Ever stare at your company’s open enrollment screen and think, I have no idea what half of this means? You’re in good company. A national survey found that 86% of employees are confused by their benefits (HRMorning, 2024).
That confusion can cost real money. Choosing the wrong plan or skipping a benefit could mean hundreds or even thousands of dollars lost each year. The good news? A few smart questions can help you make confident, money-savvy choices.
At RedSky Money, we help early-career professionals tackle real-world financial decisions with clarity and confidence. Here are five questions to ask before you hit “submit.”
1. What does each health plan really cost me per year?
Don’t just look at the monthly premium. Add up what you might spend in a year — premiums, deductible, copays, and coinsurance.
A low premium might seem like the best deal, but if you visit doctors often or take prescriptions, a higher-premium plan could actually save you money. The trick is looking at the total cost, not just what comes out of your paycheck.
2. Is there an HSA or FSA, and how do I use it?
If your employer offers a Health Savings Account (HSA) or a Flexible Spending Account (FSA), it’s worth learning how they work. Both let you use pre-tax dollars for medical expenses, which means you pay less in taxes.
An HSA is especially powerful because the money rolls over year to year and can grow over time. Think of it as a mini health investment fund that helps you save now and later.
3. What does my employer match on retirement contributions?
Your 401(k) match is one of the easiest ways to earn free money. Find out what percentage of your salary your employer will match and contribute at least that much.
Even a small contribution early in your career can grow dramatically thanks to compounding. Future-you will be very grateful.
4. Do I have access to mental health or wellness benefits?
Many companies now include perks like therapy sessions, wellness apps, or gym memberships, but a lot of employees don’t even know they exist.
Check your HR portal or benefits summary to see what’s available. Mental and physical health benefits aren’t just nice extras — they’re part of building a sustainable, healthy career.
5. When can I change my choices again?
Outside of open enrollment, most plans only let you make changes after a “qualifying life event” such as getting married, having a baby, or losing coverage elsewhere.
Knowing the rules helps you plan ahead and prevents surprises later. You don’t want to find yourself stuck with the wrong plan until next year.
Why this matters
If 86 percent of employees are confused about their benefits, you have an opportunity to do better. Understanding your options helps you make smarter choices, lower stress, and stretch your paycheck further.
Treat this process as part of your financial foundation, not just another HR task. Each benefit you understand is one more way to strengthen your financial life.
Try this week
Before you click “submit,” pick one question above and find the answer — through your HR rep, benefits guide, or company portal.
Even one confident decision can save you money and reduce financial stress for the entire year.
If you’d like a personalized money plan, RedSky Money offers free one-on-one financial coaching to help you start strong and make choices that work for your financial journey.