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Financial Well-Being Blog
September 15, 2026

5 Money Questions to Ask Before Open Enrollment

Money Management
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Open enrollment is an opportunity to make changes to your benefits that can impact your finances and overall financial health. From healthcare and retirement savings to other valuable resources your employer may offer, your benefits are an important part of your overall compensation — and making thoughtful choices can support your financial well-being both today and in the future.

 

Think of open enrollment as a chance to consider what has changed, what matters most to you and how your benefits can support your goals. Taking a little time to review your options can help you feel more prepared for the year ahead and more confident on your path toward financial peace of mind.

 

Here are five questions to ask yourself as you consider your benefit choices during open enrollment.

 

1. What Has Changed in My Life or Finances?

The benefits that worked last year may not be the best fit today. Consider whether anything has changed, or is likely to change, including:

  • Getting married or divorced
  • Having or adopting a child
  • Changes in household income
  • New or changing healthcare needs
  • Changes in expenses or financial goals
  • Changes in who depends on your income

 

Even without a major life event, your priorities may have shifted. You may be building an emergency fund, paying down debt, increasing retirement savings or anticipating higher healthcare or childcare expenses. Open enrollment is a chance to make sure your benefits still support where you are today and where you want to go.

2. What Did Healthcare Actually Cost Me This Year?

Choosing health insurance can feel complicated, but you don't need to become an expert to make a thoughtful decision. Start with how you used healthcare this year.

 

Consider:

  • How often you or your family visited a doctor
  • Regular prescriptions or ongoing treatments
  • Regular or unexpected healthcare expenses
  • What you paid out of pocket and whether those costs were difficult to manage

 

Then think about what you can reasonably anticipate for the coming year. When comparing plans, look beyond what comes out of your paycheck. Your total healthcare costs can also include deductibles, copays and coinsurance when you receive care. A plan with a lower premium isn't necessarily the least expensive option overall.1

 

If your employer offers plan comparison tools or calculators, use them alongside your healthcare history to help estimate potential costs.

3. Am I Making the Most of Tax-Advantaged Benefits?

Depending on your employer and health plan, you may have access to accounts that help you set aside money for certain expenses on a tax-advantaged basis. Common options include:

  • Health Savings Account (HSA): Available to eligible individuals enrolled in certain health plans. HSA funds can be used for qualified medical expenses, unused money generally rolls over from year to year and the account remains yours if you change employers. For 2026, the HSA contribution limit is $4,400 for self-only coverage and $8,750 for family coverage.2 In 2027, these limits increase to $4,500 for self-only coverage and $9,000 for family coverage.3
  • Health Flexible Spending Account (FSA): Allows you to set aside pre-tax money for eligible healthcare expenses. For plan years beginning in 2026, employees can contribute up to $3,400 to a health FSA. Depending on your employer's plan, unused funds may be subject to use-it-or-lose-it rules, although some plans allow a limited carryover or grace period.3
  • Dependent Care FSA: Can allow eligible employees to use pre-tax dollars for qualifying childcare or other dependent-care expenses. For 2026, the annual dependent care FSA limit is $7,500  for individuals who are single or married filing jointly, or $3,750 for married individuals filing separately.4

 

Eligibility and plan rules vary, so understand what your employer offers, what expenses qualify and any deadlines that apply. If you already expect eligible healthcare or dependent-care expenses, these benefits may help those dollars go further.

4. Am I Taking Advantage of My Full Workplace Benefits Package?

Your salary is only one part of your compensation. Look beyond health insurance and review your employer's full benefits package, which might include:

  • Retirement plans and employer matching contributions
  • Life and disability insurance
  • Employee assistance, mental health or financial wellness programs
  • Tuition, education or assistance
  • Childcare, dependent-care or commuter benefits
  • Employee discounts and other voluntary benefits

 

Some benefits have a financial value that's easy to overlook. For example, qualifying employer educational assistance can receive favorable federal tax treatment, and certain student loan payments may qualify under employer educational assistance programs.4 You may even find services you're paying for yourself that are available through work for free or at a discount.

 

5. Do My Benefits Support My Financial Goals for Next Year?

Your benefits choices can affect your:

  • Monthly budget
  • Emergency savings
  • Healthcare and childcare costs
  • Retirement savings
  • Insurance protection
  • Other financial goals

 

Think about what you want your finances to look like over the next year. Someone expecting a baby may pay closer attention to healthcare expenses, parental benefits and dependent-care accounts. Someone focused on retirement might review their contribution rate and whether they're receiving their full employer match.

 

The goal isn't necessarily to choose the most coverage or the option with the lowest upfront cost. It's to choose workplace benefits that fit your life, your finances and your goals.

Make Open Enrollment Part of Your Financial Considerations

Give yourself time to understand what your employer offers and consider how those benefits work alongside your budget, savings and other financial priorities. The right choices will look different for every household and can shift as your life changes.

 

 If you're unsure how your workplace benefits fit into your broader financial picture, a Financial Well-Being Coach can help you think through your budget, savings, debt and financial goals so you can approach your decisions with greater confidence.

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About the Author

Jeremy Davis

Financial Well-Being Coach

Jeremy Davis joined CommunityAmerica in 2022 and currently serves as a Financial Well-Being Coach at the Hickman Mills Community Access Center.

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