2025

Georgia in the summer. What can you say about it? It’s hot. The whole day through. Even at night. Especially at night. When the moonlight’s falling through the pines and it’s still 90 degrees.

I think I enjoy the drive into Savannah more than the city itself. There’s a backroad that winds through the Low Country boondocks on a meandering path to the foot of The Talmadge Memorial Bridge, which spans the Savannah River.

They’re widening part of the route now, and ruining the ambiance in the process. It used to be a wormhole to a Deep South past you never knew, but were somehow still nostalgic for. It’s an almost religious experience: Driving down that road under the Spanish moss, music on with the sunroof open so the humidity can mingle and merge with quintessentially local psalms like OutKast’s “Slump” or Goodie Mob’s “Black Ice.”

Savannah’s convenient to the island I called home for the better part of eight years. When I visit the island, I generally make the short drive over to the city to wander and eat. Or eat and wander.

When I felt the shoulder tap, I spread my napkin out on the bartop, expecting a server’s hand to reach in with the shrimp, grits and andouille sausage dish I’d ordered. When nothing came, I swiveled around to see a familiar face. I knew Jasmine as a bartender from a steakhouse on the island, but there she was, smack dab in the middle of the city wearing a key-lime green dress and holding what looked like an espresso martini.

Jasmine’s in her mid- to late-twenties, but her mannerisms and demeanor are still that of a 19-year-old. Rather than greet me like an adult, she waved her free hand in an exaggerated arc as if I were standing 50 yards away not sitting right in front of her: “Haaayy!”

“Well hey there.” I was genuinely surprised to see her. Geographically, Savannah’s only a stone’s throw from Okatie, where she’s from. But over-50 golf communities aside, Okatie’s the South Carolina backcountry. At the risk of overgeneralizing, residents of Beaufort and Jasper counties tend to find themselves serving martinis to people in dresses at nearby resort clubs, not being served martinis while wearing dresses over the state line in the region’s only cultural center.

Jasmine was a testament to that admittedly distasteful generalization: She went to Clemson to study psychology for two years, but dropped out because she found it too bumptious. (Clemson’s a good school, but it’s not exactly Harvard on the supercilious scale.)

“You look nice,” I said. “Very sophisticated.” “You look hot,” she told me. I took a nervous two-second beat. Then I realized she was talking about my clothes. “Oh! Right,” I exhaled, relieved. Despite living in the south for substantially all my life and near the coast for most of it, I have a hard time dressing for the summer. That night I was wearing a Golden Goose denim jacket over a forest green Saint Mxxxxxx sweater adorned with the silhouette of Cerberus.

“What brings you to Savannah?” I wondered. “I live here now,” she chirped. The couple to my right was paying their check. “Wanna sit? Looks like this spot’s opening up.” She was meeting a friend who turned out to be an equally bubbly twenty-something. They had appetizers while I ate dinner and dessert. I bought their food, but not their drinks. They were on stop number one of what sounded like a bar-hopping marathon and I didn’t want to contribute financially to however that might end up 12 drinks, five bars and seven hours later.

Jasmine was a star, she just didn’t know it. She had a young Halle Berry look and just enough of a sarky side to temper her otherwise over-the-top vivacity. The problem, indelicately, is that she never struck me as especially intelligent nor “street smart.” You need to be one of those two, and ideally both, if you’re going to make it anywhere in life.

This was the first time I’d seen her outside that island steakhouse, and I was grateful her friend was there to keep her entertained. Try as I might to be unpretentious, even my small talk tends to be untraversable, which is one reason I’ve taken to listening more than talking when I engage people in person these days.

She’d moved to the city with no job and a few thousand in cash, comforted by the notion that with mom and dad a mere 20 miles away and ample openings in the food and beverage industry as a fallback, Savannah was a mostly risk-free proposition. Still, I assumed there was some plan to earn money. And I assumed that plan wasn’t well thought out. Sure enough.

