Open enrollment checklist: Money moves to maximize your benefits

By Kyle C. Miller and Gina Coletti

It is that time of year again! Open enrollment has started, or will soon start, for the majority of us. Taking advantage of this period can unlock savings, reduce risk, and help impact your bottom line in ways you may not be aware of. This is your once-a-year opportunity to take a holistic look at your benefits, and this article aims to aid your thoughtful analysis.

What is open enrollment?

Open enrollment is the annual period when employees can choose or make changes to their workplace benefits, typically, including vision, dental, and health insurance, as well as flexible spending accounts (FSAs), health savings accounts (HSAs), and other optional benefits.

During this window, you can:

• Enroll in new coverage you previously waived.

• Switch between available plans (for example, from an HMO to a PPO).

• Add or remove dependents.

• Adjust contributions to tax-advantaged accounts.

When is the open enrollment period?

• Employer plans (group benefits): Typically, two to four (2–4) weeks in the autumn (Oct–Nov) for coverage beginning January 1. Exact dates vary by employer, so watch for HR emails and portals.

• ACA/HealthCare.gov (individual and family plans): November 1 through January 15 in most states. Enroll by December 15 for coverage effective January 1; later enrollments (by January 15) usually start February 1. State-based exchanges may differ slightly.

• Medicare (people 65+ or with certain disabilities): Annual open enrollment October 15 through December 7 to change Medicare Advantage/Part D for next year; Medicare Advantage Open Enrollment runs January 1 through March 31 for Advantage plan changes.

Once the window closes, your choices generally stay in place for the full plan year unless you experience a qualifying life event, such as marriage, birth of a child, or loss of other coverage. Employers typically announce open enrollment dates in advance, so mark them early to give yourself time to compare options and make informed decisions.

How to maximize your financial benefits

Open enrollment isn’t just about picking health insurance plans—it’s an opportunity to take a closer look at how your benefits fit into your overall financial well-being. From healthcare costs to tax-advantaged savings and income protection, the right decisions now can have a big impact on your budget for the year ahead. Use the following checklist to make confident, informed choices and ensure you get the most value from your employer-sponsored benefits.

Price the package, not just the premium

Don’t let a low premium distract you from the true annual cost. Compare plans using the full amounts of premiums, deductibles, copays, coinsurance, and the out-of-pocket maximum. Consider expected healthcare needs for the year, such as planned surgeries, orthodontics, or recurring prescriptions, and explore costs under each plan. Confirm that your doctors, facilities, and medications remain in-network; out-of-network surprises can quickly erase any perceived savings. If you’re married, compare your plan to your spouse’s, as one spouse’s plan may offer better value for family coverage.

Know your window and plan around life events

You can get started by confirming your employer’s enrollment period and setting reminders. Missing these deadlines can be costly, forcing you to carry suboptimal coverage for the remainder of the plan year. Outside of open enrollment, changes are generally permitted only upon qualifying life events, such as marriage, birth of a child, or loss of other coverage. Typically, you have sixty (60) days from the event to make mid-year changes. A job loss or layoff that causes loss of access to insurance can also trigger this window.

Leverage tax-advantaged accounts and added benefits

Review your options across medical, dental, and vision, and take a fresh look at your flexible spending account (FSA) and Health Savings Account (HSA) elections.

• FSAs allow you to set aside pre-tax dollars for eligible expenses and can be particularly useful for predictable costs on the horizon.

• HSAs, when paired with a qualifying high-deductible health plan, deliver triple tax advantages on contributions, tax-deferred growth, and eligible withdrawals.

In addition to FSA and HSA options, don’t overlook employer-sponsored wellness programs, mental health sessions, and fitness reimbursements—these are real financial benefits that can offset healthcare costs.

One-year commitment

Open enrollment choices are locked in for a year—this can empower you and should not paralyze you! If a plan underperforms and fails to align with your needs, you can course-correct next year. When considering your options for the next year, focus on reducing risk while balancing predictable expenses, and don’t forget to revisit life and disability insurance elections to ensure income protection remains aligned with your household needs.

Avoid surprises by verifying insurance information

To prevent coverage issues, you will need to verify your personal and dependent information. Be sure to review and reconfirm addresses, coverage levels, and beneficiary designations each year. After changes take effect, promptly share your updated insurance details with your doctors, pharmacies, and any recurring providers. Failing to update can lead to costly surprises like denied claims, delays, and avoidable out-of-pocket expenses.

A smarter approach to annual enrollment

A disciplined open enrollment review blends financial analysis with practical planning. Know your deadlines, evaluate the total cost of care, optimize tax-advantaged accounts, and align coverage with your family’s needs. Nixon Peabody Trust Company’s experienced advisors can help you determine how your open enrollment choices can align with your greater financial health strategies. With a few focused hours each fall, you can meaningfully improve both your financial resilience and your healthcare experience in the year ahead.

Kyle C. Miller
Trust Advisor
+1 617.345.6052
kcmiller@nixonpeabody.com

Gina Coletti
Chief Fiduciary Officer
+1 617.345.1110
gcoletti@nixonpeabody.com