Oct 4, 2025
When Venus Williams was asked by a reporter why she had come back to participate in (and win) her first singles tournament in 16 months, she smiled and said to her adoring fans, “I had to come back for the insurance because they informed me earlier this year I’m on COBRA. So I was like, I got to get my benefits on!” (1) She added, “Nobody wants to be on COBRA, right?” (2)
COBRA, short for the Consolidated Omnibus Budget Reconciliation Act of 1985, lets workers keep their employer health plan for up to 18 months after losing their job or hours are cut. But unlike when you’re employed, you have to pay the full premium yourself, which can make it one of the most expensive coverage options.
Advertisement
Venus’ response showed how even a multimillionaire athlete can get caught between jobs, plans and deadlines in the U.S. health insurance system. It’s a situation many Americans find themselves in when they’re between jobs. Here’s how employer-sponsored health insurance can leave people exposed, and what you can do to stay covered when your job ends.
Thanks for subscribing!
Read the best of Moneywise in 5 minutes or less.
By signing up, you accept Moneywise Terms of Use, Subscription Agreement, and Privacy Policy.
Why health insurance is complicated — even for celebrities
For most Americans, health coverage comes with full-time employment. In 2023, about 60 percent of people under 65 had employer coverage, and more than half of firms offered health benefits, with nearly all large employers doing so. (3)
That system is efficient for corporations and health insurance companies, as employer-sponsored health insurance (ESI) is exempt from federal income tax. But with the rise of contingent work, the gig economy and a much higher likelihood you won’t stay with one employer over the course of your career, it leaves many Americans feeling anxious about the stability of their benefits. (4,5)
The Affordable Care Act changed the landscape fifteen years ago by creating health insurance marketplaces, subsidies for lower-income earners, and protections for people with pre-existing conditions. It also created a special enrollment window so that if you lose job-based coverage, you generally have 60 days to enroll in a marketplace plan, so if you lose your job or miss open enrollment, you still have a chance to get covered.
The One Big Beautiful Bill, recently passed in Congress, is estimated to increase the population of uninsured Americans by about ten million between now and 2034 by reducing federal health spending by more than one trillion dollars over ten years. These changes could make coverage more volatile for adults who cycle in and out of work. (6)
Must Read
- The ultra-rich use these 5 real estate strategies to build wealth while they sleep — you can start with just $100
- Here’s the average income of Americans by age in 2026. Are you keeping up or falling behind?
- Insurance companies profit most from drivers who auto-renew without shopping around. Comparing 100+ quotes takes 2 minutes and costs nothing
Join 250,000+ readers and get Moneywise’s best stories and exclusive interviews first — clear insights curated and delivered weekly. Subscribe now.
How to stay covered when your job ends
The safest move is to plan for transitions before they happen. If you are losing job-based coverage, you can apply for a marketplace plan up to 60 days before your old plan ends so coverage starts on the first day of the next month.
If you choose COBRA, compare its total cost to marketplace options, because subsidies can make ACA plans cheaper, and you can still switch to a marketplace plan when COBRA runs out or the employer stops contributing.
Advertisement
As always, you need to keep documentation of your prior coverage, since marketplaces require proof when you claim a special enrollment period. If your income drops, check Medicaid eligibility right away.
For people like Venus Williams and other contractors who rely on association plans (for example, an actor who gets their insurance through the Screen Actors Guild), confirm the exact rules for maintaining membership status during periods between jobs, layoffs or injury breaks, and be sure to ask how COBRA works for dependents.
Williams’ story shows that even those at the top of their field can’t escape the gaps in the U.S. system — a reminder for anyone to stay proactive about their own coverage.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
The Washington Post (1); Tennis.com (2); KFF (3, (6); BLS (4); World Economic Forum (5)
You May Also Like
- JP Morgan sees gold hitting $6,000/oz before 2027 — and a Gold IRA lets you hold the physical metal while deferring the tax bill. Get your free guide from Priority Gold
- Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake — here’s what it is and the simple steps to fix it ASAP
- Thanks to Jeff Bezos, you can now become a landlord for as little as $100 — and no, you don't have to deal with tenants or fix freezers. Here's how
- Millionaires under 43 are reshaping investing — just 25% of their portfolios are in stocks. Here’s where their money is going
Will Kenton is a personal finance writer with a Master's degree in Economics who has been published in Investopedia, AP News, TIME Stamped and Business Insider among other publications.
