Not the word as metaphor — as actual fact. The idea that you can take something ordinary, something that exists only in your head, something you haven’t told anyone about yet because you’re not sure it’s real, and transmute it into a room full of people breaking bread at golden hour at The LINE Hotel in Los Angeles while Elaine Welteroth sits across from you and says the word “Oprah.”

That happened. To me. In real life. On film.

I want to tell you what it felt like to sit across from her, but first I have to tell you what it felt like to want to.

I was in New York when Elaine Welteroth became Editor-in-Chief of Teen Vogue. I was paying attention to culture the way you do when you’re in your twenties in that city and you believe, with your whole nervous system, that something important is always about to happen. And then it did. She was 29. She was the first. And I watched it the way you watch someone do a thing you didn’t know was possible — not with envy, but with a recalibration. A quiet internal adjustment. Oh. So that’s what’s available.

I didn’t know her. But I have been in conversation with her work for a decade.

So when she walked into the room on the evening of our season finale, and the room shifted the way rooms shift when a certain kind of person enters, I had to remind myself I was the host.

The evening was intimate by design. Fifteen women. Dinner. A show. An invitation from It’s Good — who understood from the beginning that the most powerful thing you can do for a community is seat them together and let something real happen.

What happened was this:

We talked about surrender. About the particular difficulty of being a driven, purposeful, arrow-shooting Sagittarius woman — her words, with great enthusiasm — who has to learn, over and over again, how to be still. How to wait for direction instead of manufacturing momentum.

She described the season before every major pivot of her career as one of terror. Of going quiet. Of stopping the parties and the socializing and sitting with the question: what did God put me here to do? And then listening. Actually listening. Not for the answer that made sense on paper, but for the one that arrived with conviction.

“God’s voice doesn’t confuse you,” she said. “If you’re confused, that’s probably not God.”

The room got very still.

She talked about her birth. About finding Black midwives. About having an experience so transcendent, so confronting with her own power, that she emerged from it with what she called downloads. Initiations. A sense of herself as something ancient and capable and not done.

She said she’s a warrior who is learning how to lay her weapons down.

I said I understood that completely.

We talked about motherhood as a master class in tenderness. About how the very things that made us successful — the drive, the intensity, the forward motion — are not always the things that make us good mothers. About how the universe keeps asking us to soften, and how softening is not the same as shrinking. About how she melts in the presence of her children in ways she could not have predicted and does not fully understand and loves completely.

I told the room I don’t carry a lot of mom guilt.

She did not flinch. She understood exactly what I meant.

At some point I asked her a question — I won’t spoil it, it’s in the episode — and she looked at me and said: “Okay, Oprah.”

I am still not fully okay about it.

Here is what I want you to know about this evening, and about this season, and about why it ends here:

I built Cool Moms because I was the first of my friends to become a mother and I needed the wisdom of women I admired. I didn’t know that eight years later I would be seated across from one of them, at a dinner I produced, in a room of women I chose carefully, talking about the things that actually matter. Purpose. Pivot. Tenderness. Faith. The alchemy of turning an idea into a room.

Elaine Welteroth gave this evening everything. Not as a celebrity doing a favor. As a woman who believes in what happens when you gather the right people and let them be honest with each other. She stayed. She ate. She talked to every person who wanted to talk to her. She is exactly as warm in person as you hope she is, and she is also funnier, and she is also doing the work, quietly and persistently, on the parts of herself that don’t make the highlight reel.

That’s the thing about sitting across from someone in real life. You stop seeing the resume and you start seeing the person. What I saw was a woman who is in her becoming — not arrived, but deeply, intentionally, joyfully in motion.

I am grateful she let us witness some of it.

This is the season finale. The conversation is long because it had to be. Watch it with dinner. Watch it in pieces. Watch the moment she talks about Ava DuVernay’s couch and tell me you don’t feel something shift inside you.

Thank you to It’s Good for making this evening possible, and for understanding that good food and good conversation are not separate things — they are the same offering.

Thank you to every Cool Mom who has shown up this season. In Los Angeles, in DC, in cities I haven’t gotten to yet.

I’m coming.

Not like a regular mom.

xx Elise

Cool Moms LIVE with Dr. Wendy Osefo is out now!

I need to tell you about the day before this episode dropped, because it almost didn’t feel like it was going to happen at all.

My order from SSENSE hadn’t arrived. My hair wasn’t cooperating. I was at a new venue without my usual crew, which meant sound issues, lighting issues, and me quietly spiraling in a way I hope didn’t show on camera. I had put so much into getting home — to DC, my actual hometown — to bring Cool Moms LIVE to the people who knew me before any of this existed. My sister was there. My aunt was there. People who have watched me build this thing from the beginning were finally in the room.

