It’s come to my attention that I have a lot of loyal, consistent, and quiet readers on here—first and foremost, thank you!! You have my entire heart.
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I’m an extremely privileged person.
At 28 years old, I have found myself in a rare position. I am working a corporate job I truly enjoy—one that I haven’t prepped an exit strategy for.
If you were to tell me that 10 years from now I would still be commuting to this same office, sitting at my cubicle which is decorated with mini-figures of Taylor Swift and Elphaba and pictures of friends, writing about commercial real estate, I would be relieved. (Hopefully, by then, I’ll be commuting in a car, not the bus.)
This is the first time I have ever felt this way. I have held two other full-time corporate jobs. The first, a glorified cold-calling job, I wanted to quit before my first week of training was over. The second, as an account manager for a PR agency, I actually enjoyed but knew was going under. I was kept on until the company went out of business, and I got a nice severance payout.
My current job may not be what I was dreaming of while racking up six-figure student loan debt at NYU, but it provides me with a great work-life balance, the flexibility to work on passion projects like this newsletter, and the ability to keep my freelance clients in the personal finance space. I get paid a great salary, especially for a copywriter, plus healthcare, PTO, and other social benefits that come with working with a group of people whose company I actually enjoy.
I promise I’m not writing this to brag, but I am writing this to publicly acknowledge how rare this is in today’s job economy—and how rare it is for my age group of “vaguely 30.”
This was one of those topics that came to me, and once I had it in my head, I began to see connecting threads all around me.
First, it was in a post by Jack Raines in his newsletter Young Money, titled “The Late-20-Something's Professional Dilemma.” In this post, Jack writes, “But as you approach 30, people quit caring about your potential (or, at least, it certainly feels that way), and they want to see what you’ve done with it.” Damn.
Then, it was a post titled “Youth” by Jared Young of Tolstoyan, where he writes:
“To do a thing young is a shortcut to greatness. Everything you do right is evidence of your great potential, and all your mistakes are the mistakes of inexperience, which will be corrected, surely, by the passing of time.”
“The years that pass eat up your margin for error until there is no margin left. The mistakes you make are no longer flaws of inexperience, they are flaws of character. To be young is to be constantly on the precipice of perfection – just a little further and you’ll get there – but you never get there, and suddenly you’re old, and find yourself in a permanent state of imperfection, which you must reckon with.” Damn x2.
(Honestly, it was hard for me not to quote his entire piece. Go ahead and read it for yourself.)
These quotes tied a perfect knot on a trend I had been noticing in my real life, and it all began with a spontaneous weekend trip to New York City.
It was miraculous, really. I flew in for the double holiday weekend (Valentine’s and Presidents Day), and every single one of my friends was in town. For New Yorkers, this is truly unheard of.
I booked out my weekend with two goals:
1. Eat all the food I had been craving for the last two years.
2. See as many friends as possible.
(Happy to report I accomplished both quite successfully.)
A few days into holding back-to-back meetups, I noticed I was having the same conversation over and over again—and it wasn’t just my overly dramatic life updates of the past few months. Almost every single one of my friends, ages ranging from 27 to 32, was in the midst of what I am affectionately calling a career renaissance—but for many of them, it feels like a crisis.
M (32) works for an NGO, which, under current Trump policies, is only guaranteed funding through September of this year. She has already begun applying for jobs.
Alexa (27) is going back to school to learn UX design after being miserable in three separate corporate and sales-related jobs. She is currently working as a dog walker to earn some money on the side while she studies and plans her upcoming wedding. She doesn’t have health insurance.
Melanie (29) is relying on her husband’s income after realizing her job in media production was not the career she had hoped for. She isn’t sure what her next move will be but is considering working for herself. She is tired of being shamed for not working.
H (30) got laid off in May 2024 from a corporate job that he didn’t love but that had allowed him to travel the world. He has been applying and interviewing since then to no avail.
Alyssa (31) just had her second kid and is a stay-at-home mom despite being extremely passionate about her degree in Art History and Museum Studies. The cost of child care for two kids under three years old in NYC costs her family more than she would be earning in her dream job.
These weren’t even all the friends I talked to—and this was just over the span of one weekend.
