Embracing a Side Hustle After Retirement: A Thriving Guide for Chewy Employees

Healthcare Provider Update: Healthcare Provider for Chewy Chewy Inc. primarily collaborates with CarePlus, its dedicated healthcare arm, to provide various pet wellness and insurance plans to its customers. CarePlus aims to enhance the health and wellness of pets through comprehensive healthcare services and plans. Potential Healthcare Cost Increases in 2026 In 2026, Chewy employees may face significant increases in healthcare costs, primarily driven by anticipated record hikes in Affordable Care Act (ACA) premiums. With reports indicating some states could see premium jumps exceeding 60%, coupled with the potential expiration of enhanced federal premium subsidies, many employees could experience monthly costs rising by over 75%. As Chewy employees evaluate their healthcare options, understanding these dynamics will be crucial for their financial planning and healthcare budgeting in the face of rising costs. Click here to learn more

In the current retirement planning landscape at Chewy, engaging in part-time work or side hustles is becoming increasingly popular. Even though retirement is often seen as a time for relaxation, today it frequently includes activities that generate income and maintain mental engagement.  A survey by MarketBeat.com  of 3,000 retirees reveals that those pursuing side hustles generally earn about $379 per month. The reasons vary: 47% engage in side hustles to supplement their retirement income, 34% to keep mentally active, 10% to pursue a passion, and 9% to enhance interpersonal relationships.

Preparation is key

It’s valuable for Chewy retirees to consider their post-retirement work plans early on. Advisors recommend starting to plan 5 to 10 years before retirement. This foresight can ease financial constraints and reduce the monotony that might unexpectedly arise. Financial professionals caution against retiring prematurely without adequate financial preparation, likening it to 'pulling the ripcord and jumping out of the plane.'

Weighing the return to work

Deciding whether to work part-time is important for those transitioning from Chewy. Financial advisors play a critical role in making these decisions, assessing the necessary income levels and preferred work stress. Key considerations include the need for health benefits, especially for those ineligible for Medicare. Financial professionals highlight the importance of carefully addressing these “serious questions.”

Choosing enjoyable pursuits

Selecting work that brings joy can make it feel less like a chore. Some financial professionals encourage finding employment in areas that spark personal interest. For animal lovers, dog walking or pet sitting could be suitable, while sports enthusiasts might enjoy managing youth events. John Jones from Heritage Financial shares a client example, where, despite being financially stable, the client chose to learn golf partly to remain active and mentally engaged.

Financial implications on Social Security and Taxes

Earning a salary during retirement can affect social benefits and taxes. Those receiving Social Security benefits before full retirement age must consider the income limit that could affect their benefits. Additionally, retirees need to monitor their income to prevent moving into a higher tax bracket, particularly when making Required Minimum Distributions (RMDs). Jennifer Kohlbacher, who oversees wealth strategy at Mariner, advises structuring side hustles carefully. She suggests using a sole LLC to prevent legal disputes and discusses potential deductions for expenses like equipment and mileage.

Continuing retirement savings

Working during retirement can also help extend the lifespan of retirement savings. Other financial professionals highlight a case where a retired Chewy executive chose consulting to reduce withdrawals from his personal retirement account (IRA), allowing the account to grow tax-deferred and increase its financial value for his heirs.

Adaptability and ongoing evaluation

Life’s unpredictability calls for flexibility in retirement plans.  There are real-life examples of a retirees returning to work to support their spouses during early parental leave. It’s beneficial to perform regular financial reviews to confirm that the side hustle meets ongoing financial and emotional needs.

In conclusion

The evolving perspective on retirement now sees it as a phase that may include ongoing work activities, reflecting shifts in financial strategies, personal fulfillment, and social structures over time. As this trend grows, retirees are encouraged to view self-employment not only as a financial supplement but also as an opportunity to stay engaged and involved in society.

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Participating in side hustles can significantly improve the cognitive health of retirees.  According to a 2020 study by the American Psychological Association , retirees engaged in productive activities, such as part-time roles or self-employment, reported better psychological health and increased cognitive capacity compared to those fully retired. This stimulation from active work supports mental alertness, crucial for personal financial management and effective problem-solving in retirement.

Navigating retirement with a side hustle is like sailing through a peaceful retirement haven with a sturdy little motorboat. Just as a sailor uses the motorboat to explore new coves and shores freely, extending the journey beyond set boundaries, an alternative activity during retirement allows individuals to pursue new passions and opportunities while maintaining their financial stability. It’s the perfect blend of exploration and income generation, allowing retirees to boost their income on their own terms, maintain mental resilience, and expand social networks—all while mastering the dynamics of their post-professional life.