Health Care Costs in Retirement: What Overstock.com Employees Should Know Before It’s Too Late

Healthcare Provider Update: Healthcare Provider for Overstock.com Overstock.com provides its employees with health insurance options through major insurers offering Affordable Care Act (ACA) plans, including well-known providers like UnitedHealthcare and Anthem. Potential Healthcare Cost Increases in 2026 In 2026, employees at Overstock.com are expected to face significant increases in healthcare costs, driven by anticipated premium hikes in the ACA marketplace. Projections indicate that some states might see premium increases exceeding 60%, exacerbated by the potential expiration of enhanced federal premium subsidies. As many employees may bear a larger share of healthcare expenses, it is crucial for Overstock.com workers to stay informed about their benefits and explore strategies to manage rising costs. The combination of inflated medical expenses and changing employer strategies could lead to a challenging healthcare landscape, stressing the importance of proactive financial planning. Click here to learn more

'Overstock.com employees should treat rising health care costs as a central part of retirement planning, not an afterthought, by integrating realistic medical expense projections into their overall financial strategy early on.' — Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'Overstock.com employees who factor health care inflation into their long-term retirement plan can better maintain financial stability and flexibility throughout their later years.' — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. The rising cost of health care in retirement and its impact on long-term outcomes for your finances.

2. Strategies Overstock.com employees can use to estimate and manage future medical expenses.

3. Smart ways to integrate health care planning into your overall retirement strategy.

You’ve been saving, working, and planning your retirement for decades. Yet many Overstock.com employees are still surprised by one expense that can quietly disrupt even the most careful plans: health care.

Even if your mortgage is paid, your pension elections are set, and your retirement travel mapped out, health care costs can alter your financial path if not taken into account early.

According to Wealth Enhancement financial adviser Kevin Won, CFP®, “Health care inflation is the hidden tax on retirement. People often budget carefully for living expenses and travel, but underestimate the long-term costs of health and longevity.”

The Price of Health Care in Retirement

Industry research shows the average 65-year-old couple may need roughly $345,000 to cover premiums, prescriptions, and out-of-pocket expenses in retirement—not including long-term care. ¹  Depending on health and lifespan, total costs could reach higher amounts. For Overstock.com retirees, these expenses can reduce decades of pension and 401(k) savings if not addressed appropriately.

Between 1989 and 2019, prescription drug prices surged over 200%, and hospital care costs climbed about 450%, far outpacing general inflation. ²  This reinforces the need for Overstock.com employees to plan for the future cost of medical care well before retirement.

Why Estimating Health Care Costs Is So Difficult 

Everyone’s retirement health story is different, but several key factors shape expenses:

Life Expectancy
Many Americans now live well into their 80s. For Overstock.com couples retiring at 65, there’s nearly a high chance at least one partner will live past 80 ³ —meaning additional years of premiums and prescriptions.

Personal Health
Even retirees in good health will face costs for age-related procedures, such as joint replacements, dental, and vision care. As Won notes, “Being healthy gives you choices, but not immunity from medical costs.”

Location
Where you live after leaving Overstock.com can have a major impact. Medical procedures may vary by tens of thousands of dollars depending on the state or region.

Insurance Options
Medicare provides core coverage, but it doesn’t cover everything. Overstock.com retirees who transition from company health benefits should understand that dental, vision, and long-term care are excluded from Original Medicare (Parts A and B).

The Ongoing Trend of Medical Inflation

Medical costs continue to rise faster than general inflation. While new technology improves outcomes and longevity, it also increases expenses. For Overstock.com retirees living on fixed pensions, this trend can place pressure on household budgets over time.

Won cautions, “The challenge isn’t today’s prices—it’s tomorrow’s uncertainty. Retirees who base planning on current medical costs may face shortfalls in 10 to 15 years.”

Turning Concern into Control

You may not influence the health care system, but you can influence your preparation. Overstock.com employees can start by estimating their current expenses—including out-of-pocket costs, copays, and premiums—and using an annual health care inflation rate of 5–6% to model potential future needs.

Regularly review your insurance coverage, including any Overstock.com retiree medical benefits you qualify for, and adjust as plans and costs change. Flexibility is essential—having a buffer is better than facing a shortfall during retirement.

Smart Strategies for Paying Health Care Costs

1. Understand Medicare Coverage ⁴

• Part A: Covers hospital stays, usually with no premiums but with deductibles.

• Part B: Covers outpatient care with monthly premiums and copays.

• Part D: Offers prescription coverage through private insurers.

• Part C: (Medicare Advantage): May include dental and vision benefits.

2. Account for Long-Term Care
About 70% of retirees will need some form of long-term care. ⁵  Costs can range from $70,000 to $75,000 annually for assisted living. ⁶  Overstock.com retirees should consider long-term care insurance or hybrid life policies, since Medicare does not cover custodial care.

3. Use Health Savings Accounts (HSAs)
Employees enrolled in a high-deductible health plan can fund HSAs with triple tax benefits: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. After age 65, funds may be applied to Medicare premiums and dental or hearing costs.

4. Keep a Medical Emergency Fund
Set aside six to 12 months of medical expenses to handle dental implants, surgeries, or out-of-network care. This helps avoid liquidating investments during market downturns.

5. Balance Your Investments
Health care inflation often exceeds overall inflation. A mix of growth and income investments can help Overstock.com retirees preserve purchasing power and maintain cash flow for health needs.

6. Review Prescription Options
Compare prices between pharmacies, consider mail-order services, and choose generic medications when available to reduce costs.

7. Include Health Care in Your Income Strategy
Treat health care as a fixed expense in your retirement budget. “When health care becomes part of your income plan, it can stop being a source of fear,” says Won.

8. Stay Informed Without Overreacting
Laws and benefits change frequently. Focus on what you can control—your savings rate, coverage selections, and plan reviews.

Your Health and Finances Are Connected

A well thought-out health care strategy can support both your wealth and your peace of mind. Whether you’re still working at Overstock.com or approaching retirement, now is the time to strengthen your plan.

“This is the stage where your preparation pays off,” says Won. “We want health care to be part of your retirement story, not a surprise ending.”

How The Retirement Group Can Help

Health care planning doesn’t have to be overwhelming. The Retirement Group can assist Overstock.com employees in designing a customized retirement and health care strategy aligned with their goals and benefit options. To speak with a retirement planning consultant about your pension, 401(k), or health care choices, call (800) 900-5867.

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Sources:

• 1. Fidelity Investments. ' Fidelity Investments Releases 2025 Retiree Health Care Cost Estimate ,' July 30, 2025.

• 2. Rakshit, Shameek, Emma Wager, Paul Hughes-Cromwick, Cynthia Cox, and Krutika Amin.  “How Does Medical Inflation Compare to Inflation in the Rest of the Economy?”  Peterson-KFF Health System Tracker, 2 Aug. 2024,  www.healthsystemtracker.org/brief/how-does-medical-inflation-compare-to-inflation-in-the-rest-of-the-economy/ .

• 3. Social Security Administration. ' Actuarial Life Table .' Period life table, 2022, as used in the 2025 Trustees Report.

• 4. Centers for Medicare & Medicaid Services.  “What’s Not Covered?”  Medicare.gov, 6 months ago (access date Oct. 30, 2025),  www.medicare.gov/providers-services/original-medicare/not-covered .

• 5. Administration for Community Living.  “How Much Care Will You Need?”  U.S. Dept. of Health & Human Services, 18 Feb. 2020 (page updated), acl.gov/ltc/basic-needs/how-much-care-will-you-need.

• 6. Where you live matters. ' How Much Does Assisted Living Cost? ' May 13, 2025.