Off Campus, based on Elle Kennedy’s beloved hockey romance series, is the latest, and I loved it. But I’m not here to debate what they changed from the books or whether I liked the casting. There are whole Reddit threads for that, and I trust you can find them.

What I want to talk about is three specific scenes that made me want to give the whole team a standing ovation. Not dramatic scenes, not iconic ones. Quiet, almost throwaway moments that normalize something we apparently still need to normalize: men who are actually good to women. (Note: spoilers ahead)

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The first one is small. Our lead, Hannah, doesn’t drink at parties. She mentions this to Garrett, the hockey player love interest, and he goes back into the kitchen to track down something else for her. He runs into his friend John Logan and asks if there’s anything non-alcoholic.

Garrett: Do you see anything non-alcoholic? It’s for Hannah.

Logan: She doesn’t drink?

Garrett: She said not at parties.

Logan: (picks up an unopened can) Here, try this. Closed cans are safer, bro.

Logan doesn’t make it weird. He doesn’t ask why. He reads the room — I don’t drink at parties communicates exactly what it communicates — and he gives a simple, practical solution. Garrett takes it back to Hannah. She thanks him and kisses him on the cheek.

What’s remarkable about it is how unremarkable it is. A woman signals something without having to explain it. The men around her read the signal. One of them hands over something specific and useful. Nobody makes a moment out of it. It just happens.

This is the bar. It is not a high bar. And yet…

The second scene is more substantive. Hannah has some history that makes physical intimacy complicated, and she’s asked Garrett to help her work through some of it. He’s nervous because he cares deeply about getting it right. He’s in the gym doing bench press when his teammate Dean walks over to spot him and senses something is up. Garrett asks Dean (who by general consensus has a significant amount of sexual experience) for advice.

What follows is one of the best conversations between two men I have watched on television in recent memory.

Garrett: I really want it to be good. For her.

Dean: If it’s her first time, she might not come.

Garrett: Not an option. She has to come.

Dean: Respect. Well, there is one thing that helps women come. The single most effective, highly recommended, enjoyed by all tool at your disposal. Trust. That’s it. She just has to feel completely safe. Completely relaxed. But consent is key. And she can’t consent if she doesn’t feel safe. So you just have to figure out what makes her feel safe.

Garrett: I’m just not sure I’m the kind of guy she should be trusting with this.

Dean: Well, if she asked you, she thinks you are. Which is fucking hot.

Two hockey players. In a gym surrounded by weights. Talking frankly about a woman’s pleasure and safety as the stated goal of the conversation. No irony, no discomfort, no machismo getting in the way.

This is the cultural argument I keep making: when you actually watch what romance audiences respond to, the pattern is right there. Women do not want watered-down men. They want men who are strong and present and fully themselves and who treat women like full human beings. Those things have never been in conflict, no matter how loudly the internet insists otherwise.

The third scene is a change from the book, and I think it was the right call.

After the breakup, Hannah hears about a campus-wide “hands off” policy — a declaration that she’s off limits to other men. She assumes Garrett issued it. She’s furious, and she confronts him.

He’s genuinely confused. It turns out the freshmen on the team had taken “he’ll lose his shit if someone hits on Hannah” as a threat rather than an expression of feelings. They apologize. And Garrett turns to her and says he would never do that. She should be with whoever she wants to be with.

That’s the whole scene. He just states clearly that putting a “no trespassing” sign on a woman without her consent isn’t romantic. It’s removal of autonomy, and it’s disrespectful.

There’s a loud argument online happening right now that respecting women costs men something. And then here we see three men who are coded as hyper masculine in every traditional sense—hockey players, conventionally attractive, physically imposing—and they are just... good. Attentive and protective and direct and trustworthy, and none of those qualities cost them anything.

These scenes work because nobody in them is trying to make a point. That's just what good men look like when you write them accurately.

This is what I mean when I say women’s stories are worth more than the industry gives them credit for. The audience for this genre has always known what it wanted: men who lead with care as a default rather than a concession. The show is currently #1 on Amazon, which tells you everything you need to know about what audiences actually want.

For the record, I also know that this is not some female fantasy version of men. I know so many men who are good like this. The bar isn’t imaginary. We just rarely see it onscreen.

Someone at Amazon looked at the romance novel market and decided that audience deserved more, and I am here for it!

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“Another one!” I said.

She sent back a string of laugh-cry emojis. We’ve both lost count.

In the last several months, so many of the most accomplished millennial women in my life have either left their corporate jobs or are taking time off to recover from burnout before figuring out what’s next. This is not a story about people who couldn’t cut it. These are the women who put in the hours, did the work, earned the titles, and have the track records to prove it. They are not looking for an easy way out. They are looking for a way out of something that stopped making sense.

The LinkedIn posts keep coming. We see them, we send them to each other, we cheer. And somewhere underneath the cheering is the shared recognition that we are watching something real happen, and it is happening to almost everyone we know.

For the record: I am genuinely thrilled for all of them. I’ve been working for myself for eight years and it is the best professional decision I’ve ever made. But I also know this pattern is not a coincidence, and it is not a lifestyle trend. It is a signal pointing to something that needs to be named.

The Great Millennial Career Crisis

If you haven’t heard the term “Great Millennial Career Crisis” yet, you may have felt it. It’s the slow burn of doing everything you were told to do and watching the promised payoff quietly fail to materialize. It’s being in what looks on paper like a good job, and still living paycheck to paycheck, still unable to afford things that feel embarrassingly basic, still wondering why you feel so financially behind when you’ve worked so hard. It’s the specific exhaustion of realizing that the formula you were handed wasn’t designed for the economy you actually graduated into.

Career coach Janel Abrahami, who coined the term, describes it as “a collective breakdown”—an entire generation realizing that the career contract they were promised doesn’t exist anymore. That’s the most accurate description I’ve come across. It’s not burnout exactly, though burnout is part of it. It’s something more structural: a mismatch between what we were told work would deliver and what it’s actually delivering, playing out simultaneously across an entire generation.

If you’re a millennial woman reading this: you are not failing at adulting. You are not bad at money. The system was not built to support the life it told you to want.

And if you’re a boomer reading this—especially if you’re looking at a daughter or a niece or a younger colleague and wondering why she seems so exhausted and so stuck—this is for you too. This is what’s happening to the women in your life, and it did not start with their choices.

