We Didn't Turn Out OK with Jennie Monness

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

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

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

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

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

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

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

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

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

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

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