Drinks with the Girls®

What if the life you planned isn't the life you got… and what if that's actually a good thing?

When the kids grow up, relationships change, careers shift, or the roles that once defined us no longer fit, it's easy to wonder: Who am I now?

This week on Drinks With the Girls, Karen and Lisa welcome writer, editor, and book coach Carolyn Flynn for a heartfelt, funny, and refreshingly honest conversation about midlife reinvention and the possibility of a second adulthood.

Carolyn shares her experience of navigating major life transitions, questioning the identities she'd built her life around, and discovering that starting over doesn't have to mean starting from scratch.

Together, we explore the friendships that remind us who we are, the courage to let go of what no longer serves us, and why life after 40 or 50 might be an opportunity to become more ourselves than ever before.

Because maybe midlife isn't about winding down. Maybe we're just getting warmed up!

The life you planned versus the life you got: What happens when your carefully imagined future takes an unexpected turn?

Finding yourself beyond your roles: Remembering that being a mother, partner, or professional is part of who you are, not all of who you are.

Empty nesting and identity: Navigating the emotional shift when children grow up and family dynamics change.

The power of female friendship: How our friends can remind us of the parts of ourselves we've forgotten—and why we don't have time for mean girls anymore. (Seriously, they're still around?)

Letting go and starting over: Learning what to keep, what to release, and how to move forward without having everything figured out.

Your second adulthood: Why life after 50 can be a time for meaningful choices, creativity, adventure, and purpose.

Making room for yourself: Asking what you want after years of prioritizing everyone else's needs.

Carolyn Flynn is a writer, editor, and book coach who helps people bring their stories to life. A former editor of Sage magazine, she has interviewed inspiring women, including Gloria Steinem, and writes about reinvention, storytelling, and living boundlessly.

In this episode, Carolyn shares experiences that shaped her own reinvention and the lessons she's learned about identity, resilience, and the possibilities of a second adulthood.

Inspired to write your own story? Carolyn has two special opportunities for Drinks With the Girls listeners!

Free 30-Minute Writing Consultation

If you've been thinking about writing your story but aren't sure where to begin, Carolyn is offering listeners a complimentary 30-minute Find Out More consultation.

Whether you're exploring an idea for a book or finally ready to put your experiences into words, this is an opportunity to connect with Carolyn and talk about your writing goals.

Book your free consultation:

Free Monthly Writing Community on Zoom

Looking for a little encouragement, dedicated writing time, and a warm-hearted community?

Carolyn also hosts a free monthly Zoom gathering featuring writing time and supportive community. Our listeners are welcome to join any month!

When: The last Monday of every month.

Register for the free Zoom gathering:

Explore Carolyn's writing, books, book-coaching services, and more at:

Website: https://carolynflynn.com

Carolyn also writes on Substack about living boundlessly and storytelling, and discusses her June 2027 writing retreat in Dingle, Ireland.

Have you ever reached a point where the life you planned no longer fit the person you'd become?

We'd love to hear what reinvention means to you—and whether you're beginning to imagine your own second adulthood.

Pour yourself a cocktail or a cup of coffee and join us for a conversation about finding yourself, embracing change, and asking one deliciously hopeful question:

What if it's better?

If this episode resonates, share it with a friend who might need to hear it, and follow Drinks With the Girls for more real, raw, heartfelt, and often hilarious conversations about navigating midlife together.

Find us at: https://www.drinkswiththegirlspodcast.com

🍸☕ What We Were Drinking:

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💬 Takeaways — What Do YOU Think?

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🏥Medical Disclaimer:

Ever wonder why you keep people-pleasing, striving for perfection, or falling back into habits you know aren't helping you? What if the problem isn't a lack of willpower—but the ways you've learned to protect yourself?

This week on Drinks With the Girls, Karen and Lisa sit down with Lori Montry, somatic healing practitioner, creator of The Freedom Framework, and author of You're Not the Problem, to explore the connection between our nervous systems, past experiences, and the behaviors we carry into midlife.