Here’s the actual story.

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The Formula Stopped Working

Every millennial was handed the same playbook: go to college, get a good job, climb the ladder, buy a house, retire comfortably. Work hard enough and the system will take care of you.

The problem is that playbook was written for a different economy where loyalty was rewarded with stability, productivity gains flowed to the workers who generated them, and the life the formula promised was actually affordable on the salary it produced.

That economy ended somewhere around 1979. It just took a few decades for most of us to notice, because the formula kept looking like it was working. Until it didn’t.

Here is what actually happened.

The Economic Stack

Millennials didn’t encounter one bad economic moment. We encountered a sequence of them, each one compounding the last, with no recovery window in between.

The Great Recession (2008–2009) hit us at exactly the wrong moment: at entry level, or just before it. Those who graduated into it spent their formative career years in a labor market where unemployment stayed above pre-recession levels for years and wages stagnated across the board. By 2016, millennial families were approximately 34% below the wealth level economists would have predicted them to reach based on where earlier generations were at the same age.

Student debt arrived at the same time as the degree it financed became less valuable. Baby boomers paid an inflation-adjusted average of $3,519 per year for public college tuition. By 2023, that number was $9,750, a 177% increase. After adjusting for inflation, college costs grew 52% between when boomers and millennials attended university, and have spiked 143% since 1963. Millennials now carry nearly one-third of all student loan debt in the country.

Housing became the wall that ended the conversation. When most boomers turned 30 around 1985, the average single-family home cost $82,800. When millennials turned 30 around 2019, that number was $313,000. Home prices have risen approximately 1,045% since 1973. As of 2025, the average first-time homebuyer is 40 years old.

And if you’re wondering whether “lower cost of living” cities offer an escape hatch: the average sale price for a home in Nashville—the city people have been fleeing to from Los Angeles for affordable housing—hit $853,811 in May 2025. In Los Angeles, the typical home value is $946K.

There is no cheaper market anymore. There are only markets where the unaffordability arrived more recently.

And then came the pandemic, which layered hiring freezes and mass layoffs on top of an already strained foundation. Millennials have now experienced two economic catastrophes in their working lives, with no meaningful financial buffer between them.

The Pay-Productivity Divorce

Here is the part that is genuinely enraging: the economy has been producing more value per worker than at any point in modern history. We are working harder and more efficiently. The wealth exists. It is simply not going to the people who created it.

Since 1979, productivity has grown 8x faster than typical worker pay. To put specific numbers on it: from 1979 to 2025, productivity increased approximately 90.2%, while hourly compensation grew only about 33%. Before 1979, the two grew together—policy deliberately ensured that the gains of an expanding economy were broadly shared. That policy was abandoned. The divergence is not accidental.

Where did the money go? When the Bureau of Labor Statistics first started tracking this data in 1947, workers received 70% of the nation’s total income. By the third quarter of 2025, that share had fallen to 53.8%, its lowest level in 78 years. The rest is in corporate profits and returns to investors.

Meanwhile, the top 1% of U.S. households held 22.8% of total net worth in 1989. By 2024: 30.8%. The richest 1% now own half the entire stock market. The average middle-class household holds $496,000 in wealth, less than 2% of what the average household in the top 1% holds.

This is what “the economy is doing great” actually means. The economy is doing great for some people.

The Always-On Tax

Layered on top of the financial math is something harder to put a number on: the dissolution of the boundary between work and life.

The smartphone made it permanent. Remote work made it complete. What used to be a 9-to-5 with occasional late nights is now a continuous expectation of availability that doesn’t resolve on Friday at 5pm. Millennials spend an average of 40 hours per week on work communication alone—in some cases exceeding the standard workweek before the actual work has even begun. Bosses send emails at midnight. Slack messages arrive on Sunday. The unspoken agreement is that your life is always interruptible.

This matters specifically because of what we were promised in exchange for it. Boomers entered a system that rewarded that kind of dedication with stability, pensions, clear advancement, and a wage that kept pace with cost of living. Millennials got the same hustle expectation without the guarantees. We burned ourselves out chasing something that quietly stopped being available.

Millennials are now the most dissatisfied generation at work, rating job satisfaction an average of 4.6 out of 10, lower than Gen Z, Gen X, and boomers.

And here is the thing that the “millennials just want purpose” conversation always gets wrong: demanding meaningful work is not a luxury position or a personality quirk. When your job colonizes your evenings and your weekends and your nervous system, it had better mean something. The ask for purpose is not entitled. It’s proportional.

The Women’s Tax

Everything above is worse if you are a woman.

Women in the prime working-and-childrearing years of 25 to 34 do 2.3x as much household work and 2.8x as much childcare as men. This is not just a function of having children: even among childless women working full-time, women do 1.8x as much household labor as their male peers.

Meanwhile, childcare costs have risen at approximately twice the rate of overall inflation since August 2024, and parents now spend up to 20–30% of their income on childcare. Half of millennial mothers have considered leaving their jobs because the math no longer works—the cost and stress of childcare outweigh their earnings.

In 2025 alone, 455,000 women left the workforce. Caregiving responsibilities were the number one reason, cited by 42% of those who quit. The Catalyst researcher who studied this put it plainly: “Women are not opting out. Rather, they’re very literally being torn between their caregiving responsibilities and the rigid way that we continue to do work.”

The system still operates as though someone is home. Nobody is home. Both parents are working, the childcare system is broken, the second shift hasn’t shifted, and women are absorbing the cost of all three.

The Gerontocracy Problem

One reason none of this has been adequately addressed is that the people with the power to address it are not living it.

Steven Spielberg was 27 years old when he filmed Jaws, the movie that created the modern “summer blockbuster”. Lorne Michaels was 30 when he launched Saturday Night Live. The industries they were trusted to remake, at those ages, were reshaped by the bet made on them.

As The Ankler wrote about in a great piece, “Everyone Who Ran Hollywood Used to be Young. What Happened?” Today, every major Hollywood studio head is between 51 and 68, and no one on the recent shortlist for senior studio roles was under 50.

