We Didn't Turn Out OK with Jennie Monness

PODCAST · health

We Didn't Turn Out OK with Jennie Monness

For the last two decades, I've worked closely with infants, toddlers, preschoolers and their parents - listening, guiding and supporting families and their young children. I've connected with so many parents through my social media account, texts, calls, and leading moms' groups. When we have open, honest and vulnerable conversations - no matter who you are as a parent - that's how we connect, learn and grow.We also discover so much about ourselves and how that plays into our parenting. That's why I created We Didn't Turn Out Ok, a podcast where you'll hear real conversations about challenges we face in parenting, hear how we uncover the roadblocks, often from our own stuff, and listen to how we work through what's often keeping us stuck. There will be professionals in the field, noteworthy guests and everyone in between.Using my own parenting journey and approach, combined with research-backed best practices, I am determined to help us all move forward from

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    66: The Big Little Moments

    After more than fifteen years working to the top of luxury fashion, culminating in her role as COO of Brandon Maxwell, Lauren Phelps walked away. She had just lost her mother to brain cancer and was pregnant with her first son, and she realized something: the memories she carried of her mom weren’t the milestones or big moments, trips and celebrations. They were the in-betweens. The way her mother brushed hair away from her face during a bedtime story. The songs. The painting together on the back porch. She didn’t want to miss those moments with her own children. Today, Lauren is a fine artist working out of her studio at the historic National Arts Club in Gramercy Park, where her oils, charcoals, and pastels are devoted almost entirely to the bond between parent and child. She is currently illustrating a book with bestselling author Michael Sampson (out soon), with her own debut as author-illustrator launching in 2027. In this episode, Lauren and I get into the big little moments, and we bond, hard, over what it’s like to raise deep-feeling kids who show those feelings in wildly different ways. Our older ones tend to process through complication and quiet; our younger ones leave nothing unsaid. We close the conversation with Lauren in the middle of a real one: her 8-year-old is scheduled to perform an almost unbelievably complex musical piece in front of his entire school the next day, and he’s wavering. We talk through how to hold space for a child who is caught between wanting something and being terrified of it. (An update from Lauren the morning after we recorded: he performed. He was incredible.) This one is two moms pulling back the curtain on what it actually feels like to parent big-feeling children and on holding each other up while we do it. I hope it helps you and you connect with it the way we did with each other. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    65: The Stories We Inherit with Morgan Radford

    What happens when the story you’ve always believed about yourself… starts to shift? This week on We Didn’t Turn Out Ok, I sit down with Morgan Radford, journalist, co-anchor of NBC News Daily, mom, and now debut novelist, to talk about identity, unbelonging, family stories, and the quiet ways our past shapes who we become. Morgan’s new novel, Now Then, explores a mother and daughter uncovering hidden truths across generations, and our conversation goes far beyond the pages of the book. We talk about what it feels like to move through spaces where you’re deeply aware of exclusion, the tension between belonging and becoming, and how motherhood changes the way we understand our parents - and ourselves. We also talk about intentional parenting, raising children connected to culture and language, and the emotional inheritance we pass down without even realizing it. And honestly? One of the most underrated “why didn’t anyone tell me this sooner” moments from this conversation was hearing Morgan talk about the importance of looking for peace and stability in a relationship, not just chemistry, intensity, or potential. It’s one of those things that feels so obvious once someone says it out loud, but so many of us were never actually taught to value. This episode is thoughtful, emotional, reflective, and full of the kinds of conversations that stay with you long after they end. In this episode we discuss: Unbelonging and awareness of exclusion Identity and self-discovery The stories we inherit from our parents Motherhood and perspective shifts Culture, language, and intentional parenting Family secrets and emotional legacy Love, timing, and choosing peace in relationships Now Then is available now. Learn more and order at MorganRadford.com. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    64: Moving from "Why Me?" to "Now What?" with Dr. Rachel Goldman

    I sat down with my dear friend Dr. Rachel Goldman, psychologist, Clinical Assistant Professor at NYU Grossman School of Medicine, mom of two, and author of When Life Happens. In this episode, we talk about what it really means when “life happens” the moments we can’t control, the stories we attach to them, and how we can move from blame, shame, or stuckness into curiosity and repair. Rachel shares a cognitive behavioral therapy lens on parenting, body image, conflict, comparison, and the everyday thoughts that shape how we feel and respond. We talk about why “why is this happening to me?” can keep us stuck, how to ask “now what?” instead, and how to help our kids build problem-solving skills by modeling this same mindset. We also get into body image, the messages our kids absorb, why language matters, and how modeling boundaries, breathers, resets, and self-compassion may be one of the most powerful ways we teach our children how to move through hard moments. This conversation is about letting life be messy without making ourselves wrong for it and remembering that none of us are doing it perfectly, but we can keep learning, repairing, and beginning again. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    63: Is She Ready...or Am I? A Conversation Beyond Camp

    She’s going to camp…and I’m not okay.  This episode was recorded and released a little selfishly. I’m currently in the thick of preparing to send my 8-year-old daughter to sleepaway camp in just two months, and I am feeling everything. There are certain moments in motherhood I always knew would feel both gut-wrenching and joy-filled, and this is absolutely one of them. Sending my first child off to camp, the very same camp where I experienced such a deep sense of belonging, independence, and lifelong friendship, is incredibly meaningful. It shaped so much of who I am. The idea that she’ll now begin creating her own version of that magic is one of the most exciting parts of motherhood for me. And still, two things can be true: alongside that excitement is a steady undercurrent of nerves. Questions enter in my mind at all hours “She still climbs into my bed some nights… what does that mean?” “If she brushes off her younger sister’s tears as embarrassing, will she hold things in at camp?” “Will she rinse all the shampoo out of her hair?” These small thoughts somehow feel very big right now. That’s exactly why I wanted to have this conversation with Lauren Kasnett Nearpass. Lauren, alongside her mother Susan Kasnett, co-founded ⁠Summer 365⁠ in 2013 with the goal of bringing camp consulting into the modern age. While Google searches and social media can offer endless opinions, Summer 365 was built on something much deeper: lived experience. As former campers, counselors, and now mothers, their team understands firsthand the transformative power of summer camp, and the weight of choosing the right one. Their approach is deeply personal, working one-on-one with families to thoughtfully match each child with the environment where they can truly thrive. I knew Lauren personally, but I had also heard over and over how impactful her work is for families navigating this process. And this felt like the exact moment to lean on that expertise, not just for me, but for so many parents either considering sleepaway camp or preparing for it. As Lauren shares, now is often when families begin exploring options for future summers, though she’s also helping families even for this coming season. What makes this conversation even more meaningful is that Lauren is in it too. Her daughter is heading into her fourth summer at camp, and her almost 8-year-old son will be going for the first time. She speaks candidly about her own uncertainties and shares something that really stayed with me: there’s no perfect “checklist” for readiness. While some kids are clearly going to thrive, others are the ones who will deeply benefit from the experience. In this episode, we talk about everything, from how to make one of your child’s first big life decisions together, to the emotional rollercoaster of letting go, to the practical ways we can prepare our kids in the months leading up to camp. This isn’t just about camp, it’s about trusting that our children are ready to step into something new, even when it stretches us as parents (or happens without us there!) I keep coming back to something my older sister once told me after sending her kids to camp: “Once I knew they were happy and thriving, it hit me, they’d be making all these incredible  memories without me.” And I think that’s what I’m really bracing for. I somehow didn’t cry during this recording, but I can feel it all at any given moment - the ache, the pride, the letting go. So if you see me in May or June… just hug me. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    62: Everyone F*cking Matters - And So Do Our Nervous Systems

    I sat down with Dr. Brooke Weinstein, a globally recognized expert in neuroscience-based parenting, occupational therapist, and what she calls a “personal trainer for your brain.” But this episode goes far beyond strategies or frameworks. It’s about what happens when life forces you to look at yourself differently. After the loss of her husband to suicide, following a period where Brooke began choosing herself in ways she never had before, she was faced with the kind of truth most of us spend our lives avoiding: that so much of who we think we are is actually just our nervous system trying to keep us safe. We talk about: - What it really means to regulate your nervous system (and why it’s not a luxury, it’s a necessity) - When you realize you can't fix anyone and you aren't supposed to - People-pleasing, identity, and the unraveling that comes with choosing yourself - Talking to our children about hard things, and why our job is to parent the child in front of us… not the one we fear they might become Throughout the episode, we come back to this idea over and over again: everyone fucking matters. Including you. Brooke’s work blends neuroscience, sensory regulation, and real-time pattern awareness to help people not just understand their triggers, but actually change them. And in this conversation, you’ll hear what that looks like not just in theory, but in a life that’s been cracked open and rebuilt. I also share parts of my own journey this past year, and why one of Brooke’s posts hit me so hard: “People think healing is gentle. It’s not. Healing is gutting. Nothing destabilizes you more than realizing your entire personality was just your nervous system trying to keep you alive…” This episode is so honest, raw, emotional and hopefully will inspire you to never forget that you matter too. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    61: We're Not Losing Control, We're Holding on Too Tight

