Chewy Employees: Navigating Your Future When Medicare Isn't Enough

As Chewy employees approach retirement, it is very important to discuss with your family the financial and legal implications that they will incur,' says Brent Wolf of The Retirement Group, a division of Wealth Enhancement Group.

Planning for retirement is not only about the individual’s preparation; it is about the generation of a strategy and comprehension of the prepared and unprepared,' states Kevin Landis from The Retirement Group, a division of Wealth Enhancement Group.

In this article, we will discuss:

1. Legal and Financial Preparations: The importance of giving legal authority to children for financial and medical decisions and sharing detailed financial plans.

2. Property and Asset Management: Learn how to manage and transfer property and how debt affects inheritance.

3. Healthcare and Incapacity Planning: Healthcare requirements and how to make legal arrangements for the event of incapacity.

It is very important to make sure that you have made your goals known to those who will be affected by your retirement plans, especially if you have dependents like children. It is wise to involve your family in the financial and health management decisions to be made after you leave the Chewy company to benefit your family and yourself. The level of information disclosure may differ depending on the type of family relationships.

As part of your retirement preparations, it may be wise to grant your children legal authority to make financial and medical decisions on your behalf. If retirement has begun and these arrangements haven't been made, addressing this promptly is crucial. Early and open discussions about your retirement goals and circumstances are essential, especially before any potential health issues or other challenges arise.

Your House

Many retirees downsize to a smaller and easier to manage home. This decision is often triggered by various factors such as high maintenance costs, substantial property taxes, or the simple desire to change—the possibility of moving to another country or to a retirement community with additional features. This shift is both emotional and practical, especially if there are expectations about the family home’s future ownership or its sentimental value.

If the home is a large part of your assets, Chewy retirees may be able to use the equity in your home to fund a comfortable retirement. On the other hand, if you are financially able, you could transfer the property title to your child. It is crucial to know the tax consequences of such a transfer. Your child may be taxed highly if they later sell the property after you gift the house while alive since they will not be able to take a step-up in cost basis on the property.

Your Indebtedness

Chewy retirement with various debts, including credit card balances, mortgages, and even student loans, is becoming more common. You need to inform your children about these liabilities as they will affect their share of the inheritance. All non-assumable debts or home equity loans will require new financing to be settled.

Your Other Financial Assets and Retirement Accounts

Many retirees rely on the savings that they have accumulated in their working years, Social Security, and any pension that they have. The SECURE Act 2.0 has increased the age of required distributions from retirement accounts to 73, affecting the management of these assets. This is important so that your children know where your assets are located to avoid them being inaccessible when you die or become incapacitated.

Your Policy for Life

It is important to disclose the information regarding any life insurance policies since these will pay for the funeral and remaining medical expenses after your death.

Your Medical Plans

Retirement from Chewy is a major problem in terms of healthcare as many retirees rely on Medicare or other private health insurance. These details have to be discussed with your children, including those for long-term care needs that are not covered by Medicare.

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In the Event of Your Incapacity

Having legal documents like power of attorney is important in case of incapacitation that is unexpected. This ensures that your wishes on where you want to be and what you want to do with your health are respected.

Your Choice

It is crucial to review and revise your will every now and then. This can help avoid confusion and can convey to everyone any special provisions or questionable provision of resources that may lead to conflict.

Any Company You Manage

If you own a business, then the future of the business, whether it will be sold or if it will be transferred to the next generation, needs to be discussed with your children to ensure a smooth transition and to set expectations.

Overarching Thoughts

It is important to know the typical retirement age in order to make informed financial decisions. Due to the fact that people live longer than before, retirement can stretch for many years, which calls for better financial planning.

Using Tools for Financial Planning

Virtual tools like stock trading simulators can be useful to gain real life experience of handling investments with real money consequences that can be useful for current and future retirees.

Ensuring that your children know the basics of your pension and other healthcare that you will get as a retiree when you were working at a Chewy company makes the conversation easier. A 2020 report by the Employee Benefit Research Institute found that retirees are likely to be partially or completely wrong about these benefits, which means that they could have false ideas about their finances. This ensures that your children know these benefits, which are important in your retirement planning and may make them consider starting theirs.

Disclosing your retirement plans is a bit like giving the keys to a family car to your children. You can help your children understand the route you have in mind, the healthcare coverage you need, and the pension benefits you will be receiving – just as you would explain the condition and best features of a car before letting your children use it. It enables them to know what to do to continue the legacy and navigate the ‘vehicle’ correctly in the future.

Sources:

1. Warren Street Wealth Advisors: 'Chewy and Large Company Employees.' In 2025, Warren Street Wealth Advisors offers specialized financial services for Chewy employees, including one on one investment advice and retirement planning.

2. Chris Reddick Financial Planning, LLC: Reddick, Chris. 'How to Effectively Save for Retirement in Chewy Companies.' Chris Reddick Financial Planning, LLC was established in 2018 March 2, from  www.chrisreddickfp.com . This article examines the saving behaviours of different generations of Chewy companies, the movement from pensions to 401(k) plans, and other changes.

3. Willis Towers Watson: 'DB Plans a Thing of the Past for Most Chewy Companies.' The article, published on PLANSPONSOR on March 2, 2018, is available at  www.plansponsor.com . This source is cited to show the decrease of defined benefit plans in Chewy companies and other general changes in retirement planning.

4. Willis Towers Watson: 'Evolution of DB Plan Sponsorship for Chewy Companies, 1998 – 2019.' The document provided by Willis Towers Watson is the historical data of the management of pension plans by Chewy companies over the years, including the shift from traditional to hybrid plans.

5. HR Search & Rescue: 'F500 Benefits.' On the HR Search & Rescue website, you will find information on how Chewy companies can improve their benefit packages to attract and retain employees, with emphasis on retirement and other benefits.