And I was standing there holding it all together with a prayer and a flat iron.

I’m telling you this because I want you to watch this episode knowing: the production quality is different. The soul is not.

Dr. Wendy Osefo is taller than you think.

I say this as someone who has watched every season of Real Housewives of Potomac with the kind of devotion usually reserved for religion. She walked into Shanklin Hall and I had to remind myself to be a professional. She is warm in the way that genuinely confident people are warm — not performing it, just extending it. Gracious with every person in the room. Never once short on words or wisdom.

She had come straight off filming a new season. I was gagging.

What I didn’t expect was how much she would give. This wasn’t a celebrity doing a favor. This was a woman who showed up fully, to a podcast, in her hometown audience’s city, for a community of mothers she had never met, and just gave.

On finding your voice:

At one point I asked her when she knew her voice was her gift. Her answer was honest in the way that reframes the question entirely.

She said she’s still finding it. That what’s changed is she’s stopped making excuses for it. Stopped dimming it so other people wouldn’t feel uncomfortable. Someone told her once: if someone feels inferior because of your light, that has nothing to do with you. She said that changed her life.

I believe her.

She talked about being a disruptor — about walking into a company culture and asking why lunch is only ten minutes. About how that kind of disruption makes people uncomfortable not because you’re wrong, but because you’re making them ask questions about themselves they weren’t ready to answer. She said she’s made peace with the fact that some people will never like her.

“My existence irritates their spirit. And I’m okay with that.”

The room erupted. Rightfully.

On motherhood and mom guilt:

One of the audience members asked about mom guilt — specifically, how do you let it go when you’re putting yourself first? And Wendy was honest: she hasn’t conquered it. She still has it. She probably always will.

But then I pushed a little. Because I’ve been sitting with something lately.

I told the room that I don’t carry a lot of mom guilt. And I meant it, not as a flex, but as something I’ve genuinely had to work through. When you co-parent, when you’ve had to humble yourself and accept that you cannot be everything, you start to understand that your child’s world is bigger than you. That the aunties, the grandparents, the village — they’re not filling in for your absence. They’re expanding what’s possible for him.

And sometimes I’ll say it: I think mom guilt is ego. The belief that we are so essential, so central, that our children can’t thrive without our constant presence. Sargent has an entire identity outside of me. It is my job to guide him to it, not hover over it.

Wendy looked at me and said: you should write a book about that.

She didn’t have to say that. She said it because she meant it. And I won’t forget it.

What I want you to know about Wendy now:

A year has passed since we filmed this. Things look different for both of us. And I won’t pretend I don’t know what she’s navigating publicly right now, because I do, and because meeting someone in person changes everything.

She is not a character. She is someone’s mother, wife, daughter, friend. She is a woman who woke up at 5 AM the morning of this event to do Pilates and meditate before showing up fully for a room full of strangers. She is a professor who has never failed a student because she believes that just showing up in this world already earns you something.

I wish her and her family the very best outcome. Deeply, genuinely, because I sat across from her and watched her be a whole, full person who gives more than she takes. That’s rare. That matters.

This episode is for the DC girls.

For my sister who was in the front row. For my aunt who finally got to see what I’ve been building. For every Cool Mom who has shown up for this community in cities I haven’t made it to yet — I’m coming!

And for everyone who has ever held something together with a prayer and a flat iron and done it anyway: the soul was always there.

Once the room settles you’ll hear what I’ve been sitting with all week: mothering is bigger than biology. Sometimes it’s your mother. Sometimes it’s the women you call when you’re unraveling. Sometimes it’s the community that reflects you back to yourself when your own home mirror can’t.

This conversation is a love letter to that kind of mothering — and a reminder that repair is a practice, not a personality trait.

We’re joined by actor, producer, and all-around multi-hyphenate Tika Sumpter a Queens-born New Yorker who’s been building a decades-long career across TV and film, from her early hosting days to roles on One Life to Live, The Haves and the Have Nots, Mixed-ish, and her unforgettable portrayal of a young Michelle Obama in Southside with You. She’s also Maddie Wachowski in the Sonic the Hedgehog films which is exactly why my son Sargent suddenly developed perfect posture the moment he realized who was in the room.

Tika showed up warm, grounded, and funny as hell AND she brought her mother with her. That kind of generosity is its own flex. Her newest chapter is deeply aligned with what we talk about at Cool Moms all the time: giving kids language, giving kids agency, and giving ourselves permission to apologize.

