The “Before the Ball Drops” Checklist: Maximize Your Benefits and Protect Your Family
Between holiday shopping, travel plans, and closing out the work year, December is arguably the busiest month on the calendar. However, amidst the festive chaos, there is a critical window of opportunity that closes on December 31st.
Ignoring your insurance portfolio at year-end can mean leaving money on the table—or worse, discovering coverage gaps when you need them filled the most. At TheBenefits.Guru, we believe the best gift you can give your future self is a clean financial bill of health.
Here is your essential year-end checklist to ensure you maximize your benefits and secure your family’s financial future before the calendar flips.
1. The Health Insurance “Sprint”
If you have had a year with significant medical expenses, you may have already met your annual deductible or even your Out-of-Pocket Maximum.
Why does this matter? Once you hit your deductible, your insurance plan begins creating a cost-share. If you hit your out-of-pocket max, the insurance carrier typically pays 100% of covered services for the remainder of the year.
- The Strategy: If you have met these thresholds, now is the time to schedule those “put-off” procedures. Have you been ignoring a nagging knee injury? Do you need a dermatology screening or updated blood work? Squeeze these appointments in before December 31st while the cost is low or zero. Come January 1st, the deductible resets, and you are back to paying full price.
Don’t Forget the FSA (Flexible Spending Account)
Unlike Health Savings Accounts (HSAs), which roll over year-to-year, FSAs operate on a strict “use it or lose it” basis. Check your balance today. If you have funds remaining, you must spend them.
- What to buy: You don’t need to force a doctor’s visit. You can use FSA funds for prescription eyewear, contact lenses, or even over-the-counter essentials like sunscreen, first-aid kits, and thermometers.
2. The Life Insurance Audit
Life moves fast. In the span of 12 months, you might have gotten married, bought a home, welcomed a child, or perhaps gone through a divorce. Do your life insurance policies reflect these changes?
Check Your Beneficiaries
One of the most common—and tragic—mistakes in the insurance world is failing to update beneficiary designations. A life insurance policy is a legal contract; if an ex-spouse is still listed as the beneficiary, the insurance company is legally obligated to pay them, regardless of your current marital status or will. Take five minutes to log in and confirm your primary and contingent beneficiaries are accurate.
Review Coverage Amounts
Inflation has increased the cost of living significantly. A policy you took out five years ago intended to cover a mortgage and college tuition might now fall short. If your income has increased, your coverage likely needs to increase to match your family’s lifestyle needs.
3. Assessing Disability Adequacy
While most people understand the need for life insurance, disability insurance is often overlooked. This is your “paycheck protection.”
Many employees rely solely on group disability insurance provided by their employer. While this is a great benefit, it often has limitations:
- Taxation: If your employer pays the premium, the benefits are usually taxable to you.
- Caps: Group plans often cap benefits (e.g., 60% of your base salary). Bonuses and commissions are frequently excluded.
Ask yourself: Could my family survive if my paycheck was cut by 50% or more for an extended period? If the answer is no, it may be time to look into a supplemental individual disability policy to bridge that gap.
Start the New Year with Confidence
Financial anxiety often stems from the unknown. By running through this checklist, you aren’t just checking boxes; you are actively building a fortress around your family’s financial well-being.
Don’t let the busy season distract you from these essential tasks. If you are unsure about your coverage limits or how to spend down your FSA, we are here to help.

