We Didn't Turn Out OK with Jennie Monness

Jennie Monness
  • 4.8 (24)
  • SOCIETY & CULTURE
  • UPDATED WEEKLY

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 our areas of where we "didn't turn out ok." Every guest will be sharing openly and honestly knowing that it will help them grow as a parent but will also help all of you listening. Welcome to We Didn't Turn Out Ok.

  1. 50: How Loss Shapes Belonging with Jamie Kolnick

    2D AGO

    50: How Loss Shapes Belonging with Jamie Kolnick

    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

    52 min
  2. 49: Sister Episode

    JAN 8

    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

    41 min
  3. 47: The Psychology of Sleepaway Camp (for Kids and Parents) with Eva Heyman and Caroline Leventhal

    12/19/2025

    47: The Psychology of Sleepaway Camp (for Kids and Parents) with Eva Heyman and Caroline Leventhal

    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

    42 min
  4. 46: Blending not Balancing with Jenny Fleiss

    12/10/2025

    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

    48 min
  5. 45: Hear it from my girls

    12/05/2025

    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

    16 min
  6. 44: Mind Shifting with Jamie Graber

    12/01/2025

    44: Mind Shifting with Jamie Graber

    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

    46 min
  7. 43: Rethinking Education with Alpha Co Founder MacKenzie Price

    11/18/2025

    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

    43 min
  8. 42: A Journey with Heart Openers Zev Eisenberg and James Gangemi

    11/11/2025

    42: A Journey with Heart Openers Zev Eisenberg and James Gangemi

    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

    41 min
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Trailer

4.8
out of 5
24 Ratings

About

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 our areas of where we "didn't turn out ok." Every guest will be sharing openly and honestly knowing that it will help them grow as a parent but will also help all of you listening. Welcome to We Didn't Turn Out Ok.

Information

  • Creator
    Jennie Monness
  • Years Active
    2025 - 2026
  • Episodes
    50
  • Rating
    Explicit

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