The ground beneath us is shifting—again. With fresh momentum behind portable benefits and new developments in independent contractor classification, we may finally be approaching a long-overdue reckoning: Our employment system is broken, and it’s holding us back from the future of work.
For decades, we’ve clung to a binary model of employment that assumes all workers fit into one of two rigid categories: either fully employed or truly independent. That framework might have worked in the industrial era, but it’s fundamentally misaligned with today’s economy, where innovation demands flexibility, and workers increasingly value autonomy. Yet, instead of evolving, we’ve layered outdated laws onto new realities, leaving businesses caught navigating a patchwork of legal tests with vast differences of case law and interpretation, and workers without access to the benefits and protections they deserve. The system’s opacity—the vague, contradictory classification tests and standards—has halted most meaningful progress on moving work forward.
Can independent contracting be a choice?
When gig platforms first emerged—from virtual call centers to rideshare and delivery apps—the reaction from labor advocates was swift. California became the proving ground for this, with landmark court decisions like Dynamex, quickly followed by sweeping legislation like California’s AB5. AB5 codified the decision in Dynamex, which created a new “ABC” test that made it virtually impossible for platform companies to defend independent contractor classification in the state. Coupled with a unique enforcement environment that incentivized lawsuits with massive penalties, a tidal wave of litigation followed. The legal and regulatory approach was clear: Shut it all down.
And for a while, it worked. Attorneys won enormous monetary judgments, companies faced staggering penalties, and platforms were pressured to abandon innovation or risk extinction. Between class action lawsuits, increased audit, and enforcement activity by state agencies and attorneys general, I watched many startups shutter firsthand. Entrepreneurs who dared to reimagine work were forced to either pivot or perish.
The implicit message was that worker independence was inherently exploitative, and the only solution was to push everyone into traditional employment—whether it worked for them or not. But this narrative overlooked a critical fact: People want to work differently.
Flexibility as a feature
Then came Uber. With deep pockets and an unapologetic disregard for traditional regulatory pathways, Uber bulldozed its way into mainstream commerce. It forced the country to confront an uncomfortable truth: Flexibility isn’t a loophole, it’s a feature. And for millions of workers, it’s a necessity.
Of course, Uber’s approach wasn’t perfect. Its disruption drew deserved criticism and made life harder for those of us advocating for a more collaborative path forward. But in forcing a national conversation, Uber revealed a deep disconnect between how work is regulated and how it’s actually lived.
When I began my career as a lawyer for tech companies, I thought worker classification was a technical niche. But as I met single moms managing multiple gigs to support their families, people with disabilities needing control over when and how they work, and caregivers juggling appointments and aging parents, it became clear: Our current system isn’t just outdated, it’s unjust. It excludes entire communities from opportunity, not because they can’t work, but because the structure of work doesn’t work for them.
The need to reimagine work
Today, those questions of classification, protection, and participation are no longer abstract legal puzzles. They sit at the heart of our economic competitiveness. If we want an economy that fosters innovation and includes everyone, we must redesign the systems that underpin how we work.
It’s our system that’s broken.In the U.S., nearly all benefits and protections are tied to employment status. The solution isn’t to force everyone to be traditional employees. We have to reimagine work.
And businesses know this. Startups and legacy companies alike are eager to meet workers where they are. But they’re paralyzed by risk. Under current law, if a business offers even modest protections and benefits to independent workers—say, accident insurance or retirement support—it could trigger a legal reclassification that unravels its entire business model. The result? A chilling effect on innovation and workers left without a social safety net. Companies avoid doing the right thing out of legal necessity, and workers are left to navigate the economy alone.
This is not just a labor issue. It’s a business imperative.
Forward movement
Fortunately, momentum is building. States are experimenting with hybrid models. In California, voters passed Proposition 22 to create what is essentially a third category of work—preserving independence while providing some protections. At the federal level, leaders like Senators Bill Cassidy, Tim Scott, and Rand Paul have proposed legislation to support portable benefits and create clearer legal definitions. These are early, imperfect steps, but they reflect a growing recognition that we need a new compact.
Private companies are also stepping up. DoorDash, for example, partnered with Stride Health to help independent workers access benefits like health insurance and financial tools. This kind of leadership shows what’s possible when business is empowered to innovate to serve both flexibility and fairness.
What we need now is the policy infrastructure to match that spirit of innovation. That means decoupling benefits from employment status, so protections can follow the worker—not the job. It means giving companies a safe, legally sound path to support nontraditional workers. And it means building systems that reflect the way people actually work today, not the way they worked 50 years ago.
The future of work isn’t some distant horizon. It’s already here. What remains to be seen is whether our laws—and our leaders—are ready to meet it.
Regan Parker is chief legal and public affairs officer at ShiftKey.