Congress is no different. The 119th Congress, seated in January 2025, is the third oldest in U.S. history. The median age of the Senate is nearly 65. The median age of an American is 39. The people making policy are, on average, a quarter-century older than the people living under it. Research confirms that older politicians prioritize legislation benefiting older groups (like pension increases) while younger legislators are more likely to support childcare and education spending. The representation gap has policy consequences.

The market understands what this costs, even when politics doesn’t: stock prices decline when younger CEOs die unexpectedly, while the sudden deaths of older executives drive price increases.

We are, across politics, entertainment, and corporate America, living through the consequences of the same generation holding the reins for the last 35+ years. For me, the fact that Donald Trump, George W. Bush and Bill Clinton were all born in the same year (1946) within 2 months of each other showcases this problem.

You Are Not Failing. The System Isn’t Working.

Here is what I want you to take from all of this:

The thing you’re feeling—the financial precarity despite doing everything right, the exhaustion that doesn’t resolve, the quiet dissonance between your credentials and your circumstances—is not a reflection of your choices. It is the predictable output of a system that extracted maximum labor from one generation while routing the gains elsewhere.

You are not bad at money. You are living in markets where a median home costs more than four times the median household income. You are not lazy. You are working 40-plus hours a week of communication before the actual work begins. You did not fail to plan. You were handed a plan that was built for an economy that no longer exists.

The friends of mine who are going independent right now? They are not giving up. They are being rational. They looked at a system that stopped delivering on its end of the deal and made the logical decision to renegotiate the terms. That’s the most sensible response to an unreasonable situation.

And the fact that so many accomplished women are arriving at it at the same time—in the same months, across the same industries, in the same friend groups—tells me it is a signal worth paying attention to.

What Now?

I don’t have a tidy prescription for any of this. I’m in the middle of remaking my own career in response to my industry collapsing in real time. The structural problems are structural and they don’t resolve with a morning routine or a mindset shift. But I do believe that the way we start remaking the work world is by building something different and supporting each other while we do it.

One thing I want to use this space for is highlighting women who have taken the leap and gone out on their own. These are the people I find most energizing to watch because what they’re building when they stop optimizing for someone else’s org chart is genuinely worth paying attention to.

So if you’ve made the jump—consulting, freelancing, your own business, your own Substack, whatever shape it’s taken—I want to hear from you. Reply and tell me about your work. Include a link to your website, your newsletter, anywhere people can find you. I’ll be sharing them here.

The more we build in public and support each other doing it, the more collective power we have to demand something better.

If You Want to Go Deeper

Some of the voices who have been naming this in real time:

• Janel Abrahami coined the term “Great Millennial Career Crisis” on TikTok and has done smart, specific work on what she calls the “portfolio career” as a response. Her Substack, Going Places, is worth subscribing to.

• Sonya Barlow of LMF Network wrote a piece on Substack titled Millennials Are in a Career Crisis. Or Did We Just Stop Pretending? that covers the identity dimension well.

• The Bossed Up podcast, Episode 539 with Janel Abrahami goes deeper on the structural vs. personal failure question.

• Anne Helen Petersen’s 2019 BuzzFeed essay on millennial burnout, now a book Can’t Even, remains the foundational text on why this generation specifically got here.

• The Everygirl’s full feature on the millennial career crisis is a thorough, well-reported companion piece to this one.

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For women who do serious work and have unserious pleasures, and want to build a life entirely on their own terms. Essays, guides, and honest takes on working for yourself, why women's stories are worth billions, and a life built across two coasts.

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Inside was an indigenous feather headdress from South America. She looked at it for a moment and said, with excitement: “That looks like what Juma wears!”

Juma Xipaia is an indigenous chief from the Brazilian Amazon and also happens to be the protagonist of Yanuni, a documentary I worked on this year. It is a beautiful film that was shortlisted for the Academy Awards, with Leonardo DiCaprio as an executive producer and made by award winning documentary filmmaker Richard Ladkani. I brought both girls to a screening last fall, and they had the chance to meet Juma. They were learning about the Amazon in school at the time, and we talked about it for months afterward. The younger one made Juma a card that Juma has framed at her house.

Standing in that museum, in front of a display case that could easily have been just another artifact behind glass, she had context instead. She had a face, a name, a story, a real person she’d met and talked to in mind. The headdress wasn’t a historical object. It was something that belonged to someone she knew.

That is what storytelling does. It’s why I love what I do so much.

I’ve spent fifteen years in entertainment, the last ten exclusively on the social impact side—human rights films, social justice stories, feature films and documentaries about the parts of the world most people aren’t paying attention to until someone makes them impossible to look away from. I went freelance eight years ago and built a real business doing this work, and the belief I’ve carried the entire time is this:

A news story doesn’t make an eleven-year-old stop in a museum and recognize something as belonging to a person she knows. A film does. That has always been true and it will keep being true, regardless of how the industry changes.

What I’m grieving is that the industry seems to have forgotten it.

Trump ruined everything.

In Q1 of 2025, the cuts came fast and the damage was long-term. As soon as the funding cuts to USAID, the National Endowment for the Arts, and all the other DOGE casualties came through, the funding infrastructure that made impact work viable vanished seemingly overnight. Filmmakers rely on philanthropic funding to support their impact campaigns—grants, individual donations, key partnerships, and institutional support—and it is what made it possible for so many films to get out into the world and make real change. The cuts, coupled with the new pressure on private philanthropy to fill the gaps of institutional funding cuts, means that a significant amount of that is simply gone now.

And separately but certainly related, the industry got scared. The studios and streamers that used to have moral courage—that told stories people were afraid to tell, that understood their own power to open a door or shift a perspective or make someone’s reality impossible to ignore—have gone very quiet. Nobody wants to touch anything that might be perceived as “political”. Nobody wants to be a target. The industry I was drawn to because it was full of artists who understood that art has always been at the center of social change has become, in a lot of rooms, an industry of people waiting to see what’s safe and profitable.

I have friends who have worked consistently their entire careers—people who were turning down jobs a few years ago because they simply had too many offers—who have had no work. Not a slow season. No work. These are experienced, talented, sought-after people, and the thing they built their entire professional lives around has become uncertain in a way none of us have seen before.

The career I thought I’d have forever.

There’s a particular kind of grief that comes from loving something that can’t love you back the way it used to. It’s not heartbreak exactly, but it’s more like watching someone you deeply admire go through something that’s changing them, and not knowing yet who they’ll be on the other side, and having to keep showing up in the meantime.