We're talking about why conflict can feel downright terrifying, why women so often put everyone else's needs first, and how perfectionism, people-pleasing, and other coping behaviors can become so familiar that we mistake them for our personalities.

Karen opens up about her response to conflict, Lisa shares a personal connection to masking and neurodivergence, and Lori explains why understanding our protective patterns may be the beginning of meaningful change.

Plus, we get into the difference between knowing why you do something and actually feeling safe enough to do it differently.

If you've ever thought, "Why am I still doing this?"—pull up a chair. This conversation might help you ask a completely different question.

And the conversation doesn't end there. Join us for After Hours on Patreon, where Karen and Lisa take a closer look at their own patterns and the ways they've learned to protect themselves.

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🍸☕ What We Were Drinking:

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If you could go back and talk to your 40-year-old self, what would you say about motherhood, marriage, finding yourself, and navigating the messy middle of life?

Karen and Lisa are taking a trip down memory lane, revisiting two very different versions of life in their 40s. For Karen, it was a decade of rediscovering herself while quietly navigating a marriage that was falling apart. For Lisa, it was a whirlwind of fertility struggles, raising young children, working full-time, and learning to parent a neurodivergent child.

From questioning whether they were good enough mothers to wondering who they were beyond the roles they played, they're sharing the struggles, surprises, and hard-won wisdom that shaped the women they are today.

And here's the thing: Looking back, maybe their younger selves didn't need more advice. Maybe they needed more grace, a little less self-doubt, and permission to trust themselves.

If you're a woman in your 40s, 50s, or 60s who's ever felt overwhelmed by motherhood, questioned your marriage, lost sight of yourself, or wondered whether you're doing any of it right, this conversation is for you.

Grab your favorite drink and join us for a heartfelt, funny, and refreshingly honest look at the women we were, the women we've become, and why both deserve a little love. Cheers! 🥂____________________________________________________________________

🎧Show Notes:

🍸☕ What We Were Drinking:

Sun Kissed Ice Tea + Vodka Raspberry

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Hormone replacement therapy (HRT), breast cancer risk, and menopause—why is it still so hard for women over 40 to get straight answers about their health?

For Part 5 of our Celebrating the Twins series, Karen and Lisa welcome Dr. Betsy Greenleaf, a quadruple board-certified physician and women's health expert, for a candid, eye-opening conversation about hormones, breast health, and taking back control of our midlife wellness.

When Lisa can't get her estrogen patches but Viagra seems readily available, the frustration gets REAL. And for Karen, whose mom battled breast cancer, the fear surrounding hormones hits especially close to home.

Together, they unpack the confusion around HRT and breast cancer risk, explore bioidentical hormones, challenge menopause myths, and tackle why women's sexual health and quality of life are still too often overlooked.

If you're navigating perimenopause or menopause, worried about breast cancer risk, struggling to find a doctor who actually listens, or simply tired of being told to live with your symptoms, this conversation is for YOU.

Because midlife shouldn't mean settling for less. It's time to ask better questions, advocate for our bodies, and feel empowered to make informed decisions about our health.

Grab your favorite drink and join us for some truth, a little outrage, plenty of laughs, and a reminder that you deserve to be heard. Cheers! 🥂

🎧Show Notes:

Guest: Dr. Betsy Greenleaf

🍸☕ What We Were Drinking:

Lisa’s Arbonne Cocktail 

Myos & Protein Milk with Decaf Coffee

Pause Labs.health - Exclusive discount code for 6 mos free for listeners: DRINKS

🎧Podcast Episodes

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The hidden cost of caregiving for women goes far beyond exhaustion—and the “Daughter Tax” could be costing you more than you ever imagined.

Women are still so often the default caregivers: raising kids, supporting family, caring for aging parents, managing everyone’s needs—and adjusting careers, income and retirement plans to make it all work. But when you’ve spent decades being the dependable one, where do you draw the line between loving your people and losing yourself?

