The way we work has fundamentally changed—but our benefits system is still stuck in the 1950s. Here's why that needs to change, and what a fairer future could look like.
---
Picture this: You drive for a rideshare company in the morning, do freelance graphic design in the afternoon, and teach online fitness classes in the evening. You're hustling, you're thriving, you're exhausted—and you have absolutely zero health insurance, no retirement savings, and if you get sick tomorrow, your income simply stops.
Welcome to the gig economy, where flexibility comes with a hidden price tag.
According to the Bureau of Labor Statistics, approximately 57 million Americans participate in gig work in some capacity. That's roughly 36 percent of the U.S. workforce operating outside the traditional employment model. And while the freedom to set your own schedule and be your own boss sounds incredible (because honestly, it kind of is), there's a massive gap in the system that's leaving millions of workers vulnerable.
The core problem? Our entire benefits infrastructure was designed for a world where you worked for one company, probably for decades, and that company took care of you. Pension, healthcare, paid vacation—all tied to that single employer relationship.
But that world doesn't exist anymore for a growing number of workers. And pretending it does isn't just outdated thinking—it's actively harmful.
---
Here's the mental model that changes everything: What if your benefits followed you instead of your job?
Portable benefits are exactly what they sound like—benefits that workers can take with them from gig to gig, job to job, regardless of who they're working for at any given moment. Think of them like a backpack versus a company uniform. The uniform stays when you leave; the backpack comes with you everywhere.
Under a portable benefits system, every time you complete a rideshare trip, deliver a package, or finish a freelance project, a small contribution goes into your personal benefits account. These funds accumulate across all your different income sources and can be used for:
The key principles of portable benefits include:
1. Pro-rata contributions: Companies contribute based on the actual work performed, proportional to earnings or hours.
2. Multi-employer compatibility: Benefits accumulate regardless of how many platforms or clients you work with.
3. Worker ownership: The benefits belong to the worker, not any single company.
4. Flexibility: Workers can choose how to allocate their benefits based on their individual needs.
This isn't just theoretical anymore. Several states and organizations are actively building these systems right now.
---
Let's get real about what's at stake here.
The gig economy isn't just a side hustle phenomenon. For many workers, it's their primary income source. A 2023 McKinsey report found that approximately 36 percent of employed respondents identified as independent workers, up from 27 percent in 2016. And this number continues to grow.
The human cost of the current gap is staggering:
Research from the Aspen Institute found that gig workers are significantly less likely to have access to employer-sponsored health insurance, retirement plans, or paid leave compared to traditional employees. This isn't because they don't want these benefits—it's because the system literally wasn't built for them.
Consider the ripple effects: A delivery driver who can't afford to take a sick day might work while ill, potentially spreading illness to customers. A freelance writer without retirement savings might have to work well into their seventies. A rideshare driver injured on the job might face financial ruin without workers' compensation.
The flexibility paradox is this: The very thing that makes gig work attractive—the freedom and independence—is also what makes workers most vulnerable. It's a trade-off that shouldn't have to exist.
---
This isn't just policy wonk fantasy. Real organizations and governments are creating portable benefits systems today.
One of the earliest examples of portable benefits in action, the Black Car Fund has been providing workers' compensation coverage to for-hire vehicle drivers in New York since 1999. Here's how it works: A small surcharge is added to every ride, creating a pool that covers drivers regardless of which company dispatches them.
The model proves something important: portable benefits can work at scale. The fund covers over 130,000 drivers and has paid out millions in claims.
Alia represents a groundbreaking approach to benefits for domestic workers—housecleaners, nannies, and caregivers who often work for multiple households. Families contribute a small amount after each cleaning, and workers accumulate benefits including paid time off and life insurance.
What makes Alia remarkable is its simplicity. Through a user-friendly platform, even workers with multiple part-time clients can build meaningful benefits over time.
Washington has been at the forefront of legislative efforts to establish portable benefits. While comprehensive legislation is still evolving, the state has explored models that would require gig companies to contribute to worker benefit funds.
While not strictly a portable benefits law, Colorado's legislation requiring pay transparency and equal treatment has created frameworks that could support future portable benefits initiatives.
The Aspen Institute's Future of Work Initiative has been instrumental in developing portable benefits frameworks and bringing stakeholders together. Their research and convenings have helped shape how policymakers and companies think about this challenge.
---
Here's something that might surprise you: Portable benefits could actually be good for business.
The current classification battles between companies and workers are expensive, time-consuming, and damaging to brand reputation. Companies like Uber, Lyft, and DoorDash have spent hundreds of millions of dollars fighting legal challenges over worker classification.
A well-designed portable benefits system could offer a third way—allowing companies to maintain workforce flexibility while providing meaningful support to workers.
Potential business advantages include:
Reduced legal risk: Clear frameworks for benefits contributions could decrease costly misclassification lawsuits.
Improved worker retention: Workers with access to benefits are more likely to stay engaged with platforms.
Better public relations: Companies supporting worker wellbeing gain positive brand perception.
Workforce quality: When workers aren't stressed about healthcare or emergency savings, they perform better.
Some gig companies are beginning to explore voluntary benefits programs, though these often fall short of comprehensive portable benefits. DoorDash, for example, has offered some accident insurance and earnings protection. Uber has piloted various driver support programs. These are steps—but they're not yet the systemic change workers need.
