Somebody Had to Insure the Freelancers

Working Today, Then the Freelancers Union

When Sara Horowitz incorporated Working Today in New York in 1995, the country was in the middle of a quiet but significant shift in how work was structured. Temporary staffing agencies were growing, personal service contracts were multiplying, and the Bureau of Labor Statistics would run its first Contingent Worker Supplement that same year — confirming that a substantial portion of the American workforce lacked the protections attached to standard employment. Horowitz came from a labour-lawyer background and understood the core problem precisely: the benefits that American workers relied on — health insurance above all — were designed around the assumption of a single, continuous employer relationship. People working outside that relationship had nowhere to go.

Working Today operated initially as a nonprofit advocacy organisation, lobbying for portable benefits and drawing attention to the growing population of independent workers. But advocacy without infrastructure has a limited reach, and by the early 2000s Horowitz had concluded that the organisation needed to offer something concrete. In 2003, Working Today relaunched as the Freelancers Union, with a structure built around member services rather than collective bargaining in the traditional sense. The name changed; the underlying diagnosis stayed the same.

The Health Plan as Foundation

The Freelancers Union's first significant product was not a strike fund or a contract template. It was health insurance. In 2008, the organisation launched the Freelancers Insurance Company, a member-owned insurer that pooled the risk of a population — freelancers, independent contractors, the self-employed — that commercial carriers had largely priced out or excluded outright. The logic was straightforward: individuals buying coverage on their own faced underwriting standards and premium rates calibrated for high-risk pools, because insurers had no mechanism for treating a scattered population of solo workers as a group. The Freelancers Union created that mechanism.

At its peak the health plan covered tens of thousands of members in New York State. The model demonstrated that aggregating non-employees into a purchasing group was operationally possible, even if it depended on regulatory conditions specific to New York. When the Affordable Care Act came into force in 2014 and established the individual marketplace exchanges, the competitive landscape for the Freelancers Insurance Company shifted materially. By the end of 2014 the insurer had wound down its health plan, finding that the exchange market — with its subsidies and standardised tiers — had absorbed the function the union had been filling at considerable administrative cost. The organisation acknowledged the closure straightforwardly: the ACA had made one of its primary products redundant.

That outcome looked like a defeat but was also a form of validation. The Freelancers Union had spent years arguing that independent workers needed a group-based insurance mechanism. Federal law eventually agreed, though it chose a different vehicle.

What the Structure Said About the Strategy

The Freelancers Union's approach — building infrastructure before, or instead of, seeking collective bargaining rights — reflected a clear-eyed reading of US labour law. The National Labor Relations Act of 1935, as consistently interpreted by the National Labor Relations Board, does not extend collective bargaining rights to independent contractors. A union whose members are self-employed is therefore a union that cannot negotiate a contract with an employer, because by legal definition its members have no employer. Horowitz's response was not to fight that classification directly but to work around it: if the union could not bargain for wages, it could still aggregate purchasing power, lobby for policy change, and build the kind of associational infrastructure that converted a dispersed population into something resembling a constituency.

By the early 2010s the Freelancers Union reported a membership in the hundreds of thousands — a figure that rested on a free-to-join model rather than dues payment, and which critics noted was difficult to verify independently. The organisation's influence on policy debates, particularly around portable benefits legislation at the state level, was more clearly documented. Its 2013 partnership with Upwork's predecessor platforms on the Freelancing in America survey series brought statistical weight to arguments it had been making for nearly two decades.

The Freelancers Union did not solve the problem of benefits portability in the United States. What it demonstrated, durably, is that the absence of an employer does not have to mean the absence of collective structure — and that sometimes the most radical thing a union can do is offer its members health insurance.