Tom McQuillan on the Two Retirement Questions People Often Answer Too Late
By: Carson Bernard
For most of a working life, retirement planning gets measured in a single number. People compare the 401(k) balance to a target and assume that once it is large enough, the planning is finished.
Then two questions arrive that the number does not answer. The first is about health coverage: which version of Medicare to choose and what it will and will not cover. The second is about cash flow: where the money shows up each month once the paycheck stops. Both decisions land in a narrow window, often in the same year, and both are difficult to undo later.
The number of people facing that window is unusually high right now. More than 4.1 million Americans will turn 65 each year through 2027, roughly 11,200 a day, according to research from the Alliance for Lifetime Income, which has called the period the Peak 65 zone.
Thomas J. McQuillan, RFC®, has spent the past decade working with people inside that window. He and his wife, Sherri, founded My Retirement Store, a family-owned agency in Hoover, Alabama, that specializes in Medicare and retirement income planning. The pairing is deliberate. In McQuillan’s experience, people rarely arrive with only one of those questions, even when they think they do.
“Retirement confidence comes from knowing where your dependable income will come from after the paycheck stops, and how your healthcare coverage will work,” McQuillan says.
The Medicare Decision Nobody Prepares For
Turning 65 does not come with instructions. It comes with mail.
In 2026, the average Medicare beneficiary can choose from 32 Medicare Advantage plans with prescription drug coverage, and 39 individual plans in total, according to KFF. That is before the separate path of Original Medicare with a supplement and a standalone drug plan, and before networks and premiums shift from one year to the next.
McQuillan says the questions he hears most often are more basic than plan comparison. People want to know when to enroll, what happens to coverage from a former employer, and whether a specific doctor will still be in network.
“People are not confused because they are careless,” he says. “They are confused because nobody has ever explained it to them in plain language, and the material they receive in the mail is not written to explain it.”
Where the Paycheck Comes From
The second decision: retirement income planning, has no fixed deadline, unlike Medicare enrollment. Nobody mails a reminder that it’s time to determine whether your ensured income will cover your monthly expenses.
McQuillan starts with an inventory rather than a recommendation. Clients identify the income they can count on, including Social Security and any pension benefits, and then compare that total to their essential monthly living expenses. If there’s a gap between the two, that’s the problem worth solving.
“Once people see the gap in writing, the conversation changes,” McQuillan said. “It stops being an abstraction about whether they have enough. It becomes a specific number they can plan around.”
When a gap exists, the discussion may include annuities. Depending on how they are structured, annuities are insurance contracts that can provide ensured income for a specific period or for life, subject to the contract terms and the claims-paying ability of the issuing insurance company.
“Annuities are tools,” McQuillan said. “For many retirees, the most valuable use of an annuity is creating ensured lifetime income when Social Security and other warranty sources are not enough to cover essential expenses. Other annuities are designed to protect principal, while some offer benefits that can help with long-term care costs. The key is matching the tool to the problem.”
My Retirement Store is an insurance agency. It does not manage investments or provide individualized investment advice, and McQuillan says being clear about that boundary is part of the job.
Education Before Products
The agency holds roughly 18 to 20 educational seminars a year across the Birmingham area, covering Medicare basics and retirement income planning. Attendance does not require an appointment afterward, and McQuillan says a meaningful share of attendees never become clients.
“If someone leaves a seminar and decides they can handle it themselves, that is a good outcome,” he says. “They are making an informed decision instead of a default one.”
That is also how he defines the work.
“Retirement is more than the money you saved,” McQuillan says. “It is knowing how your healthcare works and knowing what shows up in the account every month. When people have both of those answered, they stop worrying about running out and start actually living. Retirement should be lived, not survived.”
Disclaimer: The information provided in this article is for general informational and educational purposes only. It is not intended as financial, insurance, tax, or professional advice. Medicare plan availability, benefits, and costs vary by location and by year. Annuity guarantees are subject to the terms of the contract and the claims-paying ability of the issuing insurance company. Readers should not rely solely on the content of this article and are encouraged to seek guidance tailored to their specific circumstances. We disclaim any liability for any loss or damage arising directly or indirectly from the use of, or reliance on, the information presented.