    This solo episode is all about what’s actually underneath the behaviors we’re trying so hard to fix, and why the more we try to control them, the more disconnected things can feel. I collected questions from you guys beforehand and almost every question I got sounded different on the surface like: How do I get my child to listen? To stop lying? To be fair? To go to school without a fight? To feel ok when they're not included? …but underneath all of them was the same question: How do I get my child to behave and react in the way I think they should? So in this episode, I’m breaking down why that approach and mindset, while so understandable, is often the very thing getting in the way. I talk about: why “old tricks” stop working (especially around age 3–5) the problem with forcing moral behavior what lying actually means in child development school resistance, bedtime struggles, and what behavior is really communicating and even how we show up in our own adult experiences (like not being included) This episode is about shifting from control to connection and reacting to understanding (so hard guys! I know!) But our role isn’t to control every moment,…it’s to support our kids (not control them) as we allow them to move through it. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    60: From School Admissions to Building Life Skills

    In this episode, I sat down with my friend Brooke Parker, someone who started as an Instagram connection and quickly became one of those rare, deeply trusted mom friends. We met in the most “New York mom” way possible - sitting across the hallway from each other after having our second babies. Fast forward four years, our kids ended up in the same preschool class and became incredibly close… and so did we. Brooke is an early childhood educator turned consultant, helping families navigate the often overwhelming (and very imperfect) private school admissions process in NYC. Through her work, she not only guides parents toward the right fit for their child, but also works directly with kids to help them feel confident, capable, and prepared. But beyond her professional lens, Brooke is that mom friend - the one everyone texts about everything. From products to transitions to “what do I do in this moment?” - she somehow always has an answer. It’s what led her to create her platform, @justaskbrooke, where she shares practical, thoughtful guidance for every stage of childhood. In this conversation, we get into: - Why she believes preparation (not perfection) is the foundation for confidence - Her biggest “no’s” (including no wipe warmers, skipping sippy cups, and ditching the stroller earlier than you think) - How to introduce a new sibling in a way that actually supports both children - The small, intentional choices that build real-life skills over time We also talk about something I find so compelling about Brooke, how she approaches parenting and life with a level of thoughtfulness and organization that feels grounding, not overwhelming, making sure to share the imperfections with her children as teachable moments. This episode is full of tangible takeaways, but also something deeper: a reminder that when we prepare our children (and ourselves), we give them something much more lasting than ease - we give them confidence. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    59: I Don't Believe in Homework

    This episode started with a simple story I shared on Instagram: “the way my soul just does not believe in homework.” That sparked a conversation with my friend and longtime follower, Caitlin Greer Meister, who reached out to say she’s actually done extensive research on this topic. So of course… we had to sit down and talk. Caitlin is a specialist in strengths-based learning, neurodiversity-affirming practices, giftedness, and executive functioning. She’s a parent educator, instructional leader, and mom of two, with training from the Harvard Graduate School of Education and in Orton-Gillingham. She’s also the founder of Joyfully Learning, a NYC-based tutoring and educational consulting practice, where she supports families and schools in raising confident, capable kids. Her work has been featured in The New York Times, The Wall Street Journal, New York Magazine, Parents, and more, and you’ll feel why the second you hear her speak. In this episode, we explore my instinctual, emotional reaction to homework alongside Caitlin’s research-backed perspective and her real-life experience advocating for less (and in some cases, no) homework for her own children. This isn’t about dismissing school or structure, it’s about questioning what actually supports our kids: their learning, their nervous systems, and their connection at home. Rather than summarizing it all here, I want you to listen, reflect, and decide where you land. And maybe… consider this with me: Less homework. More connection. Less pressure. More presence. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    58: I Used To Roll My Eyes at “Woo”...

    I used to roll my eyes at the word “woo.” You know the kind of things I mean — energy healing, psychics, plant medicine, spiritual practices that some people swear by and others dismiss immediately. I probably would have dismissed them too… until I didn’t. About a year ago, a guest on this podcast shared how she used psychedelics to rewire her brain. What struck me wasn’t the mysticism — it was the science behind it. That conversation opened a door for me that eventually led to four of my own plant medicine journeys, a lot of meditation, and a growing curiosity about what we label as “woo.” Then I met Ariana Cleo — someone who didn’t discover the woo world later in life, but was raised in it. Her childhood included psychic parties and energy healing from her grandmother whenever she was sick. In this episode, we talk about what it’s like to grow up surrounded by those practices, the fine line between magical family traditions and things that can feel embarrassing as a kid, and how she decided what parts of that world she wanted to carry forward. Ariana shares how these spiritual practices became a refuge that helped her navigate deep trauma — and how, after experiencing pregnancy loss, they ultimately led her to create her own podcast, Into The Woo, where she explores the mystical and spiritual with curiosity and openness. At one point Ariana was seeing seven healers a week, so if you’re even a little curious about what people mean when they talk about “woo”… this episode is a fascinating place to start. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    57: Raising Grounded Kids with Jill Kargman

    In this episode, I sit down with the brilliant and hilarious Jill Kargman, someone I’ve long admired for her authenticity and ability to make me laugh out loud. Jill started writing in small pockets of time while she was a stay-at-home mom raising young kids in a Brooklyn walk-up. That writing eventually led her to become a bestselling author, screenwriter, and actress. Her work has been adapted into television, and now film, with her directorial debut Influenced coming soon. What fascinated me most was hearing how Jill built a creative career as a mom in her 40s with young children—and how she now shows up as a parent to teenagers. I had a feeling she would bring the kind of refreshing honesty and perspective we all need, and she absolutely delivered. Jill describes herself as having had a “perfect upbringing,” so this wasn’t a typical “breaking cycles” conversation. But as we talked, it became clear how certain parts of her childhood quietly shaped who she is today - as a creator, a person, and a mom. We also talk about raising kids in New York City without getting swept up in the intensity of what the city can become. Jill is deeply intentional about keeping her family grounded and grateful in an environment that can easily pull you in the opposite direction. At one point I told her she’s basically a parenting expert, not because she claims to be one, but because of the calm confidence and clarity she brings to raising thoughtful, grounded kids. The steadiness she speaks with throughout this conversation feels like a window into the way she shows up as a mom. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    56: What Your Birth Date Reveals About You and Your Kids

    What if you could understand your child — and yourself — on a deeper level? To truly meet them where they are. In this episode, I’m joined by Ipek Gray, founder of The Born Method — a numbers-based system that uses birthdates and meaningful numerical patterns to create a personalized 20-digit code. Through a blend of data, ancient wisdom, and research, Ipek helps people uncover how they’re wired: how they communicate, where their natural strengths lie, where they may carry wounds or shadows, and what their “zone of genius” might be. I had a private session with Ipek the day before we recorded this — and it moved me so much that I asked her to come on and walk through my children’s numbers so you could hear the process in real time. What unfolded wasn’t about prediction or perfection. It was about awareness. About timing. About understanding how each person in a family might experience the world differently. We talk about how tools like this shouldn’t create pressure to “get it right,” but instead offer a roadmap for deeper connection — helping us see our partners, our children, and ourselves more clearly. Because when we understand how someone is built, we stop trying to change them — and start learning how to support who they already authentically are. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    55: Giving Our Kids the Voice We Didn't Always Have

    In this episode, I talk with Kelly Oriard and Callie Christensen, the founders of Slumberkins, a parenting resource designed to help both parents and children build resilience through meaningful stories, characters, and emotional tools that families truly see themselves in. From transitions and repair to grief, gratitude, emotional courage, and the development of a loving inner voice, what they’ve created reaches far beyond plush dolls and books. At its core, Slumberkins speaks to something universal: the inner child we all carry, and how parenting our own children often reveals the voices we needed but didn’t always receive. We connected deeply over our own seemingly “great” childhoods that still held moments of not feeling fully seen or heard, and how those experiences shaped us into people-pleasing adults who struggled to set boundaries without questioning our lovability. Kelly and Callie share vulnerably about stepping away from marriages where emotional safety wasn’t present, choosing instead to model honesty, courage, and self-respect for their children as single mothers. This one felt really special to record, and I’m so grateful for the work and community they’ve created. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    54: What is Confidence Really?

