7 Smart Open Enrollment Strategies to Maximize Your Benefits (and Your Savings)

If you’re like most of my clients, that annual open enrollment email from HR lands in your inbox with a mix of dread and confusion. Between comparing plan options, deciphering insurance jargon, and making decisions that will impact your family for the next 12 months, it’s easy to feel overwhelmed. And if you’re the primary breadwinner in your household? The pressure to get these decisions right feels even heavier.

The trust is that open enrollment is one of the most important financial planning opportunities you’ll get all year, and the decisions you make now can save (or cost) you thousands of dollars. After working with women and families for over a decade, I’ve seen firsthand how smart open enrollment strategies can make a meaningful difference in your financial wellbeing, especially when you’re juggling career, family, and maybe even aging parents.

So let’s cut through the confusion and make sure you’re not leaving money on the table this year.

1. Start With Your Family’s Healthcare Reality Check

Before you click “keep my current plan,” take a hard look at how your family actually used healthcare this past year. I can’t tell you how many times I’ve sat with clients who realize they’ve been overpaying for coverage they rarely use—or worse, underpaying and getting hit with massive out-of-pocket expenses.

Think about what’s really happening in your household. Is your college student still on your plan? Are you in perimenopause and seeing your doctor more frequently? Is your partner managing a chronic condition? Are your aging parents increasingly relying on you to help navigate their healthcare, reminding you that your own needs will change soon?

One of the most effective open enrollment strategies is to review your actual claims from the past year (most insurance portals let you download this information). Add up what you spent on premiums, deductibles, copays, and prescriptions. Then, use your employer’s comparison tools to see if a different plan would have saved you money.

Here’s what I tell my clients: if you’re the breadwinner and your family depends on your income and benefits, you can’t afford to guess. Run the numbers. A high-deductible health plan (HDHP) with an HSA might save you thousands if your family is generally healthy, but if someone needs regular care or you’re managing your own health issues, a PPO with higher premiums but predictable copays might give you the peace of mind you need.

2. Max Out Your HSA (It’s the Triple Tax Advantage You Can’t Ignore)

If you are eligible for a Health Savings Account, this is your golden ticket. It’s especially powerful if you’re thinking about retirement in the next 10-20 years. An HSA offers a triple tax advantage that no other account can match: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.

For 2026, you can contribute up to $4,400 for individual coverage or $8,750 for family coverage, with an additional $1,000 catch-up if you’re 55 or older. If you can afford it, max out your HSA contribution and don’t touch the money. I know that’s easier said than done when you’re managing a household budget, but hear me out. Pay your current medical expenses out of pocket if possible and let that HSA grow for decades. After age 65, you can withdraw HSA funds for any purpose without penalty (though non-medical withdrawals are taxed like a traditional IRA).

Think of it as a stealth retirement account that also gives you a safety net for healthcare costs, something we all know gets more expensive as we age. 

3. Don’t Sleep on Your FSA Options (Especially Dependent Care)

Flexible Spending Accounts are the ultimate “use it or lose it” benefit, but they’re incredibly valuable if you plan correctly. For 2026, you can contribute up to $3,400 to a healthcare FSA.

Consider your predictable expenses: your hormone therapy, your daughter’s contact lenses, your son’s ADHD medication copays, your own therapy sessions (yes, mental health counts!), or those orthodontia payments you’re still making. Many people don’t realize that FSA funds can cover so much more than doctor visits—sunscreen, first aid supplies, reading glasses for when you’re helping with homework, and even menopause-related products.

But here’s the benefit I see too many women overlook: Dependent Care FSAs. If you’re part of the sandwich generation—still supporting kids at home while also helping care for aging parents—this is huge. You can contribute up to $7,500 per household pre-tax for childcare or adult daycare for a qualifying dependent.

Let me paint a picture: maybe you’re paying for after-school care for your youngest while you’re at work. Or perhaps you’re paying for adult daycare for your mother a few days a week so you can focus on your career. That’s money you’re already spending. Running it through a Dependent Care FSA gives you an immediate 20-30% return through tax savings. 

