Conversation?

From Silence to Strength: A guide for women who are ready to set boundaries and speak their truth.

Jessica Neighbor's avatar
Jessica Neighbor
Apr 30, 2025
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Love Your Voice
Do I Need to Have This Difficult Conversation?
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Have you experienced this?

You sense that something is off in a relationship at work, at home, or with a friend, yet you choose not to address it.

“This will blow over,” you hope. You swallow your concern and try to carry on as usual.

But that funky feeling gets funkier.

You end up avoiding this person or overthinking until you've imagined a conflict and outcome, all without them being present.

Remaining silent is not helping, but you’re not sure if having the conversation is worth it. Or safe.

This week, we’re taking the first step in exploring how to say the hard thing, and IF we should bother.


💬 Week 1 Focus: Should I even have this conversation?

It might sound simple, but it’s not. Many women in midlife have spent years tiptoeing around other people’s emotions and reactions.

As women, we are taught to be “nice” and pleasant. We’re often praised for keeping the peace at the expense of our happiness. As a recovering people pleaser, I can so relate.

What I learned for myself and with my communication clients over the years is that setting boundaries or naming what matters isn’t rude, it’s a powerful gift.

If you have a pressing issue with your client, boss, or friend that's keeping you awake at night, it may be worth discussing it with them.

This week, I want you to pause and ask:
Is there a conversation I need to have that I’ve been avoiding?

You don’t have to dive into it yet. This is just the beginning. We’ll explore this topic weekly in May.


Try this:

Use this 3-question gut check from my From Silence to Strength guide:

  • Have I felt dismissed, disrespected, or drained in this relationship or dynamic?

  • Have I said anything about it, or kept it to myself?

  • Is this a meaningful relationship that affects my life directly?

If you answered yes, it might be time to speak up.


🖊️ Writing Prompt of the Week:

What boundary have you felt lately that’s ready to be honored?

Share your reflections in a journal or start a private note or voice memo on your phone (my new favorite). This is a powerful invitation to be honest with yourself.


📅 Save the Date:

We’ll meet live on May 22 at Noon PST to walk through this process together in a supportive workshop. Bring your questions, reflections, and scripts, and I'll be there to coach you through.


🎁 Free for Paid Subscribers:

Paid members of the Love Your Voice Community can download my newly updated communication workbook:
👉 From Silence to Strength: A Woman’s Guide to Setting Boundaries and Speaking Your Truth.

My guide takes you through a step-by-step process to prepare for and have a difficult conversation while maintaining your composure and integrity. You can download the PDF guide HERE:

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