Make the Most of Employee Benefits Season

It’s that time of year again—fall travel, football season, and family gatherings are just around the corner. It’s also Employee Benefit Enrollment season for many, typically running from mid-October to mid-November.

While reviewing benefits isn’t as exciting as our family’s fall break plans, I know that Neil’s employee benefits are just as important to our financial future as our time together is to making memories. Each year, I take the reminder postcard and place it next to my keyboard in my home office. The enrollment window often opens while we’re on fall break, so I need it front and center during my downtime.

What Do We Review?

Health, Dental, and Vision Insurance

Every year, we carefully review our health insurance options and read the fine print. We typically choose between a co-pay PPO plan and a High Deductible Health Plan (HDHP). We always take time to think through any anticipated expenses so we can select the plan that fits our needs.

Because both Neil and I have access to insurance through our employers, I double-check the eligibility rules to ensure I can remain on his family plan. Some companies allow this, while others charge a “working spouse” surcharge—or don’t allow it at all. Staying on one family plan helps us meet a single deductible and out-of-pocket max, which is important for our cash flow planning.

We also review our dental and vision insurance. Some medical plans include coverage for children’s vision and dental (up to age 19), while others offer separate family coverage. Neil and I both need vision coverage (I’m quickly heading toward bifocals), but the kids still have great eyesight. One year, we upgraded to enhanced dental to take advantage of orthodontics coverage, but now that we’ve hit our lifetime max, we’ve returned to basic coverage.

Bottom line: Read the fine print and think carefully about what your family needs for the upcoming year.

Savings Plans

In connection with our health coverage, we review whether to use a Health Savings Account (HSA)—available only with HDHPs—or a Flexible Spending Account (FSA). Both can reduce our taxable income, but they have different rules. Some employers now contribute to HSAs on behalf of employees, which is an added bonus worth considering.

We also used to use a Dependent Care FSA when our childcare costs were higher. While that benefit isn’t as useful to us now, it was a great tax-saving tool when the kids were younger. (And yes, they’re still expensive—just in $20+ increments instead of daycare checks. See my article on that!)

For long-term savings, we review both Neil’s 401(k) plan along with mine, looking at:

• Company match opportunities
• Pre-tax or Roth (post-tax) contributions
• Our overall retirement savings strategy

For our family, a mix of pre-tax and Roth contributions makes the most sense.

Other Benefits

We also review:

• Life insurance
• Disability insurance
• Critical illness or cancer policies
• Group long-term care insurance (when available)

These group policies are often offered at low rates and may be portable, meaning you can keep them if you leave your job. Still, it’s important to compare them with individually owned policies. I highly recommend speaking with your advisor at Rather & Kittrell to evaluate what’s best for your specific family needs and costs.

Note: This list isn’t exhaustive—companies are always rolling out new fringe benefits to attract and retain talent. Be on the lookout!

Final Thoughts

Spending a few hours reviewing benefits may not be the most exciting part of fall break—but it’s essential for our financial well-being. It’s not just about retirement planning; it’s about having a plan for the years leading up to retirement, too.

If you’re still working, take the time to thoroughly review your options. And if you’ve already retired, encourage your employed loved ones to do a thorough review of their benefits. Don’t assume last year’s choices are still the best. Be intentional about your benefits for 2026 and beyond.

Amanda Howerton, CFP® is a Senior Advisor with Rather & Kittrell.