Is Everyone Pretending to Have Jobs?

No one wants to admit they don't have to work

You know the way your smile freezes for a second when someone you just met turns, cocktail in hand, and casually drops that ubiquitous little question: “so what do you do?”

During the tiny pause as you inhale and open your mouth, you have to decide which version of yourself to present. Do they seem like someone you should try to impress, or does it feel polite to downplay your status?

How you spin your answer may depend on whether you’re looking for a new job, a date, a client referral - or a swift exit.

For many of us, at least during “the accumulation years” in retirement forum parlance, there’s a straightforward response at the ready. You brighten, stand a little straighter, and flash your LinkedIn headshot game-face: I’m a [job title or idealized function] at [company or industry, whichever sounds cooler]!

Or maybe you’re a full time parent, in which case you might vacillate between mild embarrassment (recounting what you used to do) and conspicuous pride (portraying parenting as an all-consuming, reverent calling). Unless you’re a dad - then you’ll probably just pretend to be self-employed.

That seems to be the preferred strategy of late for anyone who’s wealthy enough to not have to work. If you visit any online retirement forum, you’ll find fraught discussions about how to explain your workforce exit. Surprisingly, admitting you’re retiring is rarely considered.

Jordan Grumet posits that anxiety about what others will think is a primary obstacle for those otherwise ready to retire. He focuses on familial concerns (spousal hesitation, wanting to set an example for kids, disappointing parents), but I think it’s a broader issue.

Few people want to acknowledge publicly that they can afford not to work. They want to continue pretending to be “normal” and “middle class” (and perhaps also “young”).

This worry has always seemed overblown to me, though maybe that’s because I spent my career in finance in Dallas, a materialistic bubble where humble-bragging about your annual bonus or company sale price is far from taboo.

This 2024 Wall Street Journal article stopped me in my tracks though, and I think about it often. It describes how many powerful women in finance have “doting househusbands:”

One stay-at-home dad whose wife works in private wealth at an investment bank says he sometimes tells other men that he manages real estate—technically true because the family owns a few buildings. He says he can identify other men in his position at private-school functions when they say they “manage investments” or “run a boutique hedge fund.”

“We’re all out there, but we can’t say anything about it,” he says.

One I learned it, I heard this secret language everywhere.

Most of my private bank clients had millions invested and didn’t actively earn much, if any, money. Some were middle-aged and had sold a business; others were young adults with big trust funds. Many were aging former execs who invested over decades and had formally retired from a corporation.

But nearly all of them still self-described as workers.

They aren’t lying exactly. A “portfolio manager” might spend time day trading his Fidelity IRA. A “real estate developer” might have inherited some family land. I’ve even met “CFOs” and “family office directors” who actually just preside over their own wealth - though golfing and dining with your network of bankers and attorneys is a sort of occupation, I suppose.

The tldr is that wealthy people commonly use terms of labor to obfuscate their ownership of capital.

Basically, they pretend to have jobs.

That isn’t to say they don’t work at all. But if you’ve ever wondered how a yoga instructor can afford a $700K townhome, or how that executive can play so much golf, or why gyms and malls are full during the day, or how your “normal” friends can travel for seemingly half the year - ding ding ding!

And I get it! Really I do.

Many people prefer to practice “stealth wealth” and actively hide their resources, sometimes even from their own families. They take pride in living frugally and will not abandon their middle class identity no matter how many millions they amass (they make great bank clients, when they aren’t nitpicking fees and interest calculations).

Even big spenders born into generational wealth don’t generally want to advertise it, at least if they’re classy. No one wants to reply to “what do you do?” with “oh, you know, I passively accumulated ownership of the means of production and now spend my days quite at leisure.”

This is America, baby - hard work isn’t just celebrated, it’s required.

What bugs me is the discrepancy between how wealthy men and women manage this message. The stay-at-home-dads in the WSJ article all pretend to have high status jobs, usually related to managing their money (presumably to retain their identity as “provider,” even if unconsciously).

Meanwhile women with just as much wealth seem content to identify as moms (even if they have nannies or their kids are grown) or portray themselves in lower status jobs related to their hobbies (writer, influencer, volunteer, artist).

This exacerbates the perception of gender inequality when it comes to money, career, parenting, and household division of labor.

Work or Play?

The phenomenon is particularly glaring when viewed through the lens of dating apps, the rare place you are prompted to specifically and publicly announce your job / employer.

It’s not necessarily rude to be vague in person where you can easily expand the “what do you do?” question beyond work.

I’ve recently hopped on the mahjong bandwagon and am obsessed! Do you play?

My kids’ sports schedules are keeping me absolutely frantic; can you relate?

I have been noodling on a book idea actually; one of my goals this year was to start writing.

A party or networking event establishes relational, geographic and socio-economic proximity, so job titles are not as relevant.

In the vast digital world of dating though, any thinking person woman is going to want more context than a few photos to decide whether to proceed. Creative evasions may raise suspicion, and refusals to answer (“worker bee” at “none of your business”) can come off as aggressive.

I had recently retired from my banking career when I joined the online dating scene over a year ago. Scanning profiles of men in their late 30s to late 50s, I realized quickly that vague job titles like “President,” “Investor,” and “Founder” can signal “wealthy / retired” or “unemployed / broke.”

It turns out you don’t have to be rich to pretend to have a job.

I don’t generally care (initially, anyway) as long as you’re cute and want to buy me a cocktail. It’s usually obvious though - maybe because of the 20 years I spent as a private banker, a job that on a basic level boiled down to sussing out strangers with money, meeting them at upscale restaurants, and getting them to like me.

The big difference is now I can’t expense it.

I struggled to categorize my (lack of) employment on my own profile. As a woman, my job doesn’t matter nearly as much as my pictures - which is annoying and unfair, if sometimes convenient.

My fluency in the secret fake-job language of the wealthy supplied plenty of options though:

• I am still a licensed Financial Advisor and a Registered Investment Advisor, though those titles imply employment at a broker dealer - and sound more like a LinkedIn profile than a dating one.

• I remain a Certified Financial Planner™ so that’s an easy non-lie. Though that alone implies (to insiders at least) that I’m under- or even un-employed.

• I toyed with “Retired Banker” during a defiant period after noticing men around my age who identified as retired. Why shouldn’t I? Equal representation!! (Maybe because it reeks of “masculine energy” and might “intimidate” men, terms I wish I didn’t regularly encounter.)

• I added Writer after a mastermind retreat last year - mainly to affirm that identity and manifest a writing practice. Though it can invite somewhat embarrassing questions about what I’ve (not yet) written - and implies poverty.

• I could use President (of my LLC), real estate investor (totally passive), or many of the other investment-centric titles mentioned above. (Also allegedly squelchers of “feminine energy.” Also I don’t give a shit.)

I’ve been using “Financial Strategist” since opening my consulting practice. You can interpret “consultant” to mean well-paid overworked employee who travels weekly for work, or unemployed, or early retiree with a few clients who travels monthly for fun.

My smile might still freeze as I watch your brain scan me for the most likely definition. But I’ll enjoy my cocktail either way.

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I help people get organized and use wealth to design a life that feels secure and aligned. A former Wall Street banker and CERTIFIED FINANCIAL PLANNER™, I act as an unbiased advocate without selling products or managing investments. To learn more, visit my website.

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