Why Venus Williams Came Back for the Insurance

While her comment was delivered with some degree of humor, the remark hits close to home for so many working Americans. Following an employer separation, continuation of health coverage is notoriously expensive and often administratively opaque. Even for one of the world’s most elite athletes, the reality of navigating a complex benefits system became a deciding factor in her return to work. 

Health insurance has deep roots in the American labor system and originated during the Industrial Revolution, when “sickness funds” and employer-sponsored injury coverage provided early forms of worker protection. These benefits laid the groundwork for today’s group health plans. Developments continued over time, including the establishment of workers’ compensation, the rise of employer-based health plans, and the introduction of Medicare and Medicaid, reshaping how healthcare is accessed and paid for in the U.S.

By the late 20th century, employer-sponsored health insurance had become a standard part of total compensation. In 1986, the Consolidated Omnibus Budget Reconciliation Act (COBRA for short), ensured that after leaving a job under certain conditions, employees could retain the insurance their employers provided–but at their own expense.

For many workers today, health insurance is not just a benefit; it’s a reflection of employer values. According to a 2022 MetLife study, 73% of employees said that the benefits offered by their employer make them feel more loyal, and 52% said health benefits in particular affect their decision to stay at or leave a job.

The cultural relevance of this shift isn’t lost on public figures. When a tennis legend jokes about being “back because I’m on COBRA,” it strikes a nerve because it’s rooted in truth. Healthcare decisions increasingly influence career decisions, whether that means delaying retirement, staying in a role they’ve outgrown, or navigating a complex system to maintain continuity of care.

As an HR consulting firm, we encourage our clients to ask: Are we treating health insurance like a fixed cost—or like a dynamic lever for engagement, equity, and growth?

Venus Williams isn’t alone in her return-to-work moment. A growing wave of Americans are making career decisions based on accessing healthcare and changing financial priorities. This includes a surprising number of baby boomers. A group of baby boomers, dubbed “Boomerang Boomers,” are re-entering the labor market in record-breaking numbers. According to LinkedIn’s Economic Graph, the share of retirees returning to work jumped nearly 24% in 2023, with 13.2% of older Americans exiting retirement—the highest level in five years. 

Financial necessity, fueled by inflation, market volatility, and rising living costs, is a major driver. This trend aligns with broader demographic shifts: as of 2025, about 19% of adults aged 65 and older are still working, nearly double the rate seen in the mid-1980s. Employers are starting to embrace this shift by offering flexible, part-time, or mentorship roles to workers re-entering the workforce. In hospitality, for instance, a 10% rise in boomers working casual shifts is helping fill critical gaps while leveraging the reliability and experience they bring. 

There are currently four generations in the workforce. There is not a one-size-fits-all benefits plan. For example, varying needs could be a 26-year-old aging off a parent’s plan, a mid-career employee navigating long-term care for a loved one, and a retiree rejoining the workforce to regain coverage. The needs of today’s workforce are deeply individual and constantly shifting, yet many benefits packages are still designed as if all employees are in the same life stage, with the same priorities.

This is a missed opportunity. Flexible, responsive benefits are becoming a competitive differentiator, especially as the workforce grows more age-diverse and life paths become less linear. Employers that offer extended eligibility to part-time workers, build phased-retirement benefit options, or provide portable access to mental health support aren’t just checking boxes; they’re meeting real people where they are.

And benefits flexibility doesn’t have to mean complexity. Shorter waiting periods, less complicated plan explanations, or benefits education tailored by age and role can make a difference in how employees perceive value. The goal isn’t just coverage, its connection, care, and a benefits experience that adapts to life’s curveballs, whether someone is just starting their career or coming out of retirement.

When Venus Williams said she came back for the insurance, it was funny—because it rang true. But for employers, it poses questions:

• Would your employees come back for your benefits?
• Would they stay because of them?
• Do they even understand what they have?

In an era where career decisions are shaped as much by healthcare access as by salary or title, benefits are no longer just a back-office function. They’re a frontline signal of your company’s priorities, values, and adaptability.

From boomerang boomers to Gen Z new hires, the future of work depends on how well your benefits strategy meets people where they are—and where they’re going. The question isn’t just what you offer, it’s how clearly, flexibly, and consistently you deliver it.