“See this?” She turned to me, grinned and pointed with her index finger at one of her top teeth. “The food stuck in there?” I joked. She snapped her lips shut. “I’m just kidding, there’s no food.” She slapped me on the knee and grinned at me again. “See it?” “What? That — what is that? A diamond?” “Not a real one, silly!” “Yeah, I assumed–” “It’s a tooth gem!” she exclaimed. I had nothing: “Never heard of them. That’s a thing?” “Oh yeah, it’s big,” she gleamed, motioning to her friend who nodded enthusiastically: “It’s a killer side hustle.”

She showed me someone’s Instagram page. A girl in California who supposedly makes a lot of money hustling tooth gems. “So, what’s the business model?” I asked. “Well, you buy them and then you put them on people. You start with your friends and then you go from there.”

I had questions. Like, “Shouldn’t a dentist do that?” And, “What happens if the gems come off and someone swallows them? Is there liability there?” And so on. I knew she didn’t have the answers, so I didn’t ask. I did ask about the margins, though. She gave me some numbers — how much the kits cost and how much she could charge to bond the faux gems to people’s teeth.

I pulled out my phone as if to respond to a text message. I Googled an overview of Savannah’s demographics and did some quick math on my calculator app. She’d need to put tooth gems on more or less every Savannah resident aged 14 to 25 to make a respectable living. An optimistic scenario for market penetration — which implicitly made even more optimistic assumptions about her dedication, discipline and marketing prowess — projected a maximum annual haul of $10,000, maybe $12,000.

There was no point telling her that. The only thing more infinitesimal than the chances of that business succeeding were the odds of me ever seeing her again.

“Well, I guess there’s only one question,” I said, slipping the phone back into my messenger bag. “What are you gonna call it?” She lit up: “Jazzy Jewels!” I shook my head: “No, no, no.” She turned serious. “You don’t like it?” “It’s ok,” I said. “But ‘Jewels by Jasmine’ sounds more sophisticated.”

She looked pleased. “Maybe I’ll go with that. Think it’ll work?” I wanted to be polite, but I didn’t want to lie. In this case, the two were mutually exclusive, so I deflected. “Well, I once quit a restaurant job for a hustle,” I told her. She was intrigued: “Did it work?” I paused. “Yes and no.”

Yesteryear’s luxury

“Americans Are Side-Hustling Like We’re in a Recession,” The Wall Street Journal declared on June 18.

The article was notable not so much for the debate about whether the prevalence of second, third and fourth jobs is a recession portent, but rather for the extent to which it suggested that, to quote directly from the piece, “holding one job at a time is on the way to becoming a luxury for emerging generations.”

The columnist from whose digital pen that line sprang probably wasn’t aiming for Olympic-level perspicacity, but the characterization of a work life defined by gainful employment in a single occupation as a “luxury” no longer available to most economic agents in America is actually quite profound.

Americans have long mourned the demise of the apocryphal blue-collar aristocrats, the disappearance of pension jobs and related shifts blamed for the slow-motion decline of the middle-class, a phenomenon which began to accelerate in the 1980s. Young adults were encouraged to get four-year college degrees as a kind of insurance policy against labor market obsolescence. Then it was four-year degrees plus a Master’s. When MBAs and the like became a dime a dozen, you needed a PhD to distinguish yourself.

Now, in the 2020s, we seem to have reached a point where job opportunities for college graduates — who’re saddled with $30,000 in debt on average when they enter the labor market after obtaining a bachelor’s degree and $75,000 after receiving a postgraduate degree — are becoming more scarce due to, among other things, oversaturation.

In today’s US economy, demand for trade labor’s on the rise, but the legacy of mistakes made decades ago is manifesting in shortages. As McKinsey & Co. put it in an April 2024 study, “Gen Z workers report persistent cultural barriers to vocational training.” Although vocational enrollment’s rising marginally, it’s impeded by “a stigma associated with choosing vocational school over a traditional four-year university.” Specifically, eight in 10 respondents to McKinsey’s poll “said their parents wanted them to pursue a college education after high school, while only 5% said the same about vocational school.”

