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New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

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Overstock.com Employees: Discover the Rising Trend of 'Work for Pleasure' in Your Retirement Journey

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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

A recent Fidelity Investments poll illuminates new trends in the ever-changing retirement planning landscape.  Notably, 66% of respondents envision a phased-in approach to retirement, which deviates from the conventional full-stop strategy.  This choice shows a shift towards flexible retirement solutions across generations, as evidenced by the significant interest shown by both Gen Zers and millennials.

The wide-ranging implications of this trend point to the necessity of flexibility in retirement advice and planning when preparing to retire from Overstock.com. The departure from traditional retirement models highlights a more comprehensive reassessment of retirement goals and work-life balance, reflecting shifting perspectives toward the end of your Overstock.com career. Advisors who want to fulfill their Overstock.com clients' complex needs must have a thorough understanding of these preferences as retirement planning continues to change.


A growing number of retirees who desire social connection and intellectual stimulation in addition to financial security are adopting the idea of 'Work for Pleasure' in phased retirement, a viable option for Overstock.com employees.  According to an American Psychological Association study, continuing to work after retirement can enhance mental well-being, increase life satisfaction, and facilitate the transition to complete retirement. Retirement is now seen as a new chapter with opportunity for learning, growth, and contribution rather than as an end. This is especially true for seasoned professionals from high-ranking roles. 

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Retirement is becoming less and less like the unexpected curtain call at the end of a play and more like a well planned art display. Similar to how an exhibition progressively moves from one theme and era to another, providing visitors with an extensive array of experiences, the modern retirement trip, as defined by Fidelity Investments, takes place in stages. With this method, people can combine the elegant brushstrokes of their personal passions and hobbies with their professional creations. Today's retirees and soon-to-be retirees find joy and fulfillment in doing work that pleases them, much like an artist who paints for the love of art even after their formal career has concluded. This is creating a retirement experience that is as nuanced and fulfilling as a well-curated gallery.

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.

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For more information you can reach the plan administrator for Overstock.com at , ; or by calling them at .

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