HENRY Diaries: 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.
MEET… JACKSON
Jackson works in middle-market private equity. He makes $275K all-in. He still works out like he’s training for the NFL Combine, is married to a stay-at-home wife he genuinely adores, and has two toddlers who have collectively decided that he is no longer entitled to REM sleep.
Jackson moved from NYC to Chicago 6 months ago because everyone told him it would mean “more space, more balance.”
They lied. He has different stress now. Not less.
He is the Chicago Finance Bro: High Earner, Not Rich Yet.
Let’s walk through Jackson’s day.
5:12 AM — The Toddler Alarm Clock Goes Off
Jackson wakes up not because of his iPhone, but because his youngest is screaming “DADDYYYYY” like she’s summoning him for battle.
He scoops her up and walks to the kitchen.
His wife is already up because, frankly, she’s built different. He kisses her forehead - the one loving gesture he can reliably deliver before sunrise.
He makes coffee. He downs coffee. He stands there staring at a toddler dumping Cheerios on the floor and thinks:
“…this was not in the employee manual for fatherhood.”
He used to wake up at 7:30 in New York. Now Jackson wakes up at 5. Fatherhood is a contact sport.
6:00 AM — “Athlete At Heart” Workout
Jackson hits East Bank Club — Mecca for Chicago finance bros who still swear they “could’ve gone pro.”
Membership: $235/month
Mental stability: included
He runs through:
20 minutes incline treadmill
Chest day (its always chest day)
Sauna time with other men named Matt, Mike, or another Matt
In the sauna, conversations go:
“Your fund picking up deal flow?”
“You guys adding any portcos this quarter?”
“Thinking about buying in West Loop — worth it?”
“Rates are insane.”
“Bro… we’re building generational wealth.”
Internally, Jackson is like: “…are we though?”
7:15 AM — Commute: Solitude in the Tahoe
Jackson drives his 2022 Chevy Tahoe from Lake View to the West Loop.
He left New York for “more balance.” Now his commute is 27 minutes instead of 11. It gives him more time to think…
Which is honestly worse.
His brain spiral soundtrack: Rent or buy? Rent or buy? Rent or buy?
West Loop condos are $700K–$1.2M and interest rates feel like a personal attack.
Jackson wants stability. His wife wants roots. He wants to give her that.
But he also wants to not feel like he’s voluntarily stepping into financial quicksand.
7:29 AM — Office Arrival: Dark Roast & Deal Pressure
Jackson walks into his office — a steel-and-glass ecosystem that looks like a WeWork on a Red Bull binge.
He grabs a cold brew.
Bites into a protein bar.
Opens his laptop.
His calendar is a parade of finance bro obligations:
Internal diligence meeting
Founder pitch
Portfolio ops call
One-on-one with SVP
LP update review
Low-key?… Jackson likes this life.
High-key - Private equity hits the same competitive nerve sports used to hit. This is where he thrives.
8:00 AM — Deep Work Mode (Jackson’s Actually Great at This)
Jackson opens a CIM. His brain switches into Terminator Mode.
He rips through:
Add-backs
Customer concentration
EBITDA margins
Founder risk
Capital structure
This is the one part of his life where anxiety doesn’t exist.
Jackson isn’t scared of hard work. He isn’t scared of pressure. He isn’t scared of performance.
His anxiety is about everything outside these spreadsheets.
10:30 AM — Text From Wife: “Do We Have Room for Swim Lessons?”
His wife sends a photo of the toddlers in a bath, trying to drown each other playfully.
Swim lessons are $160/month per kid.
His instinct: “Yes.” His internal monologue: “Oh God…”
His actual text: “Absolutely, sign them up.”
Jackson wants to be the dad who never makes his kids choose between opportunity and cost.
He just hasn’t figured out how to financially plan for all this.
12:12 PM — Lunch With the SVP
Jackson heads to Kuma’s Corner because Chicago finance bros aren’t above eating burgers the size of their egos.
He orders the Slayer Burger.
SVP asks, “You settling in okay?”
Jackson shrugs, “Trying to. Toddlers are wild.”
