Hey neighbors, happy Thursday. This week we have a great Cash Confessional lined up, but before that 👇
I came across an article this week about ‘the death of the corporate job’ (ridiculous title). Not through layoffs, but through a slow erosion of the belief that the work actually matters. Not too dissimilar to what Ted Kaczynski called 'surrogate activities.' Whoa, okay folks, don't get extreme out there.
What’s interesting though is what's replacing it. People using their corporate roles as funding mechanisms to build something of their own on the side or to exit corporate life at some point. The author of that article calls it “corporate entrepreneurship.”
Engineers building SaaS tools that solve problems they see at work
An HR professional selling sourdough on the side whose about to open a bakery
A project manager offering Notion setup services to solopreneurs, aiming to make it her main income soon
If that's you and you’re building or running a business or side hustle, let’s chat. Reply to this email and let’s feature your story in an upcoming newsletter!
Okay, let’s get to it 👇
Worth checking out:
🖼 Reopening: MoMA Design Store Soho reopened and reimagined at 81 Spring St. New "Modern Mural" series debuts with Nina Chanel Abney's "LOVE NYC." Curated design meets contemporary art. Visit.
🍺 Hot Event: Stone Street Oktoberfest runs six Saturdays (Sept 21-Oct 26), Noon-11pm in FiDi. German beer garden vibes. Pretzels, wurst, live music, games. Free entry. Cheers.
⛰ Weekend Escape: Modern, creekside cabin near Livingston Manor in the Catskills. XL windows, fire pit, fully stocked kitchen. 15-min to town. 2 hrs from NYC. Dog friendly. Book it.
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Markets 📈
YTD
Nasdaq | $22,807.02 | +18.30% 🟢
S&P 500 | $6,705.55 | +14.26% 🟢
Bitcoin | $120,037.99 | +28.43% 🟢 (we’re so back)
Cash Confessional 🤑
Early 50s "late bloomer" feels very behind with $1M net worth & $200k salary

Union Pool in Williamsburg. This advertising professional’s favorite spot to reminisce about the early 2000s.
Cash Confessionals are weekly stories where NYC locals peel back the curtain and expose their money habits. Wanna submit one? Go here.
"I feel really far behind where I should be. I didn't cross $100k salary until my 40s. I was a late bloomer. I spent my youth having fun and moving around the country. I wouldn't change anything, but it impacts where I am now."
Career: I'm an Account Director in Advertising making $200k, basically at the top of my career. Sometimes I get a bonus, but it's pretty small, like $10k. I love my job. Every day I get to solve different client problems, do creative stuff, attend video shoots, go to events, and play with products that aren't on the market yet. This is a young industry, and seeing how creative and focused my coworkers are makes me very hopeful for the future.
My career goal is to stay relevant as long as I can. This is a very ageist industry and I'm at the wrong end of it. I would love to get another five years taking a paycheck, then figure out how to do some consulting or teaching work to supplement.
Living situation: We rent in Greenpoint for $2,400 from a Polish friend of a friend who owns a couple of buildings. I'm handy, so I'm his unofficial handyman/super sometimes, dealing with other tenants and contractors since he lives in New Jersey. In return, he gives me a deal. I can do whatever I want to my apartment- paint, flooring, etc. I've spent probably $10k of my own money to fix it up in the eight years I've been here. It pays to live in a neighborhood for a long time and talk to your neighbors. I wouldn't have my apartment without making friends with parents at my kid's school, going to Community Board meetings, and hanging out at local bars.
If money was no object, I'd live in Soho in some giant artist's loft like the one in "Desperately Seeking Susan." On the other hand, I love the youthful, diverse, queer energy in places like Ridgewood. It would be fun to retire and move to a further out neighborhood like that.