Karen and Lisa get real about the Daughter Tax and the invisible price women pay for unpaid caregiving. Karen shares how caring for her stepmom after a stroke affected her sisters’ jobs and livelihoods—and what it felt like when her dad simply expected his daughters to step in. Lisa opens up about the financial reality of dropping work to help family, the guilt and pushback that came when she finally started setting boundaries, and the complicated expectations wrapped up in being a “good daughter.”

And then there’s the number. The estimated lifetime financial cost of unpaid caregiving for women stopped us in our tracks. We’re not spoiling it here—but trust us, you’ll want to hear it.

This conversation moves from resentment and guilt toward something every midlife woman deserves: permission to care deeply without disappearing in the process.

If you’re a woman in your 40s, 50s or 60s juggling kids, parents, work, family expectations—or wondering why everyone else’s needs always seem more urgent than your own—this episode is for you.

Grab your drink. We need to talk about the Daughter Tax.

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🎧Show Notes:

🍸☕ What We Were Drinking:

To Us! Sparkling Beverage Wine Alternative - Looks like it is only available regionally 😥

🎧Podcast Episodes

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Why do friendships change so much in midlife—and how do you know which friends are safe enough to see the real you?

Author Lisa Najarian joins Karen and Lisa to unpack the emotional baggage women carry, the friendships that help us put it down, and what happens when we grow into a version of ourselves that some longtime friends don’t quite understand.

Lisa, author of Girl Unpack That: The Trip That Changed Me and the Framework That Can Change You, shares how one girls’ trip became the catalyst for her book—and why getting away with trusted friends can create space for conversations we’ve been avoiding for years.

Together, the girls get real about automatically saying “I’m fine” when you’re anything but, carrying the invisible emotional load for everyone around you, friendship ruptures, outgrowing old dynamics, and realizing that not every friend deserves the same level of access to your heart.

Because by midlife, you’ve lived enough to know that history doesn’t always equal emotional safety. But finding the people who truly get you? That can feel like a safety net—and sometimes, like medicine.

This conversation is for you if you’re navigating changing friendships, questioning whether an old relationship still fits, craving deeper connection, or simply tired of carrying everything by yourself.

Grab your drink and join us as we unpack what women carry, who we trust enough to unpack it with, and the life-changing power of being truly known.

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🎧Show Notes:

🎙️Guest: Lisa Najarian

🍸☕ What We Were Drinking:

📺TV

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Ready to stop people pleasing and start choosing yourself in midlife? For women over 40, giving yourself permission to want more can feel surprisingly uncomfortable—especially when your choices disappoint the people you love.

Karen and Lisa are entering their Permission Slip Era, and they’re talking about what happens when you stop waiting for approval and start trusting yourself. From setting boundaries that make other people uncomfortable to protecting your peace, taking the trip, wanting more joy (and more naps!), and realizing you don’t have to keep explaining your choices—this conversation gets real about the guilt that can come with finally putting yourself back on the list.

Because here’s the messy part: choosing yourself doesn’t mean the guilt magically disappears. People may push back. Old good-girl conditioning may come roaring back. And sometimes you have to let someone be disappointed in you without rushing in to make everything okay.

If you’re a woman in your 40s, 50s, 60s or beyond who’s tired of people pleasing, questioning your boundaries, or wondering whether it’s selfish to want more from this chapter of your life, pull up a chair.

Nobody is coming to hand you a permission slip.

Maybe it’s time to write your own.

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🎧Show Notes

🍸☕ What We Were Drinking:

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Exhausted, foggy, overwhelmed—and wondering if this is just what menopause and midlife feel like now? Functional medicine practitioner Dori Martin joins us to talk about midlife burnout, mineral balance, hormones, stress, and why doing all the “right” things doesn’t always make you feel better.

