We Didn't Turn Out OK with Jennie Monness

Jennie Monness
  • 4.8 (24)
  • MENTAL HEALTH
  • 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. 54: What is Confidence Really?

    6D AGO

    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

    17 min
  2. 53: Doing This for the First Time

    FEB 5

    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

    40 min
  3. 52: Breaking Cycles and Becoming Ourselves

    JAN 29

    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

    43 min
  4. 51: Step into the Group Chat

    JAN 22

    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

    53 min
  5. 50: How Loss Shapes Belonging

    JAN 15

    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

    52 min
  6. 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
  7. 47: The Psychology of Sleepaway Camp (for Kids and Parents)

    12/19/2025

    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

    42 min
  8. 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
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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
    54
  • Rating
    Explicit

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