    In this short solo episode I'm sharing what I think confidence really is - not praise, not performance, not getting everything right and not even owning a room. It's a belief in oneself as we are. I introduce the powerful role we play as parents in shaping that belief through our reactions, tone and presence. I also share on how stumbling upon meditation gave me the ability to pause and choose how I react to my kids. It gave me more control over how I respond to them - and I even attempt to guide you through a 60 second meditation practice on how you can start this. TLDR: raising confident kids starts with the work happening inside us. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    53: Doing This for the First Time

    Rebecca Smith is a friend of my sister’s but she’s also the founder of Mamala Organics, a new mom brand born from a very real moment: becoming a mother and realizing how hard it was to find even a few minutes to nourish herself. She began noticing something so many of us do, dipping into our children’s snacks just to get through the day, and Mamala grew from that shared truth into something meant to feel like a hug for mothers when they need it most. But this conversation goes far beyond a brand story. Rebecca and I naturally found ourselves talking about grit, as founders, as mothers, and as people deeply triggered by the idea of “giving up" and feelings around things we quit as a kid. We explored what it means to keep building for our children, the role our partners play as safe places when we hit those I can’t do this anymore moments, and how that safety is exactly what we hope to become for our own kids. We talk about energy, confidence, and the quiet realization that none of us were born knowing how to do any of this. We’re all learning. We’re all doing this for the first time. I love this episode. It feels like a snapshot of where I am right now, in parenthood, in work, and in life. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    52: Breaking Cycles and Becoming Ourselves

    Erika and I met through the mom influencer world, but our connection felt instant and deeper than coincidence - like one of those meetings that’s meant to happen. Since then, the universe has kept weaving our lives together in ways this conversation brings to light. This episode begins with me in the middle of a full-blown “hot mess mom week,” opening up about the spiral of self-judgment, the fear of other people’s judgment, and how easily we turn inward when we’re overwhelmed. From there, we talk each other through the ways we’re hard on ourselves, and the ways we’re learning to meet ourselves with more grace as we actively break generational patterns, navigate our marriages, and raise daughters we want to grow up unburdened, proud, and free. You’ll hear Erika’s origin story, losing her job at nine months pregnant at the start of COVID, continuing to follow her purpose through uncertainty, and now arriving in a completely different season of life as she approaches nine months pregnant with her second child, six years later. We also talk about her bringing her brand to life with⁠ Eden⁠ - a women’s clothing line designed for every season of motherhood, with quality and comfort at its core, pre, during, and post-partum. But what’s most powerful is that Eden isn’t just a product, it’s a symbol. A vehicle for her real purpose: building support, safety, and community for mothers. This is a conversation about identity, resilience, alignment, and becoming - in motherhood, partnership, and selfhood. You’re going to fall in love with her, just like I did. 💛 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    51: Step into the Group Chat

    In this episode, I got to Zoom-hang with three women who feel like instant soul-friends: Allison Williams (Girls, M3GAN, Get Out) and her lifelong best friends Hope Kremer (early childhood educator) and Jaymie Oppenheim (therapist). It’s a four-way Zoom, so it feels exactly like being dropped into a private group chat, the kind where nothing is curated and everything is real. We talk about momming on meds, realistic expectations changing our parenting lives, confidence and bag size (yes, really), the pressure we put on moments that maybe don’t deserve it, and the ways we all carry high stakes without even realizing it. What surprised me most wasn’t just how honest the conversation was,  it was how familiar it felt. Different lives, different paths, same nervous systems. Same fears. Same gratitude. Same joy. Same constant recalibration of who we are and who we’re becoming as mothers. And that’s exactly the energy they’re bringing into the world with what they’ve created through Landlines: connection, honesty, and a sense of you’re not doing this alone. This episode doesn’t need a long explanation. Just know this: It feels like listening to a lifelong group text thread between three best friends who became moms -  and suddenly realizing it sounds exactly like your own. And that’s the magic. Join their substack.  Listen to their pod. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    50: How Loss Shapes Belonging

    In this episode, Jamie Kolnick peels back every layer. As a mom of three, Jamie is constantly navigating her own growth and healing, shaped by profound loss after losing both of her parents and her brother. Many know her as the founder of the beloved children’s music brand Jam with Jamie. What you may not know is how much inner work she has done - and continues to do - to make sense of grief, belonging, and identity. Rather than summarizing this conversation, I want to urge you to listen. This is one of the most raw episodes yet. Jamie opens up about losing her brother at just 13 years old, how the attention and popularity surrounding that loss shaped her understanding of belonging, and how those early experiences still echo in her life today, as a parent, a partner, and a public figure on social media. Through therapy, medication, deep reflection, and honest self-inquiry, Jamie has come into herself in ways that feel both brave and deeply relatable. She speaks candidly about couples therapy, learning her triggers, the lifelong work of feeling “enough,” and what it really means to live alongside loss rather than try to move past it. Jamie also shares about spearheading Little Jam Fest, offering classes through Jam with Jamie, and her ongoing fundraising work with the Reach for the Stars Foundation. This episode will stay with you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    49: Sister Episode

    In this episode, I sit down with my sisters for what started as a “get to know us” conversation, and quickly turned into something much deeper. At some point, we forgot we were recording and simply began reminiscing. It felt like therapy. It felt grounding. And it felt especially meaningful during a time when we’re navigating some of the hardest things we’ve faced together. What kept coming back to us was this: getting through life together has always been our anchor. We reflect on our childhood and the sisterhood we share, one that, surprisingly, was never rooted in competition or jealousy. We don’t remember being at odds (aside from a few scratch marks from toddler toy disputes). As a mom of two young girls close in age, currently deep in the trenches of sibling rivalry, I found myself wondering how our experience was so different… and what, if anything, I can learn from it. Listening back to this episode, what moves me most are the moments you can’t fully hear: the quiet looks, the tears, the shared smiles. Those nuances are what hold this conversation together. I hope this episode gives you a glimpse into my upbringing, the shaping experience of being the middle of two sisters, and the quiet magic that sibling relationships, especially sisterhood, can hold. You’ll also meet my sisters: Katy Leinoff, my younger sister, is a collage artist living in Florida with her husband and their 3-year-old daughter. She’s currently seven months pregnant with her second child. Lindsey Lamchick, my older sister, is a real estate agent, title owner, and the founder of Project Disco Ball, a nonprofit inspired by her journey through breast cancer. She lives in Florida with her husband, their 16-year-old twins, and their 6-year-old daughter. There will be more sister episodes in the future, I’m already sort of hoping I can create a spin off podcast for the three of us to have regular sessions. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    47: The Psychology of Sleepaway Camp (for Kids and Parents)

    This week I’m joined by the hilarious, honest NYC moms behind the podcast Mic’d & Medicated, Eva Heyman and Caroline Leventhal, in what starts as a conversation about sleepaway camp turns into something much deeper (and very funny). Sleepaway camp might sound niche, but it’s a topic I get asked about constantly ever since I started sharing about how we were looking at camp for Tess this upcoming summer (I can’t believe she’s leaving us so soon!). I get questions  from parents all over the world. Why do we send our kids away for the summer? Who is it really for? Our kids? Us? Both? We unpack the phenomenon behind camp and all the questions that come with it: – What age is “right”? – Co-ed or single gender? – How long is too long? – Is camp about independence, identity, resilience… or parents needing space to breathe? – And how much of our own childhood experiences shape the decision? We also go inward, sharing whether we went to camp ourselves, the experiences that stayed with us (good and hard), and how those memories quietly inform the choices we’re making now as parents. For me, camp was the first place I truly felt like I belonged. It shaped who I became, gave me lifelong friendships, and remains one of the most formative chapters of my life. That belief deeply influenced the schools I chose for my daughters and the camps we explored together. This episode is real, reflective, laugh-out-loud funny, and full of nuance. It’s a conversation about sleepaway camp not just as a parenting decision but as a decision about giving your child an experience where they discover who they are, who they can be without us and what it feels like to truly belong.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    46: Blending not Balancing with Jenny Fleiss

    Today’s conversation with Jenny Fleiss is one that stayed with me long after we stopped recording. You may know Jenny as the co-founder behind major ventures like Rent the Runway and Jetblack, or recently from Roll Rider, the kids’ luggage company she dreamed up with her children. She’s also been recognized with awards such as Inc.’s 30 Under 30, Fortune’s 40 Under 40, and Most Powerful Women Entrepreneurs — but what we explore in this episode is the part of her story that accolades don’t capture. We dive into the inner work of adulthood and parenting: the moments when we realize we’re not validating what matters to our kids, even though we’ve spent our whole lives wishing others would validate what matters to us. We talk about how this work doesn’t necessarily get easier, but it becomes clearer… and how awareness is often the biggest shift of all. Jenny shares why she doesn’t believe in the word balance — and why blend is the more honest, compassionate way to approach working motherhood. We talk about what happens when we include our kids in the worlds we’re building, how it softens us, surprises us, and reveals the parts of ourselves still in need of slowing down, rewiring, or healing. It’s a warm, honest, deeply human conversation about ambition, presence, stress, creativity, and raising kids while still raising ourselves. Discount for listeners: Get 20% off Jenny’s kids’ luggage scooter company Roll Rider with code RollOK. This one is just SO GOOD. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    45: Hear it from my girls