When people ask what I would do if this work stopped being viable, I genuinely don’t have an answer. I’ve thought about it, but the reality is, there isn’t one. The stories, the work of getting people to see them, the belief that a film can do something a news story or policy paper cannot. That’s not just a “job” to me. It’s a conviction I’ve had since before I knew it was a career. And it makes this moment harder, not easier, because it would be so much cleaner if I’d simply outgrown the work or wanted something different after fifteen years. Instead I want exactly what I’ve always wanted, in an industry that is contracting around me in real time.

Yanuni didn’t get distribution. A film shortlisted for the Academy Awards, with one of the most recognized climate advocates in the world attached as an executive producer and an award-winning filmmaker behind the camera. And it didn’t get distribution. I’m still not totally over it. The work was extraordinary. The story mattered. And the industry, in this particular moment, didn’t have room for it.

Why didn’t they have room? Because it’s a documentary that is not pop culture, true crime, sports, or celebrity-driven. It’s about climate activism in an era where everyone wants to play safe.

These are the exact kinds of films that are the most important for people to see, and now audiences don’t get the thing that would have opened something in them. The eleven-year-olds won’t have the context when they stop in front of the display case.

The truth is, I wanted to do this forever. I knew the shape of the work would evolve over time—that’s the nature of any industry, and honestly I’ve always loved the problem-solving that comes with change. But I didn’t expect it to fall off a cliff. I didn’t expect the industry to be taken over by corporate conglomerates whose primary relationship to art is as a line item, who are more afraid of catching the ire of this administration than using the cultural power they actually have to stand up for something.

I’m grieving what entertainment used to be. The moral courage of it. The belief, shared widely enough to act on, that stories could change things and that was reason enough to tell them.

Eight years of working for yourself teaches you a few things, and one of them is that you can adapt. That pivoting isn’t failure—it’s just what you do when the ground shifts under you, and the ground has shifted under me more than once. I know how to find the new footing. I’m doing it right now, actually, figuring out what the next version of this work looks like and building toward it with the same stubbornness I’ve brought to everything else.

I’ll be okay. I know I’ll be okay.

I’m just also sad. And I think that’s allowed.

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I’m Kathleen, a creative strategist and small business owner with 15 years in entertainment. I run awards and impact campaigns for clients like Netflix, A24, Apple TV+, Amazon, and HBO, build impact partnerships, and write about work, romance novels, and living a bicoastal life.

And I remember thinking: well, if Shonda’s doing it, it must be legitimate.

So I read them. All of them. Quickly and without apology, which was new for me.

That last part is the part worth examining.

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I was a mathlete growing up. Genuinely, like competitions with excused absences from school, the whole thing. I loved it. I was a math and science person, deeply academic, and I cared about serious things: human rights, social justice, making some meaningful contribution to the world. And for the record, that’s not a phase I grew out of. It’s still what I do. I work in the impact side of entertainment—serious films about serious subjects—and I love it.

But somewhere in the process of becoming that person, I had drawn a quiet line around what I was allowed to consume and enjoy. Books that were too escapist. Stories that were too romantic. Things that were, in my own internal ranking system, unserious. Below me.

Looking back, this is hilarious. I have read countless romance novels since that first Bridgerton book. I have LOTS of opinions about the genre and recommendations on which authors and series I like best. The version of me who thought she was too serious for this was not protecting her intellect. She was just limiting her picture of herself, and not even consciously. She had absorbed a hierarchy about what counted as worthy and then lived inside it so completely she forgot it was a choice.

Permission to color outside the lines

Around the same time I was reading my way through the Bridgerton series, I was also turning 30 and looking up from my life for what felt like the first time.

I had left my job to work for myself. I was single. I was genuinely uncertain whether I wanted kids, which was its own unsettling realization because I had always assumed I’d eventually want the things you’re supposed to want. The relationship, the house, the timeline that more or less followed the script. I had never really asked myself the question directly. I had just assumed the answer was yes.

When I finally asked, the answer was: I don’t know. And in a lot of ways, no.

That surprised me more than I expected. I had done everything I was supposed to do. And now I was looking at a life that didn’t follow the lines, not because I had blown anything up, but because I had just quietly, incrementally built something different, without ever deciding to. Without ever giving myself “permission”.

The romance novels were smaller than all of that, obviously. But they were part of the same thing. The same pattern of waiting for external validation before letting yourself want what you actually want. Needing Shonda Rhimes to option the series before I’d let myself read it. Needing the life to already be built before I’d let myself call it intentional.

Aspiring Rich Wine Aunt

I’ve had “Aspiring Rich Wine Aunt” in my Instagram bio for years.

It started as a joke, but it has stayed because it feels like the most honest description I have for the life I want. Not wealthy in the generational wealth, retire early, buy a yacht sense. Not hustling toward some version of success that requires me to be serious about everything all the time. Something more like abundant. Expansive, generous. And ultimately, mine.

The aunt who travels and has stories and shows up with good wine and better advice. Who has done something a little different and is honest about what she learned from it. Who has figured out that the script was optional and who wants you to know that too.

That’s what this is. Essays about working for yourself, and the financial infrastructure nobody explains when you start. Honest takes on why women’s stories—the ones the industry keeps underestimating—are worth billions. Notes from a life split between Los Angeles and New York, and what it actually looks like to build something outside the lines.

Serious work. Unserious pleasures. No apology for either.

You don’t need Shonda’s permission. I just wish someone had told me that sooner.

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I work in awards campaigns. I didn’t work on Sinners. And I really, really hope it wins.

Not just because it’s a great film, though it is. But because of what a win would signal for the future of this industry.

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The Radical Act of an Original Story

Perhaps the most remarkable thing about Sinners is also the simplest: it’s an original story.

Not a sequel. Not a remake. Not an adaptation of a bestselling novel, a comic book, or a podcast. Just a film built from an idea.

That used to be the norm. But over the past two decades, Hollywood has steadily shifted toward existing intellectual property as the foundation of its business model. Today, only about a quarter of major studio films are based on original ideas. The rest are sequels, remakes, and adaptations… built on the logic that familiar is safer, easier to market, easier to justify to a corporate board.

