A ghostwriter on Substack earns $165K a year. A New York Times bestselling author earns less than a third of that.
A fashion newsletter creator pulls in $275K. A daycare worker in the same city makes $31K.
New York Magazine recently surveyed 60 New Yorkers about what they actually earned in 2025. The responses ranged from $4,000 (a newsstand owner) to $17 million (a consultant). A dog walker earning close to six figures. A Broadway actress at $42K. An Upper East Side doorman at $75K.
The piece is a fascinating window into how fractured our assumptions about income have become. Prestige doesn't predict pay. Neither does how essential the work is to society.
But as I read through each profile, I kept coming back to a question nobody in the article was asking: what does each of these people pay for health insurance?
The part salary surveys always skip
Many of the highest earners profiled in the piece are independent. Freelancers, consultants, self-employed specialists. They're making real money. They're also navigating the individual insurance market alone.
The average full-price marketplace premium in 2025 was $619 a month. For a 40-year-old with a family, unsubsidized plans can easily run above $1,500. No employer contribution. No group rate. And as of 2026, the enhanced ACA subsidies that kept costs manageable for millions of people have expired, pushing premiums even higher for middle-income earners who now fall above the subsidy cliff.
Now look at the other end of that salary survey. The daycare worker making $31K, the home health aide at $23K. They likely have access to employer-sponsored coverage. But "access" is doing a lot of heavy lifting.
The average family premium for employer-sponsored insurance hit nearly $27,000 in 2025, according to KFF's annual survey. Workers cover about 26% of that, roughly $6,850 a year. For someone earning $31K, that's over 22% of their gross income going to premiums alone, before deductibles, copays, rent, or food.
Two broken systems, side by side
What the salary data really shows is two separate health insurance problems running in parallel.
If you're independent and earning well, you're making decisions about deductibles and networks without guidance, and could be overpaying for coverage that could still allow you to be financially wiped out after a single catastrophic health event.
If you're employed and earning modestly, you technically have coverage. But the math barely works. And if that job goes away, whether through a layoff, a restructuring, or a career change, your coverage goes with it. The typical next step is COBRA, which means paying the full premium your employer used to subsidize, plus a 2% admin fee. For most people, that's a sticker shock moment that forces impossible choices.
I know this firsthand. When I was laid off, the cost of health insurance for my family went up over 700%. One day I had employer-sponsored coverage at a manageable rate. The next day I had a COBRA notice with a monthly number that felt like a typo.
The real gap in the workforce
The gig economy, the creator economy, the independent workforce. We celebrate the freedom and flexibility of these paths. But our health insurance system was built for a world where most people worked for one employer for decades.
That world is gone. The infrastructure hasn't caught up.
More than 154 million Americans under 65 still rely on employer-sponsored coverage. And yet, the modern labor market is producing more independent workers, more career transitions, and more moments where people fall between the cracks of a system designed for stability, not movement.
Family premiums have increased 26% in the last five years. Deductibles have jumped 17%. And the people most affected are the ones in the middle: earning too much for meaningful subsidies, not enough to absorb the full cost of coverage without flinching.
What this means for employers
If you're running a company, this isn't just a policy conversation. It's a talent conversation. The people leaving your organization, whether voluntarily or through a restructuring, are walking into one of these two broken systems. And how you handle that transition says something about your values.
For self-insured employers specifically, it's also a cost conversation. COBRA participants generate 2 to 3x higher claims than active employees. Every departing employee who defaults to COBRA because they didn't know they had other options is a financial risk that negatively impacts plan performance.
At When, we built a platform to close that gap. We help departing employees compare COBRA against ACA plans, private options, and Medicare, so they can find coverage that actually fits their needs and budget. For employers, that translates to lower claims exposure, reduced COBRA participation, and an exit experience that reflects the same care they put into onboarding.
But regardless of what tool you use, the first step is recognizing that salary is only half the story. Every person in that New York Magazine piece has a health insurance story attached to their income. We're just not asking about it yet.
And maybe it's time we started.
