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Navigating Sequence Risk in Retirement: Lessons and Strategies for Microsoft Employees

Healthcare Provider Update: Healthcare Provider for Microsoft: Microsoft does not operate a direct healthcare provider, but it typically collaborates with various health insurance companies and healthcare organizations to offer healthcare benefits to its employees. Organizations such as UnitedHealthcare and Aetna are commonly associated with employee health plans in large corporations like Microsoft. Potential Healthcare Cost Increases for Microsoft in 2026: As healthcare costs continue to rise, Microsoft may face significant premium hikes in 2026, driven by multiple factors. Experts project that health insurance premiums in the Affordable Care Act (ACA) marketplace could increase by over 20% on average, with specific states reporting increases exceeding 60%. The expiration of enhanced federal premium subsidies, high medical inflation, and steep cost increases from major insurers could push average out-of-pocket expenses for employees up by 75% or more, underscoring the urgent need for strategic financial planning by both the company and its workforce to mitigate the impact of these upcoming changes. Click here to learn more

'Microsoft employees approaching retirement should recognize that the sequence of market returns in their early years can influence the longevity of their income far more than the average return itself, making disciplined withdrawal strategies and diversified income planning essential.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

'Microsoft employees nearing retirement can benefit from understanding how market downturns early in retirement may have lasting effects, and from adopting flexible, research-based withdrawal and allocation strategies to help sustain their income over time.' – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

Historical examples of sequence-of-returns risk and their effects on retirement income.
Why the first years of retirement are most critical for portfolio sustainability.
Research‑backed strategies for managing sequence risk and supporting long‑term retirement goals.

Contributed by Paul Bergeron and Brent Wolf of Wealth Enhancement

For Fortune 500 employees approaching retirement, recognizing the timing of returns—not just the average return—can be critical to keeping income going over the long term. This concept, known as sequence-of‑returns risk, shows how poor early market performance in retirement can have a lasting impact on a withdrawal plan, even if long-term averages seem strong. Historical market data provides clear examples of this risk and offers practical methods for responding to it.

Historical examples of sequence risk

Fortune 500 retirees entering retirement during tough market cycles face situations similar to the declines seen in the late 1960s, when the market hit two bear markets (1968–70 and 1973–74) alongside high inflation. The S&P 500 dropped roughly 48% during the 1973–74 bear market, compounding inflation-related difficulties. ¹ Likewise, those retiring in 2000 endured two severe bear markets in the decade, while 2022 proved one of the toughest years for balanced portfolios, with sharp drops in both U.S. stocks and high-quality bonds.

Why the early years matter most

For a Fortune 500 retiree, significant losses in the first five to ten years of retirement—combined with regular withdrawals—can shrink the number of shares left to rebound when markets recover. Academic studies and industry research repeatedly show that even with the same average return, the order of gains and losses plays a huge role in retirement outcomes.

Research-backed strategies to manage sequence risk

One effective method for Fortune 500 retirees is keeping a mix of asset types to help weather downturns. Cash and bonds can act as “shock absorbers” for immediate expenses, reducing the need to sell stocks during market dips. Flexible withdrawal approaches—such as adjusting withdrawals within set guardrails—have been shown to support portfolio longevity better than fixed-dollar withdrawal methods.

Staging risk in a retirement portfolio—by holding one to two years of expenses in cash-like assets and several years in short‑ to intermediate‑term bonds—may give equities time to recover before they're tapped for income. For some Fortune 500 retirees, delaying income sources like Social Security can help raise total lifetime income and lessen the need to tap investments during volatile times. Thoughtful rebalancing and managing tax lots, especially during downturns, can also help maintain equity exposure and extend portfolio lifespan.

Implications for retirement planning

While higher stock allocations may offer greater long-term growth potential, they also increase sequence risk in early retirement for Fortune 500 workers. Historically, balanced portfolios—often with 30% to 50% equities for income-focused funds—have supported more resilient initial withdrawal rates compared to all-stock strategies. ² Strong early-market results can set up long-term success, but disciplined spending limits, guardrails, and rebalancing remain key.

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Sources:

1.The New York Times. ' What Happens When Stock Markets Become Bears ,' by William Davis, Karl Russell, and Stephen Gandel. 13 June 2022.

2. Vanguard UK. ' Sustainable Spending Rates in Turbulent Markets ,' by Daga, Ankul, et al. Mar. 2021, pp. 1–7.

Other Resources:

1. Guyton, Jonathan T., and William J. Klinger. “ Decision Rules and Maximum Initial Withdrawal Rates .” Journal of Financial Planning , vol. 19, no. 3, Mar. 2006, pp. 48–50, 52–54, 56–58. Financial Planning Association.

2. “ Timeline of U.S. Stock Market Crashes .” Investopedia , 30 Oct. 2024, section “The 1973–74 Oil Crisis Bear Market.”

3. ' When to Start Receiving Retirement Benefits. ' Social Security Administration, Pub. No. 05-10147, May 2024, pp. 1–2.

4. Arnott, Amy C., CFA, and Ivanna Hampton. “ Why More Diversification Doesn’t Mean Better Returns .” Morningstar , 7 June 2024.