So, we killed yesteryear’s labor market and replaced it with one focused almost entirely on jobs which require four-year degrees or better, but now that labor market may be dying too and we can’t go back because after all these years — and in most cases without meaning to — we’ve instilled in ourselves the notion that there’s no honor or pride in being an electrician, a plumber or a carpenter. Jesus, after all, was an investment banker and later taught graduate economics courses.

What’s a young person to do in America? The factory’s out. Literally. There aren’t any anymore. Seemingly every other headline laments the plight of heavily-indebted college graduates forced to move back in with their parents, which sounds terrible, but choosing trade school is to be ridiculed by those same parents for resigning to a life of hammers and wrenches.

Enter the hustles. Everyone under 35’s a “hustler” now, in case you haven’t noticed. The figure below gives you a rough, stylized sense of how challenging the US economy’s becoming, and how Americans are coping.

Suffice to say interest in side hustles has exploded over the past 10 years.

To be clear, that chart’s “for illustrative purposes only,” as the boilerplate caveat goes. It might even be more accurate to say it’s for entertainment purposes only. Google Trends can only track interest for terms which have some cultural relevance. The idea of a side hustle is as old as the hills, but side hustles weren’t always called “side hustles.” (Once upon a time, this was “moonlighting.”) So what you’re seeing in the Google Trends data is, in part anyway, just a vernacular shift.

Still, the popularity of the term in search results among US citizens tells us something — namely that Americans spend a fair amount of time researching what they might do to make extra money in an economy where, according to a May Indeed poll of 1,256 currently-employed or job-seeking US adults, most people need at least one side hustle to make ends meet.

Can’t knock the hustle

Although pretensions to financial independence are by no means the exclusive purview of younger Americans, the notion that the road to El Dorado is paved with side hustles is more prevalent among Gen Zers and young Millennials, who Intuit recently dubbed “The Side Hustle Generation.”

Similarly, Bankrate in September proclaimed that economic actors under 40 are redefining the American dream — one side hustle idea at a time.

In the 2024 vintage of Bankrate’s annual side hustle survey (and the fact that such surveys are being conducted regularly says a lot on its own) showed that 48% of Americans aged 18-27 and 44% of those 28-43 have a side hustle.

The figure above gives you a sense of how difficult it is to create and sustain a meaningfully lucrative side venture. Just 14% of Millennials said they earn more than $2,000 a month on their side hustles, and that was the highest share of all age cohorts. Among Gen Zers with a side hustle, nearly four in 10 reported making $50 or less each month for their trouble.

When you look at the averages — which are presumably pulled higher by a handful of outliers — you come away with a somewhat more encouraging picture. For example, Bankrate was keen to note that among Millennials, the mean extra monthly income from side hustles was $1,129. That sounds ok — until you multiple it by 12, at which point you realize we’re talking about less than $14,000 per year.

A 2024 LendingTree survey showed more or less the same thing. 55% of Gen Zers and Millennials polled said they had a side hustle, and the self-reported average monthly supplemental income was $1,253.

The nature of these hustles varies widely, and LendingTree didn’t try to obscure the extent to which some Americans are inclined to less socially acceptable hustles. As the figure below shows, 8% of side hustlers in the poll are selling drugs. So, actually hustling.

OnlyFans made the list too. Although managing an OnlyFans account isn’t “illicit,” per se, it can be explicit. Note that the figures in the chart add up to far more than 100%, which is to say many respondents are engaged in more than one of those side hustles.

The Bankrate survey showed the overwhelming majority of side hustlers are new to the game. Even among Gen Xers, only 12% said they’ve been hustling for a decade or more. With the typical payout as low as it apparently is in the side hustle business, one wonders how long newcomers will stick with it.

They may not have a choice. A third of survey responds said they’ll likely “always” need a side hustle to make ends meet. As Bankrate credit card analyst Ted Rossman put it, “While it’s admirable that so many Americans are putting in extra time and effort on their side hustles, it’s unfortunate that most are doing so simply to fund their expenses.”

The LendingTree survey found that more than eight in 10 Americans with “side gigs” said they’re now more dependent on those hustles due to “the current economy.” That, at a time when the unemployment rate in America remains historically low.