    This was the most I have learned from any guest so far. It was a 45 minute episode cut down to 12 minutes because of how moving this entire conversation was I felt compelled to keep the majority of it private. What I left in, I hope helps give you ideas for questions you can ask your own kids, letting them know you are curious about what they think and that it sparks conversations like the one I had here. I was able to hear some of their innermost thoughts and what I am sharing here I hope puts perspective on how their minds work, they want magic, they want presence, they want us. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    44: Mind Shifting

    This episode is all about rewiring ourselves. In this episode, I sit down with mind shifter and meditation coach Jamie Graber for the meditation conversation I’ve always wanted but never heard: a true back-to-basics, “start at square one” guide to what meditation actually is and how it rewires us as parents and people. I have always wanted someone to talk to me about meditation in the most basic, approachable way. She breaks it down and explains how the practice of meditation reshapes the nervous system, helps us see our thoughts instead of being ruled by them, and softens our reflexive thoughts and reactions (this is especially in motherhood when we find ourselves triggered or reactive to things we aren’t even aware of).  We each share our own before/after moments, including how meditation gave us perspective on the stories running in the background of our minds. If you’re curious about meditation but feel intimidated or confused - or if you’re like me, skeptical - then this is your starting point. You can also be guided by Jamie through her app Shift with Jamie. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    43: Rethinking Education with Alpha Co Founder MacKenzie Price

    Many parents feel it: that the current education system doesn’t fully reflect how kids actually learn. We’re craving something more aligned, more human, and more empowering, a model where children feel engaged, capable, and genuinely excited to learn because the experience itself is meaningful. I love my girls’ school and feel privileged to have been able to choose it. But I also feel there’s often a disconnect between what any current school teaches and what kids actually need to thrive in real life: confidence, communication, social skills, executive functioning, curiosity, and a true love of learning. That curiosity is what led me to learn more about Alpha School. This week I am joined by its co-founder, MacKenzie Price, who started Alpha after watching her own daughters lose their love of learning early in elementary school, and decided to create a school that brought it back. Alpha uses Time-Back Learning, an approach where AI customizes academics to each child’s level. Core academics are completed in about two hours a day, which opens up the rest of the school day to what children truly need - time to explore interests, build real-world skills, collaborate, create, and grow at their own pace. In this episode, MacKenzie and I talk about why the legacy model is failing so many kids, what truly prepares children for life, how personalized pathways can unlock potential we’ve never tapped into, and what school could look like when we design it around how children actually learn. This conversation is not about choosing a school, it’s about reimagining an entire system. It’s about believing that kids deserve environments where they grow, stretch, collaborate, problem-solve, and discover their own agency. If you’ve ever felt like something about school just isn’t working… this episode will feel really exciting and will give a glimpse into what education could really become. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    42: A Journey with Heart Openers

    This episode is one that I have been waiting to release, because it introduces one of the the most meaningful experience I've ever had. Last spring, I experienced a guided psychedelic journey with James Gangemi and Zev Eisenberg, the couple behind Heart Openers. They are not only gifted guides individually, but their partnership, the way they hold space together, and the energy they bring as a couple is truly remarkable. You feel safe, supported, and seen in a way I can only describe as being "held." That safety became the foundation for the most transformative experience I've ever had. I wanted this episode to talk about the neuroplasticity that occurs on a "journey" and the huge rewiring opportunity it gives us in the way we think. I also wanted it to help clarify the many misnomers around a psychedelic journey. Every "journey" is different and everyone experiences them differently. This journey was not ayahuasca. It didn't feel like I was out of control, I didn't feel sick, it felt gentle, grounding and deep. It was about sitting with myself, not escaping. Seeing what's been inside all along with the support of plant medicines and with guides who knew exactly how to hold the emotional and spiritual container for that to happen. In this episode you'll be introduced to the process, learn the purpose of it all and really get a glimpse into how special Zev and James are. It feels like the start of so much more that really touches on the truest expression of what this podcast has always been about: understanding where we "didn't turn out OK" and discovering what becomes possible when we finally turn toward those areas with understanding and love. James and Zev are extraordinary guides, an extraordinary couple and extraordinary humans. I'm so honored and excited to share this conversation - and this part of my story - with you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    41: Be Nice, Try Hard and Have Fun

    In this episode I sit down with Brynn Putnam and Kevin Thau for a conversation about ambition, reinvention, blended family life, and what it really means to build connection at home. Brynn is the entrepreneur behind Mirror - the interactive fitness company acquired by Lululemon - and now the creator of The Board, a new tool designed to help families stay connected in a tech-saturated world. A former professional ballerina and mom of two (and step-mom of three), Brynn brings a unique blend of creativity, discipline, and a deep belief in designing for presence. Her husband, Kevin Thau, is a longtime tech leader and investor known for helping scale companies like Twitter and Vine. As a dad to three daughters and partner in raising a blended family of five kids, he brings thoughtful perspective on technology, growth, identity, and parenting across every age and stage. We talk about: The inspiration behind The Board and using tech to bring families together, not pull them apart Parenting a blended family with kids ranging from toddler to college-aged Perfectionism, identity shifts, and what entrepreneurship teaches us about raising humans Reclaiming family quality time in a world that moves fast and pulls our attention everywhere Letting go of who we thought we had to be in order to show up to parenting - and life - more fully And in true WDTOOK fashion, we explore where Brynn and Kevin feel they “didn’t turn out ok,” how those patterns show up in parenting, and what they’re doing to rewrite them - including the family mantra: be nice, try hard, have fun. This is a conversation about building things - companies, families, and new ways of being - and remembering that the most meaningful things we build happen at home. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    40: Redefining Success with Rebecca Minkoff

    Rebecca Minkoff is a designer, founder, best-selling author of Fearless, co-founder of the Female Founder Collective, host of Superwomen with Rebecca Minkoff, and mom of four. In this episode, Rebecca opens up about what it really took to build her vision - from hand-sewing pieces in her apartment and styling clients to fund her dreams, to the moment she could finally stop checking her bank account before ordering dinner. She shares how following her “opportunity tentacles” - her term for staying alert to possibility - kept her always one step ahead, even when the path wasn’t clear. We go deep into what success means after you’ve achieved it - how Rebecca has redefined it as being fully present. She shares how she’s teaching her kids to negotiate (a skill she once resented learning herself), why she refuses to chase balance, and how labeling ourselves with “imposter syndrome” keeps us stuck in a false story. It’s an honest, inspiring, and very real conversation - from her ill-fated reality TV experience to the moment her child talked a seller down to a $10 Labubu. What we both came back to again and again: how hard, and important it is to model meaningful work for our kids while still trying to figure out how to message it right. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    39: Finding Meaning on the Other Side with Chloe Harrouche

    At just 23 years old, Chloe Harrouche was diagnosed with breast cancer. Instead of spiraling or feeling defined by the diagnosis, she chose to meet her journey with purpose, trusting that meaning would reveal itself on the other side. A decade later, that belief became the foundation for The Lanby, her concierge medical company created to bridge the gap between medicine and wellness, bringing together the best providers to empower people with integrative care. In this episode, Chloe opens up more vulnerably than ever before. She shares why she cried only once during her cancer journey - until a fertility struggle years later opened the floodgates. She reflects on the way her mom parented her differently from her sisters - stricter, more focused on academics - and how she now sees both the gifts and the challenges of that approach. Chloe also discusses how cancer shaped her as a parent: the pull toward routines, structure, and wellness, and the simultaneous reminder from her kids to rediscover silliness and presence. What makes Chloe’s story remarkable is her willingness to hold all of it - her upbringing, her diagnosis, her resilience, her vulnerability - and her belief in a greater purpose running through it all. Her path to founding The Lanby feels not only logical but destined. In honor of Breast Cancer Awareness Month, this conversation honors the club no woman wants to join but that holds some of the strongest members. As I share in this episode, my own sister is part of that club too. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    38: From Forbes 30 Under 30 to Father of Two Michael Perry's True Measure of Success

