Why Dropbox Employees Are Embracing Retirement Jobs – It’s Not Just About Money

'Increasingly, Dropbox retirees are recognizing that their retirement plans need to evolve with rising costs and changing expectations—side gigs provide not only additional financial security but also a sense of purpose and fulfillment, crucial for a well-rounded retirement experience.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement Group.

'Many Dropbox retirees are finding that returning to work in some capacity offers more than just extra income; it enhances their mental and social well-being, providing both financial and personal fulfillment during their post-career years.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement Group.

In this article, we will discuss:

1. The financial challenges retirees are facing, including inflation and rising healthcare costs.

2. The growing trend of retirees pursuing side jobs or gigs for additional income and personal fulfillment.

3. The broader benefits of working in retirement, such as maintaining mental health, purpose, and social engagement.

Many Dropbox retirees are discovering that their ideal retirement scenario is not as financially stable as they had imagined, especially as the financial landscape continues to shift. The reality of living on a fixed income has brought unexpected challenges for many. A record 11.2 million Americans over 65 are employed today, with this number expected to rise to 14.8 million, or 8.6% of the workforce, by 2033, according to the U.S. Bureau of Labor Statistics. Once thought to be uncommon, this trend is becoming more widespread as retirees look for additional income to cover rising living costs and maintain their desired lifestyles.

While many factors contribute to this shift, money concerns are at the core of the challenges retirees face today. A recent D.A. Davidson survey reveals that 60% of retired Americans wish they had a side career or gig, compared to just 8% who already do. A startling two out of five retirees say they can’t afford their dream retirement, emphasizing the growing financial strain on this group, including those who retired from Dropbox.

Undoubtedly, inflation has played a significant role in this shift. In recent years, the cost of living, including essentials like groceries and gas, has seen a sharp increase. Many retirees, including those who spent years at Dropbox, are finding that their money doesn’t go as far as they had hoped, especially after entering retirement with expectations about their lifestyle. The uncertainty surrounding Social Security only adds to the problem. While the Social Security trust fund is not expected to run out of funds until 2035, many retirees are concerned about the future of this vital financial support, particularly as life expectancies rise and the fund’s long-term viability is questioned.

Retirement planning is also affected by personal factors beyond inflation and Social Security concerns. Many retirees, even those from companies like Dropbox, don’t have enough saved for retirement, and some even carry significant debt into retirement. Additional financial pressures, such as supporting aging parents or adult children, can also strain retirement funds. Medical costs only make matters more challenging; according to Fidelity Investments, a 65-year-old retiring in 2024 can expect to spend an average of $165,000 on healthcare throughout retirement. These costs can create a significant gap between expectations and reality, highlighting the need for additional income.

A side job can provide more than just financial stability, even for retirees who aren’t facing immediate financial challenges. Many find that working in retirement helps them stay engaged and gives them a sense of purpose. According to the D.A. Davidson poll, 55% of seniors with retirement gigs cite maintaining social or mental engagement as their primary motivator, and 93% of retirees with side jobs report that they love their work. This highlights the broader reality that employment, even in retirement, provides a framework that supports mental and physical well-being for retirees, including those who worked at Dropbox.

Take Andy Roy, a 74-year-old retiree from Saratoga Springs, New York. After a long career working for himself, Roy began mowing the grass at the Albany Rural Cemetery a few days a week four years ago. Roy admits that while the job pays well, the true benefit is the sense of purpose it provides. “It’s beneficial. I feel like I’m helping. It serves as a small anchor during the day and gives me a sense of purpose,” he says. Beyond the work, Roy has formed close friendships with his coworkers and developed an interest in the rural cemetery movement. While the pay is appreciated, he acknowledges that the sense of fulfillment is the true reward, something Dropbox retirees may also discover after leaving their careers.

Similarly, 72-year-old Merry Farnum, a retiree from Falmouth, Maine, has taken on a new challenge as a launch driver at Handy Boat, a local boatyard. After working as an Associated Press news photographer, Farnum now spends her days transporting people between land and their boats, a job that keeps her active and outdoors. “The biggest payoff is the challenge and the structure it gives my life,” she says, noting that the money is useful, but the real motivation is the sense of accomplishment. Farnum’s experience demonstrates that working in retirement can offer financial stability while enriching one’s life, just like retirees from Dropbox who take on new challenges in their post-career years.