Original films are harder to model. But they’re also where the most interesting storytelling tends to live.

People Actually Showed Up

Here’s the thing that keeps striking me: almost every non-industry person I’ve talked to this awards season has seen Sinners. In many cases, it’s the only Best Picture contender they’ve seen.

That shouldn’t be remarkable. But it is.

Over the past decade, the Oscars have drifted further and further from mainstream audiences. Many nominated films are critically admired but culturally invisible: respected within the industry, largely unseen by the public. Sinners became something closer to a cultural moment. People talked about it. Recommended it. Dragged their friends to see it.

A Best Picture win for Sinners would be a rare alignment between awards recognition and actual audience engagement. And the Oscars desperately need that alignment if they want to stay culturally relevant.

It Broke the Awards Calendar Too

Awards campaigns follow an unofficial playbook. Films most likely to win arrive late in the year, carefully timed to stay fresh in voters’ minds. Sinners premiered last April—a timeline that would normally place it at a serious disadvantage.

And yet here we are.

If it wins tonight, it will challenge another quiet assumption about how this industry works: that awards success can only be engineered through release timing and careful campaign mechanics. These assumptions and mechanics pay my bills, but we need to remember that sometimes cultural momentum—audiences discovering a film, championing it, refusing to let it fade—matters just as much.

Culture, Folklore, and the Power of Story

The part of Sinners that I keep thinking about most isn’t the horror. It’s the history.

The film draws deeply from the blues and the cultural life of Black communities in the American South—the juke joints, the music, the gathering spaces that served as safe havens during a period defined by segregation and racial violence. It even includes a nod to the lesser-known role of Chinese grocers in the Mississippi Delta, a real and fascinating piece of that region’s social history that almost never gets told.

And then there’s the central villain: an Irish vampire. Which isn’t just a horror trope. It’s allegory.

Irish immigrants in America were once marginalized outsiders who ultimately gained power through assimilation into whiteness. In Sinners, the vampire arrives drawn to the vitality of the culture he encounters, and what begins as fascination quickly becomes domination. Colonization. Cultural extraction. The repeated historical pattern of dominant groups entering spaces they didn’t build, taking from them, and destabilizing them in the process.

Sinners doesn’t present any of this as a lecture. It embeds it inside genre storytelling: music, horror, folklore, performance. That’s what powerful cultural storytelling does. It turns history into narrative. It lets audiences experience political and historical truths emotionally, through story.

That’s the reason I work in this industry. Film and television are the only mediums that build empathy at scale. The more we see each other—really see each other—the more human we become.

The Ownership Question

The story behind Sinners is almost as important as the story on screen.

Ryan Coogler negotiated a deal with Warner Bros. that granted him significant creative control and long-term ownership rights over the film. In the modern studio system, that’s genuinely rare. And it matters because ownership determines who benefits from cultural success, not just today but decades from now.

As studios have consolidated and IP has become the central asset in entertainment, filmmakers have steadily lost leverage over the stories they create. Rights get centralized within corporations. Creative talent gets treated as contractors.

Coogler pushed in the opposite direction. And the result was one of the most culturally significant films of the year.

A Word on One Battle After Another

I’ll be honest: I didn’t love the other major contender in this race. I found it narratively unconvincing in ways that have been well-documented by people far more eloquent than me. I’ll leave it at that. What I’ll say is this: the contrast between the two films sharpens the point. One made me feel something, made me care enough to listen to interviews, google more about aspects of the history. The other didn’t.

Awards seasons are full of films the industry decides matter. Fewer are films that actually do.

What a Win Would Actually Signal

Sinners did something rare: it captured critical recognition and genuine cultural momentum at the same time. Its historic 16 nominations reflect that. But if it wins Best Picture tonight, the significance goes beyond the trophy.

It would signal that original stories, made by filmmakers who actually own their work, for audiences who actually show up… those films can still win. And if they can still win, maybe more of them will get made.

In an industry increasingly shaped by corporate logic and franchise economics, that’s not a small thing.

That’s the whole thing.

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Hi, I’m Kathleen,

and I’m here to share what 15 years working in entertainment and strategy, eight years of which have been self-employed, has taught me about business, work, and culture.

Today we’re here to talk about the one piece of advice that has saved me thousands of dollars and probably many panic attacks and was the best piece of advice I got when I started working for myself eight years ago.

It is unsexy, but it is the key to creating the foundation of a good business.

Drum roll, please.

Yes, we are here to talk about taxes.

The thing that nobody wants to talk about, but this time of year is incredibly important.

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When I first started working for myself — or was thinking about it — I met with several people that had been doing it longer than me.

One person gave me this piece of advice that I try to pass on to everybody as often as I can:

Always pay your estimated taxes.

At that point, I didn’t even know what estimated taxes were.

I was used to being a W-2 full-time employee where all of my taxes were handled by my company and HR.

And suddenly I was staring down the barrel of working for myself and having to handle every single aspect of running a business on my own.

It was overwhelming.
It was intimidating.

He told me that if you work for yourself, you have to pay estimated taxes to the government four times a year.

And if you don’t, there is a penalty — which I had no idea even was a thing.

Obviously, I knew that I would have to pay taxes at some point and in some way. But from the very beginning of working for myself, I did the thing that I’m about to share with you.

And it has saved not only thousands and thousands of dollars over the years, but so many panics, so many headaches, so many moments that I’ve seen other people walk through.

So let’s start with the basics.

There are tax deadlines four times a year.

If you work for yourself, you have to pay estimated taxes on these four deadlines:

• April 15th

• June 15th

• September 15th

• January 15th

Essentially, you pay estimated taxes for what you made in the quarter preceding the deadline.

So for April 15th, you’re paying estimated taxes on the money that you made from January through March.

There are many ways of calculating this. I would recommend talking to an accountant about it.

But you pay your estimated taxes to the government — and you do it four times a year.

The second point:

If you do not do this, there are penalties.

It’s structured as a percentage penalty for inadequate payment.

For every day that you have not paid the adequate amount, there is a penalty.

Nobody wants to pay penalties when you can just get ahead of it.

There is a huge temptation to say:

“Oh, I need the cash flow now and I will deal with taxes later in April when it’s the tax deadline.”

I understand that temptation.

