HENRY DIARIES: Jessica, The 37-Year-Old LA Creative Who Looks Like She Has a G-Wagon but Drives a Nissan
37. Creative agency girl. Six-year relationship. Makes $190K. Orange County roots. LA lifestyle addict. Nissan Altima driver with G-Wagon aesthetic. Student loans almost gone. Savings fat. Credit card balance fatter. Not moving to the Valley. Ever.
MEET JESSICA
Jessica is 37. She’s a Creative Director at a boutique-but-secretly-powerhouse agency in Los Angeles. She makes $190K - and honestly, she should be making more, but she’s too busy producing perfection to negotiate aggressively.
She’s been with her boyfriend for six years. They live together in a rent-controlled apartment in Mid-City that is technically “cozy” but realistically “we need a second bathroom.”
She’s from Orange County, which means:
she grew up around surf moms and Botox dads
she had a mild identity crisis in high school
she escaped to LA for “creative freedom”
she learned quickly that rent in LA is a personal attack
She drives a silver 2018 Nissan Altima. Not because she can’t afford a nicer car. But because she refuses to pay $1,800/month for a G-Wagon lease just to sit on the 405 for two hours a day.
Also because she knows deep down: “My Altima gets me there the same time your G-Wagon does, babe.”
But she still dresses like someone who would have a dedicated spot at the Edition valet. And honestly? She pulls it off.
Her vices:
oat milk matchas
Erewhon hot bar
spontaneous Palm Springs resets
hotels she has no business staying at
Santa Barbara wine weekends
“but it was 30% off” purchases
credit card reward points (her true love language)
Her strengths:
saving
hoarding cash
manifesting abundance
looking expensive on a Nissan budget
thriving in LA’s creative pressure cooker
avoiding the Valley at all costs
Her weakness: She cannot get her credit card balance under control because being in LA is basically being in a full-time situationship with temptation.
Let’s walk through her day.
7:12 AM - The Soft Girl Wakeup
Her boyfriend is already awake because he works in tech and thinks waking up at 6 AM is a personality trait.
She wakes up when she feels like it. Which today is 7:12.
Her alarm is the same song she’s used for six years: “Keep Ya Head Up” by Tupac. If she changes it, she’ll accidentally sleep until noon.
She checks her phone. Instagram first. Then email. Then Slack. Then Instagram again because she forgot she already looked.
She scrolls through LA girl content:
pilates at 6am
smoothie bowls
rooftop sunsets
“my hot girl walk to Alfred Coffee”
girls wearing outfits she could pull off if she actually woke up on time
Jessica stretches, sighs, and whispers: “I’m gonna get my life together tomorrow.”
She lies every morning.
7:45 AM - The LA Morning Tax
She grabs her Altima keys and makes the sacred pilgrimage to: Alfred.
Her order: Iced matcha, oat milk, light sweetener, $9.25 + tip because she is not a monster.
Then she swings by Erewhon “just to grab breakfast.” Which translates to:
$17 coconut yogurt parfait
$14 ginger shot she didn’t need
$8 bottle of water because she forgets she owns a Brita
She tells herself: “Health is wealth.”
Her bank account says: “Be serious.”
9:10 AM - Work Mode: Serving Excellence
Jessica gets to her agency in Culver City. She’s early for once. She feels powerful.
Her day:
client creative reviews
brainstorming sessions
last-minute “quick asks” that are never quick
rewrites
deck building
the occasional existential crisis
Her team loves her. Clients worship her. Her boss depends on her more than he admits.
She earns her salary. Every. Damn. Penny.
The problem isn’t income. It’s Los Angeles.
This city has a way of turning $190K into $2.75 real-world dollars.
11:40 AM - A Text From Her Mom
Her mom: “Are you saving? Are you investing? When are you buying a house? You're almost 40.”
Jessica: “Hi mom :) yes working on it.”
Her mom grew up in scarcity. Jessica grew up in hustle. Her mom doesn’t understand LA rent, wedding prices, 32% taxes, creative burnout, or what a down payment looks like in 2025.
Her mom thinks she’s one call away from buying a $600K starter home in Orange County.
Jessica laughs. Cries. Laughs again.
12:32 PM - Lunch That Was Supposed to Be Cheap
She and her coworkers decide to “grab something quick.”
In LA, “quick” means:
$21 salad
$6 water
$5 parking
$9 cookie “because I deserve it”
She eats it outside while discussing:
creative concepts
weekend plans
astrology
why none of them want to move to the Valley
One girl mentions Riverside County.
Jessica clutches her chest. Starts sweating. Visibly recoils.