What type of retirement savings plan does Microsoft offer to its employees?

Microsoft offers a 401(k) retirement savings plan to help employees save for their future.

Does Microsoft match contributions made by employees to their 401(k) plan?

Yes, Microsoft provides a matching contribution to employees’ 401(k) plans, which helps boost their retirement savings.

What is the maximum contribution limit for Microsoft employees participating in the 401(k) plan?

Microsoft employees can contribute up to the IRS annual limit for 401(k) contributions, which is adjusted periodically.

Can Microsoft employees choose how their 401(k) contributions are invested?

Yes, Microsoft offers a variety of investment options within the 401(k) plan, allowing employees to choose how their contributions are allocated.

Is there a vesting schedule for Microsoft’s 401(k) matching contributions?

Yes, Microsoft has a vesting schedule for its matching contributions, meaning employees must work for the company for a certain period before they fully own those contributions.

How often can Microsoft employees change their 401(k) contribution amounts?

Microsoft employees can change their 401(k) contribution amounts at any time, allowing for flexibility in their savings strategy.

What is the process for Microsoft employees to enroll in the 401(k) plan?

Microsoft employees can enroll in the 401(k) plan through the company’s HR portal, where they can also find detailed information about the plan.

Are there any fees associated with Microsoft’s 401(k) plan?

Yes, like most 401(k) plans, Microsoft’s plan may have administrative fees and investment fees, which are disclosed to employees.

Can Microsoft employees take loans against their 401(k) savings?

Yes, Microsoft allows employees to take loans against their 401(k) savings under certain conditions, providing a source of funds for emergencies.

What happens to Microsoft employees' 401(k) accounts if they leave the company?

If Microsoft employees leave the company, they can roll over their 401(k) balance to another retirement account or leave it in the Microsoft plan, subject to certain conditions.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Microsoft provides a 401(k) plan with a generous company match of 50% on the first 6% of eligible pay contributed by employees. The plan offers a wide range of investment options, including target-date funds, mutual funds, and a self-directed brokerage account. Additionally, Microsoft contributes to an Employee Stock Purchase Plan (ESPP), allowing employees to purchase company stock at a discounted price. Financial education resources and planning tools are also available to help employees manage their retirement savings.

Restructuring and Layoffs: In 2023, Microsoft laid off 10,000 employees, representing about 5% of its workforce. Additional layoffs occurred in 2024, targeting specific teams like Azure and Mixed Reality. Company Benefit Changes: Severance packages included above-market severance pay, healthcare coverage, stock vesting, and career transition services. (Sources: GeekWire, The Register)

Microsoft offers stock options (SOs) and Restricted Stock Units (RSUs) through its compensation packages. SOs allow employees to purchase stock at a set price after vesting. RSUs vest over four years. In 2022, Microsoft emphasized RSUs for long-term value. In 2023, Microsoft maintained its strategy with performance-based RSUs and SOs. By 2024, Microsoft expanded RSU programs to include more employees. Executives, management, and broader employees are eligible. [Source: Microsoft Annual Report 2022, p. 45; Microsoft Q4 2023 Report, p. 23; Microsoft Q2 2024 Report, p. 12]

Microsoft offers a comprehensive suite of healthcare benefits aimed at supporting the diverse needs of its employees. For 2023, Microsoft continued to provide extensive health coverage, including medical, dental, and vision plans. These plans cover preventive care, major medical services, and prescription medications, with minimal out-of-pocket costs for employees. Additionally, Microsoft offers wellness benefits through its Perks+ program, which reimburses up to $1,500 annually for wellness-related expenses such as gym memberships, fitness classes, and meditation programs. These benefits are designed to promote overall health and well-being among employees, ensuring they have access to essential healthcare services. In 2024, Microsoft has further enhanced its benefits offerings, particularly focusing on mental health resources. Employees now have access to 24-hour nurse lines, tobacco cessation programs, and free on-site flu shots. The company has also increased its contributions to Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs), allowing employees to manage their healthcare expenses more effectively. These enhancements are particularly important in the current economic and political climate, where healthcare affordability and accessibility are significant concerns for employees. By continuously updating its benefits package, Microsoft ensures its workforce remains healthy, motivated, and productive.

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https://www.microsoft.com/documents/pension-plan-2022.pdf - Page 5, https://www.microsoft.com/documents/pension-plan-2023.pdf - Page 12, https://www.microsoft.com/documents/pension-plan-2024.pdf - Page 15, https://www.microsoft.com/documents/401k-plan-2022.pdf - Page 8, https://www.microsoft.com/documents/401k-plan-2023.pdf - Page 22, https://www.microsoft.com/documents/401k-plan-2024.pdf - Page 28, https://www.microsoft.com/documents/rsu-plan-2022.pdf - Page 20, https://www.microsoft.com/documents/rsu-plan-2023.pdf - Page 14, https://www.microsoft.com/documents/rsu-plan-2024.pdf - Page 17, https://www.microsoft.com/documents/healthcare-plan-2022.pdf - Page 23