The future of benefits are portable, but how do we get there?

Legislation is spreading across the country to allow the creation of Portable Benefits for non-traditional workers (freelancers / gig / independent). A bill introduced in Congress in 2023 would fund national pilots of the same, and the debate has re-emerged this summer.

As someone who built her early career on a portable major medical plan for NY freelancers, I’ve seen how this can work in practice. What we need are trusted associations, non-profits and social-purpose businesses to provide key infrastructure for portable benefits and a multi-stakeholder approach to funding them. This cannot be left to big tech & venture capital.

  • There is no doubt that the nature of work is changing at all levels of the economy. More flexible. More on-demand. More tech-enabled. Shorter term. Based on networks and platforms. More part-time, simultaneous and fluid. The current system is not built to handle this.

  • We have also seen that not every group needs the same care. By allowing different sectors, industries and employers to select appropriate options for their employees, we have a patchwork system for traditional employees that allows for some customization. While deeply flawed, when it works, it works. Giving arts organizations, associations and other purpose-built platforms the same flexibility, we can create portable benefits that are tailored to different communities.

  • Artists and freelancers have told us that flexibility is it’s own form of safety. By diversifying their income streams most flexible workers mitigate the risk of economic downturns by no longer relying on a single employer for their livelihood. Avoiding “job lock” (where you’re stuck at one employer, platform or work source) is a key strategy to maximize income and efficiency that must be preserved when looking at portable benefit options.

Earlier this month, I co-authored a Snapshot on Portable Benefits with Creatives Rebuild NY and the Artists at Work Program. You can read it here.

Ann Boger

Ann Boger is the founder of Bramble & Bird Consulting and Managing Director of Velarium Labs, a new benefits incubator launching in 2026. She is a fractional executive across multiple healthcare and insurance startups; was previously VP of Scaling for Coterie Insurance and Chief Operating Officer of Freelancers Union and Insurance Company before health reform. She splits her time between New York City and coastal Maine.

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