I left the city with a heavy sense of dread and guilt for how many of my friends were feeling lost—and how I had just updated them on how much I was loving my new job. (I’m sorry!!)
I asked my friends if they would be willing to share their stories here for The B Word, and because they are all incredible people, they agreed.
“I spent five years in jobs I never enjoyed, and after finding myself suddenly unemployed, I knew I needed a change,” says Alexa.
“I’ve thought about learning a new skill to change jobs for years, but it always sounded like a hassle, and money would be an issue. Even now that I’m taking a course, I still keep thinking about the money I’m missing out on for the next year. I’m old enough where making a change is hard, but I’m young enough where I can’t go on in jobs I hate for the next 30 years.”
Even for my friends who are able to rely on their partner’s income, the sentiment is similar.
“While being a stay at home mom is incredibly fulfilling, it’s not what I had intended for myself,” says Alyssa. “Initially I had hoped to get my masters in library science, but due to the high cost of further education I had to end my academics after graduating with my bachelors. Now, eight years after graduating, I have had to pause my professional career due to the rising cost of childcare.”
“For a short while I attempted work with sending my first child to daycare. After taxes, it ended up costing me money to go to work every day. It wasn’t sustainable. I tried to work remotely with my child but it’s near impossible to split your attentions to such demanding tasks.”
“Now I’m a full time stay at home mom. I miss the social aspects of working as well as the paychecks. I know this is a short term situation but I worry for my family’s financial future due to my inability to add a second salary to our gross income.”
There are a few truths for late-20s/30-somethings in 2025:
The economy sucks & inflation is scary.
The job market feels hopeless.
Home ownership is a laughable dream.
No employment sector is safe anymore.
That might sound dramatic, listed out like that, but it’s how many of us feel. My friends are all well-educated, living in a high-earning city, with impressive résumés, but none of them feel better off for it.
In response to the current market—where no job feels safe and no career feels guaranteed—people are turning to self-employment, something I tried (and failed at) in 2024.
“I’m in a pretty privileged position,” says Melanie. “I know that for the most part, jobs are a paycheck and a way to keep the lights on, but I feel as I’m getting older, the stakes are so much higher to do something I truly enjoy for the next 40 years.”
“I’m not interested in settling this late in the game or starting something new where I’m leagues behind. But, I’ve never envisioned myself just being a stay at home mom one day. I know I have more to give mentally and I miss being able to exercise my brain. I miss finding solutions to problems, but maybe I’m just meant now to be finding solutions to my own problems and working for myself, out of the corporate world. Just a lot of maybes.”
For H, who has spent the last 10 months searching for a job, the journey to employment has been a brutal lesson in self-reflection. “This past year has been trying and unexpected to say the least. I am the type of person that has struggled with detaching my identity and sense of self-worth from my work, something that I was made aware of throughout my early career by those closest to me.”
“I would not have been able to maneuver this crazy job market without losing myself in the process, if I did not learn to detach what I do for a living from my identity a long time ago. But, with all that said, this experience has made me rethink that very topic: why is attaching part of your worth to your work that detrimental?”
When we hung out over the weekend, H told me about a business idea he has, which perfectly combines his passion, personality, and the impact he wants to make in the world. We are both super excited about it.
“While we are all far more than what we do to make a living, we are what we leave behind. This experience made me understand that you can not a should not leave the choice of what you put out into the world in someone else’s hands, especially when you put your all into your work as I have and cannot help but continue to do. For me that means continuing forward in the career that I have built and enjoy, while more importantly working to build a business of my own that allows me to be proud of attaching my worth to what I put out in the world.”
I don’t have a grand reflection or prophetic wisdom to share here. I don’t have the answers—I’m only 28!!
However, I wanted to give my friends a platform in the hope that someone might resonate with the feeling of being more lost than ever and exhausted from the judgmental glares of others scrutinizing how they chose to cash in their college-aged potential, even if it's just among ourselves.
The future certainly remains uncertain, but there are two truths that will keep me going: sharing your experiences makes you feel less alone. And tossing pizza dough in the air? That will never not be hot.
Dying to hear your thoughts on this one! Please leave a comment and share with your community of other vaguely 30 year-olds.
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