By Matt D’Amico, CFP®, ChFC®

You have a life insurance policy you bought in 1998, a long-term care brochure that came in the mail last week, and a Medicare packet arriving sometime around your 65th birthday. But you haven’t been given the financial advice you need to figure out: 

  • Which do you still need? 
  • Which one stopped earning its premium years ago? 
  • Which one you should have looked at before now. 

These questions come up in nearly every meeting with people in their late 50s and early 60s. Insurance gets bought one policy at a time, across 30 or 40 years, so by the time retirement is close, you own a stack of coverage assembled for a version of your life that has already ended. Sorting it out starts with reading what you already have.

Start With the Policies Already in Your Filing Cabinet 

Three categories deserve your attention before you shop for anything new.

Life Insurance 

Find the death benefit, the named beneficiary, and the annual premium on every policy you own, then ask what job that coverage is doing today. A policy bought to replace a paycheck for a young family may be addressing a concern you’ve already solved.

Coverage is still a smart move in a few situations. When one spouse dies, the household stops collecting the smaller of the two Social Security benefits, and a pension may drop to a survivor percentage or end altogether, so life insurance can fill that income gap. It also creates cash for a family that owns something hard to divide, such as a rental property or a business interest, so nobody is rushed into a sale.

Universal life policies deserve extra attention, since some were sold on 1990s interest assumptions that never held and now need a larger premium to stay in force. Ask your carrier for an in-force illustration, a projection of whether today’s premium will carry the policy to age 90.

Long-Term Care

Medicare covers far less than people assume. It pays for skilled nursing care after a qualifying hospital stay, covering days one through 20 in full and charging $217 a day for days 21 through 100 in 2026 (projected to rise to $223.50 a day in 2027), then stopping altogether. 

Custodial care, which helps with bathing, dressing, eating, and moving around, is not covered at any point, and it is the kind that goes on for years. The national median runs around $133,462 a year for a private room in a nursing home, $6,386 a month for assisted living, and $36.05 an hour for a caregiver at home.

Timing works against you on this one. Coverage is priced on your age when the policy is issued and your health when you apply, and both move in one direction, so a diagnosis at 66 that feels minor can close the door entirely. People who ask between 55 and 60 see the widest set of options, including standalone policies, life insurance with a care rider, and setting aside a pool of your own assets for it.

Supplemental Coverage

Original Medicare leaves you responsible for 20 percent of most outpatient costs with no annual ceiling, on top of a Part B premium of $202.90 a month in 2026 (projected to rise to $209.50 per month in 2027). Medigap and Medicare Advantage are two different answers to that exposure, and you cannot hold both at once. Your six-month Medigap window opens when you turn 65 and enroll in Part B, and it is the one stretch when carriers cannot ask about your health. 

Annual open enrollment runs October 15 through December 7, when plans revise their networks and the drugs they cover.

The Two Ways People Get This Wrong 

Over-insurance shows up as premiums with no job attached, like a term policy that’s renewed several times at the old rate or a hospital plan bought through work that now duplicates something Medicare handles. That money is not funding the part of the plan that’s thin.

Under-insurance is harder to spot because the gap stays hidden until a crisis hits. The most common example is a family assuming they can simply “self-fund” long-term care out of their savings. They often don’t realize that paying for a few years of custodial care can drain the very portfolio meant to support a surviving spouse for decades. 

Finding your place between the two requires knowing what the rest of the plan needs the insurance to do.

Where Insurance Belongs in the Plan

Our Retirement GPS process covers five areas: income planning, investment planning, tax planning, healthcare planning, and legacy planning. Insurance fits directly into two of those areas: healthcare planning dictates your Medicare choices and long-term care strategy, while legacy planning uses life insurance to shield surviving spouses and transfer wealth.

That placement drives the order Networth Advisors works in. We start with your income needs, your tax situation, and what you intend to leave behind, then answer coverage questions against what we find. 

No insurance company owns us, so we’re not limited to one carrier’s shelf, and as fiduciaries, we’re obligated to put your interests ahead of our own.

Do you own policies that have never been read alongside the rest of your retirement plan? That’s the review you want to book. Bring the paperwork and we can go through it policy by policy, and tell you what each one costs and whether it still belongs.

To start the conversation, call (800) 822-3639, email schedule@networthadvisorsllc.com, or schedule a time online.

Frequently Asked Questions

Do I still need life insurance after I retire?

Only when the policy still has a job to do. Coverage is usually worth its premium when:

  • A surviving spouse would lose Social Security or pension income
  • Your estate holds property that is difficult to divide among heirs
  • You intend to leave a set dollar amount to heirs

If none apply, you may be paying for coverage you no longer need.

Does Medicare cover long-term care?

No. Medicare pays for skilled nursing care for up to 100 days after a qualifying hospital stay, and only the first 20 days come at no cost. It doesn’t provide custodial care, the daily help with bathing, dressing, and eating that most families eventually need. That cost falls to you, Medicaid, or a long-term care policy.

What’s the difference between Medigap and Medicare Advantage?

Medigap pays part of what Original Medicare leaves you owing and lets you use any provider who takes Medicare. Medicare Advantage replaces Original Medicare with a network plan that often bundles drug coverage. You can hold one, never both. The Networth Advisors team evaluates the two against your health, your travel, and your budget before you enroll.

About Matt

Matt D’Amico, CFP®, ChFC®, is a registered Investment Adviser Representative and financial advisor at Networth Advisors, LLC, a financial planning and wealth management firm in Canonsburg, PA. The firm is dedicated to helping clients enjoy a successful retirement, specializing in income planning and legacy preservation for pre-retirees and retirees. Matt excels at simplifying complex retirement concerns to help clients make smart financial decisions.

Matt discovered his passion for finance in college, inspired by a trusted mentor, and earned a degree in finance and business management from Saint Vincent College. Before joining Networth Advisors, he gained valuable experience at New York Life and MassMutual, where he obtained his Life, Accident & Health Insurance Licenses. Matt is also a CERTIFIED FINANCIAL PLANNER® professional and Chartered Financial Consultant®.

Outside of work, Matt is a sports junkie and music enthusiast. He enjoys spending time with friends, embarking on adventures with his wife, Kayla, and their mini labradoodle, Nellie. He is also the co-author of Networth for Retirement: Mapping Out Your Journey. To learn more about Matt, connect with him on LinkedIn.