Her debut children’s book, I Got It From My Mama, centers on what kids absorb from us and what happens when we model repair. And if you’re trying to reduce screen time without turning into the Screen Time Police, she’s also building a whole audio world for kids through her podcast Adventures of Curiosity Cove, anchored by stories like “Ella the Curious.”

“Apology does not take power away from you. You’re giving your child a power they’ll thank you for later.”

This episode is about truth without fluff, motherhood without perfection, and becoming someone your child (and your people) can consistently return to even when you’re being held accountable by a small person with big opinions.

Last year, in a room full of women at The Line Hotel in Los Angeles, I sat across from someone I’ve quietly admired for a very long time.

Long before panels and podcasts and personal brands, I knew Jeannie Mai as the woman on How Do I Look? warm, funny, stylish, and somehow always talking to women instead of at them. She felt like the cool older cousin who told you the truth, fixed your eyeliner, and sent you back out into the world a little braver.

So when she joined us in front of a live audience mothers, aunties, women in various stages of figuring it out the energy shifted immediately. Not performative. Not polished. Just present.

Not like a regular mom. I’m a cool mom.

What unfolded was not a keynote or a highlight reel. It was a conversation. The kind that moves between laughter, side comments, and moments that sneak up on you when you are not trying to be profound.

We talked about dating including my poorly timed decision to go on a date with a white man on Day 1 of Black History Month. We talked about why our nervous systems cling to what is familiar even when it is not serving us. We talked about cringe moments being proof that you actually tried. About changing your mind out loud and letting your past selves exist without dragging them.

The nervous system will choose a familiar hell over an unfamiliar heaven.

Jeannie spoke with a kind of honesty that did not rush toward a takeaway. She talked about healing in pieces. About motherhood reintroducing her to herself. About raising a child with emotional regulation and unapologetic confidence in a world that will absolutely try to humble you early.

And then she would say something that cracked the room open and follow it with a laugh that reminded you this was not therapy. This was life.

No risk, no story.

Then we opened it up to the room.

This is our Ask A Cool Mom segment where the audience gets to ask the questions they are actually carrying. Not dressed up. Not theoretical. The kind that come from living a little and still wanting clarity.

How do you know if a decision is coming from a healed place or a hurt place

Ask A Cool Mom turned the conversation communal. Aunties. Mothers. Women brave enough to ask without over explaining. Less interview. More collective exhale.

There were moments that felt tender. Others that felt messy. A few that felt like inside jokes you did not realize you needed. That is the thing about being in a room like that you are not consuming content. You are witnessing something.

This episode was recorded last year but watching it now it still feels exactly on time. Because these are the questions we keep circling back to. About identity. About choice. About how we stay soft without losing ourselves and how sometimes staying soft looks like laughing at your own bad decisions.

This video lives here on Substack exclusively for subscribers because it deserves space. Because it deserves to be watched without multitasking. Because some conversations want your full attention and maybe a glass of wine.

Press play.Pull up a chair.Welcome to Cool Moms!

“Bitch, it’ll get done. It always gets done.”

I’ve been trying to have this conversation with Ilana Glazer for a long time — not the fictional Ilana Wexler, but the real Ilana: the mother, the artist, the Aries who refuses to learn the astrological big three but instead finds faith, the human who can move between chaos and clarity in a single sentence. When we finally sat down together in the daylight at Ace Hotel Brooklyn, something in the room unlocked. It felt exactly like the best afternoon conversations do: a little chaotic, a little holy, very funny, and surprisingly honest.

We talked about motherhood and identity, the slow deepening of faith, the spiritual ickiness of hope, and the strange pressure of being an “elder millennial” trying to hold it all together. We asked whether it’s PMS, perimenopause, paranoia, or just the culture collapsing. Ilana opened up about the early days of Broad City, what still drives them creatively, and how they are learning to parent, partner, and participate in the world with more intention.

There were jokes about astrology, questions about race and belonging, confessions about corporate alter egos, and the kind of soft power only another mother in the room can recognize. And the audience brought their own fire — naming the parts of motherhood that feel isolating, liberating, or both at the same time.

The conversation ended the way all truly good Cool Moms moments do: with a hug, a knowing smile, and the reminder that everyone in the room is just doing their best to live, evolve, and take themselves seriously in a world that rarely makes space for it.

Ilana Glazer is not Ilana Wexler — the reality is sharper, funnier, and far more compelling. And in this episode, all of that comes through

.— Elise

Photography by Jamie Pearl