But oftentimes what I see happen—with friends, with colleagues, with people who ask me about this—is that they spend the money and do not save it.

Then April 15th comes along and they have not accounted for taxes.

And suddenly they’re stuck owing thousands of dollars in taxes plus penalties that they have not planned for.

And it sends people into an understandable panic.

So here’s my advice:

If you build this habit as soon as possible, it becomes so easy to maintain.

What I did when I first started working for myself, before I had incorporated my business and had separate checking and savings accounts, is I opened a separate savings account in my bank.

I put 30% of everything that I made straight into that savings account.

And I pretended like it didn’t exist.

I didn’t spend it.

When the tax deadlines came up for that quarter, I would work with my accountant to figure out what I needed to pay.

I would pay my tax estimates, and I would keep the rest of that 30% sitting in the savings account.

At the end of the year, if there was any leftover, I used that to fund retirement accounts—because you’re also still on the hook to figure those out for yourself as well.

It made such a big difference to just put a set percentage away directly into that savings account and pretend that it didn’t exist.

I never spent it.

And in all eight years that I’ve worked for myself, I have never owed taxes.

I’ve actually gotten refunds most years—small refunds, but still a refund—because I paid my taxes throughout the year.

I have never come into tax season in April with a huge surprise tax bill that I did not know how to pay.

And it has probably saved my business.

It has definitely saved me thousands of dollars, and many hours of therapy and panic and anxiety.

So if I’m going to give anybody a piece of advice when they’re first starting, it is this:

Please, please, please pay your estimated taxes every single time.

Do not wait.
Do not say you’re going to figure it out later.

It will be the one thing that can really set your business apart from a sustainability perspective and allow you to keep working for yourself in the long term.

So please save this.

Share it with a friend who you know is thinking about going freelance or is in the middle of it.

You can always start paying your estimated taxes and start saving for it.

It’s tax season, so pass this advice along.

It is the unsexy parts of working for yourself that make the biggest difference.

That’s what I want to share it with more people. Because it’s something that helped me tremendously, and I want to make sure that as many people as possible can get that same help.

I appreciate that someone gave it to me.

So I want to pay it forward.

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Exit Interview is the honest debrief on work, power, and culture. I'm Kathleen—I've spent 15 years working in entertainment, advocacy, and strategy, and the past eight building a business on my own terms. This is where I say the quiet part out loud: how power actually moves, how careers really evolve, and what I've learned since stepping off the corporate ladder.

My name is Kathleen, and I have spent 15 years working in the entertainment, marketing, and impact sectors. The past eight years of that, I’ve spent working for myself and running my own business.

I started this Substack (and this subsequent Substack podcast) to help pass along the hard-earned insights and lessons I’ve learned along the way.

When I started working for myself eight years ago, I didn’t really know anyone who was doing it yet. I was 28, almost 29 at the time, was leaving a really toxic work environment and decided to try my hand at freelancing to see if it could buy me a little bit more time to find the next right job.

And within six months, I was making more than I had before. I doubled revenue year over year for the first four to five years. And I ended up working for myself longer than I ever planned to from the from the get go.

I what I had planned to be a three to six month stopgap turned into the best career decision I’ve ever made.

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I am now in my mid to late 30s and I have so many friends that are facing their own career fork in the road decisions. So many millennials who have spent their careers climbing the corporate ladder, doing all of the things we were told to do to get ahead and finding themselves up against a glass ceiling of possibility due to the current economic realities, the looming threats of AI, the contracting and consolidation of wealth and power to the very few hands at the top, the lack of corporate turnover in terms of leadership and a whole number of factors that leave us burnt out, overwhelmed, overworked and unsatisfied.

So many people are thinking about what it looks like to take on consulting projects or work for themselves, and I personally love it because I think taking your career and your work into your own hands and stepping into that level of empowerment is one of the best decisions you can make for yourself. I also know that it’s risky—when I did it I did not have kids, I was not married, I had a roommate. My degree of responsibility was a little bit different than what a lot of people are considering now, and my hope and my goal is that some of this content can help de-risk the decision.

That it can help make you feel a little bit more comfortable, a little bit more secure in how to put the pieces together and structure moving forward.

The reality is that working for yourself, yes, it comes with a lot of freedom. I’ve done many a work days abroad and on trips that I wouldn’t have been able to otherwise.

But it also means doing every part of running a business.

It means paying taxes.
It means figuring out retirement and health insurance.
It means planning ahead.
It means forecasting.
It means business development.
Etc.

And that can that can be overwhelming.

And so many people are used to their companies handling so many of the logistics and back end systems that make a business run and just being responsible for doing their particular job function. And suddenly you’re facing having to do a lot more.

So my whole goal with this Substack and with this podcast is to share some of the lessons and insights I’ve learned along the way. Probably share some stories from people that are walking through it right now or have navigated it differently or in different industries than I have.

And to use it as a space to reflect on what it means to rethink work in this current moment when we’re all facing such big looming questions about our futures and the future of work in general.

I also want to share the business lessons and insights I learned from working in an industry—entertainment and culture and impact—that have tremendous impact on the world and in the way that we understand things.

So this podcast, though not really a traditional podcast, more of a place to have conversations from another human being, is where I hope to do that.

So thank you for listening, for coming along to this somewhat crazy experiment that I’m running as someone who doesn’t like being in the spotlight. But I do really want to help people navigate these really big looming questions and make it seem a little less scary, a little less overwhelming, from the perspective of someone who’s done it for almost a decade.

So thank you for listening to Exit Interview, where we get honest about the realities of work and power and culture and have some of the conversations you can only have when you walk out the door.

I’m Kathleen, and thank you so much for listening along!

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Exit Interview is the honest debrief on work, power, and culture. I'm Kathleen—I've spent 15 years working in entertainment, advocacy, and strategy, and the past eight building a business on my own terms. This is where I say the quiet part out loud: how power actually moves, how careers really evolve, and what I've learned since stepping off the corporate ladder.

Men talking about it seriously on hockey podcasts. Women dissecting scenes like they’re case law. Professional athletes coming out and naming the show as part of what made them feel ready.

That kind of cultural saturation doesn’t happen by accident.

A couple of Saturdays ago, I finally watched Heated Rivalry. All six episodes in one sitting. Downloaded the book immediately after. Read that in a day too. Then, yes, watched it again.

