Family Wealth blog

Medicare Open Enrollment Checklist

A man's hand moves one of several wooden blocks with checkmarks on them. The title reads Medicare Open Enrollment Checklist.

For Medicare members, October 15 is a very important red-letter day. That’s when the annual three-week Open Enrollment period starts.1 As you may already know, Open Enrollment Decisions a person makes during Medicare Open Enrollment aren’t just about immediate health needs. They can ripple through an investor’s financial landscape, impacting everything from monthly budgets to long-term retirement goals. An integrated approach that considers both health needs and financial objectives is essential. So, as timing is everything, here is a primer to help you prepare for this year’s Open Enrollment.

What Can I Change?

During Open Enrollment, you can make changes in the following general areas:

• Switch from Original Medicare (Part A & Part B) to a Medicare Advantage Plan (Part C) and vice versa.

• Enroll, switch, or drop a Medicare Prescription Drug Plan (Part D).

• Switch from one Medicare Advantage Plan to another.

• Join or drop a Medicare Medical Savings Account Plan.

Getting Ready for Open Enrollment

This section will guide you through essential steps to ensure you’re equipped to navigate the many choices available, from assessing your health needs to comparing plan options. These steps aim to demystify the process and align your choices with both your health and financial goals.

Important Steps:

• Review Your Current Coverage

• Assess Your Health Needs

• Create a List of Your Medications

• Research and Compare Plans

• Consider the Financial Implications

• Finish the Open Enrollment Process

Remember, the decisions you make during the Open Enrollment period will be effective starting January 1 of the following year.

Help is Available

If you thought enrolling for Medicare was a bit too complex, don’t get your hopes up too much for the Open Enrollment routine. You will find some resources by going directly to, [2] but you may want to go to your financial advisor for guidance.

A financial advisor’s role primarily revolves around helping clients understand the financial implications of their choices, ensuring they make informed decisions based on their financial health and future needs. When it comes to Medicare choices that make sense within your overall plans, a financial advisor would most likely assist with the following:

Review Your Current Coverage: An advisor can help you understand any changes in costs and benefits of your current plan, which could affect your financial planning.

Assess Your Health Needs: While this is primarily a health concern, an advisor might discuss potential upcoming medical expenses and how they could impact your finances.

Research and Compare Plans: Financial advisors can assist in weighing the financial pros and cons of various plans, ensuring that clients make decisions that align with their financial goals. Some advisors have access to excellent planning tools that help them focus on those plans that align with your needs.

Look Beyond the Premium: Advisors emphasize the importance of considering all costs. They’ll help you assess deductibles, copayments, and coinsurance, not just the upfront premium, to ensure you’re making a financially sound choice for the long term.

Seek Assistance: While they will provide financial guidance, advisors can also recommend seeking out additional help, especially for the non-financial aspects of Medicare.

Mark Your Calendar: An advisor will often help clients stay on top of important financial deadlines, ensuring they don’t miss opportunities or face penalties.

Confirmation: After making changes, a financial advisor might remind you to ensure everything is processed correctly to avoid unexpected expenses.

Financial Considerations

For many retirees or even those who haven’t retired quite yet, Medicare is a crucial part of their financial strategy. Understanding the financial implications of different Medicare plans can be quite complex. That’s why it’s important to consider asking your financial advisor for help in working through these six key considerations for wealth management in relation to Medicare:

1. Cash Flow Considerations:

Premium Costs: The cost of premiums, whether for Original Medicare or a Medicare Advantage Plan, can significantly impact your monthly expenses. It’s essential to factor this into your budget.

Out-of-Pocket Expenses: Co-pays, deductibles, and out-of-network fees can eat into your disposable income. Estimating these yearly costs can help you adjust your budget accordingly.

2. Long-term Health Costs:

Future Needs: If you anticipate significant health changes, such as surgeries or treatments, you might want to opt for a plan offering broader coverage, even if it comes with a higher premium. This can prevent draining your savings.

Prescription Coverage: As medication needs change, it’s crucial to select a plan that covers new or anticipated medications. Failing to do so can lead to unexpected and significant out-of-pocket costs.

3. Investment Implications:

HSA Compatibility: If you’re enrolled in a High Deductible Health Plan (HDHP) and using a Health Savings Account (HSA) as a tax-advantaged investment vehicle, your choice of Medicare plan might impact your HSA eligibility. [3]

Tax Planning: Some Medicare premiums are income-related. If your income increases due to capital gains or other sources, you might end up paying higher Medicare premiums called IRMAA (Medicare Income-Related Monthly Adjustment Amount). This interplay should be factored into your tax and investment decisions.

4. Retirement Savings Longevity:

Drawdown Rate: Health care costs can influence how quickly you deplete your retirement savings. If more is spent on health care, you might need to adjust your withdrawal rate or investment strategy.

5. Risk Management:

Coverage Gaps: Without comprehensive coverage, an unexpected health event can lead to significant costs, possibly requiring the liquidation of investments at inopportune times.

Long-term Care: Medicare typically doesn’t cover long-term care. If you’re considering long-term care insurance, weigh the premium and potential benefits against the risk of future long-term care needs.

6. Legacy & Estate Implications:

Your Legacy: If your goal is to leave a financial legacy, substantial health care costs can reduce the estate’s value. Proper coverage can help safeguard assets intended for heirs.

Again, Medicare is more than just a health insurance program; it’s a crucial part of your financial strategy. By understanding the financial implications of different Medicare plans, you can make informed decisions that align with your wealth management goals.

The Takeaway

Yes, this is a lot to take in, and the time to prepare it now. The good news is that Open Enrollment only happens once a year. The bad news is that it does happen every year. But, as the choices made during the enrollment period can have such impactful and long-lasting effects on one’s finances, it’s extremely important to approach this annual routine with as much attention as one would with managing a financial portfolio. Another reason why getting your financial advisor involved is a worth considering sooner than later.





Disclosure: This information is for educational and informative purposes and shall not be considered a specific recommendation. Readers are advised to speak with their advisor at JL Bainbridge to determine their specific recommendations that meet their investment objectives and to review their portfolios. The material being provided is thought to be accurate. However, the information is compiled from multiple resources and may become outdated or otherwise rendered incorrect by new research or corrections without notice. J.L. Bainbridge & Co., Inc., is not a broker dealer and does not offer tax or legal advice. Please consult your tax or legal advisor for assistance regarding your individual situation. It should neither be assumed that future results will be as profitable or that a loss could not be incurred. For more information related to our firm, please see our disclosure brochures at and

The Family Wealth newsletter logo, which is a forest green square with white letters on it.

Are you already a subscriber? If not, click here so you don't miss anything!