    Michael Perry could be introduced as the founder of Maple, the creator of KIT (acquired by Shopify), and a Forbes 30 Under 30 entrepreneur. But he’ll tell you the only introduction that matters is: husband to an incredible wife and father to two amazing sons. Michael found himself on food stamps in his 20s, sold cars for a living, and only dreamed of the symbols of success - financial security, the house, the car, the validation that he had “made it.” And he achieved all of it. But when faced with the possibility that he might never have children, he realized none of it mattered. Through IVF, he and his wife went on to welcome two beautiful boys, and fatherhood became his greatest accomplishment and deepest purpose. Of course his recap of this unleashed all the emotions for me, because this was such a gift to have this reminder from him that I feel such a sense of urgency to share with all of you.  In this episode, Michael shares the story of how his wife’s unwavering belief in him unlocked his potential, how redefining success transformed his life, and why every achievement felt almost superficial in comparison to being present for his family. Now, with his new venture Maple - which stands for “Making All Parents’ Lives Easier” - he’s building a tool for parents rooted in that same belief: that family is everything, and that being there for the practices, the drop-offs, the moments in between (when we can be) is what really matters.  My favorite quote from this episode is when he said "everyone is greedy about something and I'm really f*cking greedy about time with my kids." If there’s one message you were meant to hear as a parent, let it be this: validation and success are fleeting, but showing up for the people you love will always be enough. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    37: Solo on When Our Kids Trigger Us...and More

    In this episode, I’m answering a mix of questions I’ve gotten from you - things like: “Why does my kid’s behavior trigger me so much?” “How do I know if I’m reacting to them or to something in me?” “What do I do when they refuse to apologize?” I share a real moment in the car after apple picking where I slipped into that familiar place of making their emotions about my expectations. Not because I don’t know better - but because maybe I’m still unlearning what I absorbed growing up. The work isn't about being perfect in the moment - it's about noticing it later and repairing . I also talk about something so many of us do without realizing it: parenting for the people watching instead of the child in front of us - especially when we feel judged, embarrassed, or responsible for how our kids make us “look.” Here’s what else I get into: Why certain behaviors, like refusing to apologize, hit such a nerve How to tell if your reaction is about your kid—or about you What to say instead of forcing an apology in the moment How to repair later without using shame Parenting for approval vs parenting for connection Why noticing a trigger is actual growth, not proof you’re failing This is basically my first full solo episode, and I’d really love to hear what you think. Do you want more episodes like this? What topics should I do next? Send me a DM, leave a review, or message me one of your questions - I’d love to build future solos around what you’re actually navigating. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    Episode 36: Business and Life Partners Olivia Landau and Kyle Simon on Delegating at Home and Work

    What happens when you build a business with your spouse before you even start dating? For Olivia Landau and Kyle Simon, co-founders of The Clear Cut, that was the foundation of their love story, their multi-million-dollar company—and now, their parenting journey. In this episode, Olivia and Kyle open up about: How Kyle believed in Olivia’s idea before she did, pushing her to grow a blog hobby into a thriving business. How even her parents doubted her early on - and how that early lack of belief shaped her journey as a founder.  Why they wish they had given themselves more time to adjust to parenthood instead of jumping back into work too quickly. The surprising freedom they’ve found in releasing control—delegating at home and in business—and why it doesn’t make them any less of entrepreneurs. The ways their “not okay-ness” shows up—Olivia as a recovering perfectionist, Kyle as someone working on being more present—and how they’re navigating those patterns as new parents. It’s an honest, funny, and relatable look at the intersection of marriage, entrepreneurship, and parenthood—proving that success isn’t about doing it all yourself, but about learning when to lean on each other and your village. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    Episode 35: Enoughness and the Mother Daughter Dynamic with White Hair Wisdom

    Imagine getting an inside glimpse into the dynamic between a mother and daughter—their reflections on who they are, where it all comes from, and how it shapes the way they show up in their own parenting. Imagine hearing not only the beauty, but also the “not so okay” parts, spoken with honesty and without hiding behind perfection. That’s exactly what you’ll hear in this episode with Lynn Shabinsky, known to over a million followers on Instagram as White Hair Wisdom, and her daughter, Marissa Savrick, her Director of Operations and mom of three. Together, they share not only what inspires them, but also the challenges, doubts, and growth edges that have shaped their bond as both mothers and daughters. We explore everything from the traps of “toxic positivity,” to the struggle of feeling like enough, to the freedom that comes from embracing who you are. Lynn’s ability to self-reflect with honesty—not with resentment or regret, but with awareness and empowerment—proves why White Hair Wisdom is the perfect name for her platform. This is a conversation that reminds us why sharing stories across generations matters. You'll relate to it, want to call your mom from it and learn so much from it. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    34: Marriage after Parenthood with My Husband Matt Monness

    You guys sent in your questions, he answered! Everything from finding time for intimacy, what he feels changed the most since becoming parents and what it's like to be married to someone on social media. This one is short but sweet so I'll keep the description the same. Let us know what you think and what Matt should answer next time! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    33: Lucie Fink on Ambition, Motherhood and the Stories We Tell Ourselves

    In this episode I sit down with Lucie Fink - lifestyle host, podcast host of The Real Stuff and, who I like to call, an epic story teller. I was first drawn to Lucie because of her incredible way of telling stories, not just the way she shared the brands she believed in but how she shared her life. It’s sometimes silly, often beautifully edited but also so authentic and real. Her shift into motherhood solidified my intrigue because of how seamlessly she seemed to keep her videography abilities which I know can be all consuming. She just exudes effortless in so many ways and I was excited to see what was behind it.  Lucie and I got into her origin story at Refinery 29 (and probably spend longer there than planned because of my genuine fascination), but the most powerful takeaways are how she shares her ambition—an ambition she once thought would fade when she became a mom - actually carried her into the most creative stage of her career. We also talk about her parents, in-laws, her experience as a twin, and more. But the most powerful takeaways from this conversation are how Lucie shares the way in which her ambition, one she thought wouldn’t matter anymore once she became a mom, not only stayed with her but pushed her into her most creative stages of her career. We also talk about her parents, her in-laws, her experience as a twin and more.  What inspired me most was Lucie’s way of keeping her own projections out of parenting - something so difficult to do when our children’s experiences bring up memories of our own. This conversation truly feels like one of those long coffee chats with someone who inspires you as both a professional and a mom. Lucie and I also dig into how we each frame our work to our kids, and how important it is to dismantle the myth of “doing it all” - because none of us can, nor should we aspire to. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    32: Big City Readers x We Didn't Turn Out OK with Beth Gaskill

    In this episode, I sit down with Beth Gaskill, the reading and learning specialist behind Big City Readers. We dig into the disservice many schools unintentionally create when it comes to teaching reading - and how that often leads to a “third grade slump” - when children can no longer keep up and we learn that they need a more comprehensive tool box. Beth explains why this happens, and what parents can do to better support their children’s reading journey. We talk openly about my own experience with my daughter - how her confidence took a hit in kindergarten when she compared herself to friends who’d already had reading tutors - and how that shaped the way she’s embraced reading since. Together, we explore why confidence is just as critical as fluency, and why schools should avoid sharing reading levels with parents or children. Instead, it’s about honoring each child’s unique pace and path toward becoming a lifelong reader. Beth shares tactical skills, tools, and strategies parents can use right away, including when it might be time for a symbolic “homework bonfire” to push back against cookie-cutter assignments that don’t serve our kids. We also reflect on: How our own childhood reading experiences can contribute to areas in which we didn’t turn out OK - and how to break that cycle for our kids. The tension I’ve felt between play-based learning and the pressure to teach kids to read early. Practical ways to build confidence, foster a love of learning, and keep reading fun. Whether your child is just starting out or already navigating reading challenges, this episode will leave you with reassurance, perspective, and actionable tools to support them. Beth is the best - follow her!  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    31: Waking Up - The Beginning of My Life After Zoloft

    In my first-ever solo episode, I’m sharing something deeply personal — my journey with anxiety, medication, and what it’s been like to come off Zoloft after nearly half my life. This conversation isn’t the full story of how I got here — that’s for future episodes. There’s a deeper beginning, one rooted in a lifetime of people-pleasing, seeking acceptance, and slowly losing sight of who I really was. But today, I’m starting with the moment I began to question whether I was truly living or just coasting, and the decision that shifted everything: stepping away from the medication I thought I’d take forever. I share why I made that choice, what it’s been like to feel more deeply than I have in years, and how I’m now navigating life — and parenting — without numbing. This is where the story starts… but there’s so much more to come. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    30: It Starts With Us — Nervous System Regulation with Alyssa Blask Campbell