4. Review Your Life Insurance and Disability Coverage (This Is Non-Negotiable)

This is where I see people leave the most money on the table, and it’s also where I get the most pushback. I know nobody wants to think about these scenarios. But if you’re the primary breadwinner, if your family depends on your income, or if you’re a single parent, this isn’t optional.

Many employers offer group life insurance equal to one or two times your salary—often at no cost to you. But if you’re earning $100,000 and your employer provides $200,000 in coverage, is that enough to replace your income, pay off the mortgage, and fund your kids’ college? Probably not.

Your employer’s basic coverage rarely meets this need. The good news? Group supplemental life insurance through your employer is often significantly cheaper than buying an individual policy, especially as we move into our 50s and 60s and those premiums start climbing. However, it’s important to note that this coverage often isn’t always portable. 

And let’s talk about disability insurance—something that is often overlooked. If you’re in your peak earning years, your ability to earn income is your most valuable asset. Disability insurance replaces a portion of your income if you become unable to work due to illness or injury. Most employer plans cover 60% of your salary, but make sure you understand whether benefits are taxable and if there’s a waiting period before coverage kicks in. If you’re the one everyone depends on, this protection is critical.

5. Take Advantage of Retirement Plan Changes (Your Future Self Is Counting on You)

Open enrollment is the perfect time to review and adjust your retirement contributions—and this is especially important if you’re in your 40s through 60s. The unfortunate reality is that women still face a retirement savings gap.

If you received a raise this year, increase your 401(k) contribution by at least half of that raise amount. You won’t miss money you never saw in your paycheck, and your future self will thank you. If you got a 4% raise, bump your 401(k) contribution by 2%.

For 2026, the projected 401(k) contribution limit is $24,500, with an additional $8,000 catch-up contribution if you’re 50 or older. That catch-up provision exists specifically for people like us who are in our prime earning years and need to accelerate our savings. Take advantage of it.

At minimum, contribute enough to get your full employer match. That’s literally free money, and you can’t afford to leave it on the table. If your employer offers a Roth 401(k) option, consider splitting your contributions between traditional and Roth accounts for tax diversification in retirement.

6. Explore Newer Benefits You Might Be Overlooking

Many employers have added valuable benefits in recent years that often get overlooked during open enrollment—benefits that can make your life as a working woman managing multiple responsibilities significantly easier. These might include:

• Legal services plans that provide access to attorneys for estate planning (critical if you have kids or aging parents), power of attorney documents for your parents, or reviewing contracts
• Employee assistance programs offering free counseling (because let’s be honest, managing career and family is stressful), financial planning sessions, or elder care navigation services
• Wellness incentives that reduce premiums for completing health screenings or fitness challenges
• Fertility and family planning benefits if you’re considering expanding your family 
• Menopause support programs that some progressive employers now offer

Review your entire benefits package, not just the insurance options, to make sure you’re utilizing everything available to you. These benefits exist because you’ve earned them. Use them.

7. Document Your Decisions and Set Calendar Reminders

Finally, one of the most underrated open enrollment strategies is simply keeping good records, something we often neglect when we’re busy taking care of everyone else.

Create a simple spreadsheet documenting what you chose and why. Note any anticipated medical expenses for the coming year: your daughter’s wisdom teeth removal, your own mammogram and colonoscopy (yes, we’re at that age), your son’s allergy shots, your mother’s upcoming knee surgery that you’ll be helping coordinate. Estimate your out-of-pocket costs and make sure your FSA election covers it.

Set reminders for mid-year to check in on your FSA spending, HSA contributions, and whether you’re on track with your retirement savings goals. Schedule that preventive care appointment for yourself, not just for your kids or your parents. And definitely set a reminder for next October to start thinking about open enrollment before you’re rushed and making decisions in the last 24 hours.

The Bottom Line

As women who are managing careers, families, and often the financial wellbeing of multiple generations, we can’t afford to treat open enrollment strategies as just another checkbox to complete. These decisions matter. They protect your family, maximize your compensation, and build your financial security.

The strategies you implement during this window can save you thousands of dollars and provide essential protection for your family’s future. Take the time to understand your options, run the numbers, and make informed decisions. 

And if you’re feeling overwhelmed, don’t hesitate to reach out to a financial professional who can help you evaluate your choices in the context of your overall financial plan. You don’t have to figure this out alone.