SVP grins, “You thinking about buying?”
Jackson sighs, “Trying to decide. West Loop pricing is nuts.”
SVP laughs, “Welcome to being an adult, man.”
Jackson laughs too while internally screaming.
1:45 PM — Owner Call: Founder Energy Meets Dad Fatigue
Jackson hops on Zoom with an owner pitching a B2B SaaS bolt-on acquisition that allegedly “revolutionizes logistics.”
Jackson asks two questions. Founder rambles and crumbles.
The deal is dead. He knows it in 90 seconds.
He logs off. Drinks cold brew. Moves on — emotionally unavailable to bad pitches.
3:30 PM — Zillow Spiral (Again)
Between calls, Jackson breaks his promise to himself and opens Zillow.
He scrolls:
3BR, $815K
4BR, $1.1M
HOA fees that feel like organized crime
He runs mortgage calculators. Closing cost calculators. Property tax estimators.
He hates what he sees. Closes the tab.
Reopens it. Hates it again.
Closes it “for real this time.”
Jackson wants the condo. He wants the certainty. He wants to give his wife the home she dreams about.
But he also wants to not feel financially suffocated.
This is the HENRY paradox.
High earner. No wealth. All stress.
4:58 PM — Quick Gym Stop: Part 2 of Sanity Maintenance
Jackson goes back to East Bank Club because being a former athlete means therapy is spelled W-O-R-K-O-U-T.
He deadlifts.
He sweats.
He resents Zillow.
He sees other dads wearing Patagonia vests and On Clouds and thinks:
“We are literally all the same NPC with slightly different LinkedIn profiles.”
It comforts him.
6:15 PM — Dinner, Dad Mode, and Paw Patrol Hellscape
Jackson comes home. A toddler sneezes directly into his mouth. Another throws spaghetti at the wall.
Dinner is loud. Messy. Overflowing with chaos and love.
He loves these tiny humans. He also sometimes misses silence.
7:42 PM — Bath Time War
Bath time is a war zone.
One kid splashes.
One cries.
One pees.
(He only has two kids, but somehow three crises happen.)
His wife laughs because he looks like he’s battling demons.
Jackson soldiers on.
8:30 PM — Post-Bedtime Zombie Hour
Kids: unconscious.
Living room: destroyed.
Jackson and his wife: shells of people.
His wife asks softly, “Do you think we should buy soon?”
Jackson pauses.
“I want to… I really do. I just want to be sure we’re ready, you know?”
She nods.
She trusts him. That trust feels like love - and pressure.
He wants to be the rock. The planner. The one who “knows what to do.”
But he’s never been a one-income family before. Never budgeted for two kids, a wife, and a mortgage. Never navigated Chicago property taxes or condo assessments.
He’s making $275K. He is doing well. He just feels like he’s flying blind.
He clicks on an Instagram notification from his friend sharing the 15th reel of the day. More crying laughter emojis. 😂
9:45 PM — Late-Night Doomscrolling
Jackson opens ChatGPT like it’s a confessional booth.
He types:
“How much should I have saved by 32?”
“Is renting throwing money away?”
“Buying vs renting West Loop 2025”
“Private equity dad budget help”
“Should I open a 529?”
“Will interest rates drop?”
“Is it irresponsible to buy right now?”
His pulse rises.
He closes the browser.
Enough.
10:30 PM — The Realization
Jackson isn’t afraid of work. He isn’t afraid of pressure. He isn’t afraid of being the provider.
He is afraid of:
Making the wrong financial decision
Not planning well enough
Not saving enough
Failing his family financially
Living beyond their means
Missing opportunities
Not knowing what he doesn’t know
He looks at his sleeping wife.
Thinks about their kids.
Feels the weight of responsibility - and the weight of possibility.
And he finally says to himself: “I need help. Real help. A real plan. For us.”
This moment is where every HENRY’s life pivots.
Where the paycheck meets purpose. Where ambition meets adulthood. Where fear becomes strategy. Where vibes become clarity.
This is the moment Jackson decides: It’s time to get our financial sh*t together.
