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Life Insurance — 8 questions

I know the face value of my life insurance policy. If you don't know the number, you can't know if it's enough.

My death benefit would replace at least 5–10× my annual income for my dependents. The common rule: enough to cover income replacement, mortgage payoff, and education costs.

I know when my current policy expires — if it's term insurance. A lapsed term policy at age 68 with poor health is nearly impossible to replace affordably.

My beneficiaries are current — spouse, children, and contingent beneficiaries are up to date. An ex-spouse or deceased parent listed as beneficiary is a common and costly oversight.

I understand whether my policy has a cash value component — and whether it's performing as illustrated. Whole life and IUL policies can underperform projections. Know what yours is actually doing.

My coverage accounts for my current debts — mortgage balance, business loans, co-signed debt. Income replacement isn't enough if there's debt that would outlive you.

I have a plan — not just a policy. I know what the money is supposed to do. Most people bought a product. Fewer have thought through the actual job it needs to perform.

My policy is through a carrier — not just a group benefit I'd lose if I left my job. Group life disappears with employment. Portability matters.

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Health Insurance — 9 questions

I know my deductible — and I have that amount available if something happens tomorrow. A $6,000 deductible you can't actually cover isn't real protection.

I know my out-of-pocket maximum — and what counts toward it vs. what doesn't. Surprise bills often come from costs excluded from the OOP max: out-of-network, specialty drugs, balance billing.

My doctors and specialists are in-network on my current plan. Networks change. Verifying once a year at open enrollment prevents a mid-year surprise.

My regular prescriptions are covered under my plan's formulary at the tier I expect. Formularies change annually. A tier shift can double or triple your drug cost overnight.

I have dental coverage that actually covers the procedures I'm likely to need. Most dental plans cover cleanings and basic work well — but major restorative work has strict annual limits and waiting periods.

I have vision coverage and I know what it covers for frames, lenses, and contact lenses. Stand-alone vision plans are often underused because people don't know exactly what's included.

I understand what my plan covers for mental health and therapy — same as other medical visits or different. Mental health parity laws apply, but coverage details still vary significantly by plan.

If I lost my job tomorrow, I have a plan for health coverage — COBRA cost, marketplace options, or a spouse's plan. COBRA is often $700–$1,500/month. Knowing the number beforehand removes panic from the decision.

I've reviewed my plan options at the last open enrollment — not just auto-renewed. Carriers restructure plans annually. Auto-renewal can mean paying more for less without realizing it.

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Medicare — 8 questions

If I'm within 3 years of 65, I know my Initial Enrollment Period — and whether I need to act before my birthday. Your IEP is the 7-month window around your 65th birthday. Missing it without qualifying coverage means permanent penalties.

I understand the difference between Medicare Advantage and Original Medicare + Supplement. These are fundamentally different structures. Switching out of Advantage back to Original Medicare can be difficult after age 65.

I know whether my income triggers IRMAA — the Medicare high-income surcharge — and by how much. If your 2024 income exceeded $109,000 single / $218,000 joint, your 2026 Part B and D premiums are higher. Many people find out at enrollment.

My Medicare Part D drug plan covers my current prescriptions at a tier I can afford. Part D plans should be reviewed every year during Annual Enrollment (Oct 15–Dec 7). Formularies change.

I know that Medicare has no out-of-pocket maximum under Original Medicare alone — and I have a plan for that. Original Medicare Part A + B has no OOP cap. A Medigap supplement or Medicare Advantage fills this gap differently.

I understand what Medicare doesn't cover — dental, vision, hearing, long-term care. These are the four most common Medicare surprises for new enrollees.

If I'm still working past 65 with employer coverage, I know how my employer plan coordinates with Medicare. Employer size determines whether Medicare or your employer plan is primary. Getting this wrong can result in unpaid claims.

I've reviewed my Medicare plan in the last 12 months during Annual Enrollment Period. Advantage and Part D plans change every year. Staying in the same plan without reviewing it can cost you significantly.

Note: This checklist is general educational information, not individualized insurance, tax, or legal advice. Coverage needs vary based on your age, health, income, family situation, and state of residence.

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