    In this episode, I sit down with Alyssa Blask Campbell - founder of Seed and Sew, host of the Voices of Your Village podcast, and bestselling author of Tiny Humans, Big Emotions and the upcoming Big Kids, Bigger Feelings. A mom of two, Alyssa has spent years researching emotional intelligence in children - only to realize that many adults, including herself, never had the tools modeled for them in the first place. We talk about what it really means to support emotional development, starting with ourselves. Alyssa shares how regulating our nervous systems isn’t just a self-care buzzword - it’s the foundation for helping kids navigate their own emotions. She walks us through the simple yet powerful practice she used with her students (and now with her kids): checking in with her body cues, modeling emotional awareness, and embracing rupture and repair. We also dive into why regulation is never one-size-fits-all - why it’s okay to lose it sometimes, and how the true goal is quicker recovery and connection afterward. Alyssa talks about the importance of saying, “That wasn’t about you, that was about me. I’m sorry I yelled,” and how moments like that can rewire relationships and build true emotional safety. She also shares why she created the S.E.E.D. Certification® (Schools Excelling in Emotional Development) - a new model of professional development for educators that prioritizes emotional support for the adults in children’s lives. We wrap by discussing Alyssa’s two game-changing books: ✨ Tiny Humans, Big Emotions - A guide to helping kids navigate big feelings like tantrums, separation anxiety, and overwhelm while building a foundation for emotional intelligence from the start. ✨ Big Kids, Bigger Feelings - Available now for pre-order, this is the much-needed next step: a guide for supporting kids ages 5–12 through the emotional complexities of the elementary years—name-calling, meltdowns, cliques, and more. If you’ve ever wondered how to actually help your child with their big feelings - without losing your own mind - this episode is your starting point. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    29: Bridging the Emotional Gap in Marriage: Partnership and Parenthood with Alex Sall and Mosh Oinounou

    Ever wonder how you’ll ever bridge the gap between you and your spouse’s wildly different ways of handling emotions and challenges? Me too. That's why this episode is for you, me, all of us. In this deeply honest episode, I sit down with journalist Mosheh Oinounou—who you may know as Mosheh of Mo’ News—and his wife, my dear friend, marketing agent Alex Sall. We talk about how they’ve built their relationship from the inside out. From a couples retreat at Kripalu, six months into dating to navigating parenthood with a shared vision, they’ve done the work before the chaos, and it shows. We unpack how their childhoods—shaped their early dynamics, how they’ve bridged emotional gaps with tools like the Gottmans’ Bringing Baby Home and Eve Rodsky’s Fair Play Deck, and how they hold space for one another in both the everyday and the heavy moments (including Mosheh reporting the news daily). We talk emotional labor, people-pleasing, breaking generational patterns, and how parenting on the Upper East Side brings its own set of values to navigate. Alex opens up about her journey to stop pleasing everyone and start pleasing herself (with Mosheh cheering her on), and Mosheh shares how he’s learning to listen and validate instead of fixing. And yes—we also talk about the real difference between protecting kids from the news and empowering them to understand it. This episode is a must-listen for any couple navigating the emotional push-pull that comes with different upbringings, communication styles, or parenting values. Whether you’re just starting out or deep into raising kids, Alex and Mosheh offer a refreshingly honest look at how to bridge the kinds of emotional and cultural gaps that can quietly make—or powerfully strengthen—a relationship. Their story will leave you inspired to do the work, have the conversations, and build something intentional, together. Correction: In this episode, Alex references an astrology app when she says “time passages” but she is referring to “the pattern.” Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    28: Is This Normal? Navigating Early Development with Tots on Target Dr. Allison Mell

    As someone who believes in letting gross motor development unfold naturally—without rushing babies into positions they can’t get into (or out of) themselves—I’ve always had questions about how we support movement in early childhood. So in this episode, I sat down with the amazing pediatric physical therapist behind Tots on Target, Dr. Allison Mell, to dig into all of it. I’ve followed Tots on Target for years because of the way she breaks down early development in a way that’s clear, thoughtful, and totally empowering for parents.  We talk about when to reach out for support, what mini milestones really tell us, and how even well-intentioned early classes can place performance expectations on infants and toddlers before they’re ready. Together, we explore the tension between trusting a child’s timeline and knowing when intervention matters—and how to reframe what it means to support a child’s development without pushing them too far, too fast. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    27: Redefining What Play Looks Like with Hart & Hero

    What if the toys our kids play with could help shape them into more compassionate, balanced, and open-hearted ? In this episode, I sit down with Hart & Hero founders—and fellow moms—Chanie Brod and Musya Eckhaus to explore how toys can do so much more than just entertain. We dive into the quiet power of care, the beauty of duality, and how to bridge the gender play gap in a world that too often puts kids in boxes. From their origin story to the values behind their thoughtfully designed products, Chanie and Musya share how they’re raising both sons and daughters with the freedom to be strong and soft, nurturing and brave. I share a deeply personal parenting moment that challenged my own assumptions about femininity, reflecting on how easily we pass down gendered expectations—sometimes without even realizing it. We also explore how the roles kids take on in play can shape the roles they default to in adulthood—particularly when it comes to caregiving and the “default parent” dynamic. When nurturing is only encouraged in girls, we miss the chance to raise boys who are emotionally fluent, capable caregivers too. This conversation is a powerful reminder that play isn’t just play—it’s practice for life. We cover: Why care is one of the most radical, under-celebrated strengths How to support boys in embracing nurturing roles and girls in stepping into leadership—without forcing either The impact of representation and inclusive toys on identity formation How duality helps raise whole, resilient humans How early play patterns can shape future family dynamics Whether you’re a parent, educator, or just someone who cares about raising the next generation with intention, this episode will leave you inspired to notice the micro moments—and make them count. Learn more about Hart & Hero at @hartandhero Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    26: From Guarded to Grounded with Whitney Port

    When I tell you that this may be one of the most moving conversations on We Didn’t Turn Out Ok so far, I’m still not doing it justice. Having Whitney Port on brought me back to growing up what felt like with her—from watching The Hills, where she seemed to live in an alternate world from my "Varsity Blues" suburbs in NJ to following her journey as she began filming for The City, where she carved her space in fashion and seemed to have everything fall into place. She met her now-husband Timmy (then a producer on the show), and began creating what she calls “beautiful things”—both professionally and personally. But if you’ve followed along with Whitney’s story, you know she’s opened up bravely and publicly—about how things didn’t stay perfectly “in place.” About how pregnancy didn’t feel magical, how her experience of starting motherhood felt really sudden and how she’s now navigating an ongoing six-year fertility and surrogacy journey. Her honesty has been incredibly powerful for those who follow her, they feel connected, seen and supported in her sharing. I wondered what was left to uncover. It turns out—so much more that we will all connect to— in different ways.  In this conversation, Whitney shares the feeling when she sees another mom in a moment, how that can feel easy to judge until we then experience the same in her own parenting. She talks about how realized that it’s not about judging anyone else or ourselves, but about awareness and confidence in how we are showing up as a parent. She shares the emotional landscape that’s shaped her: from being one of five siblings in a home where it sometimes felt like her feelings often didn’t have space, to seeing a beautiful example of a marriage in her parents, to the boundaries that were set forth for her and her siblings, to learning what emotional safety really means—first for herself, and now for her son, Sonny. This is a conversation about permission: to feel, to be unsure, to heal, and to show up—even when it feels like we don’t know exactly how. To be the kind of parent who’s still learning, still healing, still growing. Spoiler: we both shed tears reflecting on how we were raised, and how that contributed to who we are today. She’s amazing. This one’s special. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    25: Beyond the Comparison Trap - Identity After Motherhood with Dale Stabler and Annabel Lawee

    In this episode, I sit down with Dale and Annabel - the funny, real and deeply honest voices behind We Are More Than Moms, a community and podcast that supports moms in navigating identity, ambition, and the messy in-between moments of modern motherhood. We talk about the many layers that shift when we become moms - from how we see ourselves to how we compare (to other moms, our pre-mom selves, even our own kids). We dig into the power of recognizing when we’re not OK, and how those moments can actually spark real growth - especially when we allow ourselves to ask for help. Dale and Annabel also share the inspiration behind their brand-new coaching program - a supportive space designed to help moms reconnect with who they are now and step into their next chapter with confidence, clarity, and self-trust. If you’ve ever felt like you’re somewhere between who you were and who you’re becoming, just know we’ve all been there - and as Dale and Annabel say, motherhood might just be your 2.0 version… the one where you become your best self, if you can just allow yourself to see it. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    24: Parenting without Panic, Emily Oster on Tech, Routines and more

