HENRY DIARIES: Darren - The Boston Strategy Consultant Making $216K, Traveling Weekly, and Still Wondering Why He Feels Broke
35. Lives in Boston. Strategy consultant. Makes $216K. Travels constantly. Loves live sports, concerts, and nice things he pretends were “on sale.” Has grad school loans. HENRY energy.
MEET DARREN
Darren is 35. He lives in Back Bay - not because he’s rich, but because he refuses to live anywhere that requires crossing the Charles on a weekday.
He makes $216,000 a year. Consulting salary. Consulting lifestyle. Consulting exhaustion. Consulting financial confusion.
He’s single. Partially by choice, partially by Delta Airlines.
He travels weekly. He’s always jet-lagged. He owns hotel slippers he didn’t technically “steal,” but also didn’t technically not steal.
He loves:
live sports (Celtics, Bruins, Red Sox - he’s an equal-opportunity fanboy)
live music (House of Blues, Big Night Live, random indie shows he pretends to discover first)
overpriced cocktails at spots where everyone looks like they work in tech
He also has grad school loans and a cost-of-living situation that feels like a financial chokehold.
He is the quintessential Boston HENRY: High earner. Not rich yet. Not even close.
Let’s get into his day.
5:07 AM - The Consultant Curse
He wakes up naturally because his body has given up on normal human rhythms.
Checking his phone is an Olympic sport:
Slack
email
two new calendar invites
a flight alert
a text from his manager that says “Quick Q” (never good)
sports scores he fell asleep before watching
He lies there for a minute thinking: “Didn’t I just go to sleep?”
Because… yes. He did.
6:15 AM - The Boston Ritual
He goes to Tatte because that’s what Bostonians do when they want to feel something.
Orders:
cold brew the size of his head
a breakfast sandwich he debates paying for in cash to pretend it doesn’t count
He people-watches:
grad students crying
biotech bros pretending to work
women in Lululemon who definitely have their life together
He scrolls through scores from last night’s Celtics game and genuinely wonders if he should’ve splurged on those $600 seats.
He didn’t.
He regrets it anyway.
8:00 AM - Laptop Open, Soul Closed
Consulting mode = activated.
His day includes:
client call
deck review
“just add a few slides” (which means 18)
data he’s supposed to magically conjure
internal team sync
travel arrangements
He’s good at this. Really good. Fast thinker. Sharp analyst. Good in front of clients.
He thrives under pressure - or at least appears to.
The problem isn’t work. The problem is money. His budget is basically:
rent
loans
Uber
flights
concerts
sports tickets
eating out
rinse and repeat
He gets paid well. He spends well. He saves… eventually.
Sometimes. Kind of.
10:42 AM - The “Quick Sync” That Hijacks His Life
His manager pings him:
“Got a sec?”
He never has a sec. He always says yes.
This becomes:
1 urgent workstream
3 deliverables
2 deadlines
0 emotional support
Consulting is just professional whiplash.
12:30 PM - Lunch: Boston Prices Should Be Illegal
He grabs Sweetgreen because he hates himself financially.
$18.07 for lettuce, chicken, and humiliation.
He checks his credit card balance and feels his soul leave his body.
He has savings. He has a good salary. But somehow Boston still feels like it’s pickpocketing him on a daily basis.
2:15 PM - The Sports Ticket Debate
Group chat lights up: “Bruins game Thursday? We found resale seats, $285 each.”
He stares at the message.
He wants to go. He really wants to go. He works his ass off. He deserves fun. But also… $285??
He says: “I’m in.”
Because life is short. And because HENRYs always choose experiences now and worry about the rest later.
3:45 PM - Travel Prep
He checks into his flight for tomorrow.
Chicago → Dallas → Boston.
He packs mentally. He has packing down to:
laptop
chargers
noise-cancelling headphones
black quarter-zip
Patagonia vest
toiletries
“client-ready face”
He’s like a corporate Marine.
5:40 PM - Equinox to Cope
He hits Equinox because therapy is expensive and sweat is free.
He lifts. He runs. He stares at himself in the mirror like he’s challenging Future Darren to get his shit together.
He feels alive for the first time today.
7:30 PM - Dinner & Music
He meets a coworker friend at Row 34.
They hit:
oysters
craft beer
the kind of dinner that looks affordable until the bill arrives
Then they head to a small show at Paradise Rock Club.
He lives for nights like this. Good music. Good friends. Good energy. The tiniest break from the grind.
10:55 PM - The TikTok Spiral
He gets home and collapses into bed.
Then he opens TikTok.
Motivational reels. Finance bros screaming about “investing early.” Consulting humor. Boston apartment tours he can’t afford. Sports analysis. Concert highlight clips. A random “side hustles you should start” video.
He OD’s on:
productivity content
wealth content
lifestyle content
His brain is like: “You’re rich! You’re broke! You’re thriving! You’re failing! Buy a multifamily! Move to the suburbs! Never leave the city!”
He slams his phone down dramatically.
11:48 PM - The HENRY Epiphany
Lying there, he thinks: “I make great money. Why do I feel like I’m sprinting on a treadmill?”
He knows why:
Loans
Rent
Travel
Lifestyle
No real financial plan
He’s doing everything right professionally. He’s doing everything vibes-based personally.
He whispers to himself: “I don’t need more salary… I need a strategy.”
This is the universal HENRY awakening. The moment where ambition meets adulthood. Where lifestyle meets reality. Where the income is high but the clarity is zero.
Darren finally admits: He doesn't need:
another Celtics ticket
another flight
another vest
another inspirational TikTok
He needs someone to help him get his financial sh*t together.
