We Didn't Turn Out OK with Jennie Monness

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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