    This episode is really special to me. I got to sit down with Emily Oster — someone whose work has been a constant companion in my parenting journey. Emily is an economist, bestselling author, and professor at Brown University who has become a trusted voice for parents looking to make informed, grounded decisions. You might know her from her books Expecting Better, Cribsheet, The Family Firm, and The Unexpected. Her work takes complicated data and turns it into something we can actually use — not to be perfect, but to feel less lost and more confident in how we parent. I first found Emily when I was thinking about getting pregnant and searching (desperately) for trustworthy information on whether it was okay to stay on my Zoloft. Her calm, rational, and deeply human voice stood out immediately. She didn’t just share the data — she helped me feel like I wasn’t alone in trying to figure it all out. Meeting her in person was surreal, and also… so normal. She’s a mom, just like us, and she’s as down-to-earth as she is brilliant. In this conversation, I got to ask the questions that have been on my mind for years — and her answers did not disappoint. We talked about: Kids and technology — what the data actually says, how to think about screen time, and when kids might be ready for things like phones. (Her “frontal lobe” metaphor changed how I think about it.) Routines — why they matter not just for our kids, but for us. Emily shared how having routines early on (even just for sanity) laid the foundation for flexibility later on. “Hurried Child Syndrome" — the eye rolly term that has scared us all since it started trending on instagram, Emily shares the difference between rushing through life and pushing kids ahead too fast, and how slowing down has helped her kids take more ownership in the mornings. The power of saying no — how her family protects their weekends, talks through what really matters, and why sometimes skipping a birthday party is exactly what everyone needs. At the end, I asked Emily if there was one parenting hill she’d die on — and her answer honestly surprised me. She reminds us that no single choice makes or breaks our kids. What matters most is what makes your family happy and work well together. This episode felt like the kind of conversation I needed as a parent — grounding, smart, and totally freeing. I’m so excited to share it with you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    23: Chipping Away to Your True Self: Conscious Parenting with Erin Morrison

    The Conscious Mom, where do I start? Back in 2020, when I was supporting other moms through virtual groups—craving a bit of that support for myself—I stumbled upon Erin Morrison, a.k.a. The Conscious Mom, on Instagram. What started as a digital connection during COVID quickly became a real friendship, even though we had never met in person. Fast forward five years, countless DMs, and near-misses in Florida (where Erin lives with her two kids, Ellie, 9, and Jonah, 11), and we finally made it happen. Erin flew up, and we got to share this conversation in person—a full hour of heart, insight, and so much truth. In this episode, we dive into Erin’s brilliant new book, Three Minutes for Mom, which I genuinely think is the only tangible tool every mom should have on their nightstand. It’s like a morning hug in book form—something I reach for before anything else, especially my phone. Here are some of my favorite takeaways from our conversation: The culture of over-involved motherhood: We unpack how stepping back and trusting our kids can unlock their creativity, independence, and resilience—not just from boredom, but from life’s bigger challenges. Discomfort and distraction: We talk about how the emotions hardest to tolerate in our children are often the ones we avoid in ourselves—and how our phones have become quick escapes from that discomfort. Urgency culture & boundaries: Erin and I are both recovering people-pleasers, learning to protect our mental space with boundaries—turning off notifications, reclaiming quiet moments, and modeling that for our kids. Loving boundaries: Erin shares a powerful reflection on the boundaries her own parents set that felt hard in the moment—but made all the difference. A reminder that boundaries are love in action. Weathering the storm: Erin beautifully captures the hardest part of parenting—“You have to withstand the storm of their emotions.” We talk about what it means to hold steady through our kids’ disappointments, big feelings, and heartbreaks—without taking them on as our own. Chipping away: A theme we kept returning to—how parenting (and personal growth) is all about chipping away at the noise, the pressure, the self-doubt, to get closer to who we truly are and how we want to show up. Not only is this episode reflective and relatable but it’s a conversation that will stick with you - or at least it has for me—in the moments when you need to access something to help you know you’re doing it right, when you’re setting a boundary and your kids push back, when your kids tell you their bored, when you go to look at your phone first thing in the morning instead of grounding yourself, when you really reflect and “chip away” at the stuff that’s making you think you don’t have it all within you, because you really do.  Also, buy her book immediately.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    22: Movement as Medicine with Katia Pryce, Founder of DanceBody

    In this episode, I’m joined by Katia Pryce, the powerhouse founder and CEO of DanceBody, a dance-based fitness brand built on the belief that movement is medicine—something I deeply resonate with. What struck me most in our conversation was learning how DanceBody was born from Katia’s rock bottom moment. After moving to New York in her early twenties with dreams of being on Broadway, Katia landed a job at the iconic Tracy Anderson Studios—only to have it taken from her without warning. From that space of uncertainty and loss, she chose to keep moving—literally. DanceBody was created out of necessity, resilience, and a refusal to stop dancing. Her story embodies the idea that life doesn’t happen to us—it happens for us, a theme that runs through this episode. Now a mother to an almost two-year-old daughter, Katia opens up about the ever-evolving challenges of body image in motherhood. She’s passionate about helping women feel more connected to their bodies—more confident, more present, and ultimately, more joyful. Key Takeaways: – Katia’s energy is magnetic, especially when she talks about dance as a healing tool. She shares how movement isn’t about aesthetics for her—it’s about boosting serotonin, dopamine, and reclaiming mental wellness from the inside out. – She reflects on her upbringing, where work ethic was modeled as “non-negotiable,” and how her early experiences with dance, pom, and extracurriculars laid the foundation for self-earned confidence and community. – We dive into how DanceBody helps women build confidence, even if they walk in full of self-doubt. Katia has created an environment where women feel safe enough to let go and gain a new sense of self. – As someone who needs music and movement to stay grounded, I felt such a connection with Katia. Dance is my form of meditation, a way to connect with my girls, and my go-to for lifting the mood. To speak with someone who built an entire business on the transformative power of dance—it was everything. Whether you’ve danced your whole life or not at all, this episode is a reminder that movement isn’t about performance—it’s about coming home to yourself. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    21: Siblings, Sisters and Psychedelics with Cameron Rogers

    In this episode, I sit down with Cameron Rogers - longtime content creator, podcast host of Conversations with Cam, and mom of two boys. Cameron is as real as they come - unapologetically honest, refreshingly open, and someone who always has a way of making you think, “Wow, I feel the same way, but I never knew how to say it!” We dive into so many topics - starting with how Cameron has learned not to internalize negativity from others, and whether anything from her upbringing helped her build that resilience. We chat about how therapy and simply growing into herself have shaped her confidence, and she shares how she’s been working through the “role” her family gave her growing up as the so-called “bitch” of the family. Cameron, like myself, is the middle of three girls, so it was fun to relate and get into birth order, sibling dynamics, and how those patterns play out not just in our own lives, but in the relationships we see forming in our kids. Cameron opens up about her childhood as an athlete, how the need for external validation drove her, and how her high-functioning anxiety and ADHD impacted her - especially in motherhood. We also share a little sneak peek into a recent “journey” we both embarked on that included psychedelics (more on that in a future episode!). Cameron is one of those people you can talk to about anything - she’s an open book with a gift for sharing and somehow does it all.  After this conversation, I’m even more obsessed with her new journal (which I already loved!) because I understand the heart behind it. Listen for a raw, honest, and inspiring conversation that was one of my favorites.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    20: How Childhood Shapes Parenthood a Conversation with Alexa Leigh Mufson

    Alexa Mufson is the founder and CEO of Alexa Leigh Jewelry and a mom of three - ages 9, 6, and 3. Before this episode, Alexa and I actually recorded one that got lost (I know!) - so this is our second take. Honestly, I welcomed the redo because I can get totally lost in conversation with Alexa. She’s so open to diving deep into parenting, exploring her own childhood, and coming up with tools that work for her - and that’s exactly what I hope this podcast inspires more parents to do. Before we recorded, I asked Alexa what she wanted to talk about, and she shared something close to home: one of her sons has been experiencing anxiety. It’s something she remembers from her own childhood - and still feels at times. In our first recording, I suggested she try the “worst case scenario” exercise, something I personally use when I’m feeling anxious. So often when our kids (or we) are overwhelmed, the instinct is to say “don’t worry, it’ll be fine,” but there’s real power in facing the fear and asking, “what’s the worst thing that could happen?” Alexa has since used that exact approach with her son when he’s anxious about being late. She’ll pause and say, “what are you afraid will happen if we’re late?” And in doing so, she’s giving him the gift of resilience - a set of tools he can carry with him for life. Some other moments that really stood out: Alexa shared a bedtime ritual she’s created with her kids - especially her middle son, who feels things deeply. Every night, they go around and share three feelings from the day. She even shares her own three feelings which also helps her kids feel "less alone" in their own. It came from her own memories of lying awake at night as a child, anxious with no outlet. Now, she’s created a space for her kids to release those feelings, and in doing so, she’s healing something in herself, too. She also opened up about her own experience with postpartum anxiety, specifically a rare hormone-related condition where she’d get intrusive thoughts every time her milk let down. It was her mom who first noticed it, which helped her name and prepare for it before her second baby was born. Naming it gave her power over it—just like she’s now helping her son do with his own worries. We talked about how powerful it is to raise emotionally intelligent kids—and how that starts with modeling it ourselves. From labeling emotions to creating safe spaces for expression, Alexa is doing that daily. It’s not just about managing anxiety; it’s about understanding feelings, connecting through them, and building emotional awareness that will serve her children far beyond childhood. Alexa describes herself as a “recovering perfectionist.” Recently, she handed over control of her professional @alexaleigh Instagram account to her team and is focusing on her personal account @alexamufson. While she said it was to separate business from personal, I can’t help but see it as a big step in her journey away from perfectionism and into trust and delegation. There’s so much more in this episode - it was so open, honest and heartfelt. I adore Alexa, and I think you will too. I’m also so excited to share that we’ll be partnering again on our separation bracelets just in time for back-to-school. Spoiler: there may be a version just for boys this time around. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    19: From Dating Doubts to Mom Confidence with Lindsey Metselaar