2008

“You know my parents love you, right?” Christi was maybe 35 at the time. Her parents, who definitely weren’t Italian, ran the best Italian restaurant in town and had for almost three decades. And they did love me. More even than their own children, I sometimes imagined.

We were sitting in the office, a cramped space wedged uncomfortably between the kitchen and the bar. “Umm, yes I’m well aware,” I said. She looked like she knew something I didn’t. “If you got something to tell me, now’s the time, because–” We heard the back door open and shut. “Whatever it is we’ll talk about it later,” I said. “They’re here.”

We hurried out of the office, through the server alley, around the hostess stand and into the bar area, where she and I spent the morning arranging white balloons and roses. It was the same setup every year. They always humored us by acting surprised.

“Happy Anniversary!” we yelled, as they rounded the corner from the office hallway which led into the back bar. She gave them her gift (I can’t remember what it was) and I presented them with mine: A bottle of Perrier-Jouët. That year, I splurged on the gift box which came with a set of hand-painted flutes.

He shook his head. “You know you don’t have to do this,” he told me, sighing. His wife came around the bar and gave me a bear hug. A college volleyball player once upon a time, she was a formidable woman even in her sixties.

He wasn’t stupid. And he’d known me by then for a little over four years, a period during which I’d metamorphosed from an endearing 4.0 political science major with a near six-figure side hustle repertoire and designs on law school, to something more subtly sinister. I was never harmless, exactly, but the nature of the hazard was changing. 2006’s Veuve Clicquot anniversary gift was a manipulative gesture. 2008’s Perrier-Jouët boxset was understated coercion.

I didn’t see it that way at the time, or if I did, I don’t remember being cognizant that I was changing. Certainly, he was more attune to my personal phase shift than I was. And he let me know about it that day.

It was just after 10 in the morning. We opened for lunch at 11. The servers were starting to show up, bedraggled and bleary-eyed. Christi and her mother set about clearing away the anniversary balloons and nursing waitstaff hangovers with hot toddys and aspirin. He called me out to the loading dock where one of our liquor and wine reps was carting in cases of Ruffino.

“Do you know how I kept this place open when I first bought it?” he asked me, looking out wistfully at the parking lot. “I, uhh” — I did know, but I wasn’t sure where he was going, so I played it safe: “I’ve heard stories.” He nodded and chuckled.

After an uncomfortably long pause, he turned to me and put his hand on my shoulder. “You know I don’t care about the bootleg DVDs, the valium –” I tried to interject: “It’s not vali–” He took his hand off my shoulder and put it in front my face to stop me. “Whatever it is, I never cared about it or any of the rest of it, but this…” He fished a piece of a plastic straw out of his pocket and held it up. “… this I can’t have.”

I played dumb. “My drug of choice is amber, liquid and legal.” He shook his head: “You’re gonna insult my intelligence now?” “No, I just– I’m not–” “I didn’t say you were. What I am saying is that for all the sh-t I let you do, I can’t let you suck the life out of this place by turning my staff into junkies.” He paused. Then started up again. “If you want to keep coming in here for a W-2, you gotta keep this sh-t outta here,” he scolded, wagging the cut-off straw at me like it was a finger. “Do you understand?”

I put on my crestfallen face. “Don’t give me the act,” he said. “Just tell me you understand.” “I understand,” I said, pulling out a pack of Turkish Golds. I offered him one as joke. He didn’t smoke and he hated that his wife did. He turned and walked back inside.

I sat down, dangling my legs off the loading dock and dragged on the Camel. I heard the door open again behind me. “Thanks for the champagne,” he called out. The door clanged shut. He hadn’t waited for a reply. “Yeah, you enjoy that,” I muttered, under my breath. “Cheers.”

Rise of the polyworkers

There’s a human resources-friendly euphemism for side hustling: Polyworking.

As The New York Times wrote in a May piece, that term “began cropping up after the pandemic as an upbeat spin on Millennial workers’ reputation for taking on side hustles, trying to monetize hobbies and eschewing 9-to-5 work.”

