Our TDWS conversation with filmmaker and writer Betsy Chasse felt like one of those conversations where everybody watching kept nodding along going, yes, exactly that.
We started with her essay “Maybe I Should Have Married Rich,” which is really about a tax bracket and emotional reality nobody talks about enough: not poor enough to qualify for help, not wealthy enough to stop constantly calculating. The kind of life where you can technically be “doing okay” while quietly wondering why every basic thing suddenly feels impossibly expensive.
And from there, the conversation just opened up.
We talked about being GenX parents raising kids in a world that feels dramatically less stable than the one we were promised. FAFSA rage. College tuition insanity. The hidden costs nobody prepares you for. The dawning realization that what once counted as a solid middle-class life now barely feels sustainable.
Betsy talked about literally moving to Minnesota so her son could qualify for in-state tuition at the University of Minnesota, and honestly? It made a lot of sense in this crazy timeline we’re all in.
We also got into the particular exhaustion of being a woman trying to navigate money, work, independence, and survival inside systems that seem designed to penalize you no matter what choice you make. One of the strongest parts of the conversation was Betsy unpacking the phrase “gold digger” and the impossible bind women are put in: told financial security matters, then mocked for pursuing it.
Somehow we also ended up talking about social media, progressive lenses, purging possessions, Stripe fees, Jeffrey Epstein, and a giant painting Betsy rescued from the side of the road featuring a shark with the word FUCK above it—which honestly became the accidental mascot for the entire discussion.
It was funny, sharp, deeply honest, and a deeply GenX-core conversation, the kind where everyone’s laughing a little while quietly admitting: this is harder than we thought it would be.
Thank you Untrickled by Michelle Teheux, Amy Gabrielle, Beth Cruz, LeftieProf, Peter W Shuster, and many others for tuning in, and to Karen Marie Shelton and Yanni Hamburger for moderating.
Love you, mean it!
