4 Retirement Withdrawal Strategies for Overstock.com Employees to Help Make Your Money Last

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 must carefully consider their retirement withdrawal strategies to maintain a sustainable income, as decisions on the timing and method of withdrawals can impact their financial health in retirement.' – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'By structuring the right withdrawal strategy, Overstock.com employees can better navigate the complexities of retirement, helping their hard-earned savings last throughout their retirement years while potentially managing the risks associated with market volatility and unforeseen expenses.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. Four retirement withdrawal strategies to help your savings last.

2. The impact of tax considerations, required minimum distributions (RMDs), and Social Security benefits on your retirement income.

3. The importance of planning for health care costs in retirement.

Retirement is the culmination of years of dedication, hard work, and saving. As a Overstock.com employee, you’ve likely worked diligently to build your retirement savings. However, once you’ve accumulated your nest egg, the challenge becomes converting that sum into a sustainable income to cover what could be decades of retirement. A major concern for many retirees, including those in the oil and gas industry, is outliving their savings. It’s critical to understand how to manage your retirement funds wisely to help make them last.

Having a healthy retirement fund is essential, but it’s equally important to know how to manage that fund effectively. Your retirement well-being depends on the decisions you make about withdrawing funds from your 401k, IRA, or other accounts. If you withdraw too much too quickly, you risk depleting your savings too soon, leaving yourself financially vulnerable. Conversely, if you withdraw too little, you may not be able to live comfortably. Therefore, choosing the right withdrawal strategy is key to optimizing your savings.

Below are four strategies that Overstock.com retirees can consider to help their savings last:

1. The 4% Rule: An Age-Old Method

One of the most widely recognized retirement withdrawal methods is the 4% rule. According to this approach, retirees withdraw 4% of their original retirement portfolio balance in the first year of retirement. Each subsequent year, the amount withdrawn increases to keep pace with inflation. For example, from a $500,000 portfolio, the first year’s withdrawal would be $20,000 (4% of $500,000). The following year, if inflation is 3%, the withdrawal would rise to $20,600. The 4% rule aims to strike a balance between making withdrawals and allowing the funds to grow over time.

That said, some financial professionals have raised concerns about whether the 4% rule is still the best strategy, particularly in light of market volatility. In tough market conditions, the 4% rule might accelerate the depletion of your assets. Some advisors recommend reducing the withdrawal rate to 2.4% in such cases to help safeguard long-term funds.

2. The Fixed-Dollar Approach: Consistency and Confidence

The fixed-dollar withdrawal method involves setting a specific amount to withdraw each year during retirement. This amount is periodically reassessed based on financial needs and investment performance. The primary benefit of this approach is stability, as you know exactly how much you will receive every year. However, one downside is that it doesn’t account for inflation. Over time, as living expenses increase, the purchasing power of your fixed withdrawal will decrease.

Furthermore, similar to the 4% rule, the fixed-dollar approach can be risky during market downturns. If your investments don’t perform as expected, you may end up withdrawing more than your portfolio can sustain. Therefore, it's important to regularly reassess your plan, particularly during periods of economic uncertainty.

3. The Strategy for Total Return: Emphasis on Growth Assets

The total return strategy focuses on keeping your portfolio predominantly invested in growth assets, such as stocks. You would only withdraw enough to meet your immediate living expenses while allowing the rest of the portfolio to grow. The goal of this approach is to balance long-term growth potential with withdrawal needs, letting your assets grow as much as possible while still providing the income you need.

This strategy may appeal to retirees who have a significant financial cushion and a higher risk tolerance. However, it does carry the risk of having to sell investments at a loss during a market downturn, which could affect long-term growth. It’s best suited for those who are comfortable with volatility and who have a deep understanding of market performance.

4. The Bucket Strategy: A Layered Approach to Risk and Reward

The bucket strategy divides your retirement assets into multiple 'buckets' based on when the funds will be needed. The first bucket holds enough cash for immediate expenses, typically within the next 6-12 months. This money is invested in low-risk, liquid assets like money market funds or high-yield savings accounts. The second bucket is for medium-term needs, typically one to three years, and might include bonds or certificates of deposit (CDs). The third bucket holds long-term growth assets, like stocks, mutual funds, or exchange-traded funds (ETFs), and is meant to be used in five+ years.

This strategy aims to provide both short-term stability and long-term growth by investing in a mix of lower-risk and higher-risk assets. The short-term buckets are optimally insulated from market volatility, while the long-term buckets can ride out market fluctuations for potential growth. While this approach requires careful planning and regular rebalancing, it can offer peace of mind for retirees, allowing them to manage short-term expenses while still benefiting from the growth of their investments over time.

Other Elements That Impact How Long Your Retirement Funds Last

While choosing the right withdrawal strategy is essential, several other factors can impact the longevity of your retirement funds. For Overstock.com employees, it's crucial to consider the following:

• Tax Considerations:

• Understanding the tax implications of your withdrawals is vital. Traditional retirement accounts, such as 401ks and IRAs, defer taxes on contributions and investment gains until you start taking distributions. In contrast, Roth accounts offer tax-free distributions. Planning your withdrawals to take advantage of lower tax brackets in retirement can be a smart strategy. For example, you might withdraw from tax-deferred accounts first, allowing Roth accounts to grow tax-free.

• Required Minimum Distributions (RMDs):

• The IRS requires that you begin taking minimum distributions from your traditional retirement accounts when you turn 73. Failing to take these distributions can lead to significant penalties. Since Roth IRAs are not subject to RMDs during your lifetime, delaying withdrawals from these accounts can be advantageous.

• Social Security Benefits:

• For many retirees, Social Security serves as a key source of income. The decision of when to start receiving benefits is a critical part of your retirement strategy. Starting early at age 62 results in lower monthly payments, but waiting until your full retirement age or even 70 can increase your benefits by as much as 8% per year.

• Health Care Costs:

• Health care costs are an often-overlooked aspect of retirement planning. According to a 2023 study by Fidelity, a 65-year-old couple retiring in 2023 can expect to spend an estimated $315,000 on health care costs over the course of their retirement. ¹  Planning for these expenses and adjusting your withdrawal strategy accordingly is essential to helping your savings last.

Bottom Line

Choosing the right withdrawal strategy is a critical step in making your retirement savings last. Whether you opt for the 4% rule, the fixed-dollar method, the total return strategy, or the bucket approach, each strategy offers different benefits and risks. By also considering tax implications, RMDs, Social Security, and health care costs, you can better prepare for a comfortable retirement.

For Overstock.com employees, planning ahead and using the right strategy can help you enjoy a stable, financially independent retirement. By understanding how your withdrawal strategy interacts with other elements of retirement planning, you can position your nest egg to last for the long haul.

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Sources:

1. Fidelity.  ' Fidelity Releases 2023 Health Care Cost Estimate .' 21 June 2023.

2. Colucci, Julie. 'Retirement Withdrawal Strategies To Extend Your Savings.'   Bankrate , May 2025, pp. 1–3.

3. Reichenstein, William. 'A Roth 401(k) Is a Tax Break Hiding in Plain Sight.'   Barron's , May 2025, pp. 2–4.

4. London, Hali Browne. 'Diversify or Risk Running Dry: 12 Additional Income Streams For Your Retirement.'   Investopedia , May 2025, pp. 5–7.

5. Bengen, Bill. 'The Guy Behind Retirement's 4% Rule Now Thinks That's Way Too Low.'   MarketWatch , May 2025, pp. 3–5.

6. Allianz Life Insurance. 'Ditch the Fear: A Guide to Embracing Retirement Preparedness.'   Kiplinger , May 2025, pp. 1–2.