The Lie Behind "Having It All"
How an entire generation inherited impossible expectations
I’m two weeks behind on my newsletter.
When I started this Substack, I promised myself that every Tuesday at 7 a.m., I would publish a new essay. And then I broke it, two weeks in a row.
You would think now that my husband is home I’d have more time to write. Instead, I spent the afternoons at the pool, catching fireflies with my girls, grilling dinner, and staying up way too late watching movies with my family because the truth is he’ll be gone again soon and I wanted to enjoy the little bit of summer we have together as a family.
So the essays waited.
What surprised me the most was that I couldn’t fully enjoy the reason I missed my deadline in the first place. While he was away, all I did was count down the days until we were together again. And yet now that he’s home, every afternoon I have this same nagging thought running underneath everything else: I should be writing. That’s when I realized the newsletter was beside the point. The real feeling was that no matter where I was, I felt like I needed to be doing something else simultaneously. As if I could be mentally alone with my thoughts enough to write a 1,500-word essay while chasing after my kids, catching up with my husband, and being fully present for every part of it.
A few weeks ago I was sitting with a group of moms when someone asked if I signed my daughter up for fall activities. Apparently registration opened weeks earlier. I laughed and said, “Honestly, I feel like I can’t keep up.” There was an awkward pause, then everyone exhaled, and one by one, they started admitting that they felt the same way and that they felt behind in every area: with their work, their kids, their marriage, their friendships, their home, themselves. Everything suffered a little. These were women who made completely different choices, and I kept wondering how they all landed in the exact same place.
I think it’s because we’re no longer comparing ourselves to one woman. We’re comparing ourselves to women everywhere who look like they have it all: the founder mom, the wellness mom, the Montessori mom, the mom with the best Amazon finds, or the mom with the perfectly organized house. They’re all different women, but our brains stitched them together into one impossible standard. Then we started wondering why we couldn’t become her.
For decades we’ve debated whether women can “have it all,” but along the way we turned that question into an obligation. My mother’s generation fought for opportunities women before them never had: careers, financial independence, and a seat at the table.
My generation said, “I’ll see your careers and raise you the ambition economy,” while our ovaries were quietly losing their minds.
We entered adulthood just as Lean In and Girlboss culture took over, and I went all in. Celebrities became founders, founders became celebrities. Ambition became an obsession that lived inside our pockets. Every time we opened our phones, there were funding announcements, promotions, women who somehow seemed to be at the top of their careers, raising kids, and never once looking like it cost them anything.
And underneath all of it, at the exact same time, our bodies were asking a completely different question: when are you having children? Two clocks. One biological. One cultural. Both ticking toward the same five-year window.
I remember lying on my OB’s table only half-listening to her talk about the benefits of freezing my eggs because I was answering work emails before rushing to an important meeting. Looking back, it feels almost absurd that I never questioned why the biggest career years of my life were also the years every doctor’s appointment ended with another reminder that fertility doesn’t wait.
That’s the real collision. It’s not “can women have it all.” It’s that an entire generation got handed two deadlines at once, and nobody warned us they would fall on the same due date.
And as if that wasn’t enough, motherhood changed too. It became a full-time performance review. There was suddenly a right way to feed your baby, a right way to help them sleep, a right way to play with them, a right preschool, a right amount of presence. Every choice started to feel like a referendum on whether you were doing it “right.”
We never replaced one expectation with another. We simply stacked them on top of each other. Until “having it all” stopped meaning women had more opportunities and started meaning excellence in every category of life, all at once.
Listening to Emmy Rossum on Call Her Daddy, I heard her describe what her therapist calls “the pancake problem.” She was running naked out of the shower to flip pancakes, then sprinting back to rinse the conditioner out of her hair so she could get to work on time while caring for her ten-month-old. It wasn’t really about pancakes. It was about what happens when every part of your life insists it’s the most important part. Her therapist told her something almost absurdly simple: sometimes it’s okay to do a little less.
I don’t think modern women forgot how to do less. I think we forgot how to decide what deserves less, because everything now feels equally urgent.
Mothers today spend more hours with their children than mothers did in the 1960s, even as their hours in paid work have nearly tripled. And the Fed’s own 2025 household survey found that even when both parents work full time, mothers are still more than three times as likely as fathers to call themselves the primary caregiver. The expectations placed on us multiplied, but the hours never did.
People often ask why I called this newsletter Have It All-ish. Because I want to live life in the “-ish.” The “-ish” isn’t settling. It’s accepting that you can’t have it all at once. That every meaningful life comes with invisible trade-offs, that some seasons belong more to work, others belong more to family, and that choosing one beautiful thing at a time doesn’t automatically mean you’ve failed another.
I’m still two weeks behind on my newsletter, but I got two weeks with my family.
Turns out, that's the “-ish.”



I love this so, so much. If I ever notice that writing feels like an obligation, that's when I know it's time to take a break to focus on family or work. It's just impossible to keep up with writing, school, work, family, etc. even when I so desperately want to. But then that gets me thinking... *why* do I want that? Usually it is the result of social media, cultural expectations, pressure, or something else. Something other than what I actually want. It's a lot to navigate!
Hi Hilary! I thought this was a really thoughtful essay. I think it's so important to give yourself grace in those moments when you skip a deadline or two to spend time with your kids. The world can wait, but you are the only mom they have. I especially connected with, "I don’t think modern women forgot how to do less. I think we forgot how to decide what deserves less, because everything now feels equally urgent." I really feel this way too. There is an urgency to build something, have a side hustle, get the essay out on time, connect with the subscribers. It's a lot to manage. But I think just having the perspective that we are the ones who decide where our energy goes every day. And some days it can be super family focused. And other days we can spend more time on our creative projects. Everything can have its place, just maybe not every single day.