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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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