Open enrollment comes around every fall – and for many families, it’s one of the most important (and most overlooked) financial planning opportunities of the year.
If you’re in your 30s, 40s, or 50s juggling kids, careers, and competing priorities, open enrollment may feel like just another HR task to check off the list. But taking 30–60 minutes to review your benefits can lead to smarter decisions, lower out-of-pocket costs, better protection, and more confidence in your financial plan.
Here are six key decisions to review during open enrollment – plus tips to make the process simpler and more rewarding.
1. Health Insurance: Choose the Plan That Matches Your Family’s Needs
This is the headline decision for most people – and the one that can feel the most overwhelming. Between PPOs, HMOs, HDHPs, deductibles, coinsurance, and out-of-pocket maximums, it’s no wonder many people default to last year’s plan.
Instead of focusing only on premiums, look at total expected costs:
- What’s the deductible and out-of-pocket maximum?
- How often do you visit doctors or specialists?
- Do you have recurring prescriptions or procedures?
- Are your preferred doctors in-network?
If you’re generally healthy and can afford higher upfront costs, a High Deductible Health Plan (HDHP) paired with an HSA can offer significant long-term savings. If you expect higher medical needs, a traditional PPO may offer better value.
2. HSA vs. FSA: Understand the Differences and Compatibility Rules
These tax-advantaged accounts help you cover eligible medical expenses – but they work very differently.
Health Savings Accounts (HSAs)
HSAs are available if you’re enrolled in a qualified HDHP and they offer a triple tax advantage:
- Pre-tax (or tax-deductible) contributions
- Tax-free growth
- Tax-free withdrawals for qualified medical expenses
Unused funds roll over year to year, and once the balance is large enough, you can invest it. Many families use HSAs to reduce taxes today while building reserves for future healthcare needs.
Flexible Spending Accounts (FSAs)
FSAs are use-it-or-lose-it accounts. You contribute pre-tax dollars to cover eligible healthcare expenses, but most funds must be used within the plan year (some plans allow a small carryover or grace period).
FSAs can be used for:
- Copays, coinsurance, and deductibles
- Prescription and many over-the-counter medications
- Dental care and orthodontics
- Vision care, glasses, and contact lenses
This makes FSAs especially helpful for families who expect consistent out-of-pocket medical expenses and who want to lower their taxable income.
3. Life Insurance: Make Sure Your Family is Protected
Many employers offer group life insurance equal to 1x or 2x your salary – but that’s rarely enough if you have young kids, a mortgage, or dependents who rely on your income.
During open enrollment, check:
- How much life insurance is included?
- Can you purchase additional coverage?
- How much life insurance do you need?
In most cases, it’s wise to supplement group coverage with a term life insurance policy you own privately. It’s often more affordable and flexible – especially if your job situation changes.
4. Disability Insurance: The Most Overlooked Coverage You Probably Need
Think of disability insurance as income protection. If you couldn’t work for several months or longer due to illness or injury, how would your family pay the bills?
Many employers provide short-term disability, but long-term disability insurance is where real protection kicks in. During open enrollment:
- Review what’s provided (percent of salary, benefit period, elimination period)
- Understand the difference between “own occupation” vs. “any occupation”
- Consider whether your household could manage without your income
Disability insurance is especially important for single-income households, where the loss of income can quickly disrupt your ability to cover expenses, save for goals, and maintain your lifestyle. In these situations, long-term disability coverage offers critical protection – and peace of mind – when your financial stability depends on one paycheck.
5. Dependent Care FSA: Tax Savings for Families with Young Kids
If you pay for daycare, preschool, after-school programs, or summer camps, a Dependent Care FSA (DCFSA) can save you hundreds (or more) in taxes.
For 2026, you can contribute up to $7,500 per household pre-tax ($3,750 if married filing separately) to cover eligible dependent care expenses. This includes:
- Licensed daycare centers and in-home providers
- Preschool tuition
- Before- and after-school care
- Some summer day camps
- Care for an elderly dependent living in your home
Just be sure to:
- Confirm your provider is eligible and can supply documentation
- Submit claims before your plan’s deadline
- Coordinate with the Child and Dependent Care Tax Credit, since benefits may overlap or phase out at higher income levels
6. Review and Update Your Beneficiaries
It’s not technically a “benefit,” but open enrollment is a great time to review and update beneficiary designations for your:
- Life insurance
- 401(k), 403(b), or other retirement plans
- HSA accounts
If you’ve experienced a life change – marriage, divorce, a new child, or the loss of a loved one – your beneficiary designations may need to be updated. These elections override your will, so keeping them current is critical.
Make Open Enrollment a Family Finance Check-In
Rather than rushing through forms at the last minute, use open enrollment as a chance to check in on your broader financial picture. Are your benefits supporting your goals? Are there gaps in your protection plan? Are you leaving money on the table?
At Navwell Advisors, we help families make smarter financial decisions with clarity and confidence. If you’re unsure which options are best for your situation, let’s talk.
Open enrollment isn’t just paperwork – it’s an opportunity to strengthen your financial foundation for the year ahead.
Want help reviewing your open enrollment options?
Schedule a free consultation and let’s make sure your benefits are working for you.