    In this episode, I sit down with OG podcast host Lindsey Metselaar of We Met at Acme a a show where singles turn for unfiltered dating advice. Lindsey started her podcast at 27 after being dumped on her birthday, and now she’s married, a mom, and still telling it like it is. What struck me most about Lindsey is how grounded and confident she is, even just 15 months into motherhood. She’s figuring it out in real time and learning more about herself along the way.. Key Takeaways: The Butterfly Effect of Love: Lindsey and I reflect on the tiny moments that lead us to our partners - and even the babies that feel meant for us. (Spoiler: You might be surprised by how I met Matt!) Imposter Syndrome: Lindsey shares how she once questioned herself as a host of a dating podcast before meeting “her person,” and how those doubts don’t continue to creep in as much at least - as a married mom she feels its the ultimate testament to how it all ends up working out. Real Confidence: Lindsey credits her success to letting go of what others think. Control & IVF: We both open up about our fertility journeys and how releasing control in that process prepared us for motherhood - teaching us how to trust. Perfectionism & Type-A Tendencies: From IVF to birth plans, Lindsey shares how striving for control and perfection clashed with real life - and how letting go allowed space for so much more. Parenting with Perspective: We discuss how reflecting on who we were as children helps guide the way we parent today. Handling the Haters: I talk about how I process negativity by imagining how I’d want my daughters to respond to it. It’s not about me - it’s about modeling strength for them. Mean Girl Moms: We touch on the subtle (and not-so-subtle) ways adult behavior impacts the kids we’re raising. This episode feels like a cozy hangout with two moms keeping it real. It’s open, honest, and filled with the kind of conversation you want over coffee - honestly, I’m ready to start a series with Lindsey. You can find Lindsey on Instagram at @wemetatacme and @wemetatbaby and listen to her on her own podcast We Met at Acme available wherever you listen to podcasts. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    18: Combining Tools and Understanding with Behavioral Analyst

    What happens when an empath and a behavioral analyst sit down for a conversation? An honest, and incredibly helpful discussion about the realities of parenting. In this episode, I talk with Mandy Grass - known as The Family Behaviorist -about the tools, tactics, and truths of raising children, especially when things don’t go as planned. We recorded this after a rough morning on my end, and I found myself genuinely needing Mandy’s grounded perspective. Her insights were not only validating but also actionable - and I knew I wanted to share them with you. Mandy is a go-to voice in the parenting space for her practical strategies, thoughtful courses, and accessible behavioral tools. But beyond that, she’s also a solo parent to three girls, navigating their unique needs (including ADHD) with honesty and care. In this episode, we talk about: Why avoiding unnecessary transitions in the morning can make a huge difference How to blend empathy with clear boundaries Why our kids often save their hardest emotions for us - and what that really means The importance of repairing after parenting missteps, using what Mandy calls “name without blame” The four functions of behavior - and how understanding them can change everything Parenting post-divorce, and being mindful of how we speak about our co-parents around our kids Mandy’s wisdom is filled with compassion, structure, and reality - plus she shares some of the go-to resources she’s created, like her “technology contract” and more. Remember that even the experts have chaotic mornings - and that’s exactly why this conversation will leave you feeling seen, supported, and a little more sane. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    17: Fitting In with Jyoti Chand: Identity, Motherhood and Mental Health

    I’m really excited about this episode — not just because I got to talk (and laugh a lot) with this amazing human, but because she’s about to release a book that is so important. Jyoti Chand, also known as Mamajotes, is a mom of three, a beloved social media personality, and now the author of the upcoming book Fitting Indian, releasing May 13. Order it now. Jyoti advocates for self-love, self-care, and maternal mental health -  all of which are wrapped beautifully into her book, a teen graphic novel about a young South Asian Indian girl’s search for identity growing up in America. Fitting Indian is being hailed as an authentic and powerful story that highlights the harm of mental health stigma -  and the lifesaving power of finding an honest, supportive community. That’s exactly who Jyoti is: real, honest, open, and unapologetically herself. Her social media presence is one I look forward to seeing every time I open Instagram. This was actually the first episode I recorded virtually - and Jyoti’s humor came through immediately. She told me how her husband, two dogs, and three kids were all “trapped” in the basement so she could record uninterrupted (she emphasized that it’s a finished basement, not a dungeon). What we talked about: How identity can often feel “decided” for us based on our cultural backgrounds -  but how growing up in America can complicate that. Jyoti shared how she felt “Indian at home and American outside.” The importance of owning our mental health journeys and being open about them. Both Jyoti and I have shared publicly about being on Zoloft. When we recorded this episode a month ago, I was still on it -  and now, for the first time in 17 years, I’m not. I’ll be sharing more about that soon because normalizing mental health is so important. Jyoti opened up about her mother’s silent struggles with mental health, and how stigma made it even harder. Gender roles in the home -  how both of us “wear the tool belt” in our families, but are lucky to have partners who aren’t afraid to own the kitchen, too. The importance of showing affection to our kids - especially when we didn’t grow up seeing it modeled between our own parents. There’s more, but I’ll let you hear it for yourself. Jyoti is as real as they come -  and truly one of the most fun people ever. TLDR: Taking care of your mental health is self-care - and it’s non-negotiable. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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    16: From Yes Girl to Sure Girl - Katie Sands on Motherhood, Boundaries, and Being Real Online

    In this episode, I’m joined by Katie Sands - content creator, style expert, lifestyle influencers, and now, a mom.  It’s such a real and honest conversation about how motherhood reshaped her identity both online and off. Katie opens up about her IVF journey, the spiral of postpartum anxiety and OCD, and how even well-meaning messages from followers sent her into overwhelm during those early days. We also talk about something we both initially planned to do: not share our kids online. Spoiler: It’s the real reason this podcast was created. I’ve been rethinking -  and yearning for -  a different way to share my motherhood journey and my guidance  that feels more respectful of my girls, especially as they get older. We talk about: Katie’s journey in her career, the pros and cons of working for herself especially now that she is a mom.  Katie’s experience with IVF and how she feels and supports others close to her going through it.  Katie’s unexpected experience of Post Partum Anxiety and how sharing on social media contributed to that.  The complicated decision and process  to hire a nanny -  and the emotional layers behind it - especially as this was recorded the day before  she left her baby for the first time to be able to fully focus on being a sister for her brother’s wedding.The constant “do we bring the baby or not?” tug-of-war How relationships are tested when you have babies at the same time as others but you make very different choices And Katie’s transformation from always saying “yes” to learning how to say “no.” (she’s officially a JOMO girl!) We talked about the slippery slope of “Keeping up with the Jones’s” that often comes raising a family in NYC.   Key Takeaways: We don’t know what motherhood will bring until we’re in it , and that’s part of the magic of it. We learn, we grow, we mature and we set boundaries. Sharing vulnerably online can be grounding for both us as creators and our  communities.It’s how we feel so connected to our followers. This is the reason we went from “I won’t share my kids” to “I have to share them” and how we are still on the journey to finding that real longer term plan on this topic.  Boundaries aren’t limitations -  they’re signs of growth and alignment. Every mother’s path is different, and comparison only distracts us. I hope this conversation meets you wherever you are on your motherhood journey :) f you’ve felt the pressure to be everything to everyone - online and off - this conversation is a reminder that you’re not alone, and that redefining what motherhood looks like for you is not only allowed… it’s meant to be. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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ABOUT THIS SHOW

For the last two decades, I've worked closely with infants, toddlers, preschoolers and their parents - listening, guiding and supporting families and their young children. I've connected with so many parents through my social media account, texts, calls, and leading moms' groups. When we have open, honest and vulnerable conversations - no matter who you are as a parent - that's how we connect, learn and grow.We also discover so much about ourselves and how that plays into our parenting. That's why I created We Didn't Turn Out Ok, a podcast where you'll hear real conversations about challenges we face in parenting, hear how we uncover the roadblocks, often from our own stuff, and listen to how we work through what's often keeping us stuck. There will be professionals in the field, noteworthy guests and everyone in between.Using my own parenting journey and approach, combined with research-backed best practices, I am determined to help us all move forward from

HOSTED BY

Jennie Monness

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