In recent years, the demand for such opportunities has surged. With the growth of the gig economy, retirees, including those who spent years with Dropbox, can now pursue work that aligns with their interests and abilities, free from the constraints of the 9–5 schedule. Thanks to platforms that facilitate side jobs—like tutoring, freelancing, pet sitting, and driving for ride-sharing services—retirees can find work that is both financially rewarding and personally fulfilling. This flexibility allows retirees to decide how much they want to work, balancing their financial needs with the desire for leisure and personal time.

It’s important to consider the potential benefits of side gigs beyond just the financial stability they provide. Many retirees, including former Dropbox employees, seek a sense of purpose and belonging after leaving the workforce, which can be found through freelance or part-time employment. Maintaining an active lifestyle can also boost cognitive function and lower the risk of depression, issues that are common among retirees who may feel isolated or disconnected.

However, retirees considering whether to pursue a side job should also be aware of potential impacts on taxes, health benefits, and Social Security. Income from a side job may affect Social Security benefits depending on when an individual starts receiving them and how much they earn. It is also crucial to consult a financial advisor to fully understand the tax implications of extra income and how it fits into the broader retirement strategy, especially for Dropbox retirees looking to get the most out of their post-career years.

In conclusion, more and more retirees are incorporating side gigs or retirement jobs into their retirement plans. While financial strains, like inflation and rising healthcare costs, are pushing many to seek additional income, the benefits of working in retirement go beyond just financial gain. Retirement jobs help retirees maintain an active and rewarding lifestyle, offering social interaction, mental stimulation, and a renewed sense of purpose. Whether it’s for debt repayment, growing retirement savings, or simply staying involved, retirement work is an essential component of a fulfilling post-career life for former Dropbox employees, as well as other retirees.

A recent AARP study reveals that many seniors over 65 are working not only for extra income but for mental and social engagement as well. According to the report, nearly 60% of part-time working retirees cite the opportunity to stay active and connected with their communities as a primary motivator. Work provides an organized way to maintain mental sharpness and social connections, crucial elements for well-being as individuals live longer. AARP’s December 2024 article, 'The Benefits of Working in Retirement,' discusses these findings, which also resonate with Dropbox retirees.

Examine how more and more retirees are seeking side employment for mental stimulation, purpose, and social interaction in addition to extra income. With inflation, healthcare costs, and concerns about Social Security, many retirees—including those who worked for Dropbox—are turning to flexible work options to stay active and enhance their retirement experience. Discover how part-time jobs, such as driving a boatyard launch or working at a local cemetery, are helping retirees reach financial stability while maintaining fulfilling, structured lives. The growing trend of working in retirement offers advantages that go far beyond financial gain.

Retirement is like a car that’s been sitting idle in the driveway for years. It runs fine, but without regular maintenance and direction, it may start to feel uninspired. Just like a car needs fuel, upkeep, and a destination, retirees are finding that side gigs provide more than just extra income—they give a sense of purpose, a chance to connect with others, and an opportunity to maintain both physical and mental health. Rediscovering purpose is more important than simply reentering the workforce, something many Dropbox retirees are discovering as they explore new roles after their careers.

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Source:

1. Riquier, Andrea. 'Why a Record Number of Adults Over 65 Are Working – And It’s Not Just About Money.'  MarketWatch , 30 Apr. 2025, pp. 1-2.  marketwatch.com .

2. 'Financial Impact of Side Jobs on Retirement Savings.'  AARP Research , 2018, pp. 3-4.  aarp.org .

3. 'How Side Gigs Can Improve Mental Health for Retirees.'  RL Communities Blog , 2023, pp. 1-2.  rlcommunities.com .

4. 'The Benefits of Social Engagement for Seniors.'  Baptist Retirement Community Blog , 2024, pp. 2-3.  baptistretirement.org .

5. Barron's Staff. 'Retirees Face Sticker Shock on Healthcare Costs If They Don’t Prepare.'  Barron's , 8 Aug. 2024, pp. 1-2.  barrons.com .