What struck me almost as much as the show itself was the scale of the reaction around it. And not just in an algorithm-boosted way. It was omnipresent because people actually cared and talked about it.

No paid marketing campaign can manufacture that. You can't buy genuine cultural saturation—you have to earn it.

And I can’t stop thinking about why a low-budget Canadian queer hockey romance became one of the most talked-about shows of the year, launched its stars into superstardom overnight—and what that says about who decides what gets made.

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The Numbers We Keep Ignoring

Romance is the highest-selling book genre in the world. It has been for years. BookTok has only accelerated that reality—backlists resurrected overnight, authors selling millions because readers filmed themselves crying over a single chapter.

The audience is massive. It’s loyal. It mobilizes.

And yet in film and television, romance still gets treated like it’s slightly unserious. A little indulgent. A little “for women.” We’ll spend hundreds of millions of dollars on another action franchise without blinking. But a romance—especially a queer one, especially an explicit one—still has to justify its existence in a way other genres don’t.

That disconnect isn’t about market size. It’s about hierarchy.

The Decision That Made the Difference

What’s most interesting about Heated Rivalry is that it didn’t try to make itself more acceptable.

Jacob Tierney could have diluted the intimacy. He could have chased celebrity casting to inflate the optics. He could have softened the emotional thesis in pursuit of “broader appeal.”

Instead, he made a specific choice: honor the book. Honor the audience that already existed. Trust that if you build something emotionally honest enough, the right people will show up. In fact, he walked away from bigger deals and bigger dollars to make it happen.

That's not a creative gamble. That's market intelligence.

The show didn’t apologize for being a romance. It didn’t treat desire like something that needed to be delayed or disguised. It took longing and vulnerability seriously instead of winking at them.

And audiences rewarded that conviction.

What Actually Cuts Through

Romance works because it’s about risk. About wanting someone. About choosing and being chosen. These aren’t trivial themes just because they’re often centered around women.

In fact, the reason they’ve been systematically undervalued is because they’re centered around women.

Hollywood keeps saying it wants broad appeal. But the things that actually scale are often the ones that refuse to dilute themselves. Specificity isn’t the opposite of reach—sometimes it’s the only path to it.

This is basic marketing strategy: know your audience. Build for them specifically. That specificity is what creates resonance. And resonance is what spreads. When you try to appeal to everyone, you end up mattering to no one. When you build something that a specific audience cares deeply about, that’s when you break through.

Queer stories get dismissed as 'niche' the same way romance gets dismissed as 'for women'—as if desire, intimacy, and love are somehow narrow concerns. Heated Rivalry proved what should have been obvious: universal themes don't require universal characters. They require emotional honesty.

Heated Rivalry didn’t become culturally omnipresent because it tried to be for everyone. It became omnipresent because it was uncompromising about who it was for—and that specificity gave people something to care about.

The Business Case

Here’s what I keep coming back to: industries are slow to admit when their blind spots are cultural rather than financial.

Romance has always made money. But because it’s culturally coded as feminine—because it centers intimacy instead of spectacle—it has historically received less capital, less prestige, less institutional confidence.

That’s not a market failure. It’s a power structure.

Institutional caution doesn't protect you from risk—it just ensures someone else captures the upside while you're still deliberating.

And when you consistently undervalue what women love, you don’t just reveal a bias. You reveal a structural miscalculation.

The lesson here isn’t that romance works (we know it does). The lesson is that audiences know what they want—and gatekeepers keep second-guessing them.

There’s been more written about this show in the past few months than I’ve seen about almost anything in my 15 years working in entertainment. People are analyzing the chemistry, the soundtrack, why straight women love watching desire without misogyny, what it means for queer representation. All of that matters. The cultural impact is real—I’d bet money that if someone stood on the ice after winning the Stanley Cup this year and kissed their boyfriend, the arena would erupt.

But this is a business newsletter. So what I keep coming back to is this: Heated Rivalry is a case study about who gets to decide what’s valuable, what’s serious, what deserves investment.

Eventually, the market corrects you.

Whether Hollywood learns from the correction is a different story.

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Exit Interview is the honest debrief on work, power, and culture. I'm Kathleen—I've spent 15 years working in entertainment, advocacy, and strategy, and the past eight building a business on my own terms. This is where I say the quiet part out loud: how power actually moves, how careers really evolve, and what I've learned since stepping off the corporate ladder.

Each time, it starts with something like:
“I don’t know what to do next.”

And then, a beat later:
“I’m thinking about taking on consulting projects… but I don’t even know what that really means.”

One of those conversations was with a close friend who’s in the middle of transitioning out of her current job. She’s smart, respected in her field, and far enough into her career that she knows she’s good at what she does. She’s been looking at new corporate roles, but everything feels like a lateral move at best, and a step backward at worst.

What she wants isn’t just a paycheck. She wants what most of my millennial peers want from work in their mid-to-late 30s: respect, autonomy, and ownership over her work. A sense that there’s room to grow instead of a ceiling she’s already pressed up against.

Consulting feels like it could offer all of that.
But it also feels overwhelming.

What if I can’t sign any clients?
What if I put myself out there and fail?
How do I even structure projects?
How do I build any sense of stability when nothing is guaranteed?

These are the questions that actually keep people up at night. Not “how do I freelance,” but how do I not screw this up?

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What’s actually underneath this question?

Here’s the thing I’ve noticed across all of these conversations:
The fear isn’t really about consulting.

It’s about wrapping your brain around responsibility when suddenly the edges of the container are gone.

When you’re traditionally employed, a lot of stability is handled for you by default. Someone else decides how work is scoped. Someone else defines your role. Someone else sets pay structures, handles payroll, withholds taxes, offers benefits, and absorbs risk.

When you consider consulting, all of that suddenly moves onto your plate.

And if you’re someone who’s used to being very good at your job, but has never had to play every business role at once, that shift can feel paralyzing.

So what does consulting actually look like?

When I talk through this with friends, I’m careful not to romanticize it.

Consulting is not freedom without responsibility.
It’s not vibes and pay days and magically “figuring it out” from a Parisian cafe.

Consulting is taking your existing expertise and deciding intentionally how it’s packaged, sold, and protected.