Expenses: We spend an embarrassing amount of money on going out, we love food and restaurants and it’s not uncommon to spend $2200 per month. For three people, weekly spending usually breaks down to:
Groceries: $200-250 (we have a teenager and he eats a LOT, this includes wine)
Eating out: $500 (2-3 times per week)
Live music: ~$100 (twice per month, averaged out)
Saving & investing: I save roughly $3,500 per month post-tax (about $6,500 between my wife and me). Current financial picture:
$100k in a high-yield savings account (probably too much, but my son will start college in two years)
$425k in retirement accounts
Investment property abroad bringing in $300/month after expenses (will eventually bring in $2,000/month when paid off)
I max out my 401k ($2,500 pre-tax monthly) plus the HSA. I didn't even start contributing to retirement until 2019. At first the minimum, then I got freaked out and maxed it out for a couple of years.
Worst money decision ever: Buying a condo in Williamsburg in 2014. We spent all the money we had and were so broke all the time. It took up most of our paycheck and we couldn't go out, we couldn't travel. I just hated that feeling. I even cut back on retirement contributions to afford it. When we sold it in 2019, I was in debt and thrilled to see it gone. It took me another five years to get out of debt and rebuild my savings after that.
Best money decision recently: Switching to a high-deductible health plan with an HSA. Without even trying, I have $3,000 pre-tax in a savings account that rolls over. I don't pay taxes on it when I put it in or take it out. I wish I had heard about these earlier.
Debt: We have credit cards that vary but usually $8-10k per month, a car loan for about $30k, and a mortgage in another country for about $120k (on an investment property where we used to live). We pay off credit cards every month unless there's an unexpected expense. I hate having debt. When I had the big mortgage it felt like a weight around my neck. Even now the car loan makes me feel tied down.
Final reflections
How do you feel about your financial situation? I feel really far behind where I should be. College for our kid is coming up in two years, then retirement soon after. We rent and don't own, which adds uncertainty. I didn't make much money until 15 years ago and didn't cross $100k/year until I was in my 40s. I was a late bloomer and didn't understand how much money really matters. I spent my youth having fun and moving around the country. I wouldn't change a thing, but it does impact where I am now.
What are your long-term goals? Getting ready for retirement so I can say "fuck you" to work, and contributing to my kid's college fund so he can start his adult life. Maybe having enough to buy a small cheap apartment somewhere in cash so we have low overheads. I've got about 10-12 years of this left. We still don't know where we'll end up. Maybe we'll buy a cheap apartment in the city with retirement funds or move to Europe or Asia. What I do know is we'll never retire and move to the country or Florida. It's here or not the US.
Why NYC? We can make more money here (like double any other city), my son goes to school here, my friends are all here. I love the urban lifestyle, and having a little house in the suburbs sounds like torture. I grew up that way in the 80s and never want to go back. The only place I would live besides NYC is a European city or Asia, someplace with good transit and healthcare. It's the only real city in America, for better or worse.
Submit your own Cash Confessional for an upcoming newsletter. Go here.
Side Of Money Job Board 👷
Who’s hiring in NYC?
Conversational AI Designer @ GM ($143K - $180K). Design and develop AI-based conversational and multimodal experiences for vehicle interfaces. Remote.
Performance Marketing Manager @ Grammarly ($106K - $163K). Own full-funnel paid acquisition strategy across multiple channels to drive user growth and pipeline conversion. Remote.
Sales Director, Programmatic @ The Daily Beast ($90K - $120K + commission). Own programmatic revenue strategy. Manage client engagements and strategies. Hybrid in Chelsea.
Indirect Tax Manager @ Anthropic ($230K - $300K). Develop and execute global indirect tax strategy for US sales tax and international VAT/GST. Hybrid.
☀ NYC Weather
This weekend
Friday
57°F 🌡 71°F | ⛅ | 💨 5 mph
Saturday
61°F 🌡 79°F | ☀ | 💨 3 mph
Sunday
60°F 🌡 80°F | ☀ | 💨 7 mph
You’ve reached the end.
Thanks for reading this week’s edition. If you have ideas for stories, know about new business coming soon, or want to do your own anonymous Cash Confessionals submission, let me know!
Josh
P.S.
Read something you like or maybe don’t like? Hit reply and let me know!