Welcome to Aspiring Rich Wine Aunt.
The name is both a goal and a joke, and probably exactly what you're working toward too 😉.
This is a newsletter about building a life that doesn’t look like the one you were supposed to want—and figuring out, in real time, what that actually takes.
I write about working for yourself, women’s stories and why they’re worth more than the entertainment industry gives them credit for, and what it means to design a life across two coasts that refuses to fit neatly into any one category.
If you did everything right and are quietly recalibrating what “right” even means, you’re in the right place.
As a subscriber, you can expect:
Work, Reimagined: Essays, guides, and real talk on freelancing, the millennial career crisis, and what it actually takes to build something of your own. Real numbers, real systems, no hustle culture.
Stories for the Girls: Cultural criticism, hot takes, and an unapologetic defense of romance, romantic comedy, and women’s stories from someone who has spent fifteen years working inside the industry that keeps underestimating them.
The Bicoastal Life: On place, travel, identity, and the quiet power of designing a life that doesn’t fit neatly into one city, one version of yourself, or one script someone else wrote for you.
What to expect each week:
Weekly essays — rotating across all three pillars, always free
Guides and how-tos — practical, specific, grounded in real experience
Office hours — for the questions you’re not sure who else to ask
Notes — short takes, recommendations, and things I can’t stop thinking about
Hi, I’m Kathleen!
Hi, I’m Kathleen and I have spent fifteen years working in one of the most glamorous, exacting, and genuinely fascinating industries in the world: entertainment. Eight years ago I went out on my own, and five years ago I co-founded GSD Group, a creative agency, with a business partner who pioneered social impact entertainment.
I run Oscar campaigns. I build impact partnerships. I work with filmmakers and studios and mission-driven brands to turn stories into cultural moments. I split my time between Los Angeles and New York. And I do this for myself, on my own terms, building something sustainable inside an industry that is actively rewriting its own rules.
But somewhere along the way I started noticing a pattern. The careers we were promised—the ones that rewarded loyalty, prestige, and doing everything right—were quietly not delivering. Not just in my industry. Everywhere.
Lately, more and more of my friends are asking the same questions. About designing a life outside the traditional box. About what it actually takes to work for yourself. About whether the career they were promised is still worth chasing, and what to build instead.
That’s the conversation I keep having. If you’re asking the same questions, this newsletter is for you.
Why subscribe?
Work isn’t delivering what it promised. The entertainment industry is rewriting its own rules. Women’s stories are generating billions while the industry keeps underestimating them. And the life you were supposed to want looks less appealing every year.
This is the newsletter for women who are done waiting for permission—to work differently, to love what they love without apology, to build a life that doesn’t fit neatly into one coast, one career, or one category.
Subscribe if you want clear thinking from someone 15 years inside the industry, 8 years working for herself, and deeply committed to the idea that women’s stories—in entertainment and in life—are worth a lot more than they’re getting credit for.
Welcome!
So glad you're here. Let's get into it :)
