HENRY Diaries: Meet Katie, Tech professional Crushing it in NYC
(For every woman in NYC who is killing it, spiraling, thriving, overspending, under-sleeping, and wondering how the hell she still feels broke.)
WHO THE HELL IS KATIE?
Let’s set the record straight.
Katie is 32, lives in the West Village, and pays $4,350/month for a one-bedroom that’s “charming” in the sense that if you breathe too hard the exposed brick sheds dust.
She has a six-figure job in tech that makes everyone back home think she’s “living the dream,” when in reality she is one unexpected UTI away from a financial meltdown.
She is the human embodiment of a HENRY - High Earner, Not Rich Yet.
She’s smart, driven, and easily seduced by anything marketed as “limited edition.”
She has two modes: hyper-responsible adult and goblin-girl chaos. There is no in-between.
Here is her day. 2025 NYC. Real. Brutal. Beautiful. Unhinged and aspirational at the same time.
Girl, buckle up.
HENRY Diaries: Chicago Finance Bro — The Day Jackson Realizes He’s a High Earner… Not Rich Yet
It all begins Chicago Finance Bro — The Day Jackson Realizes He’s a High Earner… Not Rich Yet
34, married, two toddlers, former NYC investment banker, newly minted PE guy in Chicago. Confident. Successful. Low-key terrified. an idea.