Dori knows this territory personally. After years of caregiving, working, parenting, and carrying all the things, she hit a wall. Her brain stopped cooperating. Small stresses felt enormous. She couldn’t sleep, lost words mid-sentence, snapped at people she loved—and realized she was running on fumes.

Sound familiar?

We get into why so many women struggle to slow down even when their bodies are begging for rest, what minerals have to do with energy and metabolism, and why Dori calls them the body’s “spark plugs.” We also talk about the emotional load women carry, the discomfort of asking for help, and why taking care of yourself isn’t something you earn after everyone else is okay.

If you’re a woman in your 40s, 50s, or 60s who feels like you’re doing everything you’re supposed to do but still don’t feel like yourself, this conversation is for you.

Maybe getting your spark back doesn’t start with doing more. Maybe it starts with finally giving yourself permission to do less. 🍸

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🎧Show Notes

🎙️Guest: 

Dori Martin, Functional Diagnostic Nutrition practitioner

🍸☕ What We Were Drinking:

Los Poblanos Lavender Lemonade

🎧Podcast Episodes

Why Am I So Tired Part 1

Why Am I So Tired Part 2

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What really changes after 45? For women in midlife, some of the biggest life lessons aren’t about getting older—they’re about finally figuring out what deserves your time, your energy, and your very limited supply of fucks.

Karen and Lisa are spilling the shizzle they’ve learned the hard way: no one is thinking about you nearly as much as you think they are, boundaries are necessary (especially with the people you love), being nice isn’t the same as being kind, and the best relationships sometimes require the hardest conversations.

Then there are the uniquely midlife realizations no one adequately prepared us for: sleep suddenly becomes sacred, your body starts renegotiating the terms of your relationship, alcohol hits differently, staying home in your comfies can sound better than the party—and being “cool” matters a whole lot less. Even if your teenager strongly disagrees.

From fuzzy-slipper school drop-offs and hiding from energy vampires to navigating family boundaries and learning to let people misunderstand you, this is an honest, funny conversation about the freedom that can come with getting older.

Because maybe one of the best things about life after 45 is realizing you don’t have to keep proving, pleasing, explaining, or showing up for everything and everyone.

This episode is for you if you’re a woman over 40 who’s questioning old expectations, protecting your peace, navigating changing relationships, listening to your body a little more closely, or simply wondering: Is anyone else figuring this midlife shit out as they go?

Grab your drink and pull up a chair. You’re definitely not the only one.

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🎧Show Notes

🍸☕ What We Were Drinking:

Pink Pomelo Limeade w/Vodka

______________________________________________________________🍸Want your very own piece of @DrinksWithTheGirls for half the cost of one bougie cocktail  per month? Enjoy exclusive bonus ad free content in After Hours. Head to Patreon and join the community! 

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Is your marriage going through a rough season—or are you quietly wondering if it might actually be over? Marriage and family therapist Dr. Becky Whetstone, author of I Think I Want Out, joins Karen and Lisa for an honest conversation about marriage crisis, emotional disconnection, separation, divorce, and whether an unhappy marriage can be saved.

Dr. Becky knows this crossroads personally. After her own marriage ended in what she now believes may have been a premature divorce, she made it her mission to understand what happens when one spouse is ready to leave while the other is desperate to hold on.

Together, they unpack the five stages of a deteriorating marriage, why emotional detachment can begin long before anyone says “I want out,” and why the end of Marriage Part 1 doesn’t always have to mean the end of the relationship. Karen and Lisa bring their own experiences with divorce, separation, and rebuilding into a conversation that gets deeply personal—and surprisingly hopeful.

If you’re in midlife questioning your marriage, feeling lonely beside the person you’ve built a life with, considering divorce, or wondering whether there’s still something worth fighting for, this conversation is for you.

Because sometimes the question isn’t simply, Should I stay or should I go? It’s: What could Marriage Part 2 look like—and do we both want to create it?

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🎧Show Notes

🍸☕ What We Were Drinking:

Guest: Dr. Becky Whetstone

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