Picture this: it’s 9:30 on a Tuesday night, and Maya — twenty-six, marketing degree from a good school, a perfectly decent salary at a logistics firm — is sitting cross-legged on her apartment floor, photographing an empty orange box. Not the Birkin. The box. The box it came in. Because on Poshmark, that empty box might sell for more than the bag she’s carrying tonight.
And that, friends, is where we are.
In The Hustle’s September 11 edition, there’s a story that keeps rattling around my head long after I finished reading it — the story of the “empty-box economy.” Original packaging for designer goods, consoles, and tech products is selling for hundreds, sometimes thousands of dollars on resale markets. eBay has more than 180,000 “empty box” listings. On Poshmark, designer packaging bundles range from three dollars to ten thousand. A 2021 study found Rolex and Omega boxes averaged around $200; some now go for well over $3,000. Who’s buying? Three crowds: resellers who know a complete set fetches more, counterfeiters who need the finishing touch on a fake, and clout-chasers who just want the box on their shelf so their feed looks richer than their bank account.
Strange? Sure. But it makes more sense than you’d think — because the side hustle itself has gone from fringe to foundation, and Maya isn’t an outlier anymore. She’s the median.
The numbers, again from The Hustle’s September 11 edition, tell the story plainly. In 2017, about 19% of Americans had a side hustle, according to Bankrate. By 2025, that share had climbed to 27%. Think about what that means in a room of fifty people at a wedding or a backyard barbecue: fourteen of them are working a second job. And these aren’t just the night-shift-and-day-shift workers of the old economy — though they deserve more respect than they’ve ever gotten. College-educated workers made up 35% of multiple jobholders back in the 1990s; by 2024, they were over half. The second job has moved upmarket. And women — especially women in their early twenties — are leading the charge, entering a job market that AI is busy rewriting under their feet.
That last detail matters. The Hustle’s piece links the surge to AI destabilizing the job market — and you can feel the logic in your bones. When your day job’s tasks are suddenly automatable, when “AI rewriting entry-level jobs” isn’t a headline but the email your boss just forwarded (Fortune’s CFO Daily has been reporting on exactly this), a second income stream stops being ambition and starts being insurance. The side hustle has become the household’s emergency fund, its hedge against the memo nobody wanted to receive.
Here’s what I keep coming back to: it’s not enough to just admire the hustle — we must listen, learn, and contribute to an economy where everyone’s second job counts as much as their first. Because there are two ways this story goes. In one, the hustle economy is empowerment: Maya sells boxes, flips sneakers, runs a spreadsheet-side consulting gig, and builds a cushion that lets her negotiate from strength at her real job. In the other, it’s precarity with better branding — a generation cobbling together 1.7 jobs to afford one life, with no benefits, no safety net, and no one asking why the first job doesn’t pay enough.
Both are true right now, and the honesty of that is uncomfortable in the way good financial stories usually are.
There’s a darker current underneath the hustle economy, and we have to look at it straight. The same Hustle edition reports the FTC’s estimate that fraud now costs Americans roughly $196 billion — nearly half of it, about $82 billion, taken from people over 60 — and that roughly 37% of fraud now involves AI. Think about that alongside the empty-box economy: where there’s a hot secondary market, there’s a counterfeit market; where there’s a counterfeit market, there are scams; and AI has industrialized the scamming. The empty-box reseller and the empty-box scammer are selling into the same demand. The difference is which side of the line the money lands on, and ordinary people — sellers, buyers, and especially older folks who didn’t grow up fluent in this ecosystem — are the ones getting burned.
And then there’s the $340 million white-hat bitcoin heist The Hustle reported in the same edition — a hacker who stole $340 million from the Liquid Network, then returned most of it after the bug was fixed, with about $47 million still unaccounted for. I won’t pretend to understand every detail of that saga, but I know what it rhymes with: an economy where the lines between clever, criminal, and “eh, close enough” are blurrier than they’ve ever been, and where the biggest paydays are often one terms-of-service violation away from a felony. That’s not a culture any of us should shrug at.
So what do we do with all of this — the hustle, the boxes, the fraud, the fear?
Start with the obvious: if you’re in the 27%, protect yourself like a business, because you are one. Separate your money. Track your hours — including the unpaid ones, the photographing-the-box-at-9:30-pm hours, because your time is the one asset this whole economy runs on. Price your work as though it has to replace your salary, because one day it might. And if you’re buying anything in the resale economy, assume the box could be lying and the listing could be lying, and let the seller’s history talk louder than the photos.
For the rest of us — the ones watching this unfold from the shore — there’s a gentler but real obligation. The people with two jobs in your life are not lazy, and they’re not greedy. They’re responding rationally to a job market that is visibly rearranging itself. The most hopeful thing in the numbers is hiding in plain sight: the side hustle has gone upmarket and mainstream, which means the stigma is dead. Nobody’s side gig is embarrassing anymore. It’s just Tuesday.
I keep thinking about Maya, on her apartment floor, getting the lighting right on an empty box. Is that a healthy economy? Honestly — I’m not sure. But is she smart, adaptable, and paying her rent on her own terms? That much I know. And whatever else we build in this new world of work, we ought to build it so that she only ever needs one job if that’s what she wants. The hustle should be a choice. That’s the take I’ll leave you with.
