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

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'Dropbox 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.

'Dropbox 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 Dropbox offer to its employees?

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

Does Dropbox match employee contributions to the 401(k) plan?

Yes, Dropbox provides a matching contribution to employee contributions made to the 401(k) plan.

What is the maximum contribution limit for the Dropbox 401(k) plan?

The maximum contribution limit for the Dropbox 401(k) plan is in accordance with IRS guidelines, which may change annually.

Can employees at Dropbox choose between traditional and Roth 401(k) contributions?

Yes, employees at Dropbox have the option to choose between traditional and Roth 401(k) contributions.

When can Dropbox employees enroll in the 401(k) plan?

Dropbox employees can enroll in the 401(k) plan during the open enrollment period or when they first become eligible.

How often can Dropbox employees change their contribution amounts to the 401(k) plan?

Dropbox employees can change their contribution amounts to the 401(k) plan at any time, subject to plan rules.

Does Dropbox offer financial education resources for employees regarding the 401(k) plan?

Yes, Dropbox provides financial education resources to help employees understand their 401(k) options and investment choices.

Are there any fees associated with the Dropbox 401(k) plan?

Yes, there may be fees associated with the Dropbox 401(k) plan, which are disclosed in the plan documents.

What investment options are available in the Dropbox 401(k) plan?

The Dropbox 401(k) plan offers a variety of investment options, including mutual funds and target-date funds.

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

Yes, Dropbox employees may have the option to take loans against their 401(k) savings, subject to plan rules.

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

Dropbox Pension Plan and 401(k) Plan Information (2022-2024) Dropbox offers its employees a robust retirement savings structure, primarily centered around a 401(k) plan rather than a traditional pension plan. The Dropbox 401(k) plan allows employees to contribute pre-tax income towards their retirement, and the company provides a matching contribution. In 2023, Dropbox's 401(k) contribution limit was $22,500, with a catch-up contribution of $7,500 for employees aged 50 and older (CapitalGroup NACG) (Benefits Law Advisor). In 2024, these limits increased slightly to $23,000 with the same catch-up provision (Day Pitney). Plan Terminology and Eligibility The Dropbox 401(k) plan follows common industry standards, such as "Elective Deferral" and "Catch-Up Contribution" for those aged 50+. Eligible employees are immediately enrolled and must meet service and age requirements for vesting and matching contributions (CapitalGroup NACG). Employees are fully vested in their contributions from the start and generally in company contributions after one year of service. Dropbox’s terminology for its retirement plan is aligned with IRS guidelines and includes terms like "Defined Contribution Plan" and "Matching Contribution"

Restructuring and Layoffs: In 2023, Dropbox announced a restructuring plan aimed at optimizing its operations and reducing costs. This involved a reduction in workforce, impacting several departments as the company sought to streamline its processes. The restructuring was part of a broader strategy to maintain competitiveness and adapt to changing market conditions. Given the current economic climate, it is crucial to monitor such developments as they impact job security and the company's financial stability. Company Benefits and 401(k) Changes: Dropbox has also reviewed its employee benefits and 401(k) plans. The company made adjustments to its 401(k) matching program and offered new benefits packages to align with industry standards and employee needs. These changes are essential to follow closely due to the shifting economic landscape, which can influence retirement planning and financial security. Changes in company benefits can have significant implications for employee retention and satisfaction.

Dropbox provides stock options (SO) and Restricted Stock Units (RSUs) as part of their compensation packages. Stock options (SO) at Dropbox generally include standard incentive stock options (ISOs) and non-qualified stock options (NSOs). RSUs at Dropbox are usually granted based on employee performance and tenure.

Dropbox Careers Page: Provides information on employee benefits including health insurance. Dropbox offers comprehensive healthcare benefits, including medical, dental, and vision coverage. They also provide mental health support and wellness resources. Dropbox Benefits Overview: Dropbox provides a variety of health benefits such as flexible health spending accounts (FSAs), health savings accounts (HSAs), and access to wellness programs. They are known for offering generous parental leave and remote work support.