It’s that time of year again—open enrollment season. Whether your health insurance comes through your employer or a state marketplace, fall is your once-a-year opportunity to review your benefits and make updates that will take effect on January 1, 2026.

For many busy families, it’s tempting to breeze through these decisions just to check the box. But this is one of the few times you can make strategic choices that directly impact your health coverage, income protection, and out-of-pocket costs for the year ahead.

Outside of this open enrollment window, changes are usually only allowed if you experience a major life event, like getting married, moving, having a child, or leaving your job.

And it’s not just about health insurance. Open enrollment also covers a range of important employer-sponsored benefits like life insurance, short- and long-term disability, and tax-advantaged accounts like HSAs and FSAs.

Because these decisions play a big role in your overall financial plan, it’s important to take time this enrollment season to evaluate your current benefits and make sure they still align with your family’s needs. Below, we’ll walk you through what to consider and how to make the most of this year’s open enrollment.

How to Review Your Employee Benefits During Open Enrollment

Even if nothing major has changed in your health this year, your benefit options may have. Open enrollment is your chance to review your needs and make sure your benefits still strike the right balance between affordability and protection from the unexpected.

As you consider your coverage for 2026, here are some key areas to review.

Choosing the Right Health Insurance Plan for 2026

First and foremost, think about your own health. Maybe you were diagnosed with a new condition, or maybe you’re feeling better than you have in years. Your current situation should guide your decisions. Relatively healthy individuals or families (including younger people with few medical concerns) may not need the same level of coverage as someone managing multiple chronic conditions or facing a family history of illness.

It’s also important to reflect on your health-related spending from the past year, particularly in relation to your deductible. If you chose a high-deductible health plan (HDHP), did the savings on premiums outweigh the higher out-of-pocket costs? HDHPs can make sense for people who don’t expect to use much care and want access to a Health Savings Account (HSA), which offers triple tax advantages and can serve as a powerful tool for managing current medical expenses or even saving for healthcare in retirement.

If you already contribute to an HSA or FSA, open enrollment is also the time to adjust your contribution amounts to reflect your anticipated needs for 2026.

Alternatively, if you had significant out-of-pocket expenses in 2025, you may want to consider a plan with a lower deductible. This can mean higher monthly premiums and no access to an HSA, but insurance would begin covering costs sooner—potentially saving you money overall.

You may also be choosing between different types of plans, like a Preferred Provider Organization (PPO) or a Health Maintenance Organization (HMO). PPOs usually offer more flexibility in choosing providers and don’t require referrals to see specialists, though they tend to come with higher premiums. HMOs often cost less but require you to stay in-network and get referrals for specialist care. Your decision should come down to what kind of access and flexibility you and your family want or need.

Don’t Overlook Life and Disability Insurance During Open Enrollment

Health coverage often gets the spotlight during open enrollment, but don’t overlook your other insurance options—especially life and disability insurance. Many employers offer access to these through group plans, but they usually require you to actively opt in, especially if you want coverage beyond what the company provides at no cost.

Take a moment to review any life and disability policies you already have. Ask yourself: would this be enough for my family if something happened to me? The default life insurance benefit is often tied to your salary, but that may not be enough to cover long-term needs like mortgage payments, college costs, or income replacement.

Disability insurance tends to fly under the radar, but it can be just as important. If an injury or illness kept you from working, would your family be able to maintain your current lifestyle? Short-term and long-term disability coverage can help replace lost income and provide financial stability while you recover.

Think about where you are today and what might change over the next year. You can’t predict emergencies, but you can prepare for them. A quick review of these coverages now can help you feel more confident about your family’s financial safety net.

Key Questions to Ask Before You Choose a Plan

As you continue to weigh your options, there may be other factors to consider. 

If your spouse also has access to workplace benefits, it’s worth reviewing their plan details alongside yours. Make sure the plan you choose as a household is the best fit overall. Sometimes it makes sense to stay on your own employer’s policy. Other times, switching to your spouse’s plan could offer better coverage or save money.

Also, think about what’s ahead in 2026. Are you considering a job change, stepping away from full-time work, or even retiring? If so, it may be simpler to switch to your spouse’s employer coverage now, assuming they plan to stay in their current role. That way, you avoid the disruption of changing plans mid-year and potentially starting over on your deductible.

Big life transitions are stressful enough. Lining up the right coverage now can help you avoid surprises and keep things running smoothly later on.

Quick Recap: What to Focus On During Open Enrollment 

• Open enrollment is your annual opportunity to review and adjust employer-sponsored benefits for the year ahead.
• Even if your health hasn’t changed, your coverage options or needs might have.
• Review your health insurance plan type (PPO vs. HMO) and whether a high-deductible plan with an HSA is still the right fit.
• Evaluate last year’s medical spending and adjust HSA or FSA contributions accordingly.
• Consider switching to a lower-deductible plan if out-of-pocket expenses were high.
• Don’t overlook life and disability insurance; employer-provided coverage may not be enough.
• Review your spouse’s benefits to determine the most cost-effective and comprehensive household plan.
• Factor in upcoming life changes, such as job transitions or retirement, to avoid mid-year coverage disruptions.

Need Help Reviewing Your Options?

Even if you don’t expect to make any changes, it’s always a good idea to review your options. Your employer (or your spouse’s employer) may provide new offerings, and this will be your only chance to opt in or out until next year’s open enrollment (barring any special enrollment periods). 

Healthcare can be a significant expense, especially if you’re stuck with inadequate coverage. Policy “overkill” can mean spending more of your income on premiums than necessary, while being under-insured can lead to large out-of-pocket costs. 

If you’d like some help sorting through your options during this open enrollment period, don’t hesitate to reach out to our team. We’d be more than happy to help you choose the coverage that best supports your broader financial plan.

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.