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Overstock.com Employees Confront the Fear of Running Out of Money in Retirement

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

'To allay long-term financial concerns, Overstock.com employees may benefit from a comprehensive retirement strategy that addresses inflation, health care costs, and tax planning.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'Proactive retirement planning—especially around inflation, health care, and shifting tax policies—can help Overstock.com employees gain clarity and reduce uncertainty in the years leading up to retirement.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

Key causes of retirement anxiety, including inflation, health care, and taxes.
Generational differences in money concerns and readiness.
The value of broad retirement planning approaches.

Retirement Anxiety is On The Rise

Employees across industries, including those at Overstock.com, have long worried about how they will fund retirement. These concerns have grown considerably in today’s economy. Nearly two out of three Americans (64%) said they worry more about outliving their resources than they do about dying, according to the Allianz Center for the Future of Retirement’s 2025 Annual Retirement Study. ¹

Main Causes of Retirement-Related Worry

The Allianz study lists several key triggers of these fears. Regarding long-term planning, 54% of respondents said inflation was their top worry. Increases in health care costs, housing, and food prices are still undermining people’s purchasing power.

Concerns around Social Security’s future and tax burdens are also high. 43% said they feared Social Security might not offer adequate support. And another 43% named high taxes as a major issue.

Generational Gaps in Money Stress

Gen X—often balancing care for both kids and aging parents—report the highest worry: 70% versus 66% of millennials and 61% of boomers. Among corporate workers, including those at Overstock.com, this dynamic underlines how family obligations can magnify retirement concerns.

The Gap Between Worry and Action

The survey shows a gap between concern and conversation: just 23% of respondents have talked about outliving their assets with a retirement specialist, down from 28% in 2024. ² That said, Americans are considering several strategies to allay these fears, ranking the following approaches as most helpful:

41% said cutting current spending to funnel more toward retirement 
44% said increasing retirement contributions 
39% said postponing retirement
While increasing contributions to retirement accounts could help address these concerns, barriers remain: daily necessities (63%), credit card debt (40%), mortgage or rent (35%) were top reasons people weren’t contributing more.

The Emotional Side of Retirement Anxiety

Retirement fears influence not just finances, but lifestyle, career choices, and family planning. Worries about independence, dignity, and quality of life often accompany fear of running short on funds.

Health care need are often underestimated too, complicating the equation. Medicare covers many basic services, but long‑term care, home assistance, and uncovered treatments can add large bills—adding uncertainty even for high‑income employees.

Broader Retirement Planning Matters

The Allianz findings emphasize planning well beyond just saving. With people living 25 to 30 years post‑work, a solid planning mindset is critical. As Kelly LaVigne, VP at Allianz Life, noted, “Americans areliving longer… your money needs to go farther. A good plan considers 25 to 30 years of retirement, not just the first ten.” ²

Key components often include:

Income strategies: setting up regular monthly disbursements from assets
Tax planning: reducing tax burdens on withdrawals
Health care planning: factoring in Medicare gaps and long‑term care
Inflation alignment: keeping income responsive to cost increases

Combined, these strategies can help build resilience, confidence, and preparedness even in uncertain times.

In Conclusion

The 2025 Allianz Retirement Study makes it clear: a majority of Americans—and Overstock.com employees among them—see the threat of running out of money as more frightening than death. Rising inflation, health care spending, and uncertainty around Social Security are central drivers. Fewer are taking direct action through planning conversations or boosted contributions.

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Yet there is opportunity. The IRS now permits catch‑up 401(k) contributions of up to $11,250 for those aged 60–63 in 2025—above the standard limit. For many, this is a practical way to fortify resources in those final working years.

A Final Thought

Think of retirement like a long sea voyage. Death may be the storm ahead, but empty savings are the leak that can sink the ship first. According to the Allianz study, 64% of Americans fear that leak more than the storm. For Overstock.com employees, the goal is to build a well-structured plan—with consistent income, planning for health costs, and tax awareness—that can keep the vessel afloat for the long haul.

Sources:

1. Allianz Life Insurance Company of North America, ' How Americans feel about retirement in 2025 ,' by the Allianz Center for the Future of Retirement ^TM , June 2025.

2. businesswire, ' Americans Are More Worried About Running Out of Money Than Death ,' April 22, 2025.

What type of retirement savings plan does Overstock.com offer to its employees?

Overstock.com offers a 401(k) retirement savings plan to its employees.

Does Overstock.com match employee contributions to the 401(k) plan?

Yes, Overstock.com provides a matching contribution to employee 401(k) plans, subject to certain limits.

How can employees at Overstock.com enroll in the 401(k) plan?

Employees at Overstock.com can enroll in the 401(k) plan through the company’s human resources portal or by contacting the HR department for assistance.

What is the eligibility requirement for Overstock.com employees to participate in the 401(k) plan?

Most employees at Overstock.com are eligible to participate in the 401(k) plan after completing a specified period of service, typically within the first year of employment.

Can employees at Overstock.com take loans against their 401(k) savings?

Yes, Overstock.com allows employees to take loans against their 401(k) savings, subject to the plan’s terms and conditions.

What investment options are available in the Overstock.com 401(k) plan?

The Overstock.com 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and company stock, among others.

How often can Overstock.com employees change their 401(k) contribution amounts?

Employees at Overstock.com can change their 401(k) contribution amounts at any time, subject to the plan’s guidelines.

Is there a vesting schedule for employer contributions to the 401(k) plan at Overstock.com?

Yes, Overstock.com has a vesting schedule for employer contributions, which means that employees must work for a certain number of years before they fully own the employer match.

What happens to my 401(k) account if I leave Overstock.com?

If you leave Overstock.com, you have several options for your 401(k) account, including rolling it over to another retirement account, cashing it out, or leaving it with Overstock.com, depending on the plan rules.

How can Overstock.com employees access their 401(k) account information?

Employees can access their 401(k) account information through the plan’s online portal or by contacting the plan administrator.