“No… no I can’t… traffic? The vibes? No.”
She will not. Cannot. Ever. Be a Valley girl.
2:45 PM - Afternoon Panic Snack
Jessica hits the snack wall.
She walks to the agency kitchen. She grabs:
a bar
sparkling water
another sparkling water
maybe a handful of almonds
She scrolls credit card transactions “just to check.”
She sees:
$312 at Sephora
$167 at Zara
$92 at Sweetgreen
$416 at a Palm Springs hotel
$213 at a Santa Barbara tasting room
She winces but also smiles. Because she lived.
4:15 PM - Creative Review Goes Great (and Then Not Great)
Client loves the first direction. Client hates the second direction. Client wants a third direction by tomorrow morning.
Jessica is:
calm.
poised.
silently screaming.
Her internal monologue: “I should be charging double.”
But she loves the work. Even the delusional clients. Even the chaos.
6:25 PM - Home, Change, Out Again
Her boyfriend is making dinner. She kisses him and immediately walks to the closet.
She changes outfits because she has drinks. With friends. At a rooftop. In West Hollywood. Where else would she be on a Wednesday?
She puts on:
$200 blouse
$170 jeans
$400 shoes
$60 makeup look
$22 earrings from some girl on Instagram
and gets into her Altima like she’s pulling up in a Maybach
She is the moment.
7:42 PM - The LA Girl Dinner: A Financial Trap in Four Courses
Jessica meets her girls at: Élephante.
The bill will be:
$18 burrata
$22 pizza
$19 cocktails
$16 fries
and a weird LA tax she can’t explain
Total personal damage: $108.74
Not including valet ($17 cash)
Or gas ($4.95 per gallon because LA hates her)
They discuss:
relationships
work hell
skincare
should they freeze their eggs??
“girl we should do a Palm Springs trip soon”
Jessica agrees. She shouldn’t. She will. And she will put it on her credit card.
Again.
10:15 PM - The Drive Home: Therapy via Headlights
Traffic is somehow bad even at 10 PM because LA is a fever dream.
She listens to SZA. She reflects on life. She cries for 14 seconds then stops because she smudged her eyeliner.
She loves LA. She hates LA. She will never leave.
But she also wonders: “Is $190K supposed to feel like this?”
10:50 PM - The IG/TikTok Motivational Doom Scroll
She opens Instagram “just to check.”
Big mistake.
Her feed:
“How I paid off $60K in 4 months”
“This is your wake-up call to invest”
“Rich moms don't wait to buy real estate”
“If you’re 37 and don’t own property, you’re behind”
“Ways to turn 100K into a million”
“Success habits you NEED to adopt in your 30s”
She spirals.
She opens TikTok.
Worse.
She sees:
soft life influencers in Cabo
finance bros telling her she needs $3M to retire
wellness girlies living in Brentwood
25-year-olds buying houses “with cash”
budgeting tips she will never, ever follow
“Stop saying you can’t afford it - you can”
She shuts the app. Chest tight.
She whispers: “Am I doing life wrong?”
11:20 PM - Bedtime Panic, But Make It LA
Her boyfriend is asleep. She turns off the light. Stares at the ceiling.
Her thoughts:
“Should I buy a house?”
“But where? I refuse to live in the Valley.”
“Should I be further ahead?”
“My savings are good… but how do I use them?”
“Should I invest more?”
“Is 37 too old to still feel financially confused?”
“How do other people do it?”
“I love LA too much to leave…”
“Am I the problem?”
No. She’s not the problem.
LA is the problem.
The lifestyle is the problem.
The cost of living is the problem.
Her entire social circle is the problem.
The algorithm is the problem.
Existence is the problem.
She is doing great.
She just doesn’t feel great.
Because no one taught her how.
Not school. Not parents. Not society. Definitely not TikTok.
She falls asleep overwhelmed, tired… and weirdly hopeful.
THE SHIFT - THE MOMENT ALL HENRY DIARIES LEAD TO
The next morning, she looks at her bank accounts. Looks at her goals. Looks at her credit card balance.
And finally says: “I need a real plan. A grown-woman plan. Not a TikTok plan.”
She wants:
clarity
intentionality
someone with a brain to tell her what to do
permission to live her LA life without drowning financially
to feel financially safe
to build wealth in her own way
to not move to the Valley ever
This? This is the hinge moment of every HENRY.
When vibe-based living stops being enough. When the lifestyle needs a strategy. When the money needs direction. When the grown-up life finally demands a system.
When she finally says: “Okay… it’s time to get my financial sh*t together.”