Apparently, that’s the pep talk a 35-year-old working days at Home Depot and nights as an Uber drive gives himself at 5:00 in the morning: “I’m not struggling to make it in the ‘gig economy,’ I’m ‘polyworking.'” Or, “Who needs steady, gainful employment when you’re ‘polyemployed’?”

The Times article’s as short as it is sad. It centers around one statistic: As of March, there were nearly nine million people in America working multiple full- or part-time jobs. The number came down a bit in April and May, but still sits at 8.6 million. Recent readings are the highest since 1994, when the BLS series begins.

The chart also gives you some context: The blue line shows multiple jobholders as a share of the employed. The situation doesn’t look so extreme on that score, but the reading for March, 5.5%, still counted as among the highest in a quarter century.

It’s fair, I think, to suggest the BLS series is materially understating the prevalence of so-called “polyemployment.” The government has no efficient, real-time way to track house-sitting gigs and Etsy stores, let alone OnlyFans revenue and cocaine sales. Indeed, based on the survey results cited above, it’s almost surely the case that the real number of multiple jobholders across the US economy is astronomically higher than the official BLS tally.

A 2022 McKinsey survey found that 36% of employed respondents identified as “independent workers.” That, the consulting firm remarked, was “equivalent to 58 million Americans when extrapolated from the representative sample.” For reference, that share was 27% in 2016. The color accompanying the study described “a seismic shift in how Americans work and support themselves.”

This phenomenon is by no means confined to Americans without a college degree. As alluded to above, more and more college-educated Americans are discovering that to the extent a four-year degree still functions as a labor market insurance policy, the premium’s enormous and the coverage is quite poor.

A St. Louis Fed study published in March found that more than half of Americans with multiple jobs have a four-year college degree. Consider this: In 1994, fewer than one in three Americans with a college degree were compelled to hold more than one job versus seven in 10 for Americans without a degree. As of December, the share of college-educated Americans “polyworking” is higher than the percentage of “polyemployed” Americans without a degree.

In a testament to just how upside down and ironic this all really is, the Journal article cited above quoted a consultant to UC Irvine’s entrepreneurship center who said “more colleges are preparing students for a world that might require them to work a second job.” So, you now go to college to learn how to cope with an economy which no longer values your college degree.

The same piece profiled a young lady whose degree in business marketing landed her a day job as a social-media coordinator for a California-based aerospace company. At night, she works as a DJ. When she’s not overseeing Facebook campaigns for an aeronautics contractor or spinning records at a nightclub, she “makes and sells rhinestone-studded clothing as a side hustle.” Someone should tell her about tooth gems.

2010

“I’m not going.” I said it flatly, without looking up from a worn copy of Bertrand Russell’s The History of Western Philosophy, which I was committed to reading again as atonement for an academic sin.

I’d just dropped an off-semester independent study in political theory and I felt vaguely bad about it. Post-graduate independent studies demand a lot in the way of disciplined self-direction. While I’m personally amenable to asceticism, the circumstances at the time weren’t, the monastic life being inherently incompatible with the pursuit of ill-gotten material wealth.

It was late-spring, but we were sitting under a money tree at the beginning of autumn. That summer would be the coldest of winters.

“Where?” she called in through the screen door. “Where are you not going?” I’d known her for nine or so months and we’d been dating for the better part of that, long enough for her to feel comfortable questioning my judgment. But she was 20 years old. Like most people that age, her dissents were easily silenced with expensive gifts.

“To the restaurant,” I said, turning a brittle page loudly. “I’m not going to the restaurant tonight.”

She finished her Marlboro Red, flicked it off the balcony and stepped back inside. “Why? Are you sick?” I laughed. “Do I look sick? I’m never sick. The Buffalo Trace keeps me internally sanitized.” She stared at me blankly. “I’m done with it. I’m not going back there.”

I heard her drawing a breath as a prelude to an objection. So I put the book on the coffee table next to her Neverfull, leaned back on the couch and crossed my legs casually in a bid to defuse a nascent argument. “Look, it’s stupid. And everybody there knows it’s stupid.”

She was still standing up. “What about tax returns? How are you going to show–” I stopped her. “I just filed. We’ll worry about it next year.” She reached down into her bag on the table, fished out a fresh pack of Reds and tapped it on her thenar eminence.

