Chappell Roan Was Right: Health Insurance Shouldn’t Depend on Your Job

On Musicians, Freelancers, and the Fight for Affordable Healthcare—including Stride’s partnership with The Recording Academy

Last night’s Grammys highlighted an urgent issue within the music industry and the broader American workforce: the need for a benefits system that works for everyone, not just those in traditional jobs. Chappell Roan, during her acceptance speech, called out the failure of her first record label, Atlantic, to provide basic support like health insurance.

Her words point to a deeper systemic problem—our country’s outdated, employer-centric benefits model.

At Stride, we were founded to serve America's 60+ million freelance and independent workers—a group that has always included the creative class: musicians, athletes, artists, and writers. Musicians like Chappell Roan have historically been left out of traditional benefits structures, despite the essential cultural contributions they make.

This problem isn't new to us. Early on, we worked with athletes and creators who faced similar challenges. Alex Honnold, the legendary free solo climber, once shared how hard it was to secure affordable coverage despite being one of the most celebrated climbers in the world. Rich Roll, an ultra-endurance athlete and author, and Evelyn Stevens, a professional cyclist, echoed similar struggles in accessing healthcare while pursuing their dreams. As Rich said “suddenly my family was without health insurance” when he quit his job to pursue athletics, writing, and building what is now a top podcast.

These stories are a stark reminder of how broken the system is for anyone outside the nine-to-five.

Chappell’s former label isn’t alone in its lack of support; they’re a product of a system that ties critical benefits like health insurance to traditional employment. If your job doesn’t provide insurance, you’re left to navigate a complex and confusing system on your own. This is why so many creatives, including musicians like Chappell, find themselves uninsured or underinsured.

But there is hope.

Stride has partnered with The Recording Academy—the very organization behind the Grammys—to help artists access affordable healthcare. We handle the heavy lifting, from enrollment to securing premium-lowering tax credits. Most artists qualify for significant financial assistance under the Affordable Care Act but often don’t realize it. It’s likely that when Chappell was working at a coffee shop in Missouri, she would have qualified for ACA subsidies—unless she fell into the Medicaid gap, a gap Missouri has thankfully since moved to close.

Some companies are beginning to take responsibility. Warner Music Group, for instance, has partnered with Stride to provide their musicians with access to coverage. As WMG COO Carianne Marshall said in Billboard “We’re not only committed to our writers’ careers and songs, but also their well-being.”

This is a step in the right direction, but we need more.

We need a shift toward a benefits system designed for individuals, not just employees. Companies should be able to contribute to the benefits of independent contractors, whether they’re under contract for a year, a tour, or a single project. And they should provide guidance from experts who understand the unique needs of freelancers. Stride has already ignited this opportunity with portable benefit contributions programs in Utah, Georgia and Pennsylvania. And will be expanding to new industries and states later this year.

Chappell Roan’s call to action at the Grammys was powerful and necessary. It’s time for the industry to step up and for our benefits system to evolve. At Stride, we’re committed to building a future where every worker, no matter their job or status, can access the coverage and care they deserve.