How to Have Hard Conversations in Your Second Act
Having conversations with people you love—but don’t always agree with—is one of the biggest growth edges in midlife.
And that’s why I wanted to have my friend, Meagan O’Nan, on this episode of the Grey Matters Podcast. Meagan, my longtime friend and human connection specialist, and I sat down to talk about something we all wrestle with: how to speak your truth without burning bridges.
Now - Meagan is WAY less than 50 years old, but her words are valuable for women of all ages. And if you’re navigating a career change after 50, like many women in this community, those conversations aren’t just personal. They’re part of your reinvention—part of reclaiming your voice, your truth, your why.
Because if you’ve made the midlife career pivot from corporate to entrepreneurship, chances are you’ve had moments where you’ve asked:
“Can I really do this?”
“Will they still respect me?”
“What if I lose people along the way?”
These aren’t just business questions. They’re identity questions. And Meagan’s story offers something powerful: not a blueprint, but permission—to be vulnerable, to lead from your why, and to trust your voice.
The Call to Reinvent — and What We Leave Behind
If you’re like many second act entrepreneurs I work with, you know what it feels like to have built a strong, respected corporate career… and yet feel like a stranger in your own skin.
Maybe you're tired. Maybe you’ve hit burnout. Maybe something in your gut keeps whispering, “It’s time for something different.”
Meagan gets it.
She left Mississippi after being outed in college and losing her entire community. Coaches. Mentors. Friends. Gone overnight.
As she shared on the podcast:
“I realized that if I was going to heal, I couldn’t just keep running away from home.”
When she chose to move back to Mississippi with her wife Claire, it wasn’t because things were safe. It was because she was ready to stand in her voice—and do the hard work of reconnecting, rebuilding, and reclaiming her identity.
It takes courage to reinvent your professional identity. To speak your truth in rooms that once silenced you. And to keep showing up when the people you love don’t see the world the way you do.
But as Meagan said:
“We all want the same things in the end—peace, safety, joy, connection. The problem is we think we have to change each other to get there.”
How to Talk to People Who Don't See the World Like You
Here’s where it gets real: building a legacy business for women over 50 isn’t just about strategy. It’s about having conversations that matter—and often, those are the ones we’ve been avoiding for decades.
For Meagan, the turning point came when she stopped trying to get people to vote for her “why” and started showing up with vulnerability. Here’s how she frames tough conversations:
“This is what I’m afraid of: that you won’t see me, that you won’t understand me, that you won’t accept me if I tell you how I feel.”
That kind of honesty shifts everything.
In fact, when Meagan finally asked her mom how she voted in a contentious election, her mom replied: “I’m nervous to have this conversation too.” They sat down. Shared their fears. Got to the why behind their choices.
The result?
“It made sense. We didn’t agree, but we understood each other.”
If that’s not purpose-driven entrepreneurship, I don’t know what is. Because this work we’re doing—this second act of meaning and alignment—it’s not just about growing your business. It’s about growing your capacity for empathy, connection, and integrity.
From Employee to Entrepreneur: The Mindset Shift No One Talks About
Whether you’re building a coaching practice, offering one-on-one business consulting, or stepping into thought leadership branding, there’s an invisible leap no one prepares you for:
You go from fitting in… to standing out.
From playing by someone else’s rules… to creating your own.
And with that comes the tender work of facing self-doubt, rebuilding confidence, and learning how to align your business with your values—especially when the people around you aren’t quite sure what you’re doing.
Sound familiar?
Maybe you’ve:
Been dismissed at family dinners when you mention your new consulting business
Lost touch with former colleagues who don’t get your new direction
Struggled to explain what “story-based branding for coaches” even is
You’re not alone.
This is where a growth mindset for midlife business owners becomes essential. Not just for you—but for your community.
Because when you share your truth—clearly, kindly, vulnerably—you model what it looks like to lead with heart.
Meagan’s Tips for Hard Conversations (That Help in Business, Too)
Here are a few takeaways from our conversation that apply just as much in the kitchen as they do in your next client consult:
1. Start with the why.
Not your position, your passion. “This is important to me because...” opens hearts.
2. Name your fear.
Try: “I’m afraid this will push us apart.” Vulnerability builds trust.
3. Be willing to listen without needing to fix.
You don’t need someone to “vote for your why” to respect it.
4. Clarify your values.
If your business is built on empathy, curiosity, or impact—say so. It becomes your compass.
5. Accept that not everyone will meet you there.
Some people will leave. It’s hard. But you’ll have clarity—and room for aligned relationships.
“Nine times out of ten,” Meagan said, “these conversations go well. But you have to want the relationship enough to risk the discomfort.”
Check out her TedX 👇🏻
Business Growth Through Personal Truth
Here’s the quiet truth no one tells you about starting your second act business:
The most powerful brand strategy for women entrepreneurs over 50? It’s built on personal clarity.
When you know who you are, what you stand for, and how to speak to it—without needing agreement—you attract clients who want that depth.
You become not just a career transition coach for women, but a messaging coach for entrepreneurs who’ve lived through real things.
That’s the beauty of second act entrepreneurship: you’re not starting from scratch. You’re starting from wisdom.
Ready to Start Your Second Act with Confidence?
If you’ve been asking:
“How do I start a meaningful business after 50?”
“How do I find my voice again after leaving corporate?”
“How do I have conversations that build trust, not destroy it?”
This episode is a must-listen.
🎧 Listen to the full Grey Matters Podcast episode with Meagan O’Nan
🌐 Learn more about Meagan: www.meaganonan.com
🎤 Watch her TEDx Talk: What to Do When You Disagree with Someone You Love
And if you’re craving support as you scale your voice and vision, explore online mastermind for female founders, group coaching for women 50+, or entrepreneur coaching after corporate right here at Beyond the Dream Board.
Because the world needs your story. Your truth. Your business. Now more than ever.
