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.
6:02 AM — “Why Am I Awake?”
Katie wakes up before her alarm, because her anxiety likes to beat the clock.
She grabs her phone, immediately regrets it, and scrolls Instagram.
Mistake #1.
Everyone is either:
Getting engaged in Santorini
Buying houses in Austin
Running marathons
Posting their perfect 4-month-old baby like it’s effortless
Meanwhile, Katie is lying in bed, crust in her eyes, contemplating whether she can get away with dry shampoo for the third day in a row.
She flips to her bank app to make sure rent cleared.
It did. It always does. It also feels like someone stole $4,350 straight out of her chest cavity.
Welcome to Manhattan, babe.
6:47 AM — Hot Girl Walk to Equinox
Katie puts on her Alo leggings-$118-and matching top-$62-because wearing a set makes her feel organized, even though she is not.
Equinox is two blocks away. $276/month because “self-care.”
She walks there in the pre-dawn quiet, dodging trash bags, rats the size of toddlers, and a man aggressively vaping blueberry mint.
It smells like money and garbage. NYC perfume.
She meets her trainer, Blake, who is $165/session and built like a renaissance statue that drinks creatine.
She hates him. She loves him. She hates that she loves him.
8:03 AM — Matcha That Costs More Than Her Childhood Lunch Money
Post-workout, she heads to her favorite café—the one with baristas who look like part-time models and oat milk priced like it’s harvested from gold-plated oats.
Large iced matcha, almond milk: $8.75
Tip: $2 because she’s not a monster
Total: nearly $11 for a cup of green anxiety juice.
She doesn't even blink.
Because girl math says:
“It’s cheaper than therapy.”
“I deserve this.”
“It’s part of my personality at this point.”
She considers buying the chia pudding but resists, feeling temporarily virtuous.
This self-control will not last.
8:48 AM — Subway? LOL No.
Katie has two choices: Take the subway for $2.90, or order an Uber for $31.17 because her suede boots cannot touch MTA floors.
This is not a decision. This is destiny.
She orders the Uber and tells herself:
“I’m supporting the gig economy.”
“The train stresses me out.”
“This is cheaper than being late and having to explain myself.”
This is the exact brand of delusion that keeps her financially mid.
9:05 AM — Corporate Slay and Imposter Syndrome
She slides into the office like she hasn’t been in an existential crisis for 2 hours.
She opens Slack ready to dominate.
Pings everywhere:
“Just circling back!”
“Gentle reminder!”
“Quick question!”
“Can we hop on a call?”
“Who owns this?”
Fortunately her motivation is stronger than her desire to cringe.
She owns EVERYTHING apparently.
Katie is great at her job, but she also feels like she’s a single typo away from being exposed as a fraud. Despite this, she crushes her morning to-dos… as per usual.
She dreams of getting promoted this year. She also Googles “symptoms of burnout” weekly.
Her entire personality is: “I’m fine. It’s fine. Everything’s fine.”
She checks email again - reads a rave response from her team lead on her latest progress report. Her departmental boss is cc’ed.
Clock it girl!
11:22 AM — Roth IRA Gate
At 11:22 AM, a coworker casually drops: “Yeah, I maxed my Roth IRA this year.”
Katie nods like she knows what that means.
She absolutely does not know what that means.
She goes to ChatGPT “what is a Roth IRA like I’m 5” and immediately panics at the charts, graphs, and words like “compound interest.”
She closes the tab.
Hard.
12:26 PM — Seamless: The Toxic Relationship
Coworkers want Sweetgreen.
Katie wants to be the kind of girl who meal preps quinoa in cute glass containers.
She is not that girl.
She orders the Harvest Bowl ($17.94 after taxes + tip) and tells herself she will “cook something later.”
This is a lie.
She knows it.
We know it.
The universe knows it.
She’ll order sushi at 9:30 PM like a raccoon with a corporate card.
1:14 PM — Reformation: The Siren Song
A notification appears:
“REFORMATION FLASH SALE — 40% OFF. ENDS IN 2 HOURS.”
Her credit card trembles.
She adds:
A floral dress ($248)
A silk skirt ($178)
A pair of boots ($298)
A sweater ($138)
A blazer ($278) that screams “hot corporate woman who has her life together,” which Katie is not, but she’d like to cosplay as one.
Cart: $1,140.
She narrows it to two pieces, and adds her cherished promo code - $218 - and checks out.
She feels a rush of dopamine.
Fun!
3:40 PM — Anxiety Tsunami Hour
Afternoons are dangerous.
Her brain turns into a mash-up of:
student loans
“will I ever afford a house?”
“what if I lose my job?”
“I’m 32 and still renting???”
“am I saving enough?”
“why is everyone around me thriving?”
“holy sh*t weddings cost HOW MUCH?”
“kids???????????”
“retirement is a scam?”
“why can’t I breathe?”
She takes a lap around the block. Uses deep breathing. Pretends the city noise is ambiance. A mental retreat to her “happy place”.
6:14 PM — Tribeca Dinner That Yeets Her Wallet Into Space
Her friends want to try a bougie Italian spot in Tribeca. Like, the kind where the host looks you up and down before deciding if you’re worth speaking to.
Katie is tired. She should go home. She knows this.
But someone texts: “Come on, live a little.”
And her FOMO is stronger than her common sense.
She goes.
She orders:
$67 pasta with truffle
$19 cocktail that is 90% ice
$17 dessert she did not want but everyone “just had to try”
Total: $128
She cringes. Then laughs with her friends until her stomach hurts.
Money can’t buy happiness… but it can buy a three-hour laughing session with people you love.
Worth it.
Regret it.
Worth it.
Regret it.
Cycle continues.
8:45 PM — Hot Girl Walk Home (AKA Mental Health Reset)
She rejects the Uber and walks home because “balance.”
New York is glowing. The cobblestones are shiny from rain. There’s a guy playing saxophone on the corner like it’s a movie.
For a second, she feels that electric NYC girl magic. The “I’m doing it. I’m actually doing my life” feeling.
10:03 PM — TikTok Sends Her Into a Spiral
She’s in bed scrolling TikTok when a finance creator says:
“If you don’t have $100k saved by 30, you’re behind.”
Katie nearly ascends out of her body.
She slams her phone down and opens her Notes app:
“I need to get my financial life together. For real this time.”
Her brain is a blender of wants and fears:
She wants:
Stability
A home
A wedding someday
A dog
Two kids
Travel every year
A safety net
Options
To stop panicking every time she checks her account
She fears:
Student loans
High rent
Emergencies
Running out of time
Ending up broke in retirement
Never catching up
She feels:
Behind.
Guilty.
Tired.
Lost.
Frustrated.
Ashamed.
Hopeful.
Overwhelmed.
Exhausted.
Human.
She doesn’t want to coupon-cut her way to financial security. She doesn’t want to live in deprivation. She doesn’t want to feel dumb. She doesn’t want to ask stupid financial questions. She doesn’t want to feel like she’s failing.
She just wants clarity.
She wants someone to help her who won’t talk down to her or make her feel incompetent.
She wants to know she’s not screwing up her life.
She wants to know she’s not alone.
THE MOMENT EVERYTHING CHANGES
This is where her HENRY era meets her hot girl healing era.
This is where chaos meets clarity.
This is where panic meets plan.
This is where Katie calls Stash Wealth.