You still have deadlines. You still answer to clients. You still need to be clear about expectations. But you gain something important in return: control over scope, who you work with, and how your work fits into your life.

Here’s the thing that I always emphasize: control doesn’t come from hustle, it comes from structure.

Here’s where things usually start to click:

In every one of these conversations, the moment things shift is when I stop talking in abstractions and start talking concretely.

I walk through how I scope projects.
I explain why I price the way I do.
I show them examples of statements of work I’ve used.
I talk through how I built stability before I felt confident.

By no means is my way the only way, but I have found that seeing a real path forward quiets the panic.

At this stage, people usually need orientation just as much as motivation.

One thing to do if you’re spiraling about this

If you’re lying awake wondering whether consulting is a viable option—or whether you’re wildly underprepared—here’s the one thing I’d focus on first:

Break it down into tangible steps. Stop thinking about consulting as a huge leap, and start thinking about it as a container to explore new possibilities.

Your job isn’t to predict the next five years.
Your job is to define one service offering clearly enough that:

• You can clearly articulate what the deliverables are (what a client will get)

• You can clearly communicate the value to a client (how it will accomplish their goals)

• You can build clear timelines and expectations (what is required to get there)

That’s it.

I have found that stability comes from building a solid structure that you can repeat. This doesn’t mean you can’t revisit your offering down the line, but the goal is to find your starting point.

I’ve been running my own consulting business for eight years. As more friends and peers start to consider consulting, I wanted a place to share what I’ve learned and help make the process feel less overwhelming for people who are trying to figure out their next step.

I had been working in a toxic environment where I was constantly undermined, and the stress was impacting every area of my life. One day, while my mom was visiting, I said, “By the time you leave, I need to have an exit strategy.” By the end of that week, I walked away from my job—no backup plan, just the conviction that it wasn’t worth sacrificing my wellbeing for a paycheck.

A friend asked if I’d ever considered freelancing. I hadn’t. But I thought it might buy me some time while I looked for the right job—not just the next job.

Within six months, I was doing better than I had at my previous full-time job. Eight years later, I’ve never looked back.

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But here’s what I didn’t know then

I wasn’t just leaving a bad situation. I was opting out of a system that’s fundamentally broken for our generation (proud millennial over here).

We did everything “right.” We went to college. We climbed the corporate ladder. We waited our turn for promotions. We were loyal. We worked late. We produced more value year after year.

And what did we get?

• Leadership pipelines that never seem to open up

• “10 years experience required” for director positions that should be within reach

• 2% raises while producing 30% more output

• Layoffs after loyalty

• “Restructuring” that eliminates upward mobility

• The constant realization that the financial security we were promised isn’t coming

• Rapidly increasing cost of living coupled with stagnating wages

The goalpost keeps moving. The system that worked for our parents doesn’t work for us. And somewhere along the way, many of us realized: we’re on our own.

The millennial work crisis no one’s talking about

I’m 36 years old. Most of my friends are in their mid-30s to early 40s. And nearly all of them are stuck.

Not because they’re not talented. Not because they’re not working hard. But because the corporate ladder they’ve been climbing leads nowhere.

They’re too senior to be entry-level, but there’s no clear path to leadership. They’re overqualified and underpaid. They’re exhausted and burnt out from doing the work of three people after “cost-cutting measures.” They’re watching their retirement timelines slip further away despite doing everything they were told to do.

And increasingly, I find a lot of my friends asking me: “How did you do it? How did you build something stable working for yourself?”

That’s why I’m building this newsletter.

This isn’t just about freelancing tips

Don’t get me wrong—I’ll teach you the systems. How to structure your business legally. How to handle taxes so you don’t get blindsided. How to set rates that actually reflect your worth. How to protect yourself with contracts. How to find clients and build sustainable income.

I’ve spent eight years figuring this out through trial and error, and I’ll share everything I wish someone had told me.

Because here’s the truth: it’s not the sexy stuff that stops people from going freelance. It’s the unsexy admin, systems, and operations stuff that feels most intimidating.

How do I actually pay quarterly taxes? What business structure do I need? How do I invoice professionally? What goes in a contract? How do I separate my business and personal finances? What about health insurance? Retirement?

These are the questions that keep people trapped in jobs they’ve outgrown. Not because they can’t do the work—but because no one knows how to manage the backend infrastructure that their companies have always handled.

That’s what I’m here for.

But this is also about something bigger than invoicing templates and tax strategies.

This is about economic autonomy for a generation that was sold a bill of goods that doesn’t exist anymore.

This is about recognizing that the system is broken—and deciding to build our own instead.

This is about finally having the freedom to:

• Set your own rates based on your actual value

• Choose who you work with

• Design your own schedule

• Build wealth on your own terms

• Never write another performance review

• Answer to yourself

What Work, Reimagined actually is

Think of this as part systems manual, part friend you’d call for advice—one who has been doing this for eight years and isn’t going to sugarcoat it.

Every week I'll write about the practical systems, honest numbers, and real frameworks that make working for yourself sustainable. Not the Instagram highlight reel version. The actual version.

This isn’t toxic positivity “follow your dreams” nonsense. I’ll be honest about how hard it is. But I’ll also show you it’s possible and how to actually do it.

Right now, everything is free. As this grows, I’ll introduce a paid tier with deeper resources, template libraries, and more intensive support. But my commitment is to make the core knowledge accessible to everyone who needs it.

Why I’m doing this now

Because I’m watching my friends hit the same wall I hit in 2018.

Because the advice our parents give us (and that worked for them) doesn’t work anymore.

Because job security is a myth and we need to build our own.

Because someone needs to say out loud: You’re not failing. The system failed you. And here’s how to build something better.

If you’re here, you’re in the right place

Whether you’re:

• Trapped in a corporate job wondering if there’s another way

• Already freelancing but struggling to make it sustainable

• Side-hustling and trying to figure out if you can go full-time

• Just exhausted by a system that keeps moving the goalpost

• Intimidated by all the backend logistics and wondering where to start

You’re not alone. And I’ve got you.

If any of that sounds familiar — you're exactly who I'm writing for. Subscribe and read along. This is just the beginning.

—Kathleen

P.S. I’m also on Instagram @aspiringrichwineaunt. Come say hi!

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