I uncrossed my legs, leaned in again and looked up at her: “Listen, it’s putting them in a bad position.” “How so? You’re–” “Darlin,’ I don’t even have a job title anymore.” “You’re a manager,” she ventured. “I don’t ‘manage’ anything. I just sit in the office. It’s a no-show job and I can’t put that on them anymore.” She shrugged: “Ok. You were the one who said we always needed W-2s.”

I stood up, walked over to her and put my hands on her shoulders. “It’ll be fine. Let’s just enjoy the summer, ok?” She nodded. I trailed my left hand down her arm and tapped the back of her right hand. “Can I have one of those?” She unwrapped the cellophane and handed me a Red.

I went out onto the balcony, leaving her standing in the living room. “When do I get to quit?” she grumbled. I’d installed her as a hostess at the same local Italian joint. Her shift was coming up in half an hour. “Not tonight,” I called back, grinning to myself and dragging on the Red. “You gotta take my copies of the restaurant keys back to them.”

I looked in through the screen door. She was on her way down the hall. “Hey! Don’t forget the keys.” She did a one-eighty, snatched the key ring off the kitchen counter and looked across the living room at me.

“What am I supposed to tell them?” she demanded. I thought about it and came up blank. “I don’t know, whatever you want.”

She let out a waspish groan, did another one-eighty, headed back down the hall and out the front door. A wind-up ballerina doing pirouettes inside of my snow globe.

The game

It’s clear to me that barely anyone writing about the side hustle trend in America knows what it means to be a hustler.

The term “hustler” is being co-opted daily by economists, pollsters and financial journalists who don’t understand the connotation. They’re inadvertently invoking and misappropriating an entire subculture complete with its own mythology, heroes and gods.

Some of those heroes, having beat the odds to retire safely from the game, will tell you that anything can be a hustle. That someone who parlays a babysitting gig into a daycare center with annual revenue in the millions is a hustler. Or that someone who turns their grandmother’s apple pie recipe into a pastry empire is a hustler. And so on.

I beg to differ. A “gig” can never be a hustle. And it’s a mistake to conflate hustling with entrepreneurship. Intuit recently conflated all three, writing that “the multiple gigs hustle is alive and thriving among Gen Z and Millennials,” more than two thirds of whom “intend to carry their entrepreneurial ventures [through] 2025.”

A gig is just a petty side job unless and until it becomes a business, at which point the business owner’s a kind of accidental entrepreneur. A deliberate entrepreneur is someone who starts a business with a plan and some seed capital or a bank loan.

To be sure, there’s a lot of overlap between serial entrepreneurship and hustling, but they aren’t, strictly speaking, the same thing. Both serial entrepreneurs and hustlers share a love for “the game,” so to speak. But that love tends to be secondary with serial entrepreneurs, whose first passion is usually to build.

In a testament to that, a 2024 Deloitte survey of Gen Zers and Millennials found that nearly nine in 10 said their work should serve a purpose, presumably one that accrues to the benefit of society. That desire to find deeper meaning in one’s work is a major factor in younger generations’ declared affinity for self-employment.

That’s admirable. It’s the stuff good entrepreneurs and business owners are made of. More importantly, it’s the kind of mentality that makes the world a better place. But it’s not the DNA of a hustler. For a real hustler, it’s not about building. And past a certain level of financial success, it’s not about the money either. It’s about the game itself. If you know, you know.

Some hustlers eventually leave the game to become entrepreneurs, or otherwise “go legit.” But for all their virtue signaling, reformist rhetoric and pretensions to self-reflection, and no matter how successful they are in the corporate world or in polite society more generally, they never truly redefine themselves, precisely because they don’t want to.

As Mekhi Phifer put it while portraying Rich Porter in the 2002 true crime drama Paid In Full, “I love the game. I love to hustle, man. I be feelin’ like one of them ball players, you know? Like Bird or Magic or somethin.’ Yeah, you know I got dough, I can leave the league. But if I leave, are the fans still gon’ love me?”

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