---
When researchers ask gig workers what they need, the answers are remarkably consistent:
Health insurance tops almost every list. The ability to see a doctor without financial devastation is a basic human need that our current system fails to guarantee for independent workers.
Emergency savings and income stability come next. The feast-or-famine nature of gig work means workers need buffers against slow weeks or unexpected events.
Retirement security matters deeply, even to younger workers who understand that Social Security alone won't be enough.
Paid time off—the ability to take a vacation, recover from illness, or care for a family member without losing income—is increasingly seen as essential rather than luxurious.
Skills development and career advancement opportunities help workers increase their earning potential over time.
The Freelancers Union, which represents independent workers, has consistently advocated for portable benefits as a core priority. Their research shows that access to benefits directly impacts worker financial stability and wellbeing.
---
Creating a true portable benefits system requires policy changes at multiple levels. Here's the current state of play:
Several proposals have been introduced in Congress to study or establish portable benefits systems, though none have yet become law. The policy conversation is active, with interest from both parties—conservatives appreciate the market-based approach, while progressives focus on the worker protection elements.
States have been the primary laboratories for portable benefits innovation. California's Proposition 22 in 2020 created a modified model for gig workers that includes some benefits provisions, though critics argue it doesn't go far enough. Other states including New York, New Jersey, and Illinois have explored various approaches.
Some cities are experimenting with local solutions. Seattle, for example, has been at the forefront of gig worker protections and has explored benefits requirements for certain worker categories.
Looking globally offers interesting insights. Some European countries have stronger protections for non-traditional workers that could inform U.S. approaches. The European Union has been developing frameworks to improve gig worker conditions across member states.
---
Here's a useful mental model for understanding different levels of worker protection:
Rung 1: Nothing — Worker receives no benefits, no protections, no contributions. This is where many gig workers currently sit.
Rung 2: Voluntary Company Programs — Companies offer some benefits voluntarily, but workers can't count on them, and they don't transfer between platforms.
Rung 3: Mandated Platform Contributions — Companies are required to contribute to worker benefits funds, but workers must navigate multiple systems.
Rung 4: True Portable Benefits — Standardized system where all contributions flow to worker-owned accounts that follow them regardless of employer.
Rung 5: Universal Basic Benefits — All workers, regardless of employment type, have access to baseline benefits as a matter of right.
Most portable benefits proposals aim for Rung 3 or 4. The goal is creating systems that work practically while significantly improving worker security.
---
Whether you're a gig worker, a traditional employee, or someone who just uses these services, you have a role to play.
Get informed about your current options. Organizations like the Freelancers Union offer resources specifically for independent workers.
Join worker organizations in your field. Collective voices carry more weight in policy discussions.
Advocate for change by contacting your state and local representatives about portable benefits legislation.
Plan proactively by setting aside money for taxes, healthcare, and emergencies even without employer contributions.
Understand the true cost of cheap gig services. When delivery or rideshare prices seem too good to be true, workers might be absorbing the difference.
Support companies that treat workers well and offer meaningful benefits.
Tip generously when using gig services—for many workers, tips make the difference between surviving and thriving.
Contact your representatives about portable benefits legislation. Consumer voices matter in these policy debates.
Explore voluntary benefits programs that can be offered without changing worker classification.
Participate in industry discussions about portable benefits standards.
Support policy solutions that create clear frameworks rather than fighting all worker protection efforts.
---
Here's the thought-provoking question at the heart of this issue: Should your access to healthcare, retirement security, and financial stability depend entirely on your employment arrangement?
The traditional employment model, for all its problems, provided a social contract. You gave your labor and loyalty; the company provided security and benefits. That contract has been broken for millions of workers, but we haven't replaced it with anything meaningful.
Portable benefits represent one possible answer—not perfect, but promising. They acknowledge the reality that work has changed while maintaining the principle that all workers deserve basic protections.
The alternative is a growing underclass of workers who enjoy the freedom of independent work while bearing all its risks alone. That's not sustainable for workers, for families, or for the economy as a whole.
---
Creating a comprehensive portable benefits system won't happen overnight. It requires:
Political will from legislators willing to craft thoughtful policy rather than all-or-nothing approaches.
Business engagement from companies willing to see worker benefits as investment rather than cost.
Worker organizing to ensure that solutions actually meet worker needs.
Public awareness because widespread support creates pressure for change.
The good news? All of these elements are growing. The conversation about gig worker benefits has moved from the margins to the mainstream. Major publications, policy institutes, and political leaders are engaging seriously with these questions.
---
The gig economy isn't going away. If anything, technological change will likely make flexible work arrangements more common. That's not inherently bad—many workers genuinely prefer the independence and flexibility that gig work offers.
But flexibility shouldn't mean vulnerability. Independence shouldn't mean insecurity. The freedom to choose when and how you work shouldn't come at the cost of your health, your retirement, or your peace of mind.
Portable benefits offer a path toward making flexibility sustainable. They represent a new social contract for a new economy—one where security follows the worker, not the job.
The question isn't whether we can afford to build these systems. It's whether we can afford not to.
Your benefits should be as mobile as your career. That's not a radical idea—it's just common sense for the world we actually live in.
---
For more information on portable benefits and gig worker rights, explore resources from the Aspen Institute Future of Work Initiative, the Freelancers Union, and the National Domestic Workers Alliance.
